Skip to Content
Merck
All Photos(1)

Documents

101346

Sigma-Aldrich

Dichlorophenylborane

97%

Synonym(s):

NSC 93889, Phenylboron dichloride, Phenyldichloroborane

Sign Into View Organizational & Contract Pricing


About This Item

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

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Danger

Hazard Statements

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

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Synthesis of 1-Indanonyl Oxepanes.
Chang M Y and Lee N C
Synlett, 23(06), 867-872 (2012)
Oxazaborolidinone-Catalyzed Enantioselective Friedel? Crafts Alkylation of Furans and Indoles with α, β-Unsaturated Ketones.
Adachi S, et al.
Organic Letters, 11(22), 5206-5209 (2009)
Total syntheses and biological reassessment of lactimidomycin, isomigrastatin and congener glutarimide antibiotics.
Micoine K, et al.
Chemistry?A European Journal , 19(23), 7370-7383 (2013)
Synthesis of a New N-Acetyl Thiazolidinethione Reagent and Its Application to a Highly Selective Asymmetric Acetate Aldol Reaction.
Zhang Y and Sammakia T
Organic Letters, 6(18), 3139-3141 (2004)
Borheterocyclen, 2. Mitt.
Pailer M and Huemer H
Monatshefte fur Chemie / Chemical Monthly, 95(2), 373-378 (1964)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service