(1S,2S)-(-)-1,2-Diphenylethylenediamine

Base Information

• Chemical Name: (1S,2S)-(-)-1,2-Diphenylethylenediamine
• CAS No.: 29841-69-8
• Molecular Formula: C14H16N2
• Molecular Weight: 212.294
• Hs Code.: 29213000
• European Community (EC) Number: 605-438-1,608-420-1
• DSSTox Substance ID: DTXSID20426127
• Wikipedia: Diphenylethylenediamine
• Wikidata: Q72473157
• ChEMBL ID: CHEMBL467308
• Mol file: 29841-69-8.mol

Synonyms:(1R,2R)-diphenylethylenediamine;diphenylethylenediamine

Chemical Property of (1S,2S)-(-)-1,2-Diphenylethylenediamine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 3.48E-05mmHg at 25°C
• Melting Point: 83-85 °C(lit.)
• Refractive Index: -103 ° (C=1, EtOH)
• Boiling Point: 353.9 °C at 760 mmHg
• PKA: 9.78±0.10(Predicted)
• Flash Point: 199.9 °C
• PSA: 52.04000
• Density: 1.106 g/cm³
• LogP: 3.78700
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: Insoluble in water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 212.131348519
• Heavy Atom Count: 16
• Complexity: 171

Purity/Quality:

99% min ^*data from raw suppliers

(1S,2S)-(-)-1,2-Diphenylethylene-1,2-diamine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, C
• Hazard Codes: Xi,C
• Statements: 36/37/38-34
• Safety Statements: 26-36-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(C2=CC=CC=C2)N)N
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H]([C@H](C2=CC=CC=C2)N)N
• General Description: (1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine, also known as (S,S)-diphenylethylenediamine, is an effective chiral organocatalyst for the asymmetric synthesis of warfarin and its analogues. It facilitates the Michael addition of 4-hydroxycoumarin to α,β-unsaturated ketones in an aqueous medium, yielding pharmaceutically relevant compounds with high efficiency (73–98% yield) and moderate to good enantioselectivity (up to 76% ee). The catalyst enables a scalable, solvent-free approach under ultrasound acceleration, demonstrating its utility in environmentally friendly synthetic protocols for producing enantiomerically enriched anticoagulants.

Technology Process of (1S,2S)-(-)-1,2-Diphenylethylenediamine

There total 124 articles about (1S,2S)-(-)-1,2-Diphenylethylenediamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

tert-butyl [(1S,2R)-2-amino-1,2-diphenylethyl]carbamate → meso-1,2-diphenyl-1,2-diaminoethane (951-87-1,5700-60-7,16635-95-3,29841-69-8,35132-20-8,107133-00-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/acs.joc.7b00306

Reference yield: 78.0%

piperidine (110-89-4) + cis-2,3-Dihydro-2,3-diphenyl-1H-1,4-diazepine (731-65-7,3187-86-8,65424-85-3) → meso-1,2-diphenyl-1,2-diaminoethane (951-87-1,5700-60-7,16635-95-3,29841-69-8,35132-20-8,107133-00-6) + 1,3-Dipiperidinopropenylium-perchlorat

Guidance literature:

With perchloric acid; In methanol; for 4h; Heating;

Reference yield: 77.0%

cis-2,3-Dihydro-2,3-diphenyl-1H-1,4-diazepine (731-65-7,3187-86-8,65424-85-3) → meso-1,2-diphenyl-1,2-diaminoethane (951-87-1,5700-60-7,16635-95-3,29841-69-8,35132-20-8,107133-00-6) + 1,3-Dipiperidinopropenylium-perchlorat

Guidance literature:

With piperidine; perchloric acid; In methanol; for 4h; Heating;

upstream raw materials:

rac-1,2-diphenylethylene-1,2-diamine

(+)-(1S,2S)-1,2-diphenylethane-1,2-diazide

1,2-Diphenyl-N,N'-bis-[1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylidene]-ethane-1,2-diamine

benzildioxime

Downstream raw materials:

(C₆H₆(CH₃)(C(CH₃)2)(O)(CHNCHC₆H₅))2

(1S,2S)-1,2-Diphenyl-N,N'-bis-[1-(2,4,6-trimethyl-phenyl)-meth-(Z)-ylidene]-ethane-1,2-diamine

(3S,4S)-3,4-diphenyl-1,2,5-thiadiazolidine 1,1-dioxide

(4S,5S)-(+)-4,5-Diphenyl-2-(2-pyridinyl)-imidazolin

Refernces

Asymmetric synthesis of warfarin and its analogues on water

10.1016/j.tetasy.2014.04.008

The research focuses on the asymmetric synthesis of warfarin and its analogues using an environmentally friendly organocatalytic approach on water, without the need for organic co-solvents. The main experiment involves the asymmetric Michael addition of 4-hydroxycoumarin to a,b-unsaturated ketones, catalyzed by organic primary amines, with a particular emphasis on the use of enantiomerically pure (S,S)-diphenylethylenediamine. This catalyst was found to be effective in producing a series of pharmaceutically active compounds in good to excellent yields (73–98%) and with good enantioselectivities (up to 76% ee). The reactions were accelerated by ultrasound, and the protocol was scalable, leading to an efficient method for the 'solids on water' formation of the anticoagulant warfarin in both enantiomeric forms. The analyses used to assess the efficiency and selectivity of the reactions included HPLC analysis on a chiral phase to determine enantiomeric excess, as well as various spectroscopic techniques such as IR, NMR, and HRMS to characterize the synthesized compounds.