(1R,2R)-1,2-diphenylethane-1,2-diamine

• ChemBase ID: 149864
• Molecular Formular: C14H16N2
• Molecular Mass: 212.29024
• Monoisotopic Mass: 212.13134852
• SMILES: c1ccc(cc1)[C@H]([C@@H](c1ccccc1)N)N
• Canonical SMILES: N[C@@H]([C@@H](c1ccccc1)N)c1ccccc1
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R)-1,2-diphenylethane-1,2-diamine
• IUPAC Traditional name: (1R,2R)-1,2-diphenylethane-1,2-diamine
• Synonyms: (1R,2R)-(+)-1,2-Diamino-1,2-diphenylethane; (1R,2R)-(+)-1,2-Diphenylethylenediamine; (1R,2R)-(+)-1,2-Diphenylethylenediamine; (1R,2R)-(+)-1,2-Diphenyl-1,2-ethanediamine; (1R,2R)-(+)-1,2-二氨基-1,2-二苯基乙烷; (1R,2R)-(+)-1,2-二苯基乙二胺; (1R,2R)-(+)-1,2-二苯基-1,2-乙二胺

Database IDs

• CAS Number: 35132-20-8
• MDL Number: MFCD00082769
• Beilstein Number: 2369988
• PubChem SID: 162244026; 24866759; 24862410
• PubChem CID: 2724998

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.8482778
• LogD (pH = 7.4): 0.31417987
• Log P: 2.1460378
• Molar Refractivity: 66.4342 cm^3
• Polarizability: 26.751324 Å^3
• Polar Surface Area: 52.04 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 79-81 °C; 79-83 °C(lit.); 80-84°C
• Optical Rotation: [α]20/D +102°, c = 1 in ethanol; [α]20/D +105±2°, c = 1% in methanol; +104 (c=1 in methanol)

Safety Information

• Storage Warning: Air Sensitive
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: UN3259
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: III
• Risk Statements: 34; 36/37/38
• Safety Statements: 26-36; 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H314-H318; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (T); 97%; 98+%
• Grade: purum
• Optical Purity: ee: 99% (GLC)
• Linear Formula: [C6H5CH(NH2)-]2

DETAILS

Sigma Aldrich - 364010

Packaging
1 g in glass bottle
500 mg in glass bottle

Sigma Aldrich - 42745

Other Notes
Used in various catalyst systems for asymmetric reactions 1,2; The bis(sulfonamide) is a powerful chiral auxiliary3

REFERENCES

• In combination with various Lewis acids, forms a number of catalyst systems for asymmetric reactions including Diels-Alder, allylation and aldol reactions: Angew. Chem. Int. Ed., 30, 455 (1991). For use in enantioselective catalytic Diels-Alder reactions, see: J. Am. Chem. Soc., 111, 5493 (1989); Org. Synth. Coll., 9, 67 (1998).
• Chiral solvation agent for determination of enantiomeric excess of chiral acids by NMR.