1,5-dibromopentane

Structural formula
General
Surname	1,5-dibromopentane
other names	Pentamethylene bromide
Molecular formula	C 5 H 10 Br 2
Brief description	colorless solid with a characteristic odor
External identifiers / databases
EC number	203-849-7
ECHA InfoCard	100.003.500
PubChem	8100
Wikidata	Q161550
properties
Molar mass	229.95 g mol −1
Physical state	liquid
density	1.70 g cm −3 (20 ° C)
Melting point	−35 ° C
boiling point	222 ° C
solubility	practically insoluble in water
Refractive index	1.5126
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319
	P: 305 + 351 + 338
	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

1,5-Dibromopentane is a chemical compound from the group of haloalkanes . It is built up from the basic structure of n- pentane with two bromine substituents at the two terminal positions.

presentation

1,5-Dibromopentane can be synthesized by reacting 1,5-pentanediol with hydrobromic acid .

{\ displaystyle \ mathrm {HO {-} (CH_ {2}) _ {5} {-} OH \ + \ 2 \ HBr \ longrightarrow}}

{\ displaystyle \ mathrm {Br {-} (CH_ {2}) _ {5} {-} Br \ + \ 2 \ H_ {2} O}}

Another possibility is the ring opening of tetrahydropyran with hydrobromic acid and sulfuric acid .

properties

1,5-Dibromopentane is a colorless compound that is liquid at room temperature and boils at a temperature of 222 ° C.

use

By reacting 1,5-dibromopentane with primary amines , N -alkylated derivatives of piperidine can be obtained.

Production of N-alkylated piperidines from 1,5-dibromopentane

Thiane can be obtained in good yield by the reaction of 1,5-dibromopentane with sodium sulfide .

{\ displaystyle \ mathrm {Br {-} (CH_ {2}) _ {5} {-} Br + Na_ {2} S \ longrightarrow}}

{\ displaystyle \ mathrm {C_ {5} H_ {10} S + 2 \ NaBr}}

Reaction of 1,5-dibromopentane with sodium sulfide to give thiane and sodium bromide .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on 1,5-dibromopentane in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
^ R. Grzeskowiak, GH Jeffery, AI Vogel: Physical properties and chemical constitution. Part XXXI. Polymethylene dichlorides, dibromides, di-iodides, and dicyanides , in: J. Chem. Soc. , 1960 , pp. 4728-4731; doi : 10.1039 / JR9600004728 .
↑ A. Hochstetter: About the action of water on pentamethylene bromide , in : months. Chem. , 1902 , 23 , pp. 1071-1074; doi : 10.1007 / BF01524939 .
↑ DW Andrus: pentamethylene bromide in: Organic Syntheses . 23, 1943, p. 67, doi : 10.15227 / orgsyn.023.0067 ; Coll. Vol. 3, 1955, p. 692 ( PDF ).
↑ J. v. Braun: The splitting of cyclic bases by cyanogen bromide. , in: Chem. Ber. , 1909 , 42 , pp. 2035-2057; doi : 10.1002 / cber.19090420286 .
↑ J. Kenyon, H. Phillips, VP Pittman: Walden inversion reactions of d-β-butyl, d-β-octyl, and d-benzylmethylcarbinyl p-toluenesulphonates , in: J. Chem. Soc. , 1935 , pp. 1072-1084; doi : 10.1039 / JR9350001663 .
↑ K. Nagasawa, A. Yoneta: Organosulfur Chemistry. II. Use of Dimethyl Sulfoxide - a Facile Synthesis of Cyclic Sulfides , in: Chem. Pharm. Bull. , 1985 , 33 , pp. 5048-5052, doi : 10.1248 / cpb.33.5048 , pdf .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on 1,5-dibromopentane in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[2] R. Grzeskowiak, GH Jeffery, AI Vogel: Physical properties and chemical constitution. Part XXXI. Polymethylene dichlorides, dibromides, di-iodides, and dicyanides , in: J. Chem. Soc. , 1960 , pp. 4728-4731; doi : 10.1039 / JR9600004728 .

[3] A. Hochstetter: About the action of water on pentamethylene bromide , in : months. Chem. , 1902 , 23 , pp. 1071-1074; doi : 10.1007 / BF01524939 .

[4] DW Andrus: pentamethylene bromide in: Organic Syntheses . 23, 1943, p. 67, doi : 10.15227 / orgsyn.023.0067 ; Coll. Vol. 3, 1955, p. 692 ( PDF ).

[5] J. v. Braun: The splitting of cyclic bases by cyanogen bromide. , in: Chem. Ber. , 1909 , 42 , pp. 2035-2057; doi : 10.1002 / cber.19090420286 .

[6] J. Kenyon, H. Phillips, VP Pittman: Walden inversion reactions of d-β-butyl, d-β-octyl, and d-benzylmethylcarbinyl p-toluenesulphonates , in: J. Chem. Soc. , 1935 , pp. 1072-1084; doi : 10.1039 / JR9350001663 .

[7] K. Nagasawa, A. Yoneta: Organosulfur Chemistry. II. Use of Dimethyl Sulfoxide - a Facile Synthesis of Cyclic Sulfides , in: Chem. Pharm. Bull. , 1985 , 33 , pp. 5048-5052, doi : 10.1248 / cpb.33.5048 , pdf .