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251259

Sigma-Aldrich

Thionyl bromide

97%

Synonym(s):

Dibromo sulfoxide, Sulfur bromide oxide (SOBr2)

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About This Item

Linear Formula:
SOBr2
CAS Number:
Molecular Weight:
207.87
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

vapor pressure

10 mmHg ( 31 °C)

Assay

97%

form

liquid

refractive index

n20/D 1.675 (lit.)

bp

48 °C/20 mmHg (lit.)

mp

−52 °C (lit.)

density

2.683 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

BrS(Br)=O

InChI

1S/Br2OS/c1-4(2)3

InChI key

HFRXJVQOXRXOPP-UHFFFAOYSA-N

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Application

Thionyl bromide (SOBr2) can be used as a brominating agent in organic synthesis for the bromination of alcohols, carboxylic acids, alkenes, and ketones.
SoBr2 can be used in the synthesis of:      
  • ortho


  • -Bromoanilides by bromination of ortho C-H bonds of the aryhydroxylamines.      
  • β-Amino bromides from β-aminoalcohols in the presence of DMF as a solvent.      
  • 4,8-Dibromobenzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole from 1,2,4,5-tetraaminobenzene tetrahydrobromide.

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Dermal - Skin Corr. 1B

Supplementary Hazards

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Palladium-catalyzed alpha-arylation of aldehydes with bromo- and chloroarenes catalyzed by [{Pd(allyl)Cl}2] and dppf or Q-phos.
Giang D Vo et al.
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[reaction: see text] A perfluorohexane layer regulates the rate of reagent transport in the bromination and chlorination of alcohols. A fluorous triphasic U-tube method is effective for lighter reagents; the thionyl chloride layer (yellow) vanishes, and the chlorides are obtained
Thionyl bromide
Ho TL, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2006)

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