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256536

Sigma-Aldrich

Phosphorus tribromide

99%

Synonym(s):
Phosphorus(III) bromide
Linear Formula:
PBr3
CAS Number:
Molecular Weight:
270.69
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor pressure

0.27 psi ( 54 °C)

Quality Level

assay

99%

refractive index

n20/D 1.697 (lit.)

bp

175 °C (lit.)

mp

−41.5 °C (lit.)

density

2.88 g/mL at 20 °C (lit.)

SMILES string

BrP(Br)Br

InChI

1S/Br3P/c1-4(2)3

InChI key

IPNPIHIZVLFAFP-UHFFFAOYSA-N

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General description

Phosphorus tribromide (PBr3) is commonly used in Hell-Volhard-Zelinsky halogenation for the α-bromination of carboxylic acids to form the corresponding acyl bromide. It is also useful for the conversion of primary and secondary alcohols to alkyl bromides.

Application

Phosphorus tribromide may be used as a reagent:
  • In a novel protocol for synthesizing 7-ethoxy-1-(p-ethylphenoxy)-3,7-dimethyl-2-octene, a synthetic juvenile hormone mimic of trans,trans,cis-10,11-epoxy-7-ethyl-3,11-dimethyltrideca-2,6-dienoate.
  • To synthesize 1,2,3-diazaphosphinane, 1,2,3-thiazaphosphinine and 1,2-azaphosphole bearing a chromone ring.
  • To synthesize 1-Bromoundec-1-ene from 10-undecen-1-ol.

Packaging

100, 500 g in Sure/Seal™
5 g in glass bottle

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

Storage Class Code

8B - Non-combustible, corrosive hazardous materials

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Organic Chemistry (2008)
Polymerized micelle-protected platinum clusters. Preparation and application to catalyst for visible light-induced hydrogen generation.
Toshima N, et al.
J. Macromol. Sci. Chem., 25(5-7), 669-686 (1988)
Organic Chemistry, 905-905 null
Organic Chemistry (1988)
Phosphorus tribromide promoted allylic rearrangement of a tertiary vinyl carbinol. Stereochemistry of the reaction product and application to the synthesis of JH-25, a potent juvenile hormone mimic.
Babler JH
The Journal of Organic Chemistry, 41(7), 1262-1264 (1976)

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