2-METHYL-5-HEXEN-3-YN-2-OL supplier

Name
DIMETHYL(VINYL)ETHYNYLCARBINOL
EINECS
CAS No. 690-94-8
Article Data26
CAS DataBase
Density 0.917g/cm³
Solubility
Melting Point
Formula C7H10 O
Boiling Point 159.9°C at 760 mmHg
Molecular Weight 110.156
Flash Point 59.9°C
Transport Information
Appearance
Safety Poison by inhalation. Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4-Penten-2-yn-1-ol,1,1-dimethyl- (7CI); 1,1-Dimethylbut-4-en-2-yn-1-ol;2-Methyl-3-hexyn-5-en-2-ol; 2-Methyl-5-hexen-3-yn-2-ol; 5-Methyl-1-hexen-3-yn-5-ol;Dimethyl(vinylethynyl)carbinol; Nazarov carbinol; Nazarov's carbinol
PSA 20.23000
LogP 0.94670

Synthetic route

: 593-60-2
Vinyl bromide

: 115-19-5
2-methyl-but-3-yn-2-ol

: 690-94-8
dimethyl(vinylethynyl)carbinol

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethylamine at 0 - 20℃; for 12h;	91%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium hydroxide In tetrahydrofuran; diethylamine at 0 - 20℃; for 12h;	91%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 23℃; for 2.5h;	84%
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethylamine at 23℃; for 2.5h;	84%
With copper(l) iodide; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃; Sonogashira coupling;	80%

: 2768-02-7
(vinyl)trimethoxylsilane

: 115-19-5
2-methyl-but-3-yn-2-ol

: 690-94-8
dimethyl(vinylethynyl)carbinol

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; copper diacetate In 1,4-dioxane at 30℃;	47%

: 593-60-2
Vinyl bromide

: 115-19-5
2-methyl-but-3-yn-2-ol

A: 5929-72-6
2,7-dimethyl-octa-3,5-diyne-2,7-diol

B: 690-94-8
dimethyl(vinylethynyl)carbinol

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 20℃; Inert atmosphere;	A 20% B 42%

...Expand

: 689-97-4
3-buten-1-yne

: 67-64-1
acetone

: 690-94-8
dimethyl(vinylethynyl)carbinol

Conditions

Conditions	Yield
With diethyl ether unter starkem Kuehlen mit KOH;
With potassium hydroxide; sodium hydroxide
With diethyl ether unter starkem Kuehlen mit NaNH2;
With potassium hydroxide In ammonia at 30 - 40℃;

: 764-41-0
1,4-dichloro-2-butene

: 67-64-1
acetone

: 690-94-8
dimethyl(vinylethynyl)carbinol

Conditions

Conditions	Yield
With ammonia; sodium amide

: 310447-99-5, 310448-01-2
3,4-dichlorobut-1-ene

: 67-64-1
acetone

: 690-94-8
dimethyl(vinylethynyl)carbinol

Conditions

Conditions	Yield
With ammonia; sodium amide

: 14763-72-5
3-buten-1-ynylmagnesium bromide

: 67-64-1
acetone

: 690-94-8
dimethyl(vinylethynyl)carbinol

Conditions

Conditions	Yield
With diethyl ether
With diethyl ether
With diethyl ether

: 689-97-4
3-buten-1-yne

: 7473-98-5
2-hydroxy-2-methylpropiophenone

: 690-94-8
dimethyl(vinylethynyl)carbinol

Conditions

Conditions	Yield
With ammonia; sodium; ferric nitrate

: 819-44-3
5-chloro-5-methyl-1-hexen-3-yne

: 7732-18-5
water

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 20728-33-0
5-bromo-5-methyl-hex-1-en-3-yne

KOH: KOH

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 819-44-3
5-chloro-5-methyl-1-hexen-3-yne

: 60-29-7
diethyl ether

silver carbonate: silver carbonate

A: 16806-78-3
1,1,3,3-Tetramethyl-4-vinyl-phthalan

B: 690-94-8
dimethyl(vinylethynyl)carbinol

C: 820-54-2
2-methyl-hexa-1,5-dien-3-yne

Conditions

Conditions	Yield
at 0℃;

...Expand

: tetrabutoxytitanium

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 96301-49-4
(C4H9O)3Ti(OC(CH3)2CCCHCH2)

Conditions

Conditions	Yield
In benzene byproducts: BuOH; react. of Ti(OBu)4 with the alcohol under azeotropic distn. of BuOH (20-60°C, 1-3 h, inert atmosphere); evapn. (< 0.2 mm), vac. distn.; elem. anal.;	95%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 1021867-45-7
1-chloro-5-methylhex-3-yne-2,5-diol

