3-bromopropine

Structural formula
General
Surname	3-bromopropine
other names	Propargyl bromide
Molecular formula	C 3 H 3 Br
Brief description	colorless to yellowish liquid with a pungent odor
External identifiers / databases
EC number	203-447-1
ECHA InfoCard	100.003.135
PubChem	7842
Wikidata	Q7250094
properties
Molar mass	118.96 g mol −1
Physical state	liquid
density	1.57 g cm −3
Melting point	−61 ° C
boiling point	89 ° C
Vapor pressure	72 hPa (20 ° C); 310 hPa (50 ° C); 535 hPa (65 ° C);
solubility	practically insoluble in water; soluble in ethanol, diethyl ether, benzene, carbon tetrachloride, chloroform;
safety instructions
H and P phrases	H: 225-301-304-315-319-335-336-361d-373
	P: 210-261-281-301 + 310-331-305 + 351 + 338-309 + 310-403 + 235
Toxicological data	53 mg kg −1 ( LD 50 , rabbit , transdermal )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3-bromopropine is a chemical compound of bromine from the group of unsaturated halogenated hydrocarbons with a C≡C triple bond.

Extraction and presentation

The compound can be obtained by reacting propargyl alcohol with phosphorus tribromide .

properties

3-bromopropine is a volatile, colorless to yellowish liquid with a pungent odor, which is practically insoluble in water. It decomposes when heated, which can produce carbon monoxide , carbon dioxide and hydrogen bromide .

It can react with aldehydes with a Barbier reaction to form alkyne alcohols:

use

3-Bromopropine was used in the 1960s to improve the effects of chloropicrine and methyl bromide . The mixture of 60% methyl bromide, 30% chloropicrin and 9% 3-bromopropine was marketed under the name Trizone until 1968 . From 2000 the use as a fumigant and substitute for methyl bromide was examined again in the USA. It is also an intermediate for the production of other chemical compounds such as allenyl magnesium bromide .

safety instructions

The vapors of 3-bromopropine can form an explosive mixture with air ( flash point 18 ° C, ignition temperature 324 ° C). The connection is unstable and requires a stabilizer for safe handling. It is usually sold dissolved in toluene or xylene .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on 3-bromopropine in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ GWA Milne: CRC Handbook of Pesticides . CRC Press, 1994, ISBN 978-0-8493-2447-5 , pp. 24 ( limited preview in Google Book search).
^ ^A ^b Lambert Brandsma: Best Synthetic Methods: Acetylenes, Allenes and Cumulenes . Elsevier, 2003, ISBN 978-0-08-054220-1 , pp. 369 ( limited preview in Google Book search).
↑ Artur Jõgi, Uno Mäeorg: Zn Mediated Regioselective Barbier Reaction of Propargylic Bromides in THF / aq. NH ₄ Cl solution . In: Molecules . tape 6 , no. 12 , November 30, 2001, p. 964-968 , doi : 10.3390 / 61200964 ( PDF ).
↑ ^a ^b United Nations Environment Program: 2002 Report of the Methyl Bromide Technical Options Committee 2002 Assessment . UNEP / Earthprint, 2003, ISBN 978-92-807-2287-1 , pp. 47 ( limited preview in Google Book search).
^ L. Brandsma: Preparative Acetylenic Chemistry . Elsevier, 2013, ISBN 978-1-4832-9003-4 , pp. 247 ( limited preview in Google Book search).
↑ Data sheet Propargyl bromide solution, 80 wt.% In toluene, contains 0.3% magnesium oxide as stabilizer from Sigma-Aldrich , accessed on July 13, 2016 ( PDF ).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on 3-bromopropine in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[G.W.A._Milne-2] GWA Milne: CRC Handbook of Pesticides . CRC Press, 1994, ISBN 978-0-8493-2447-5 , pp. 24 ( limited preview in Google Book search).

[Lambert_Brandsma-3] A ^b Lambert Brandsma: Best Synthetic Methods: Acetylenes, Allenes and Cumulenes . Elsevier, 2003, ISBN 978-0-08-054220-1 , pp. 369 ( limited preview in Google Book search).

[4] Artur Jõgi, Uno Mäeorg: Zn Mediated Regioselective Barbier Reaction of Propargylic Bromides in THF / aq. NH ₄ Cl solution . In: Molecules . tape 6 , no. 12 , November 30, 2001, p. 964-968 , doi : 10.3390 / 61200964 ( PDF ).

[United_Nations_Environment_Programme-5] United Nations Environment Program: 2002 Report of the Methyl Bromide Technical Options Committee 2002 Assessment . UNEP / Earthprint, 2003, ISBN 978-92-807-2287-1 , pp. 47 ( limited preview in Google Book search).

[L._Brandsma-6] L. Brandsma: Preparative Acetylenic Chemistry . Elsevier, 2013, ISBN 978-1-4832-9003-4 , pp. 247 ( limited preview in Google Book search).

[Sigma-7] Data sheet Propargyl bromide solution, 80 wt.% In toluene, contains 0.3% magnesium oxide as stabilizer from Sigma-Aldrich , accessed on July 13, 2016 ( PDF ).