Dichlorophenylborane Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Dichlorophenylborane Chemical Properties,Usage,Production

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.