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157783

Sigma-Aldrich

Phosphorus tribromide

97%

Synonym(s):

Phosphorus(III) bromide

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About This Item

Linear Formula:
PBr3
CAS Number:
7789-60-8
Molecular Weight:
270.69
EC Number:
232-178-2
MDL number:
MFCD00011436
UNSPSC Code:
12352101
PubChem Substance ID:
24849701
NACRES:
NA.22

vapor pressure

0.27 psi ( 54 °C)

Quality Level

200

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
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H335

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

157783-500ML:
157783-BULK:
157783-VAR:
157783-100G:
157783-5ML:
157783-5G:
157783-2.5L:
157783-100ML:
157783-1KG:
157783-500G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ4121
MKCN1481
MKCM8982
MKCL0913
MKCK1102

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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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