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78373 Sigma-Aldrich

Dichlorophenylborane

purum, ≥98.0% (AT)

Synonym: NSC 93889, Phenylboron dichloride, Phenyldichloroborane

  • CAS Number 873-51-8

  • Empirical Formula (Hill Notation) C6H5BCl2

  • Molecular Weight 158.82

  •  Beilstein Registry Number 2243576

  •  MDL number MFCD00013612

  •  PubChem Substance ID 329768143

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Properties

Related Categories Boranes, Chemical Synthesis, Reduction, Synthetic Reagents
InChI Key   NCQDQONETMHUMY-UHFFFAOYSA-N
grade   purum
assay   ≥98.0% (AT)
refractive index   n20/D 1.545(lit.)
  n20/D 1.547
bp   66 °C/11 mmHg(lit.)
density   1.224 g/mL at 25 °C(lit.)
storage temp.   2-8°C

Description

Other Notes

Reactive chloroborane; reacts with many bifunctional compounds to bora-heterocycles, e.g. pentaphenylborole; Used as catalyst, e.g. for Fiedel-Crafts type acylation of anilines with benzaldehydes; Enol-formation with ketones and highly erythro-selective aldol-reaction with aldehydes

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Application

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

Price and Availability

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2924 8(3) / PGII
WGK Germany 
3
Flash Point(F) 
57.2 °F
Flash Point(C) 
14 °C
Protocols & Articles
Peer-Reviewed Papers
15

References

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