Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

Thionyl bromide

From Wikipedia, the free encyclopedia
Thionyl bromide
Structure of the thionyl bromide molecule
Structure of the thionyl bromide molecule
3D model of a thionyl bromide molecule
3D model of a thionyl bromide molecule
Molecular arrangement in solid SOBr2 (note that this is dramatically different from the crystal structure of its chloride analogue)
Molecular arrangement in solid SOBr2 (note that this is dramatically different from the crystal structure of its chloride analogue)
Names
IUPAC name
Thionyl bromide
Other names
Sulfur oxy dibromide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.007.332Edit this at Wikidata
EC Number
  • 208-064-3
UNII
  • InChI=1S/Br2OS/c1-4(2)3 checkY
    Key: HFRXJVQOXRXOPP-UHFFFAOYSA-N checkY
  • InChI=1/Br2OS/c1-4(2)3
    Key: HFRXJVQOXRXOPP-UHFFFAOYAY
  • BrS(Br)=O
Properties
SOBr2
Molar mass207.87 g/mol
Appearancecolorless liquid
Density2.688 g/mL, liquid[1]
Melting point−52 °C (−62 °F; 221 K) ; may includesupercooling[1]
Boiling point
  • 48 °C at 20 mmHg[1]
  • 136 °C at 1 atm but1⁄3 decomposes[1]
decomposes
Solubilityreacts inHBr, acetone, and alcohol
soluble in benzene, toluene, ether
Structure
trigonal pyramidal
1.47 D[1]
Hazards[2]
Occupational safety and health (OHS/OSH):
Main hazards
Readily decomposes in air to toxic gases
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H312,H314,H332
P280,P305+P351+P338,P310
Flash pointNon-flammable
Safety data sheet (SDS)"External MSDS"
Related compounds
Related compounds
SOCl2,SeOCl2;

PBr3,Br2

Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Thionyl bromide is the chemical compound SOBr2. It is less stable and less widely used than itschloride analogue,thionyl chloride, but engages in similar reactions.[3]

Chemistry

[edit]

It is prepared by the action ofhydrogen bromide on thionyl chloride,[4] although the corresponding reaction at higher pH (i.e. alkali bromides) proceeds only with difficulty:[1]

SOCl2 + 2 HBr → SOBr2 + 2 HCl

Phosphorus trichlorodibromide (but notphosphorus pentabromide) convertssulfur dioxide to thionyl bromide. Thionyl chlorobromide appears to be a key intermediate in these syntheses, but has not been isolated.[1]

Thionyl bromide will convertalcohols to alkyl bromides and carboxylic acids to acyl bromides. Unlike with thionyl chloride, stoichiometric bases are problematic activating agents, because free bromide anions decompose thionyl bromide totribromide,sulfur dioxide, andsulfur.[1]

It can be used for brominations of certain α,β-unsaturated carbonyl compounds.[5]

It may occasionally be used as a solvent.[6][7]

Safety

[edit]

SOBr2 hydrolyzes readily in air to release dangerous fumes ofsulfur dioxide andhydrogen bromide.

SOBr2 + H2O → SO2 + 2 HBr

Decomposition tobromine andsulfur monoxide does not occur except at elevated temperatures.[1]

References

[edit]
  1. ^abcdefghiMagee, Philip S. (1971). "The Sulfur–Bromine Bond". In Senning, Alexander (ed.).Sulfur in Organic and Inorganic Chemistry. Vol. 1. New York: Marcel Dekker. pp. 271–276.ISBN 0-8247-1615-9.LCCN 70-154612.
  2. ^"Thionyl bromide". Sigma Aldrich.
  3. ^Mundy, B. P. (2004). "Thionyl Bromide". In Paquette, E. (ed.).Encyclopedia of Reagents for Organic Synthesis. New York: J. Wiley & Sons.doi:10.1002/047084289X.rt098.ISBN 0471936235.
  4. ^Booth, Harold Simmons (1939).Inorganic syntheses. Volume 1. New York. p. 113.ISBN 978-0-470-13264-7.OCLC 86223179.{{cite book}}:ISBN / Date incompatibility (help)CS1 maint: location missing publisher (link)
  5. ^Saraf, S. D. (1 August 1969)."Reaction of thionyl bromide with tropolone and phenol".Canadian Journal of Chemistry.47 (15):2803–2804.doi:10.1139/v69-465.
  6. ^Furlani, C.; Zinato, E. (May 1967). "Hexahalogenoniobates(V), Oxopentahalogenoniobates(V) and their electronic spectra".Zeitschrift für anorganische und allgemeine Chemie.351 (3–4):210–218.doi:10.1002/zaac.19673510311.
  7. ^The chemistry of the actinide and transactinide elements. Volumes 1-6 (4th ed.). Dordrecht: Springer. 2010. p. 526.ISBN 978-94-007-0211-0.
Wikimedia Commons has media related toThionyl bromide.
Sulfides and
disulfides
Sulfurhalides
Sulfuroxides
andoxyhalides
Sulfites
Sulfates
Sulfurnitrides
Thiocyanates
Organic compounds
Stub icon

Thisinorganiccompound–related article is astub. You can help Wikipedia byexpanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Thionyl_bromide&oldid=1302032524"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2025 Movatter.jp