2-bromobenzyl bromide

Structural formula
General
Surname	2-bromobenzyl bromide
other names	α, 2-dibromotoluene; 1-bromo-2-bromomethylbenzene;
Molecular formula	C 7 H 6 Br 2
Brief description	beige solid
External identifiers / databases
EC number	222-334-8
ECHA InfoCard	100.020.305
PubChem	76965
ChemSpider	69414
Wikidata	Q63059356
properties
Molar mass	249.93 g mol −1
Physical state	firmly
Melting point	29-32 ° C
boiling point	129 ° C (19 mmHg )
solubility	soluble in dioxane (1 g / 10 mL); practically insoluble in water; soluble in alcohol, ether and most organic solvents;
Refractive index	1.619 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 314
	P: 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

2-Bromobenzyl bromide is a chemical compound from the group of haloalkanes .

Extraction and presentation

2-Bromobenzyl bromide can be obtained by reacting 2-bromotoluene with bromine in carbon tetrachloride .

properties

2-Bromobenzyl bromide is a beige solid that is soluble in 1,4-dioxane , but practically insoluble in water. The connection is very irritating to tears.

use

2-Bromobenzyl bromide is used in the synthesis of substituted quinazolines , 1,2,3,4-tetrahydroquinazolines, 2- and 3-substituted indenes, and tris-2-bromo-tribenzylamine . It is widely used as a reagent to protect aldehydes and ketones in alcohol oxidation and as a coupling component in a variety of reactions.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Data sheet 2-Bromobenzyl bromide, 98% from Sigma-Aldrich , accessed on April 4, 2019 ( PDF ).
↑ ^a ^b Data sheet 2-Bromobenzyl bromide, 98% from AlfaAesar, accessed on April 4, 2019 ( PDF )(JavaScript required) .
↑ ^a ^b ^c Lance A. Pfeifer: 2-Bromobenzyl Bromide . In: Encyclopedia of Reagents for Organic Synthesis . doi : 10.1002 / 047084289X.rn00193 .
↑ PrepChem.com: Synthesis of 2-bromobenzyl bromide - PrepChem.com , accessed April 4, 2019
↑ Heinz Becker, Werner Berger and Günter Domschke, Organicum. Practical Handbook of Organic Chemistry, Addison-Wesley Pub. Co, 172-174, (1973), ISBN 978-0201055047
↑ Ronald L. Halterman, Chengian Zhu: Efficient synthesis of 2- and 3-substituted indenes from 2-bromobenzyl bromide through an enolate alkylation / Cr (II) / Ni (II) -mediated carbonyl addition sequence. In: Tetrahedron Letters. 40, 1999, p. 7445, doi : 10.1016 / S0040-4039 (99) 01541-5 .

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Data sheet 2-Bromobenzyl bromide, 98% from Sigma-Aldrich , accessed on April 4, 2019 ( PDF ).

[Alfa-2] Data sheet 2-Bromobenzyl bromide, 98% from AlfaAesar, accessed on April 4, 2019 ( PDF )(JavaScript required) .

[wiley.com-3] Lance A. Pfeifer: 2-Bromobenzyl Bromide . In: Encyclopedia of Reagents for Organic Synthesis . doi : 10.1002 / 047084289X.rn00193 .

[prepchem.com-4] PrepChem.com: Synthesis of 2-bromobenzyl bromide - PrepChem.com , accessed April 4, 2019

[5] Heinz Becker, Werner Berger and Günter Domschke, Organicum. Practical Handbook of Organic Chemistry, Addison-Wesley Pub. Co, 172-174, (1973), ISBN 978-0201055047

[DOI10.1016/S0040-4039(99)01541-5-6] Ronald L. Halterman, Chengian Zhu: Efficient synthesis of 2- and 3-substituted indenes from 2-bromobenzyl bromide through an enolate alkylation / Cr (II) / Ni (II) -mediated carbonyl addition sequence. In: Tetrahedron Letters. 40, 1999, p. 7445, doi : 10.1016 / S0040-4039 (99) 01541-5 .