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317020

Sigma-Aldrich

(−)-DIP-Chloride™

Synonym(s):

(−)-B-Chlorodiisopinocampheylborane, (−)-Ipc2BCl

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About This Item

Empirical Formula (Hill Notation):
C20H34BCl
CAS Number:
85116-37-6
Molecular Weight:
320.75
Beilstein:
5937756
MDL number:
MFCD00074807
UNSPSC Code:
12352001
PubChem Substance ID:
24859060
NACRES:
NA.22

form

solid

Quality Level

100

mp

52-56 °C (lit.)

SMILES string

C[C@H]1[C@@H](CC2CCC1C2(C)C)B(Cl)[C@@H]3CC4CCC([C@H]3C)C4(C)C

InChI

1S/C20H34BCl/c1-11-15-7-13(19(15,3)4)9-17(11)21(22)18-10-14-8-16(12(18)2)20(14,5)6/h11-18H,7-10H2,1-6H3/t11-,12-,13+,14+,15-,16-,17-,18-/m1/s1

InChI key

PSEHHVRCDVOTID-VMAIWCPRSA-N

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Application

Both (+)- and (-)-DIP-chloride are used for asymmetric reduction of prochiral ketones and for the preparation of β-amino alcohols.
Reagent used for an enantioselective reduction of (chloroacetyl) benzofurans to chlorohydrins which serve as intermediates for the corresponding epoxides and aminoalcohols. For a short paper on the preparation of DIP halides and their use in stereoselective reductions see Chem. Commun. 1053 (1994).

Legal Information

DIP-Chloride is a trademark of Sigma-Aldrich Co. LLC

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBL3397
SHBK7309
SHBJ9859
SHBH1300V
SHBG5770V

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Tetrahedron Asymmetry, 16, 3205-3205 (2005)
Katie M Cergol et al.
Nature protocols, 2(10), 2568-2573 (2007-10-20)
The protocol for the preparation of boron enolates and their subsequent reaction with aldehydes is described, providing convenient access to beta-hydroxy ketones in good yields and with high stereoselectivities. The reaction consists of three steps: first, the ketone is rapidly
Bull. Korean Chem. Soc., 26, 652-652 (2005)
Tetrahedron Letters, 35, 1511-1511 (1994)
Journal of the Chemical Society. Chemical Communications, 1053-1053 (1994)
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