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Merck
CN

251259

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
NACRES:
NA.22
PubChem Substance ID:
24855121
UNSPSC Code:
12352101
EC Number:
208-064-3
MDL number:
MFCD00011448
Assay:
97%
Form:
liquid

Key Documents

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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

200

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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

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Skin Corr. 1B

supp_hazards

EUH014

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCN7409
BCCN5029
BCCN3405
BCCD7714
BCBL3254V

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Thionyl bromide
Ho TL, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2006)
Practical bromination of arylhydroxylamines with SOBr2 towards ortho-bromo-anilides
Du Yuanbo, et al.
Tetrahedron Letters, 72, 153074-153074 (2021)
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)
Julie T Daniels et al.
The American journal of pathology, 163(5), 2043-2052 (2003-10-28)
Excessive cell-mediated tissue contraction after injury can lead to morbid contractile scarring in the body. In the eye this can cause blindness because of posterior capsule opacification, proliferative vitroretinopathy, failure of glaucoma filtration surgery, and corneal haze. During repair, transforming
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