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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/REAXYS Number:
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

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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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Tetrahedron Asymmetry, 16, 3205-3205 (2005)
Bull. Korean Chem. Soc., 26, 652-652 (2005)
Journal of the Chemical Society. Chemical Communications, 1053-1053 (1994)
Tetrahedron Letters, 35, 1511-1511 (1994)
Aldrichimica Acta, 20, 9-9 (1987)

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