Benzoyl bromide

Structural formula
General
Surname	Benzoyl bromide
other names	Bromobenzoyl
Molecular formula	C 6 H 5 COBr
Brief description	dark brown liquid
External identifiers / databases
EC number	210-544-2
ECHA InfoCard	100.009.587
PubChem	12056
ChemSpider	11559
Wikidata	Q62449071
properties
Molar mass	185.02 g mol −1
Physical state	liquid
density	1.57 g cm −3 (25 ° C)
Melting point	−24 ° C
boiling point	218-219 ° C
solubility	reacts with water
Refractive index	1.589 (20 ° C)
safety instructions
H and P phrases	H: 314-335
	EUH: 014
	P: 261-280-305 + 351 + 338-310
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Benzoyl bromide is a chemical compound from the group of benzoic acid derivatives .

Extraction and presentation

Benzoyl bromide can be obtained by reacting benzoyl chloride with bromotrimethylsilane .

properties

Benzoyl bromide is a dark brown liquid. The compound dissolves various metal bromides with electrolytic dissociation. Metal bromide hydrates can be dehydrated with benzoyl bromide.

use

Benzoyl bromide is a versatile reagent for the benzoylation of ethers . In the synthesis of carbohydrates as ethers (especially benzyl ethers ), protected hydroxyl groups can be converted into the corresponding benzoates under mild conditions in a one-pot reaction with benzoyl bromide and zinc triflate .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet Benzoyl bromide, 97% from Sigma-Aldrich , accessed on March 25, 2019 ( PDF ).
^ William M. Haynes: CRC Handbook of Chemistry and Physics, 93rd Edition . CRC Press, 2012, ISBN 978-1-4398-8049-4 , pp. 42 ( limited preview in Google Book search).
^ Richard Montgomery Stephenson: Handbook of the Thermodynamics of Organic Compounds . Springer Science & Business Media, 2012, ISBN 978-94-009-3173-2 , pp. 221 ( limited preview in Google Book search).
^ Alan R. Katritzky, Christopher J. Moody, Otto Meth-Cohn, Charles Wayne Rees: Comprehensive Organic Functional Group Transformations . Elsevier, 1995, ISBN 978-0-08-042326-5 , pp. 1334 ( limited preview in Google Book search).
↑ V. Gutmann, K. Utvary: reactions in anhydrous benzoyl. In: Monthly books for chemistry and related parts of other sciences. 90, 1959, p. 751, doi : 10.1007 / BF00902403 .
^ Tülay Polat, Robert J. Linhardt: Zinc triflate-benzoyl bromide: a versatile reagent for the conversion of ether into benzoate protecting groups and ether glycosides into glycosyl bromides . In: Carbohydrate Researche . tape 338 , no. 5 , 2003, p. 447-449 ( semanticscholar.org [PDF]).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet Benzoyl bromide, 97% from Sigma-Aldrich , accessed on March 25, 2019 ( PDF ).

[William_M._Haynes-2] William M. Haynes: CRC Handbook of Chemistry and Physics, 93rd Edition . CRC Press, 2012, ISBN 978-1-4398-8049-4 , pp. 42 ( limited preview in Google Book search).

[Richard_Montgomery_Stephenson-3] Richard Montgomery Stephenson: Handbook of the Thermodynamics of Organic Compounds . Springer Science & Business Media, 2012, ISBN 978-94-009-3173-2 , pp. 221 ( limited preview in Google Book search).

[Alan_R._Katritzky,_Christopher_J._Moody,_Otto_Meth-Cohn,_Charles_Wayne_Rees-4] Alan R. Katritzky, Christopher J. Moody, Otto Meth-Cohn, Charles Wayne Rees: Comprehensive Organic Functional Group Transformations . Elsevier, 1995, ISBN 978-0-08-042326-5 , pp. 1334 ( limited preview in Google Book search).

[DOI10.1007/BF00902403-5] V. Gutmann, K. Utvary: reactions in anhydrous benzoyl. In: Monthly books for chemistry and related parts of other sciences. 90, 1959, p. 751, doi : 10.1007 / BF00902403 .

[6] Tülay Polat, Robert J. Linhardt: Zinc triflate-benzoyl bromide: a versatile reagent for the conversion of ether into benzoate protecting groups and ether glycosides into glycosyl bromides . In: Carbohydrate Researche . tape 338 , no. 5 , 2003, p. 447-449 ( semanticscholar.org [PDF]).