Universidad de Chile Facultad de Ciencias Departamento de Química Licenciatura Ciencias mención Química
Informe de Laboratorio de Orgánica III
Autor: Profesor:
Álvaro Etcheverry Dra. Cecilia Labbé
Fecha de entrega: 09/03/2012 e-Mail:
[email protected]
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ÍNDICE 1. 2. 3. 4.
5.
6. 7. 8.
Resumen: Introducción: Objetivos: Reacciones involucradas: a. Reducción con borohidruro de sodio: b. Oxidación con bisulfato de potasio: c. Sulfonación con ácido clorosulfónico: d. Amonólisis del grupo sulfonilo: e. Hidrólisis selectiva del grupo acetamido: f. Condensación benzoínica: g. Oxidación con ácido nítrico: h. Condensación amina-carbonilo: i. Transposición bencílica: j. Condensación de Diels-Alder: Síntesis orgánica: a. Síntesis de estireno a partir de acetofenona: i. Introducción: ii. Materiales y reactivos: iii. Método experimental y observaciones: iv. Análisis de resultados: v. Conclusión: b. Síntesis de sulfanilamida a partir de acetanilida: i. Introducción: ii. Materiales y reactivos: iii. Método experimental y observaciones: iv. Análisis de resultados: v. Conclusión: c. Preparación de quinoxalina a partir de benzaldehído: i. Introducción: ii. Materiales y reactivos: iii. Método experimental y observaciones: iv. Análisis de resultados: v. Conclusión: d. Transposiciones y cicloadiciones: i. Introducción: ii. Materiales y reactivos: iii. Método experimental y observaciones: iv. Análisis de resultados: v. Conclusión: Discusión general: Conclusiones generales: Bibliografía:
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1.- RESUMEN En este informe se verán las síntesis de distintos compuestos orgánicos, mediante el uso de distintas técnicas de laboratorio y utilizando reactivos comunes en un laboratorio. Además se analizarán los mecanismos de cada reacción de manera que se puedan sugerir pequ pequeñ eñas as modi modific ficac acio ione ness al méto método do expe experim rimen ental tal con con el fin de incre increme ment ntar ar los los rendimientos obtenidos. También se analizan distintos criterios de pureza a fin de poder determinar el grado de pureza de los productos obtenidos.
2.- INTRODUCCIÓN INTRODUCCIÓN La síntesis orgánica tiene sus orígenes en el siglo XIX, específicamente en el año 1828, cuando el químico alemán Friedrich Wöhler sintetizó urea al tratar isocianato de plata (AgNCO) con cloruro de amonio (NH4Cl). Hasta ese entonces, se creía que para poder obtener compuestos orgánicos era necesario una “fuerza vital”, propia de los seres vivo vivos, s, teorí teoríaa cono conoci cida da como como vitali vitalism smoo1. La prim primeera sínt síntes esis is orgá orgáni nica ca con con fine finess 2 comerciales fue la del alcanfor por el químico finlandés Gustaf Komppa en 1903 . A partir de entonces, entonces, el desarrollo desarrollo de la química, química, y específicame específicamente nte el de la química química orgánica, ha llevado al desarrollo de técnicas y métodos cada vez más elaborados para la síntesis orgánica. Como por ejemplo, varios premios Nobel de química se han adjudicado a investigadores cuyos trabajos se han relacionado con la síntesis orgánica. Robert Burns Woodward lo recibió en 1965 debido a varias síntesis de compuestos naturales (por ejem ejemplo plo,, su sínte síntesis sis de estri estricn cnina ina en 1954 1954), ), Will William iam S. Kn Know owle less y Ry Ryōji ōji No Noyo yori ri comp compart artie iero ronn el Premio Premio No Nobe bell de Qu Quím ímic icaa el año año 2001 2001 por por el desa desarro rroll lloo de una una hidrogenación estéreoselectiva. Sin embargo, se podría decir que uno de los grandes avances en el diseño de síntesis orgánicas se le puede atribuir a Elías James Corey, quien desarrolló el análisis retrosintético por lo que obtuvo el Premio Nobel de Química el año 1990, en este acercamiento se planea la síntesis hacia atrás partiendo del producto usando reglas estándar 3. El objetivo de una síntesis orgánica es obtener un producto en forma pura, mediante el proceso más conveniente posible, considerando los rendimientos, los costes asociados y el tiempo involucrado. Además, si la síntesis es de interés comercial/industrial, también deberán tomarse en consideración el manejo adecuado de los residuos a fin de causar daños al medio ambiente. Es necesario que la síntesis contenga la menor cantidad de pasos posibles, ya que los rendimientos caen rápidamente a medida que el número de etapas aumenta. Hoyy en día la sínte Ho síntesis sis orgán orgánica ica mode moderna rna impl implica ica lleva llevarr a cabo cabo tres tres obje objetiv tivos os principales: 1. Construir Construir el esquel esqueleto eto de carbono carbono principal principal de la molécul moléculaa objetivo. objetivo. 