Saltar al contenido
Merck
Todas las fotos(5)

Documentos clave

Ver Toda la documentación

685860

Sigma-Aldrich

(1R,2R)-1,2-Bis(2-hydroxyphenyl)ethylenediamine

95% (HPLC)

Sinónimos:

(1R,2R)-1,2-Bis(2-hydroxyphenyl)-1,2-ethanediamine

Iniciar sesiónpara Ver la Fijación de precios por contrato y de la organización
Todas las fotos(5)

About This Item

Fórmula empírica (notación de Hill):
C14H16N2O2
Número de CAS:
870991-70-1
Peso molecular:
244.29
MDL number:
MFCD09751760
UNSPSC Code:
12352116
PubChem Substance ID:
24885846
NACRES:
NA.22

assay

95% (HPLC)

form

powder

optical activity

[α]22/D +62°, c = 1% in chloroform

mp

157-163 °C

functional group

amine

SMILES string

N[C@@H]([C@H](N)c1ccccc1O)c2ccccc2O

InChI

1S/C14H16N2O2/c15-13(9-5-1-3-7-11(9)17)14(16)10-6-2-4-8-12(10)18/h1-8,13-14,17-18H,15-16H2/t13-,14-/m1/s1

InChI key

MRNPLGLZBUDMRE-ZIAGYGMSSA-N

General description

(1R, 2R)-1,2-Bis(2-hydroxyphenyl)ethylenediamine or (R, R)-1,2-bis(2-hydroxyphenyl)-1,2-diaminoethane (HPEN) is commonly used in the stereoselective synthesis of enantiopure compounds.

Application

(1R, 2R)-1,2-Bis(2-hydroxyphenyl)ethylenediamine can be used as a precursor for the synthesis of:
  • Enantiomerically pure trans-3-arylpiperazine-2-carboxylic acid derivatives via diaza-Cope rearrangement (DCR).
  • 4,4′-(1,2-Diazaniumylethane-1,2-diyl)dibenzoate trihydrate by treating with terephthalaldehydic acid.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Elija entre una de las versiones más recientes:

Certificados de análisis (COA)

Lot/Batch Number
MKCP5623
MKCM7937
MKCL7014
MKCK3589
MKCG7386

¿No ve la versión correcta?

Si necesita una versión concreta, puede buscar un certificado específico por el número de lote.

Busque por un COA

¿Ya tiene este producto?

Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

Synthesis of Enantiopure Mixed Alkyl-Aryl Vicinal Diamines by the Diaza-Cope Rearrangement: A Synthesis of (+)-CP-99,994.
Kim, Miji and Kim, Hyeseung and Kim, Hyunwoo and Chin, Jik
The Journal of Organic Chemistry, 82(23), 12050-12058 (2017)
4, 4?-(1, 2-Diazaniumylethane-1, 2-diyl) dibenzoate trihydrate
Numata T, et al.
IUCrData, 1(2), x160252-x160252 (2016)
An efficient synthesis of chiral diamines with rigid backbones: Application in enantioselective michael addition of malonates to nitroalkenes.
Zhu, Qiming and Huang, Hanmin and Shi, Dengjian and Shen, Zhiqiang and Xia, Chungu
Organic Letters, 11(20), 4536-4539 (2009)
Short synthesis of enantiopure trans-3-arylpiperazine-2-carboxylic acid derivatives via diaza-Cope rearrangement
Kwon SH, et al.
Organic Letters, 14(14) (2012)
Stereospecific synthesis of C 2 symmetric diamines from the mother diamine by resonance-assisted hydrogen-bond directed diaza-Cope rearrangement.
Kim H, et al.
Journal of the American Chemical Society, 130(36), 12184-12191 (2008)

Artículos

Chiral Vicinal Diamines for Asymmetric Synthesis

Chiral vicinal diamines are of tremendous interest to the synthetic chemist as they are found in many chiral catalysts and pharmaceuticals.

Contenido relacionado

Chin Group – Professor Product Portal

The Chin group is interested in computational and experimental approaches to understanding stereoselective recognition and catalysis. Their studies in weak forces (H-bonding, electronic and steric effects) has led to a highly efficient method for making limitless varieties of chiral vicinal diamines from the 'mother diamine' that are useful for developing stereoselective organocatalysts or transition metal-based catalysts as well as for developing drugs (Acc Chem Res (2012) p1345). The 'mother diamine' is also useful for making binol, monophos and binap analogs. The Chin group is also interested in using reversible covalent bonds for stereoselective recognition and L to D conversion of natural and non-natural amino acids (EJOC (2012) p229).

Nuestro equipo de científicos tiene experiencia en todas las áreas de investigación: Ciencias de la vida, Ciencia de los materiales, Síntesis química, Cromatografía, Analítica y muchas otras.

Póngase en contacto con el Servicio técnico