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

Melting point:

79-83 °C(lit.)

alpha 

104 º (c=1.1, MeOH 25 ºC)

Boiling point:

342.14°C (rough estimate)

Density 

1.0799 (rough estimate)

refractive index 

103 ° (C=1, EtOH)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Crystalline Powder

pka

9.78±0.10(Predicted)

color 

White to light yellow

optical activity

[α]20/D +102°, c = 1 in ethanol

Water Solubility 

Insoluble in water.

Sensitive 

Air Sensitive

BRN 

2369988

Stability:

Hygroscopic

InChI

1S/C14H16N2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14H,15-16H2/t13-,14-/m1/s1

InChIKey

PONXTPCRRASWKW-ZIAGYGMSSA-N

SMILES

N[C@@H]([C@H](N)c1ccccc1)c2ccccc2

CAS DataBase Reference

35132-20-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-23

HazardClass 

8

HS Code 

29212900

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(1R,2R)-(+)-1,2-Diphenylethylenediamine Usage And Synthesis

Description

(1R,2R)-(+)-1,2-Diphenylethylenediamine is a chiral reagent widely used in the chemical industry at present, used for asymmetric synthesis and optical resolution.

Chemical Properties

white to light yellow crystal powder

Uses

(1R,2R)-(+)-1,2-Diphenyl-1,2-ethanediamine is used as chiral solvation agent for determination of enantiomeric excess of chiral acids by NMR. It is used in various catalyst systems for asymmetric reactions.

Synthesis

Add 1,2-diphenylethanedione dioxime (48g, 0.20mol) and 260ml methanol in a 500ml four-necked flask equipped with a condenser, stir to dissolve all of them, and then add 2g of activated charcoal (120 mesh), 0.5g of Raney's nickel, raise the temperature to 60 , and then add 80% hydrazine hydrate (28.75g, 0.46mol) slowly dropwise, and keep the temperature of the reaction between 58 -62 , there is nitrogen emission during the reaction, and the rate of dropwise acceleration is controlled to keep the nitrogen emission rate not too fast, and liquid chromatography tracks the reaction process. -62 , the reaction process has nitrogen release, drop acceleration control in the nitrogen release rate is not too fast as well, liquid chromatography to track the reaction process, when the raw material 1,2-diphenylethanedione dioxime disappeared after the end of the reaction, cooling the mixture, filtration of Ranieri nickel and activated carbon, to a small amount of water covered with a preserved in order to prepare for sets of use, the filtrate distillation to recover the methanol, and the residue added to 200 ml of petroleum ether heated to make all dissolved, cooled for 24 hours and filtered to get the product The residue was heated by adding 200 ml of petroleum ether to dissolve all of it, then cooled and filtered for 24 hours to obtain the product (1R,2R)-1,2-diphenylethylenediamine 41.55g, yield 98%, chemical purity 99.57%.

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