2. Intro Introdu duci cir, r, remo remove verr o trans transfo form rmar ar los los grup grupos os func funcio iona nale less para para alcanz alcanzar ar la funcionalidad del producto deseado. 3. Ejerce Ejercerr un fuerte fuerte control control de la estéreos estéreosele electiv ctividad idad en todas todas las etapas etapas en las que
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Estas Estas tres tres tarea tareass no nece necesar sariam iamen ente te debe debenn real realiza izarse rse en ese ese orden orden ni tampo tampoco co son son exclusivamente independientes, pero es necesario integrarlas plenamente para llevar a cabo una síntesis correcta. Además también es necesario considerar los rendimientos de cada cada etapa, etapa, el tiempo tiempo utilizad utilizado, o, la prese presencia ncia de grupos grupos funcio funcionale naless que produzca produzcann 4 reacciones laterales . Básicamente, la metodología de las síntesis orgánicas implican dos casos: síntesis totales o síntesis parciales. En las síntesis totales, a partir de precursores petroquímicos y reactivos inorgánicos se obtienen los productos deseados, a su vez, estas síntesis pueden ser lineales (en donde a través de etapas sucesivas sucesivas se obtienen obtienen las moléculas moléculas objetivo), o para moléculas más complejas se puede utilizar una síntesis convergente (en donde se realizan síntesis lineales para obtener intermediarios clave los que finalmente se unen para formar el producto deseado) 5. Por otro lado, las síntesis parciales implican la utilización de precursores naturales que no han sido sintetizados, si no, que han sido extraídos y purificados a partir de organismos (un ejemplo de esto, es la síntesis del LSD) 6.
3.- OBJETIVOS En los siguientes capítulos se revisarán distintos aspectos de cada una de las síntesis realizadas. Cada síntesis implica lograr una serie de objetivos, los que se detallan a continuación: •
•
•
•
•
•
Mediante el uso de distintas técnicas experimentales, lograr la síntesis de la molécula objetivo, separarla de la mezcla de reacción y purificarla para su posterior identificación. La correcta utilización de estas técnicas para efectuar las reacciones de manera efectiva y segura. Iden Identif tific icar ar los los facto factore ress que que afect afectan an el rend rendim imie iento nto de las las reacc reaccion iones es realizadas. Ser capaz de determinar el grado de pureza de los productos obtenidos mediante criterios como el punto de fusión o las cromatografías de capa fina. Inte Interpr rpret etar ar los los espe espect ctro ross obte obtenid nidos os para para pode poderr iden identif tifica icarr el prod produc ucto to obtenido, además de poder identificar el grado de pureza. Compa Co mparar rar las distinta distintass propied propiedade adess químic químicas as y físicas físicas de los produc productos tos obtenidos.
4.- REACCIONES REACCIONES INVOLUCRADAS INVOLUCRADAS Durante Durante estas estas sesio sesiones nes de laborato laboratorio rio se llevaro llevaronn a cabo cabo distinta distintass síntesi síntesiss que que involu involucra craron ron reacci reaccione oness de distint distintoo tipo: tipo: reducc reduccione iones, s, oxidac oxidacion iones, es, cicloa cicloadic dicione iones, s, transposicion transposiciones, es, entre otras. Para cada una de estas reacciones reacciones se realizará realizará un análisis en forma general, de acuerdo al orden de utilización en las síntesis que se mencionan posteriormente. a)
Reducción con borohidruro de sodio (NaBH 4):
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El borohidruro de sodio fue descubierto en 1943 por H. I. Schlesinger y H. C. Brown, sin embargo, no fue si no hasta el año 1949 cuando S. W. Chaikin y W. G. Brown encontraron su aplicación en la reducción de aldehídos, cetonas y cloruros de ácidos 7. En contraste con el LiAlH 4, el NaBH4 es insoluble en éter y soluble en metanol y etanol, y aunque es más soluble en metanol que etanol, el NaBH4 reacciona apreciablemente con el metanol, por lo que es preferible usar etanol para llevar a cabo la reacción.
