dichloro(phenyl)borane

• ChemBase ID: 145546
• Molecular Formular: C6H5BCl2
• Molecular Mass: 158.8209
• Monoisotopic Mass: 157.98613592
• SMILES: B(c1ccccc1)(Cl)Cl
• Canonical SMILES: ClB(c1ccccc1)Cl
• InChI: InChI=1S/C6H5BCl2/c8-7(9)6-4-2-1-3-5-6/h1-5H
• InChIKey: NCQDQONETMHUMY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 873-51-8
• MDL Number: MFCD00013612
• Beilstein Number: 2243576
• PubChem SID: 24846539; 162239751; 24887294
• PubChem CID: 136678

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.9312
• LogD (pH = 7.4): 2.9312
• Log P: 2.9312
• Molar Refractivity: 37.7469 cm^3
• Polarizability: 15.952129 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Liquid
• Melting Point: 7°C
• Boiling Point: 175°C; 66 °C/11 mmHg(lit.)
• Flash Point: 14 °C; 14°C(57°F); 57.2 °F
• Density: 1.194; 1.224 g/mL at 25 °C(lit.)
• Refractive Index: 1.545; n20/D 1.545(lit.); n20/D 1.547

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F)
• UN Number: 2924; UN2924
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-14-34; 11-34-37
• Safety Statements: 16-26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H314; H225-H314-H318
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2924 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (AT); 96%; 97%
• Grade: purum
• Empirical Formula (Hill Notation): C6H5BCl2

DETAILS

Sigma Aldrich - 101346

Packaging
1, 5, 25 g in glass bottle
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

Sigma Aldrich - 78373

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