Dichlorophenylborane Chemical Properties

Melting point:

7 °C

Boiling point:

66 °C11 mm Hg(lit.)

Density 

1.224 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.545(lit.)

Flash point:

−5 °F

storage temp. 

2-8°C

form 

Liquid

Specific Gravity

1.224

color 

Colorless

Water Solubility 

Soluble in water (Reacts violently).

Sensitive 

Moisture Sensitive

BRN 

2243576

InChI

InChI=1S/C6H5BCl2/c8-7(9)6-4-2-1-3-5-6/h1-5H

InChIKey

NCQDQONETMHUMY-UHFFFAOYSA-N

SMILES

B(Cl)(Cl)C1=CC=CC=C1

CAS DataBase Reference

873-51-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

F,C

Risk Statements 

11-34-37

Safety Statements 

16-26-36/37/39-45

RIDADR 

UN 2924 3/PG 2

WGK Germany 

3

F 

10-23

HazardClass 

3

PackingGroup 

II

HS Code 

29310099

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Dichlorophenylborane Usage And Synthesis

Chemical Properties

clear colorless liquid

History

In 1880, Michaelis and co-workers began to investigate aryl-boranes to determine the valency of boron which was, at thetime, debated to be three or five. They reacted gaseous BCl3with diphenylmercury at elevated temperatures in a sealedtube and observed the formation of dichlorophenylborane and HgCl2. Dichlorophenylborane was isolated via distillationand was characterized by elemental analysis and conclusivefollow-up chemistry[1].

Uses

Dichlorophenylborane is widely used as a catalyst in Antiproliferative macrolide and cell migration inhibitor lactimidomycin and in enantioselective synthesis of polypeptide segments using vinylogous Mukaiyama aldol reactions and in enantioselective Diels-Alder cycloadditions after its reaction with allo-threonine derivatives. It is a stereo selective alkylative ring opening of cyclic anhydrides and in cross-metathesis reaction of amino derivatives with olefines.

Uses

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

References

[1] Sarina M. Berger, Prof.?Dr. Todd B. Marder, Matthias Ferger. “Synthetic Approaches to Triarylboranes from 1885 to 2020.” Chemistry - A European Journal 27 24 (2021): 7043–7058.

Dichlorophenylborane(873-51-8)Related Product Information

• TETRACHLOROGUAJACOL
• Phloroglucinol
• Boron
• PHENYLBORON DICHLORIDE