1,3-dibromopropane

Structural formula
General
Surname	1,3-dibromopropane
other names	Trimethylene bromide
Molecular formula	C 3 H 6 Br 2
Brief description	colorless, pungent-smelling liquid
External identifiers / databases
EC number	203-690-3
ECHA InfoCard	100.003.356
PubChem	8001
ChemSpider	7710
Wikidata	Q408240
properties
Molar mass	201.89 g · mol -1
Physical state	liquid
density	1.98 g cm −3 (20 ° C)
Melting point	−34 ° C
boiling point	166-168 ° C
Vapor pressure	2.6 h Pa (20 ° C); 4.9 hPa (30 ° C); 11.3 hPa (50 ° C);
solubility	poor in water (1.68 g l −1 at 30 ° C); soluble in ethanol , diethyl ether , chloroform and other organic solutions.;
Refractive index	1.5197 (20 ° C, 656.3 nm )
safety instructions
H and P phrases	H: 226-302-315-319-411
	P: 210-273-302 + 352-305 + 351 + 338
Toxicological data	315 mg kg −1 ( LD 50 , rat , oral )
	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

1,3-Dibromopropane is a bromine-containing derivative of propane .

Manufacturing

1,3-Dibromopropane can be produced by a free radical addition ( e.g. photochemically induced) reaction between allyl bromide and hydrogen bromide .

{\ displaystyle \ mathrm {H_ {2} C {=} CH {-} CH_ {2} Br \ + \ HBr \ {\ xrightarrow {h \ cdot \ nu}} \ \ Br {-} (CH_ {2} ) _ {3} {-} Br}}

The reaction must not be carried out as an electrophilic addition , as otherwise the Markovnikov product 1,2-dibromopropane would be obtained as the main product.

properties

1,3-Dibromopropane is a colorless, pungent-smelling liquid that has a melting point of −34 ° C and a boiling point of 167 ° C at normal pressure . The heat of vaporization at the boiling point is 45.5 kJ mol ⁻¹ , the heat of fusion at the melting point is 14.64 kJ mol ⁻¹ . According to Antoine, the vapor pressure function results from log ₁₀ (P) = A− (B / (T + C)) (P in bar, T in K) with A = 4.43365, B = 1776.679 and C = −39.691 in the temperature range from 283 to 440 K. Above its flash point at 54 ° C, the compound forms ignitable vapor-air mixtures.

use

Since bromide is a good leaving group , 1,3-dibromopropane can be used in substitution reactions . With suitable nucleophiles it can be used for the synthesis of cyclobutane derivatives. For example, the CH-acidic cyclopentadiene can be deprotonated by the action of bases and a spiro compound of cyclopentadiene can be obtained in stages in substitution reactions .

Biological importance

1,3-Dibromopropane irritates the skin, is hazardous to health if swallowed and is toxic to aquatic organisms. It is assigned to water hazard class 2.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 1,3-dibromopropane in the GESTIS substance database of the IFA , accessed on February 8, 2017(JavaScript required) .
^ Hermann Römpp: Römpp Chemie Lexikon . 9th edition. Thieme Georg Verlag, 1995, ISBN 3-13-102759-2 , p. 941 .
^ AI Vogel: Physical Properties and Chemical Constitution. Part I. Esters of Normal Dibasic Acids and of Substituted Malonic Acids , in: J. Chem. Soc. 1934, pp. 333-341, doi : 10.1039 / JR9340000333 .
↑ Data sheet 1,3-dibromopropane (PDF) from Merck , accessed on March 17, 2011.
^ WE Vaughan, FF Rust, TW Evans: The photo-addition of hydrogen bromide to olefinic bonds . In: J. Org. Chem. 7, 1942, pp. 477-490, doi : 10.1021 / jo01200a005 .
↑ Svoboda, V .; Kubes, V .; Basarova, P .: Enthalpies of vaporization and cohesive energies of 1,1,2,2-tetrachloro-1,2-difluoroethane, 1,2-dibromoethane, 1-bromo-2-chloroethane, 1,3-dibromo-propane, and 1,4-dibromo-2,3-dichloro-1,1,2,3,4,4-hexafluorobutane in J. Chem. Thermodyn. 24 (1992) 555-558.
↑ Domalski, ES; Hearing, ED: Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III in J. Phys. Chem. Ref. Data 25 (1996) 1-523, doi : 10.1063 / 1.555985 .
^ Stull, DR: Vapor Pressure of Pure Substances. Organic and Inorganic Compounds in Ind. Eng. Chem. 39 (1947) 517-540, doi : 10.1021 / ie50448a022 .
↑ CF Wilcox, GC Whitney: Preparation of spiro [3.4] oct-1-ene . In: J. Org. Chem. 32, 1967, pp. 2933-2936, doi : 10.1021 / jo01284a076 .
↑ Data sheet 1,3-dibromopropane from Sigma-Aldrich , accessed on November 3, 2016 ( PDF ).

[gestis-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 1,3-dibromopropane in the GESTIS substance database of the IFA , accessed on February 8, 2017(JavaScript required) .

[2] Hermann Römpp: Römpp Chemie Lexikon . 9th edition. Thieme Georg Verlag, 1995, ISBN 3-13-102759-2 , p. 941 .

[3] AI Vogel: Physical Properties and Chemical Constitution. Part I. Esters of Normal Dibasic Acids and of Substituted Malonic Acids , in: J. Chem. Soc. 1934, pp. 333-341, doi : 10.1039 / JR9340000333 .

[Merck-4] Data sheet 1,3-dibromopropane (PDF) from Merck , accessed on March 17, 2011.

[5] WE Vaughan, FF Rust, TW Evans: The photo-addition of hydrogen bromide to olefinic bonds . In: J. Org. Chem. 7, 1942, pp. 477-490, doi : 10.1021 / jo01200a005 .

[6] Svoboda, V .; Kubes, V .; Basarova, P .: Enthalpies of vaporization and cohesive energies of 1,1,2,2-tetrachloro-1,2-difluoroethane, 1,2-dibromoethane, 1-bromo-2-chloroethane, 1,3-dibromo-propane, and 1,4-dibromo-2,3-dichloro-1,1,2,3,4,4-hexafluorobutane in J. Chem. Thermodyn. 24 (1992) 555-558.

[7] Domalski, ES; Hearing, ED: Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III in J. Phys. Chem. Ref. Data 25 (1996) 1-523, doi : 10.1063 / 1.555985 .

[Stull-8] Stull, DR: Vapor Pressure of Pure Substances. Organic and Inorganic Compounds in Ind. Eng. Chem. 39 (1947) 517-540, doi : 10.1021 / ie50448a022 .

[9] CF Wilcox, GC Whitney: Preparation of spiro [3.4] oct-1-ene . In: J. Org. Chem. 32, 1967, pp. 2933-2936, doi : 10.1021 / jo01284a076 .

[10] Data sheet 1,3-dibromopropane from Sigma-Aldrich , accessed on November 3, 2016 ( PDF ).

1,3-dibromopropane

contents

Manufacturing

properties

use

Biological importance

See also

Individual evidence