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101346

Sigma-Aldrich

Dichlorophenylborane

97%

Synonym(s):

NSC 93889, Phenylboron dichloride, Phenyldichloroborane

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About This Item

Empirical Formula (Hill Notation):
C6H5BCl2
CAS Number:
873-51-8
Molecular Weight:
158.82
Beilstein:
2243576
MDL number:
MFCD00013612
UNSPSC Code:
12352002
PubChem Substance ID:
24846539
NACRES:
NA.22

Quality Level

100

Assay

97%

reaction suitability

reagent type: reductant

refractive index

n20/D 1.545 (lit.)

bp

66 °C/11 mmHg (lit.)

density

1.224 g/mL at 25 °C (lit.)

SMILES string

ClB(Cl)c1ccccc1

InChI

1S/C6H5BCl2/c8-7(9)6-4-2-1-3-5-6/h1-5H

InChI key

NCQDQONETMHUMY-UHFFFAOYSA-N

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Application

Catalyst for:
  • Antiproliferative macrolide and cell migration inhibitor lactimidomycin
  • Enantioselective synthesis of polyketide segments using vinylogous Mukaiyama aldol reactions
  • Enantioselective Diels-Alder cycloadditions after its reaction with allo-threonine derivatives
  • Stereoselective alkylative ring opening of cyclic anhydrides
  • Cross-metathesis reaction of amino derivatives with olefins
  • Asymmetric acetate aldol reactions
  • The reaction of aryl aldehydes with styrene and (E)-β-methylstyrene
Dichlorophenylborane can be used as a catalyst for:
  • The synthesis of an antiproliferative macrolide and cell migration inhibitor lactimidomycin.
  • Enantioselective synthesis of polyketide segments using vinylogous Mukaiyama aldol reactions.
  • Enantioselective Diels-Alder cycloadditions after its reaction with allo-threonine derivatives.
  • Stereoselective alkylative ring opening of cyclic anhydrides.
  • Cross-metathesis reaction of amino derivatives with olefins.
  • Asymmetric acetate aldol reactions.

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H225,H314

Hazard Classifications

Flam. Liq. 2 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP0573
SHBP7601
SHBJ7464
SHBD9623V
SHBD7469V

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