ChemicalBook > CAS DataBase List > (1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine

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

Product Name
(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine
CAS No.
144222-34-4
Chemical Name
(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine
Synonyms
R-TS-DPEN;(R,R)-TSDPEN;(1R,2R)-TSDPE;(1R,2R)-TSDPEN;TIANFU-CHEM (R,R)-TsDPEN;(R,R)-TsDPEN (1R,2R)-(-)-N-;(1R,2R)-N-p-Toluenesulfonyl-1,2-diphe;(1R,2R)-(-)-N-(4-Toluenesulfonyl)-1,2-;(1R,2R)-N-P-TOSYL-1,2-DIPHENYLETHYLENE-D;(1R, 2R)-(-)-N-(4-Toluene sulfonyl)-DPEN
CBNumber
CB1180813
Molecular Formula
C21H22N2O2S
Formula Weight
366.48
MOL File
144222-34-4.mol
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(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine Property

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)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
HS Code 
29215900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
484334
Product name
(1R,2R)-(?)-N-p-Tosyl-1,2-diphenylethylenediamine
Purity
98%
Packaging
1g
Price
$97.3
Updated
2025/07/31
TCI Chemical
Product number
A1548
Product name
(R,R)-N-(2-Amino-1,2-diphenylethyl)-p-toluenesulfonamide
Purity
>98.0%(T)
Packaging
1g
Price
$87
Updated
2025/07/31
Strem Chemicals
Product number
07-2371
Product name
(1R,2R)-(-)-N-(4-toluenesulfonyl)-1,2-diphenylethylenediamine, 98% (R,R)-TsDPEN
Packaging
500mg
Price
$61
Updated
2024/03/01
Strem Chemicals
Product number
07-2371
Product name
(1R,2R)-(-)-N-(4-toluenesulfonyl)-1,2-diphenylethylenediamine, 98% (R,R)-TsDPEN
Packaging
2g
Price
$119
Updated
2024/03/01
Strem Chemicals
Product number
07-2371
Product name
(1R,2R)-(-)-N-(4-toluenesulfonyl)-1,2-diphenylethylenediamine, 98% (R,R)-TsDPEN
Packaging
10g
Price
$414
Updated
2024/03/01
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(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine Chemical Properties,Usage,Production

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

35132-20-8

98-59-9

144222-34-4

(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 Preparation Products And Raw materials

Raw materials

Preparation Products

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(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine Suppliers

Americas 1 Belgium 2 Canada 1 China 210 Europe 3 Germany 6 India 9 Ireland 1 Italy 1 Japan 4 Norway 1 Switzerland 2 United Kingdom 11 United States 33 Global 285
CMS Chemicals Limited
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View Lastest Price from (1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine manufacturers

Henan Aochuang Chemical Co.,Ltd.
Product
(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine 144222-34-4
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1Ton
Release date
2022-09-19
airuikechemical co., ltd.
Product
(r,r)-tsdpen 144222-34-4
Price
US $0.00-0.00/Kg
Min. Order
1Kg
Purity
99.9%
Supply Ability
200tons
Release date
2024-04-08
Henan Fengda Chemical Co., Ltd
Product
(R,R)-N-(p-Toluenesulfonyl)-1,2-diphenylethylenediamine 144222-34-4
Price
US $50.00-1.00/kg
Min. Order
1kg
Purity
99
Supply Ability
g-kg-tons,free sample is available
Release date
2024-01-03

144222-34-4, (1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamineRelated Search:

(1R,2R)-trans-N-Boc-1,2-Cyclohexanediamine (1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine (R)-(+)-a,a-Diphenyl-2-pyrrolidinemethanol 1,2-Diphenylethylenediamine Toluenesulfonamide Ethylenediamine (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine (R,R)-N-(p-Toluenesulfonyl)-1,2-diphenylethylenediamine(Chloro)(p-cymene)ruthenium(II) ((R,R)-2-AMINO-1,2-DIPHENYLETHYL)[(4-TOLYL)SULFONYL]AMIDO](P-CYMENE)RUTHENIUM(II)CHLORIDE (1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine (1R,2R)-N,N'-DI-P-TOLUENESULFONYL-1,2-DIPHENYL-1,2-ETHYLENEDIAMINE RUCL[(R,R)-TSDPEN](MESITYLENE) CHLORO[(1R,2R)-TSDPEN](P-CYMENE)RUTHENIUM(II) RU[(R,R)-TSDPEN](P-CYMENE) RUCL[(S,S)-TSDPEN](MESITYLENE) RUCL[(R,R)-TSDPEN](HEXAMETHYLBENZENE) CHLORO[(1S,2S)-TSDPEN](P-CYMENE)RUTHENIUM(II) RU[(S,S)-TSDPEN](P-CYMENE)

