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251496

Sigma-Aldrich

(−)-Isopinocampheylborane TMEDA complex

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Synonym(s):
(−)-N,N′-Bis(monoisopinocampheylborane)-N,N,N′,N′-tetramethylethylenediamine, (R)-Alpine-Boramine™
Empirical Formula (Hill Notation):
C13H27BN
CAS Number:
67826-92-0
Molecular Weight:
208.17
MDL number:
MFCD00077801
UNSPSC Code:
12352116
PubChem Substance ID:
24855135
NACRES:
NA.22

form

solid

mp

139-141 °C (lit.)

SMILES string

CN(C)CCN(C)C.[H][C@]12C[C@H](B)[C@@H](C)[C@]([H])(C1)C2(C)C.[H][C@]34C[C@H](B)[C@@H](C)[C@]([H])(C3)C4(C)C

InChI

1S/2C10H19B.C6H16N2/c2*1-6-8-4-7(5-9(6)11)10(8,2)3;1-7(2)5-6-8(3)4/h2*6-9H,4-5,11H2,1-3H3;5-6H2,1-4H3/t2*6-,7+,8-,9-;/m00./s1

InChI key

QNDCJVKDHWRHGS-NCHGFZPDSA-N

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Application

Chiral hydroboration reagent.This amine-borane complex has been used as a polarity-reversal catalyst for the kinetic resolution of racemic esters and ketones.

Legal Information

Alpine-Boramine is a trademark of Sigma-Aldrich Co. LLC

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H261,H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Water-react 3

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Dang, H.-S. et al.
Journal of the Chemical Society. Perkin Transactions 1, 1033-1033 (1994)
The Journal of Organic Chemistry, 45, 3543-3543 (1980)
Aldrichimica Acta, 20, 30-30 (1987)

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