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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

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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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)
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)
Oxazaborolidinone-Promoted Vinylogous Mukaiyama Aldol Reactions.
Simsek S, et al.
Organic Letters, 9(26), 5637-5639 (2007)
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