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715964

Sigma-Aldrich

(1S,2S)-N,N′-Dimethyl-1,2-diphenyl-1,2-ethylenediamine

97%

Synonym(s):

(1S,2S)-N,N′-Dimethyl-1,2-diphenylethane-1,2-diamine

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About This Item

Empirical Formula (Hill Notation):
C16H20N2
CAS Number:
70749-06-3
Molecular Weight:
240.34
MDL number:
MFCD00216956
UNSPSC Code:
12352116
PubChem Substance ID:
329763358
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

optical activity

[α]22/D −17.0°, c = 0.5 in chloroform

mp

48-53 °C

SMILES string

CN[C@H]([C@@H](NC)c1ccccc1)c2ccccc2

InChI

1S/C16H20N2/c1-17-15(13-9-5-3-6-10-13)16(18-2)14-11-7-4-8-12-14/h3-12,15-18H,1-2H3/t15-,16-/m0/s1

InChI key

BTHYVQUNQHWNLS-HOTGVXAUSA-N

Related Categories

Application

(1S,2S)-N,N′-Dimethyl-1,2-diphenyl-1,2-ethylenediamine can be used as:
  • A precursor for the synthesis of chiral imidazolinium salts, which are used as catalysts for aza Diels−Alder reaction and as shift reagents for potassium salt of Mosher′s acid.
  • A ligand in the preparation of 2,3-dihydrobenzofurans and indanes by reacting alkyl halides with alkyl electrophiles using nickel/diamine catalyst.
  • A ligand in the synthesis of carbamates, sulfonamides, and sulfones through alkyl-alkyl Suzuki reaction using Ni catalyst.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Catalytic enantioselective cyclization/cross-coupling with alkyl electrophiles
Cong H and Fu GC
Journal of the American Chemical Society, 136(10), 3788-3791 (2014)
New directing groups for metal-catalyzed asymmetric carbon-carbon bond-forming processes: stereoconvergent alkyl-alkyl Suzuki cross-couplings of unactivated electrophiles
Wilsily A, et al.
Journal of the American Chemical Society, 134(13), 5794-5797 (2012)
The preparation of new enantiopure imidazolinium salts and their evaluation as catalysts and shift reagents
Jurcik V and Wilhelm R
Tetrahedron Asymmetry, 17(5), 801-810 (2006)

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