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685860

Sigma-Aldrich

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

95% (HPLC)

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Synonym(s):
(1R,2R)-1,2-Bis(2-hydroxyphenyl)-1,2-ethanediamine, (R,R) Diaminopharm Diamine, (R,R) Jik Chin Mother Diamine, (R,R) Mother Diamine
Empirical Formula (Hill Notation):
C14H16N2O2
CAS Number:
870991-70-1
Molecular Weight:
244.29
MDL number:
MFCD09751760
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

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

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This Item
382426685879364010
(1R,2R)-1,2-Bis(2-hydroxyphenyl)ethylenediamine 95% (HPLC)

Sigma-Aldrich

685860

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

(R)-(+)-1,1′-Binaphthyl-2,2′-diamine 99%

Sigma-Aldrich

382426

(R)-(+)-1,1′-Binaphthyl-2,2′-diamine

(1S,2S)-1,2-Bis(2-hydroxyphenyl)ethylenediamine 95%

Sigma-Aldrich

685879

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

(1R,2R)-(+)-1,2-Diphenylethylenediamine 97%

Sigma-Aldrich

364010

(1R,2R)-(+)-1,2-Diphenylethylenediamine

form

powder

form

-

form

solid

form

-

mp

157-163 °C

mp

242-244 °C (lit.)

mp

157-162 °C

mp

79-83 °C (lit.)

optical activity

[α]22/D +62°, c = 1% in chloroform

optical activity

[α]20/D +157°, c = 1 in pyridine

optical activity

[α]22/D -65°, c = 0.2 in chloroform

optical activity

[α]20/D +102°, c = 1 in ethanol

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

Signal Word

Warning

Hazard Statements

H302 - H315 - H319 - H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)

Articles

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.

Related Content

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).

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