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Merck

157783

Sigma-Aldrich

Phosphorus tribromide

97%

Sinónimos:

Phosphorus(III) bromide

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About This Item

Fórmula lineal:
PBr3
Número de CAS:
Peso molecular:
270.69
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

vapor pressure

0.27 psi ( 54 °C)

assay

97%

form

liquid

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.

pictograms

CorrosionExclamation mark

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

supp_hazards

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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Organic Chemistry, 1 (1988)
Organic Chemistry (2008)
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)
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)
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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