Esquema N°1: Mecanismo de la reducción de una cetona con NaBH 4.
b)
Deshidratación con bisulfato de sodio (KHSO 4): La eliminación de agua a partir de un alcohol se denomina deshidratación. Debido a que el agua es mucho mejor grupo saliente que el grupo hidroxilo, es mejor utilizar una catálisis ácida por sobre una catálisis básica para llevar a cabo éstas reacciones. Generalmente no se utilizan hidrácidos (HX), debido a que sus bases conjugadas son buenos nucleófilos y podrían llevar a cabo reacciones de sustitución fácilmente 8. En este caso, se utiliza bisulfato de sodio
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compuesto permite desplazar el equilibrio de la reacción hacia la formación de producto, ya que se trata de un compuesto higroscópico 9.
Esquema N°2: Mecanismo de la deshidratación de un alcohol en medio ácido.
c)
Sulfonación con ácido clorosulfónico (ClSO 3H): El ácido clorosulfónico puede ser utilizado tanto para sulfonaciones como para cloros clorosulfo ulfonac nacione ioness de un amplio amplio rango rango de compue compuesto stoss aromáti aromáticos cos.. Por lo general, general, sólo un equivalente equivalente es utilizado cuando cuando se usan solventes solventes inertes para evitar la formación de subproductos. Por otro lado, también se puede usar una mayor cantidad de equivalentes para desplazar el equilibrio hacia la formación del producto deseado, lo que dependerá de la naturaleza del sustrato inicial 10.
Esquema N°3: Mecanismo de sulfonación con ácido clorosulfónico.
d)
Amonólisis de un grupo sulfonilo: La amonólisis del grupo sulfonilo procede de similar forma a la de un cloruro de ácido, donde la reacción corresponde a una sustitución nucleofílica, en este caso, mediante el ataque de una molécula de amoniaco (nucleófilo) 11.
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Esquema N°4: Mecanismo de la amonólisis de un grupo sulfonilo.
e)
Hidrólisis selectiva del grupo acetamido: Las amidas son excepcionalmente estables frente a hidrólisis ácidas o básicas, por lo son ampliamente ampliamente utilizadas como grupos protectores protectores de aminas, aminas, cuando cuando éstas (debido a su reactividad) presentan un problema en la síntesis orgánica. Son Son norm normal alme mente nte hidro hidroliz lizad adas as media mediante nte cale calenta ntamie miento nto a reflu reflujo jo bajo bajo condiciones ácidas o básicas extremas. Para la formación del grupo acetamido generalmente se hace reaccionar la amina respectiva con anhídrido acético o con cloruro de acetilo en presencia o ausencia de una base. Para la hidrólisis se pued pueden en usar usar dive divers rsos os méto método dos, s, como como la hidró hidrólis lisis is con con HCl HCl 1,2 1,2 N bajo bajo calentamient calentamientoo a reflujo, reflujo, sin embargo, embargo, es interesante la utilización utilización de la enzima acil acilas asaa prov proven enie ient ntee del del riñó riñónn de cerd cerdo, o, dond dondee la hidr hidról ólis isis is es adem además ás 12 estéreoselectiva .
Esquema N°5: Mecanismo de la hidrólisis selectiva del grupo acetamido.
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utiliza el cianuro como catalizador fue desarrollada por Nikolay Zinin en 183915.
Esquema N°6: Mecanismo de la condensación benzoínica.
g)
Oxidación con ácido nítrico (HNO 3): La oxidación de alcoholes se utiliza para la obtención de carbonilos, si se parte de un alcohol primario se obtiene un aldehído (si se usa un oxidante suave) o un ácido carboxílico (se utiliza un oxidante más enérgico), por otro lado, si se oxida un alcohol secundario se obtiene una cetona. La oxidación de un alcohol terciario no ocurre. En este caso se utiliza como agente oxidante ácido nítrico, el cual reacciona violentamente con muchas sustancias orgánicas, por lo que la concentración y la temperatura son parámetros importantes a considerar a la hora de controlar la reacción16. Es importante llevar a cabo la reacción bajo campana, debido a que se desprende dióxido de nitrógeno (NO 2), un gas de color marrón el cual es muy irritante 17.
