251259
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
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352101
EC Number:
208-064-3
MDL number:
Assay:
97%
Form:
liquid
InChI key
HFRXJVQOXRXOPP-UHFFFAOYSA-N
InChI
1S/Br2OS/c1-4(2)3
SMILES string
BrS(Br)=O
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
Quality Level
Related Categories
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:
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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Dermal - Skin Corr. 1B
supp_hazards
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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Efficient synthesis of beta-amino bromides
Nagle AS, et al.
Tetrahedron Letters, 41(17), 3011-3014 (2000)
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)
Practical bromination of arylhydroxylamines with SOBr2 towards ortho-bromo-anilides
Du Yuanbo, et al.
Tetrahedron Letters, 72, 153074-153074 (2021)
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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