Conditions

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide at 54.84℃; for 7.5h; Product distribution; Kinetics; Further Variations:; Temperatures; reagent concentrations, reaction time;	94.3%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 125510-58-9
1-bromo-5-methylhex-3-yne-2,5-diol

Conditions

Conditions	Yield
With hydrogen bromide; dihydrogen peroxide at 54.84℃; for 7.5h; Product distribution; Further Variations:; Temperatures; reagent concentrations, reaction time;	92.8%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 74-88-4
methyl iodide

: 814-57-3
5-methoxy-5-methylhex-1-en-3-yne

Conditions

Conditions	Yield
Stage #1: dimethyl(vinylethynyl)carbinol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃;	90%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 100-07-2
4-methoxy-benzoyl chloride

: 866487-22-1
4-methoxybenzoic acid 1,1-dimethylpent-4-en-2-ynyl ester

Conditions

Conditions	Yield
With pyridine at 90℃; for 14h;	89%
In pyridine at 90℃; for 14h;	89%

: C5Cl4H2C2H3COCl

: 690-94-8
dimethyl(vinylethynyl)carbinol

: C15H14Cl4O2

Conditions

Conditions	Yield
With triethylamine In benzene at 80℃; for 5h;	88%

: C5Cl4H2C2H3COClO2C2H4

: 690-94-8
dimethyl(vinylethynyl)carbinol

: C17H18Cl4O4

Conditions

Conditions	Yield
With triethylamine In benzene at 80℃; for 5h;	88%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 820-54-2
2-methyl-hexa-1,5-dien-3-yne

Conditions

Conditions	Yield
With ion-exchange resin KU-23 at 30℃; under 100 Torr; for 2h; Dehydration;	87%
With sulfuric acid at 10 - 65℃; for 4.5h;	73%
With sulfuric acid at 70℃;
With sulfuric acid
With benzenesulfonyl chloride In pyridine

: 690-94-8
dimethyl(vinylethynyl)carbinol

: (1R,2R,4S)-1,4,5,6,7,7-Hexachloro-bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride

: C15H12Cl6O2

Conditions

Conditions	Yield
With triethylamine In benzene at 80℃; for 5h;	87%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1048027-89-9
tert-butyldimethyl((2-methylhex-5-en-3-yn-2-yl)oxy)silane

Conditions

Conditions	Yield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 65℃; for 16h; Inert atmosphere;	86%

: 2435-53-2
o-tetrachloroquinone

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 66481-31-0
1,4,5,6-Tetrachloro-7-(3-hydroxy-3-methyl-but-1-ynyl)-bicyclo[2.2.2]oct-5-ene-2,3-dione

Conditions

Conditions	Yield
With hydroquinone In toluene at 108℃; for 18h;	85.3%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 2043-61-0
cyclohexanecarbaldehyde

: 1-cyclohexyl-2,5-dimethylhex-3-yne-1,5-diol

Conditions

Conditions	Yield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); isopropyl alcohol; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 90℃; for 48h; Inert atmosphere; Sealed tube; diastereoselective reaction;	85%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 69514-47-2
(E)-2-methyl-3,5-hexadien-2-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride	82%
With lithium aluminium tetrahydride; diethyl ether
With lithium aluminium tetrahydride; water 1.) ether, 20 deg C; Multistep reaction;

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 98333-78-9
5,6-dibromo-2-methylhex-3-yn-2-ol

Conditions

Conditions	Yield
With hydrogen bromide; dihydrogen peroxide at 39.84℃; for 4h;	82%
With chloroform; bromine

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 1950-78-3
p-toluenesulfonyl iodide

A: Toluene-4-sulfonic acid 1,1-dimethyl-pent-4-en-2-ynyl ester

B: 88966-64-7
5-Iodo-2-methyl-6-(toluene-4-sulfonyl)-hex-3-yn-2-ol

Conditions

Conditions	Yield
In acetonitrile at 110℃; for 96h; Yields of byproduct given. Title compound not separated from byproducts;	A n/a B 80%

...Expand

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 1021867-52-6
5,6-dichloro-2-methylhex-3-yn-2-ol

Conditions

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide at 39.84℃; for 4h;	78%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 78-84-2
isobutyraldehyde

: 2,5,7-trimethyloct-3-yne-2,6-diol

Conditions

Conditions	Yield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); isopropyl alcohol; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 100℃; for 48h; Reagent/catalyst; Time; Inert atmosphere; Sealed tube; diastereoselective reaction;	73%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 2043-61-0
cyclohexanecarbaldehyde

: C14H22(2)H2O2

Conditions

Conditions	Yield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); d8-isopropanol; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 90℃; for 48h; Inert atmosphere; Sealed tube;	72%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 67-66-3
chloroform