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h)
Condensación amina-carbonilo: La reac reacci ción ón de carb carbon onil ilos os con con amon amonia iaco co o amin aminas as prim primar aria iass form formaa compuestos denominados iminas, también conocidas como bases de Schiff (que poseen el grupo C=N). Este tipo de reacciones es de importancia en la síntesis síntesis de aminas secundarias. secundarias. A veces, veces, este tipo de compuesto compuestoss es difícil de aislar debido a la facilidad con la que las iminas pueden ser hidrolizadas, para evitar esto suelen emplearse compuestos del tipo Y-NH 2 que dan productos estables del tipo R 2-C=N-Y, además es interesante observar que se pueden formar estéreo-isómeros cuando los sustituyentes del grupo carbonilo son distintos18.
Esquema N°8: Mecanismo de una condensación entre una amina y un carbonilo.
i)
Transposición bencílica: La transposición bencílica consiste en una reacción en donde se convierte la 1,2-difeniletanodiona (bencilo) al ácido 2,2-difenil-2-hidroxietanoico (ácido bencílico). Esta reacción fue descrita por primera vez por el químico alemán Justus von Liebig en el año 1938. En general, esta reacción se aplica para 1,2 diarilcetonas para obtener ácidos α-hidroxicarboxílicos 19.
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j) Condensac Condensación ión de Diels-Alder: Diels-Alder: La reacción de Diels-Alder fue descrita por primera vez por los químicos Otto Paul Hermann Diels y Kurt Alder en 1938, quienes obtuvieron el Premio Nobel de Química en el año 1950 por su trabajo en este tipo de reacciones 20. Corresponde a una cicloadición [4+2], puesto que comprende un sistema de cuatro electrones π y otro de dos. En general, esta reacción procede con facilidad, incluso espontáneamente y, en el peor de los casos, requiere de calor moderado. La reacción transcurre vía un estado de transición que es de menor volumen que el producto y que se ve acelerada cuando se realiza a altas presiones.
Esquema N°10: Mecanismo de una condensación de Diels-Alder.
5.- SÍNTESIS ORGÁNICA a.- Síntesis de estireno a partir de acetofenona. Introducción:
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La síntesis industrial del estireno procede comúnmente por la deshidrogenación catalítica del etilbenceno22, sin embargo, la primera vez que fue sintetizado en un laboratorio se llevó a cabo mediante la descarboxilación del ácido cinámico, catalizada por hidroquinona, puesto a reflujo 23. Además pequeñas trazas de estireno pueden ser encontradas en diversas plantas y frutas 24. La síntesis llevada a cabo en el laboratorio corresponde a una distinta a la del proc proced edim imie iento nto indu indust stria riall y se lleva lleva a cabo cabo en dos dos etapa etapas, s, dond dondee se reali realiza za una una reducción de una cetona con borohidruro de sodio y una posterior deshidratación del alcohol formado con bisulfato de potasio y cobre como catalizador, como se muestra en el Esquema N°11. O
HO
CH3
HO
N
a
E
t O
4
B
CH3
H H
CH2
CH3 K
H
4
, S C0 O u
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Esquema N°11: Síntesis de estireno Este método de síntesis permite aglomerar los conocimientos de cursos anteriores de quím químic icaa en cuant cuantoo a reac reactiv tivid idade adess y la utili utiliza zació ciónn de distin distintas tas técn técnica icass de laboratorio, tales como extracción de fase acuosa y destilación simple. Materiales y reactivos: Para la síntesis de 1-feniletanol:
REACTIVOS Etanol 95% NaBH4
CANTIDAD 25 mL 0 05 mo moles
MATERIALES Vaso pp. 150 mL Probeta 50 50 100 mL mL
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REACTIVOS 1-feniletanol KHSO4 Cobre en polvo NaCl
CANTIDA D 0.09 moles 1g 0.1 g
MATERIALES Balón de 100 mL (x2) Equipo de destilación simple Manto calefactor Probeta de 10 mL Embudo de decantación Vaso pp.
