2-methyl-3-butyn-2-ol

Structural formula
General
Surname	2-methyl-3-butyn-2-ol
other names	Ethynyl methyl carbinol; Dimethylethynyl carbinol; 1,1-dimethyl-2-propyn-1-ol; 2-methylbut-3-yn-2-ol; Dimethylethynyl methanol; Methylbutynol (ambiguous);
Molecular formula	C 5 H 8 O
Brief description	volatile, highly flammable, colorless liquid with a characteristic odor
External identifiers / databases
EC number	204-070-5
ECHA InfoCard	100.003.700
PubChem	8258
Wikidata	Q209427
properties
Molar mass	84.12 g mol −1
Physical state	liquid
density	0.86 g cm −3
Melting point	3 ° C
boiling point	104 ° C
Vapor pressure	20 h Pa (20 ° C)
solubility	miscible with water, miscible with acetone , benzene , carbon tetrachloride , cyclohexanone , diethylene glycol , ethyl acetate and monoethanolamine
Refractive index	1.4209-1.4220
safety instructions
H and P phrases	H: 225-302-318
	P: 210-280-305 + 351 + 338
Toxicological data	1420 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

2-Methyl-3-butyn-2-ol (methylbutynol for short) is a chemical compound from the group of alcohols . It is in the form of a colorless liquid.

Extraction and presentation

2-Methyl-3-butyn-2-ol is obtained by ethynylation of acetone .

In Germany around 1,000 to 5,000 tons were produced in 1991, and in Austria 5,000 to 10,000 tons in the same year. This makes it one of the chemical substances that are produced in large quantities (" High Production Volume Chemical ", HPVC) and for which the Organization for Economic Cooperation and Development (OECD) collects data on possible dangers (" Screening Information Dataset ", SIDS).

use

2-Methyl-3-butyn-2-ol is used as a versatile reagent in organic chemistry (as acetylene equivalent in palladium- catalyzed coupling reactions with halides ) and for the production of isoprene , vitamins A and B , pharmaceuticals and fragrances. Furthermore, in a concentration of 3–7% by volume, it served as a stabilizer for 1,1,1-trichloroethane , which, however, was reduced further and further due to the restricted use of this compound.

safety instructions

The vapors of 2-methyl-3-butyn-2-ol form an explosive mixture with air ( flash point 20 ° C, ignition temperature 350 ° C).

Similar connections

2-methyl-3-butyn-1-ol C ₅ H ₈ O, isomer to 2-methyl-3-butyn-2-ol
2-methylbut-3-en-2-ol C ₅ H ₁₀ O
3-methylbut-2-en-1-ol C ₅ H ₁₀ O, also called prenol
3-methylbut-3-en-1-ol C ₅ H ₁₀ O

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on 2-methyl-3-butyn-2-ol in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
↑ ^a ^b Toxicological assessment of 2-methylbutyn-3-ol-2 (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.
↑ Entry on 2-methyl-3-butyn-2-ol at ChemBlink , accessed on February 25, 2011.
↑ ^a ^b ^c OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for 3-butyn-2-ol, 2-methyl- , accessed on October 3, 2014.
↑ External identifiers of or database links to 2-methyl-3-butyn-1-ol : CAS number: 584-00-9, EC number: 209-525-1, ECHA InfoCard: 100.008.661 , PubChem : 102442 , ChemSpider : 92518 , Wikidata : Q82958063 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on 2-methyl-3-butyn-2-ol in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[bgchemie-2] Toxicological assessment of 2-methylbutyn-3-ol-2 (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.

[3] Entry on 2-methyl-3-butyn-2-ol at ChemBlink , accessed on February 25, 2011.

[SIDS-4] OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for 3-butyn-2-ol, 2-methyl- , accessed on October 3, 2014.

[5] External identifiers of or database links to 2-methyl-3-butyn-1-ol : CAS number: 584-00-9, EC number: 209-525-1, ECHA InfoCard: 100.008.661 , PubChem : 102442 , ChemSpider : 92518 , Wikidata : Q82958063 .