: 4-(2,2-Dichloro-cyclopropyl)-2-methyl-but-3-yn-2-ol

Conditions

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water at 28 - 30℃; for 4h;	69%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 2-hydroxy-5,5-dimethyl-4-vinyl-1,2-oxaphosphol-3-ene 2-oxide

Conditions

Conditions	Yield
With hydrogenchloride; air; hypophosphorous acid	68%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 1079-66-9
chloro-diphenylphosphine

: 1384384-68-2
diphenyl 3-methylhexa-1,3,4-trien-3-yl phosphine oxide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at -70 - 20℃; for 5h;	65%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 89206-87-1
(5-methyl-1,3,4-hexatrien-3-yl)phosphonous acid

Conditions

Conditions	Yield
With hypophosphorous acid	62%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 13154-24-0
triisopropylsilyl chloride

: 1379656-67-3
triisopropyl((2-methylhex-5-en-3-yn-2-yl)oxy)silane

Conditions

Conditions	Yield
Stage #1: dimethyl(vinylethynyl)carbinol With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: triisopropylsilyl chloride In tetrahydrofuran at 0 - 20℃;	60%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 76-37-9
2,2,3,3-tetrafluoropropanol

: dimethylvinylethynylcarbinol 1,1,3-trihydroperfluoropropyl ether

Conditions

Conditions	Yield
With sulfuric acid; hydroquinone at 20℃; for 20h;	58%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 676-85-7
methylsulphinyl chloride

: 753007-62-4
5-methyl-3-(methylsulfonyl)hexa-1,3,4-triene

Conditions

Conditions	Yield
Stage #1: dimethyl(vinylethynyl)carbinol; methylsulphinyl chloride With triethylamine In diethyl ether at -40 - 20℃; Stage #2: In toluene for 5h; Heating;	55%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 630-19-3
pivalaldehyde

: 2,5,7,7-tetramethyloct-3-yne-2,6-diol

Conditions

Conditions	Yield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); isopropyl alcohol; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 90℃; for 48h; Inert atmosphere; Sealed tube; diastereoselective reaction;	54%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 1194-16-7
2,2-dimethyltetrahydropyran-4-one

Conditions

Conditions	Yield
With sulfuric acid; water; mercury(II) sulfate at 85℃; for 5h;	53%
With sulfuric acid; mercury(II) sulfate

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 355-80-6
2,2,3,3,4,4,5,5-octafluoropentan-1-ol

: dimethylvinylethynylcarbinol 1,1,5-trihydroperfluoropentyl ether

Conditions

Conditions	Yield
With sulfuric acid; hydroquinone at 20℃; for 20h;	53%

: 690-94-8
dimethyl(vinylethynyl)carbinol

: 613244-84-1, 71657-06-2
2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine

: 3,4-dimethyl-2-(3-methyl-1-vinyl-1,2-butadienyl)-5-phenyl-1,3,2-oxazaphospholidine 2-oxide

Conditions

Conditions	Yield
With triethylamine In benzene for 5h;	50.6%

2-METHYL-5-HEXEN-3-YN-2-OL Chemical Properties

IUPAC Name: 2-methylhex-5-en-3-yn-2-ol
The MF of 2-METHYL-5-HEXEN-3-YN-2-OL(690-94-8): C₇H₁₀O
The MW of 2-METHYL-5-HEXEN-3-YN-2-OL(690-94-8): 110.1537
Density: 0.917 g/cm³
Flash Point: 59.9 °C
Boiling Point: 159.9 °C at 760 mmHg
Index of Refraction: 1.473
Synonyms: DIMETHYL(VINYL)ETHYNYLCARBINOL;2-METHYL-5-HEXEN-3-YN-2-OL;2-Methylhexa-5-en-3-in-2-ol
The Structure of 2-METHYL-5-HEXEN-3-YN-2-OL(690-94-8):

2-METHYL-5-HEXEN-3-YN-2-OL Toxicity Data With Reference

1.	orl-rat LD50:600 mg/kg	85GMAT Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,60.
2.	orl-mus LD50:590 mg/kg	85GMAT Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,60.
3.	ihl-mus LCLo:30 mg/m3/2H	85GMAT Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,60.
4.	orl-rbt LD50:800 mg/kg	85GMAT Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,60.
5.	orl-gpg LD50:600 mg/kg	85GMAT Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,60.

2-METHYL-5-HEXEN-3-YN-2-OL Safety Profile

Poison by inhalation. Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.

Product Name

DIMETHYL(VINYL)ETHYNYLCARBINOL

Synthetic route

2-METHYL-5-HEXEN-3-YN-2-OL Chemical Properties

2-METHYL-5-HEXEN-3-YN-2-OL Toxicity Data With Reference

2-METHYL-5-HEXEN-3-YN-2-OL Safety Profile

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