Método experimental y observaciones: Para la síntesis de 1-feniletanol: - En un vaso de precipitado de 150 mL se mezclaron 25 mL de etanol al 95% y 0.032 moles (1.2 g) de borohidruro de sodio (el cual no se disolvió en el etanol). Lentamente se agregaron gota a gota 0.10 moles (11.7 mL) de acetofenona agitando continuamente con el termómetro para mantener la temperatura por debajo de los 50°C. Esto causó un aumento de la temperatura en la mezcla de reacción, el NaBH 4 comenzó a disolverse y se apreció la formación de burbujas. - Una vez finalizada la adición de la acetofenona se aprecia que la mezcla de reacción se ha puesto turbia y se deja reposar por 15 minutos a temperatura ambiente para completar la reacción. Luego se agrega gota a gota 10 mL de HCl al 10%, formándose inmediatamente un precipitado de color blanco y liberándose hidrógeno gaseoso. Cuando se ha terminado de agregar el HCl se observa un precipitado blanco insoluble, posteriormente se agregan 20 mL de agua causando que el precipitado se solubilice. - Se coloca la mezcla de reacción a baño maría para evaporar el etanol y se
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Análisis de resultados: Se representan las cantidades utilizadas de productos y las cantidades de productos obtenidas en la Tabla N°1, para el cálculo del rendimiento de los productos se utilizaron los siguientes datos 25: ρ (1-feniletanol): ρ (estireno): Masa molar (1-feniletanol): Masa molar (estireno):
Reactivos Etanol 95% NaBH4 Acetofenona KHSO4 Cobre en polvo
1.01 g/mL 0.91 g/mL 122.17 104.16 g/mol
Tabla N°1: Cantidades de reactivos utilizados y productos obtenidos. Volumen Masa Volumen Moles Productos Moles (mL) (g) (mL) 1-feniletanol 0.097 11.8 25 Estireno 0.032 1.2 0.062 7.1 0.1 12.0 1.0 0.1
Para el cálculo de los rendimientos se utilizó la siguiente ecuación 26: Rendimiento =
moles de producto obtenido ×100% moles de producto esperado
Rendimiento por etapas: - Para la síntesis de 1-feniletanol, se obtuvo un rendimiento de 97%
Masa (g) 11.9 6.5
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8
7
6
5
4 PP M
3
2
Figura N°1: Espectro 1H-RMN teórico del 1-feniletanol 27.
1
0
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(d) (e)
7.36 7.38
2 hidrógenos 3 hidrógenos
Doblete Triplete
Los hidrógenos (d) y (e), poseen señales típicas de los hidrógenos unidos a un anillo aromático. Por otro lado, los hidrógenos (a) corresponden a los hidrógenos del metilo, cuyo desplazamiento se ve influenciado por la cercanía con el átomo de oxígeno del grupo hidroxilo, al igual que el hidrógeno (c) que debería tener una señal cercana a los 5 ppm. Al comparar el espectro teórico con el obtenido podemos ver la presencia de señales que no calzan, las que se pueden relacionar con contaminantes presentes en la muestra, como por ejemplo, los solventes utilizados en la síntesis del 1-feniletanol (etanol y diclorometano), así como acetofenona que haya quedado sin reaccionar.
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8
7
6
5
4 PP M
3
2
Figura N°4: Espectro 1H-RMN teórico del estireno 28.
1
0
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Tipo de hidrógeno (a) (b) (c) (d) (e) (f)
Desplazamiento (ppm)
Integración
Multiplicidad
5.18 5.61 6.63 7.33 7.40 7.60
1 hidrógeno 1 hidrógeno 1 hidrógeno 1 hidrógeno 2 hidrógenos 2 hidrógenos
Doblete Doblete Doblete acoplado Multiplete
Los hidrógenos (d), (e) y (f), son característicos del anillo aromático, mientras que los hidrógenos (a), (b) y (c) corresponden a los hidrógenos del sistema vinílico Nuevamente, si comparamos el espectro teórico con el experimental podemos ver la presencia de señales que no concuerdan, las señales a 1.3 ppm y 1.4 ppm pueden deberse a contaminantes presentes en la muestra, probablemente solventes, al igual que las señales a 4.2 ppm, 4.4 ppm y 4.8 ppm, las que podrían estar relacionadas con la presencia de pequeñas cantidades de 1-feniletanol.