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  • (1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediaMine 98%
  • (1R,2R)-(-)-N-(4-toluenesulfonyl)-1,2-diphenylethylenediaMine,(R,R)-TsDPEN
  • N-[(1R,2R)-2-Amino-1,2-diphenylethyl]-4-methylbenzenesulphonamide, (1R,2R)-1,2-Diphenyl-N-tosylethane-1,2-diamine
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  • BenzenesulfonaMide,N-[(1R,2R)-2-aMino-1,2-diphenyl
  • )-N-p-Tosyl-1,2-diphenylethylenediaMine 98%
  • (1R,2R)-(-)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediaMine, 98% 500MG
  • (1R,2R)-(-)-N-(p-Tolylsulfonyl)-1,2-diphenylethylenediaMine
  • (1R,2R)-1-AMino-2-tosylaMino-1,2-diphenylethane
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  • N-[(1R,2R)-2-Amino-1,2-diphenylethyl]toluene-4-sulfonamide
  • (1R,2R)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine, 98+%
  • (R,R)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine
  • (1R,2R)-N-(P-TOLUENESULFONYL)-1,2-DIPHENYL-1,2-ETHANEDIAMINE
  • (1R,2R)-TSDPEN
  • (1R,2R)-(-)-N-P-TOSYL-1,2-DIPHENYLETHYLENEDIAMINE
  • (1R, 2R)-(-)-N-(4-TOLUENE SULFONYL)1,2-DIPHENYL-1,2-ETHANE DIAMINE
  • (1R,2R)-(-)-N-(4-TOLUENESULFONYL)-1,2-DIPHENYLETHYLENEDIAMINE
  • (1R,2R)-(-)-N-(4-TOLUENESULPHONYL)-1,2-DIPHENYLETHYLENEDIAMINE
  • N-((1R,2R)-2-amino-1,2-diphenylethyl)-4-methylbenzenesulfonamide
  • (1R,2R)-N-P-TOSYL-1,2-DIPHENYLETHYLENE-D
  • (1R,2R)-(-)-N-(4-toluenesulfonyl)-1,2-diphenylethylenediamine,98%(R,R)-TsDPEN
  • (1R,2R)-(-)-N-(4-TOLUENESULFONYL)-1,2-DIPHENYL-1,2-ETHANEDIAMINEC21H22N2O2S
  • (1R,2R)-1,2-Diamino-1,2-diphenyl-N1-(4-methylsulphonyl)ethane
  • N-[(1R,2R)-2-Amino-1,2-diphenylethyl]-4-methylbenzenesulphonamide
  • (R,R)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine, 98+%
  • (1R,2R)-(-)-N-(4-Toluenesulfonyl)-1,2-
  • (1R,2R)-(-)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine,98%
  • (1R,2R)-(-)-N-(p-Toluenesulfonyl)-1,2-diphenylethylenediamine
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  • (1R,2R)-(-)-N-(4-toluenesulfonyl)-1,2-diphenylethylenediamine,98%,99%ee
  • (1R,2R)-(-)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamin...
  • TIANFU-CHEM (R,R)-TsDPEN
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  • (1R,2R)-(-)-N-(p-Tolylsulfonyl)-1,2-diphenylethylenediami
  • (1R,2R)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine / R-DPEN Tos
  • (1<i>R</i>,2<i>R</i>)-(?)-<i>N</i>-<i>p</i>-Tosyl-1,2-diphenylethylenediamine
  • 144222-34-4
  • C21H22N2O2S
  • Asymmetric Synthesis
  • Chiral Catalysts, Ligands, and Reagents