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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:
29841-69-8
Molecular Weight:
212.29
Beilstein:
3201645
MDL number:
MFCD00082751
UNSPSC Code:
12352116
PubChem Substance ID:
24862409
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.)

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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(S,S)-1,2-Diphenylethylenediamine
Chiral Reagents for Asymmetric Synthesis (2003)
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
Chenier, P.J. et al.
Tetrahedron Letters, 38, 7341-7341 (1997)
Mukaiyama, T.
Aldrichimica Acta, 29, 59-59 (1996)
N M Maier et al.
Chirality, 8(7), 490-493 (1996-01-01)
Fast and efficient baseline separation of asymmetrically substituted diarylmethanols and 1,1-diarylethanols was achieved on an endcapped, amide-linked N-3,5-dinitrobenzoylated, (R,R)-1,2-diphenyl-1,2-ethanediamine-derived chiral stationary phase (CSP). Optimal enantioselectivities on this CSP were obtained using 1% 2-propanol in n-heptane as the mobile phase. Enantiorecognition
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