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dudas debió haber repercutido en los rendimientos obtenidos. Debido a esto es que que sugi sugier eree volv volver er a puri purific ficar ar los los prod produc ucto toss para para evit evitar ar post poster erio iore ress contaminaciones (y a su vez, reacciones laterales indeseadas) si se va a utilizar el estireno como reactivo en otras síntesis.
b.- Síntesis de sulfanilamida a partir de acetanilida. Introducción: La sulfanilamida corresponde a un antibiótico perteneciente a la familia de las drogas sulfa , estos antibióticos fueron los primeros fármacos que resultaron ser eficaces como antimicrobianos29. La Figura N°7 muestra la estructura básica de las drogas sulfa. R O
1
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R
3
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2
Figura N°7: Estructura básica de las drogas sulfa.
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Vaso pp. 150 mL Embudo analítico Método experimental y observaciones: Para la síntesis de cloruro de p-acetamidobencensulfonilo: - En un matraz Erlenmeyer de 125 mL se colocan 7 g de acetanilida y se calienta en mechero hasta que se funda para posteriormente esparcirlo homogéneamente por el matraz. Una vez que se enfríe, se añaden 20 mL de ácido clorosulfónico. Esta reacción procede de forma muy violenta, desprendiéndose vapores de H 2SO4 y HCl, por lo que se la deja reposar bajo campana hasta que ya no burbujee más. Luego se traspasa a un baño maría por aprox. 10 minutos para completar la reacción. - A continuación, se vierte lentamente la mezcla de reacción a una mezcla de agua/hielo, agitándose continuamente con una varilla de vidrio. Inmediatamente se aprecia la formación de un precipitado blanco. - Se filtra al vacío en un embudo Büchner y se lava el sólido con 25 mL de agua helada.
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por recristalización en una pequeña cantidad de agua caliente. Finalmente se filtra al vacío, se seca bien el producto sobre papel absorbente y se guardan. Análisis de resultados: Se representan las cantidades utilizadas de productos y las cantidades de productos obtenidas en la Tabla N°2, para el cálculo del rendimiento de los productos se utilizaron los siguientes datos 33: Masa molar (acetanilida): Masa Masa molar molar (p-ace (p-acetami tamidob dobenc encens ensulfo ulfonam namida) ida):: Masa molar (sulfanilamida):
135.16 g/mol 214.2 214.244 g/mo g/moll 172.20 g/mol
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al ser un equilibrio posee un relativamente bajo rendimiento, debido a que es necesario desplazar el equilibrio aun más hacia la formación de los productos. Se calc calcul ulóó el punt puntoo de fusi fusión ón de los los cris crista tale less de sulf sulfan anil ilam amid idaa obte obteni nido dos, s, encontrándose en un rango entre 164-166°C, en la literatura se informa que es de 165166°C34, lo que significa que existen impurezas en los cristales cristales obtenidos. obtenidos. Además se analizó su solubilidad en dos soluciones de distinto pH (HCl al 5% y NaOH al 5%), dando como resultado que los cristales eran completamente solubles en medio ácido, mientras que eran insolubles en medio básico.
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Se realizó una cromatografía de capa fina, utilizando una mezcla de DCM/metanol al 10% como eluyente. La sulfanilamida arrojó un R f de 0.45, además de que no se encontraron impurezas.
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Figura N°10: Esqueleto básico de las quinoxalinas. En gene general ral se forma formann media mediante nte la cond conden ensa saci ción ón de orto-a orto-aril rildia diami minas nas con con 1,21,2dicetonas, aunque existen diversos métodos para la síntesis de quinoxalina y sus derivados37. En este laboratorio, para poder obtener 2,3-difenilquinoxalina, se realizó una síntesis en tres etapas, partiendo de benzaldehído. El primer paso, consistió en realizar una condensación benzoínica para formar benzoína, una α-hidroxicetona según lo que se indica en el Esquema N°13 38.
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REACTIVOS KCN Etanol 95% Benzaldehído
CANTIDAD 1.5 g 20 mL 20 mL
MATERIALES Manta calefactora Condensador de reflujo Balón de 100 mL Espátula Varilla de vidrio Embudo Büchner Matraz Kitasato
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embargo, a medida que la reacción progresa, el KCN se disuelve y la mezcla se torna
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Masa mo molar (o (o-fenilendiamina):
108 14 g/ g/mol
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En general, todos los puntos de fusión de los productos son similares a los informados
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