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Merck
CN

648418

(−)-DIP-Chloride solution

50-65 wt. % in heptane

Synonym(s):

(−)-B-Chlorodiisopinocampheylborane, (−)-Chlorodiisopinocampheylborane, Chlorobis[(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]borane, Diisopinocampheylchloroborane

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About This Item

Empirical Formula (Hill Notation):
C20H34BCl
CAS Number:
Molecular Weight:
320.75
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352001
MDL number:
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Product Name

(−)-DIP-Chloride solution, 50-65 wt. % in heptane

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

SMILES string

C[C@H]1[C@@H](C[C@@H]2C[C@H]1C2(C)C)B(Cl)[C@@H]3C[C@@H]4C[C@H]([C@H]3C)C4(C)C

InChI key

PSEHHVRCDVOTID-VMAIWCPRSA-N

concentration

50-65 wt. % in heptane

density

0.895 g/mL at 25 °C

Quality Level

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Application

(−)-Diisopinocampheylchloroborane [(−)-DIP-Chloride] solution can be used as a reducing reagent for the:
  • Enantioselective reduction of α, β-unsaturated trifluoromethyl ketones into corresponding secondary allylic alcohols.
  • Asymmetric reduction of aromatic and aliphatic α-halomethyl ketones to haloalcohols.
It can also be used as a catalyst for the enantioselective asymmetric Pictet-Spengler reaction.

General description

(−)-DIP-Chloride solution is a pinane-based asymmetric reducing agent that is commonly used in asymmetric reduction reactions.

Legal Information

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

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Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

<-22.0 °F - closed cup

flash_point_c

< -30 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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