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648418

Sigma-Aldrich

(−)-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:
85116-37-6
Molecular Weight:
320.75
MDL number:
MFCD00074807
UNSPSC Code:
12352001
PubChem Substance ID:
24883579
NACRES:
NA.22

concentration

50-65 wt. % in heptane

density

0.895 g/mL at 25 °C

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

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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General description

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

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.

Legal Information

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

Signal Word

Danger

Hazard Statements

H225,H304,H314,H336,H410

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 Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

<-22.0 °F - closed cup

Flash Point(C)

< -30 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN8889
MKCN0700
MKCL5838
SHBF4173V
SHBD0508V

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