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About This Item
Linear Formula:
PBr3
CAS Number:
Molecular Weight:
270.69
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352101
EC Number:
232-178-2
MDL number:
Product Name
Phosphorus tribromide, 97%
InChI key
IPNPIHIZVLFAFP-UHFFFAOYSA-N
InChI
1S/Br3P/c1-4(2)3
SMILES string
BrP(Br)Br
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.)
Quality Level
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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.
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.
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
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Regulatory Information
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Organic Chemistry, 1 (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)
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)
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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