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Dichlorophenylborane

Catalog No. 78373 Name Sigma Aldrich
CAS Number 873-51-8 Website http://www.sigmaaldrich.com
M. F. C6H5BCl2 Telephone 1-800-521-8956
M. W. 158.8209 Fax
Purity ≥98.0% (AT) Email
Storage Chembase ID: 145546

SYNONYMS

Title
二氯苯基硼烷
IUPAC name
dichloro(phenyl)borane
IUPAC Traditional name
dichloro(phenyl)borane
Synonyms
苯基二氯硼
苯基硼二氯化物
Phenyldichloroborane
NSC 93889
Phenylboron dichloride

DATABASE IDS

CAS Number 873-51-8
Beilstein Number 2243576
PubChem SID 24887294
MDL Number MFCD00013612

PROPERTIES

Empirical Formula (Hill Notation) C6H5BCl2
Grade purum
Purity ≥98.0% (AT)
Boiling Point 66 °C/11 mmHg(lit.)
Density 1.224 g/mL at 25 °C(lit.)
Flash Point 14 °C
Flash Point 57.2 °F
Refractive Index n20/D 1.545(lit.)
Refractive Index n20/D 1.547
GHS Pictograms GHS02
GHS Pictograms GHS05
GHS Signal Word Danger
GHS Hazard statements H225-H314
European Hazard Symbols Flammable Flammable (F)
European Hazard Symbols Corrosive Corrosive (C)
MSDS Link Download
Personal Protective Equipment Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
GHS Precautionary statements P210-P280-P305 + P351 + P338-P310
RID/ADR UN 2924 3/PG 2
Risk Statements 11-34-37
Safety Statements 16-26-36/37/39-45
Storage Temperature 2-8°C
Hazard Class 3
UN Number 2924
Packing Group 2
German water hazard class 3

DETAILS

Description (English)
Other Notes
Reactive chloroborane; reacts with many bifunctional compounds to bora-heterocycles, e.g. pentaphenylborole8; Used as catalyst, e.g. for Fiedel-Crafts type acylation of anilines with benzaldehydes9; Enol-formation with ketones and highly erythro-selective aldol-reaction with aldehydes10
Application
Catalyst for:
• Antiproliferative macrolide and cell migration inhibitor lactimidomycin1
• Enantioselective synthesis of polyketide segments using vinylogous Mukaiyama aldol reactions2
• Enantioselective Diels-Alder cycloadditions after its reaction with allo-threonine derivatives3
• Stereoselective alkylative ring opening of cyclic anhydrides4
• Cross-metathesis reaction of amino derivatives with olefins5
• Asymmetric acetate aldol reactions6
• The reaction of aryl aldehydes with styrene and (E)-β-methylstyrene7
Description (简体中文)
Other Notes
反应性氯硼烷;与多种双官能化合物反应生成硼杂环,例如五苯基硼杂环戊二烯 (pentaphenylborole)8;用作催化剂,例如用于苯胺类和苯甲醛的 Fiedel-Crafts 型酰化反应9;与酮类反应形成烯醇以及与醛类进行高赤型选择性羟醛反应10
Application
Catalyst for:
• Antiproliferative macrolide and cell migration inhibitor lactimidomycin1
• Enantioselective synthesis of polyketide segments using vinylogous Mukaiyama aldol reactions2
• Enantioselective Diels-Alder cycloadditions after its reaction with allo-threonine derivatives3
• Stereoselective alkylative ring opening of cyclic anhydrides4
• Cross-metathesis reaction of amino derivatives with olefins5
• Asymmetric acetate aldol reactions6
• The reaction of aryl aldehydes with styrene and (E)-β-methylstyrene7

REFERENCES