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364002

Sigma-Aldrich

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

97%

Synonym(s):

(1S,2S)-(−)-1,2-Diamino-1,2-diphenylethane

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About This Item

Linear Formula:
[C6H5CH(NH2)-]2
CAS Number:
Molecular Weight:
212.29
Beilstein:
3201645
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

optical activity

[α]20/D −102°, c = 1 in ethanol

optical purity

ee: 98% (GLC)

mp

83-85 °C (lit.)

functional group

amine
phenyl

SMILES string

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

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-/m0/s1

InChI key

PONXTPCRRASWKW-KBPBESRZSA-N

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General description

1,2-Diphenylethylenediamine is a chiral molecule, generally used as a chiral resolving agent and as a precursor of the chiral auxiliary. It is also used as a chiral solvating agent in NMR study.

Application

Versatile ligand for the formation of metal complexes. Used in the synthesis of chiral tropocoronands which have potential utility in asymmetric catalysis.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Jérôme Long et al.
Science (New York, N.Y.), 367(6478), 671-676 (2020-02-08)
Magnetoelectric (ME) materials combine magnetic and electric polarizabilities in the same phase, offering a basis for developing high-density data storage and spintronic or low-consumption devices owing to the possibility of triggering one property with the other. Such applications require strong
(S,S)-1,2-Diphenylethylenediamine
Chiral Reagents for Asymmetric Synthesis (2003)
Mukaiyama, T.
Aldrichimica Acta, 29, 59-59 (1996)
Chenier, P.J. et al.
Tetrahedron Letters, 38, 7341-7341 (1997)
V Larsimont et al.
Journal of pharmaceutical and biomedical analysis, 19(6), 855-864 (2000-03-04)
Two tyrosine specific, HPLC methods with either electrochemical (HPLC-ED) or fluorescence (HPLC-FL) detection are described for leucine-enkephalin (LE) in cerebrospinal fluid (CSF). Both approaches involve the hydroxylation of the Tyr1-moiety of LE by mushroom tyrosinase. Production of a catechol permitted

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