101346
Dichlorophenylborane
97%
Synonym(s):
NSC 93889, Phenylboron dichloride, Phenyldichloroborane
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About This Item
Empirical Formula (Hill Notation):
C6H5BCl2
CAS Number:
Molecular Weight:
158.82
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2243576
Assay:
97%
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
Application
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.
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
signalword
Danger
hcodes
Hazard Classifications
Flam. Liq. 2 - Skin Corr. 1B
Storage Class
3 - Flammable liquids
wgk
WGK 3
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Regulatory Information
危险化学品
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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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 101346-1G | 04061838117878 |
| 101346-5G | 04061838117885 |
| 101346-25G | 04061838667823 |