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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:
507-16-4
Molecular Weight:
207.87
EC Number:
208-064-3
MDL number:
MFCD00011448
UNSPSC Code:
12352101
PubChem Substance ID:
24855121
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
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H312 + H332,H314

Hazard Classifications

Acute Tox. 4 Dermal - Skin Corr. 1B

Supplementary Hazards

EUH014

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Efficient synthesis of beta-amino bromides
Nagle AS, et al.
Tetrahedron Letters, 41(17), 3011-3014 (2000)
Practical bromination of arylhydroxylamines with SOBr2 towards ortho-bromo-anilides
Du Yuanbo, et al.
Tetrahedron Letters, 72, 153074-153074 (2021)
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.
Angewandte Chemie (International ed. in English), 47(11), 2127-2130 (2008-02-09)
Hiroyuki Nakamura et al.
Organic letters, 5(8), 1167-1169 (2003-04-12)
[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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