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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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

JAN Code

317020-VAR:
317020-100G:
317020-25G:
317020-BULK:
317020-5G:

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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Bull. Korean Chem. Soc., 26, 652-652 (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
Tetrahedron Letters, 35, 1511-1511 (1994)
Tetrahedron Asymmetry, 16, 3205-3205 (2005)
Journal of the Chemical Society. Chemical Communications, 1053-1053 (1994)
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