(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine Chemical Properties

Melting point:

128-131 °C(lit.)

alpha 

-61.5 º (c=1, CH2Cl2)

Boiling point:

537.3±60.0 °C(Predicted)

Density 

1.1440 (rough estimate)

refractive index 

-30 ° (C=0.4, CHCl3)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform, Methanol

pka

10.76±0.50(Predicted)

form 

Crystals or Crystalline Powder

color 

White to slightly yellow

optical activity

[α]20/D 35°, c = 1 in chloroform

Water Solubility 

insoluble

InChI

InChI=1S/C21H22N2O2S/c1-16-12-14-19(15-13-16)26(24,25)23-21(18-10-6-3-7-11-18)20(22)17-8-4-2-5-9-17/h2-15,20-21,23H,22H2,1H3/t20-,21-/m1/s1

InChIKey

UOPFIWYXBIHPIP-NHCUHLMSSA-N

SMILES

C1(S(N[C@H](C2=CC=CC=C2)[C@H](N)C2=CC=CC=C2)(=O)=O)=CC=C(C)C=C1

CAS DataBase Reference

144222-34-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29215900

MSDS

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

(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine Usage And Synthesis

Chemical Properties

white to slightly yellow crystals or crystalline

Uses

Chiral diamine ligand for cooperative metal-Bronsted acid catalyzed greener reductive amination using hydrogen gas.

Metal-Br?nsted Acid Cooperative Catalysis for Asymmetric Reductive Amination

Uses

(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine is used as a catalyst in stereoselective preparation of aromatic ketone derivatives as well as other chiral organic compounds.

General Description

This product has been enhanced for catalytic efficiency.

Synthesis

(1) (R,R)-1,2-diphenylethylenediamine (20 mmol) was dissolved in dichloromethane (30 mL) and cooled to 0°C in an ice bath. A solution of p-toluenesulfonyl chloride (20 mmol) dissolved in dichloromethane (30 mL) was slowly added dropwise to the above solution at 0 °C (dropwise time 30 min). After the dropwise addition was completed, the reaction was continued at 0°C for 1 hour. After completion of the reaction, the solvent was removed by concentration under reduced pressure by rotary evaporator to obtain the crude product. The crude product was purified by column chromatography (eluent: dichloromethane/methanol=10:1, v/v) to afford the target product (R,R)-(-)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (15 mmol) in 75% yield.

References

[1] Tetrahedron Letters, 2008, vol. 49, # 27, p. 4289 - 4291
[2] European Journal of Organic Chemistry, 2000, # 12, p. 2247 - 2252
[3] Tetrahedron Asymmetry, 2009, vol. 20, # 6-8, p. 910 - 920
[4] Molecules, 2010, vol. 15, # 4, p. 2551 - 2563
[5] Patent: CN107286089, 2017, A. Location in patent: Paragraph 0078; 0148-0149

(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine(144222-34-4)Related Product Information

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