157783

Sigma-Aldrich

Phosphorus tribromide

97%

Synonym(s):
Phosphorus(III) bromide
Linear Formula:
PBr3
CAS Number:
Molecular Weight:
270.69
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

vapor pressure

0.27 psi ( 54 °C)

Quality Level

assay

97%

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 a-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.

Packaging

100, 500 g in Sure/Seal™

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Target Organs

Respiratory system

Supp Hazards

EUH014

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

C

Risk Statement

14-34-37

Safety Statement

26-45

RIDADR

UN 1808 8 / PGII

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Organic Chemistry (2008)
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)
Reaction of 2-cyano-3-(4-oxo-4H-chromen-3-yl) prop-2-enamide with some phosphorus reagents: synthesis of some novel diethyl phosphonates, 1, 2, 3-diazaphosphinanes, 1, 2, 3-thiazaphosphinine and 1, 2-azaphospholes bearing a chromone ring.
Ali TE & Hassan MM
Research on Chemical Intermediates, 44(1), 173-189 (2018)
Organic Chemistry, 1 (1988)
Andrey S Mereshchenko et al.
Nature chemistry, 7(7), 562-568 (2015-06-24)
'Roaming' is a new and unusual class of reaction mechanism that has recently been discovered in unimolecular dissociation reactions of isolated molecules in the gas phase. It is characterized by frustrated bond cleavage, after which the two incipient fragments 'roam'...

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