Product Name

  • Name

    1-Buten-3-yne

  • EINECS
  • CAS No. 689-97-4
  • Article Data187
  • CAS DataBase
  • Density 0.709g/cm3
  • Solubility
  • Melting Point 203 °C(Solv: water (7732-18-5))
  • Formula C4H4
  • Boiling Point 5.1°C at 760 mmHg
  • Molecular Weight 52.0758
  • Flash Point
  • Transport Information
  • Appearance
  • Safety Low toxicity by inhalation. Forms explosive peroxides with air or oxygen. Very exothermic decomposition when heated. Reacts explosively when heated with 1,3-butadiene or oxygen. Reacts with silver nitrate to form the explosive silver buten-3-ynide. When heated to decomposition it emits acrid smoke and irritating fumes. See also ACETYLENE COMPOUNDS and ALKYNES.
  • Risk Codes R20/21/22
  • Molecular Structure Molecular Structure of 689-97-4 (1-Buten-3-yne)
  • Hazard Symbols Xn
  • Synonyms 1-Butenyne;1-Butyn-3-ene; 3-Buten-1-yne; 3-Butyn-1-ene; Butenyne; Ethene, ethynyl-;Monovinylacetylene; Vinylacetylene; Vinylethyne
  • PSA 0.00000
  • LogP 0.80560

Synthetic route

trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

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

3-buten-1-yne

Conditions
ConditionsYield
With potassium hydroxide; 2,3-dimethyl-2,3-butane diol; Aliquat 336 In Petroleum ether for 1.5h; Heating;70%
With potassium hydroxide; calcium oxide In dimethyl sulfoxide; xylene at 120℃;
With potassium hydroxide; 2-Butoxyethanol In ethylene glycol at 170℃; for 1h; Yield given;
With potassium hydroxide; 2,3-dimethyl-2,3-butane diol; Aliquat 336 In various solvent(s) at 135℃; for 1.5h;
1,4-dichloro-2-butene
764-41-0

1,4-dichloro-2-butene

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

3-buten-1-yne

Conditions
ConditionsYield
With potassium hydroxide; cetyldimethylbenzylammonium chloride In dimethyl sulfoxide at 90 - 100℃; for 1h;69%
With ammonia; sodium amide
In ethylene glycol at 50℃; Inert atmosphere;
1-cyclobutyl-2-(triphenylphosphoranylidene)ethan-1-one
6048-18-6

1-cyclobutyl-2-(triphenylphosphoranylidene)ethan-1-one

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

3-buten-1-yne

Conditions
ConditionsYield
at 800 - 850℃; under 0.01 Torr;67%
at 850℃; for 3h;67%
benzoic 2-methyl-3-furoic anhydride
1335114-45-8

benzoic 2-methyl-3-furoic anhydride

A

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

3-buten-1-yne

B

4-methylene-2-cyclobuten-1-one
42827-31-6

4-methylene-2-cyclobuten-1-one

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
at 550℃; under 0.01 Torr; Pyrolysis; neat (no solvent);A 55%
B 17%
C n/a
benzoic 3-methyl-2-furoic anhydride
1335114-46-9

benzoic 3-methyl-2-furoic anhydride

A

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

3-buten-1-yne

B

4-methylene-2-cyclobuten-1-one
42827-31-6

4-methylene-2-cyclobuten-1-one

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
at 550℃; under 0.01 Torr; Pyrolysis; neat (no solvent);A 50%
B 15%
C n/a
Z-piperylene
1574-41-0

Z-piperylene

A

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

3-buten-1-yne

B

1-methylbuta-1,3-diene
2004-70-8

1-methylbuta-1,3-diene

C

4-methyl-2-pentene
4461-48-7

4-methyl-2-pentene

D

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

E

buta-1,3-diene
106-99-0

buta-1,3-diene

F

acetylene
74-86-2

acetylene

Conditions
ConditionsYield
at 20℃; under 0.4 Torr; Product distribution; Irradiation; variation of pressure and additives;A 0.2%
B 0.3%
C 0.13%
D 0.25%
E 0.09%
F 0.22%
2-methyl-but-2-ene
513-35-9

2-methyl-but-2-ene

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

3-buten-1-yne

Conditions
ConditionsYield
bei der Einw. dunkler elektrischer Entladungen;
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

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

3-buten-1-yne

Conditions
ConditionsYield
With potassium hydroxide at 105 - 110℃;
methane
34557-54-5

methane

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

3-buten-1-yne

(2R,3S)-1,2,3,4-Tetrabromo-butane
2657-67-2

(2R,3S)-1,2,3,4-Tetrabromo-butane

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

3-buten-1-yne

Conditions
ConditionsYield
With potassium hydroxide at 120℃;
2,3-dichlorobut-1-ene
7013-11-8

2,3-dichlorobut-1-ene

A

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

3-buten-1-yne

B

chloroprene
126-99-8

chloroprene

Conditions
ConditionsYield
at 530℃; im Quarzrohr;
3,4-dichlorobut-1-ene
310447-99-5, 310448-01-2

3,4-dichlorobut-1-ene

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

3-buten-1-yne

Conditions
ConditionsYield
With ammonia; sodium amide
4-bromo-3-ethoxy-but-1-yne
13487-52-0

4-bromo-3-ethoxy-but-1-yne

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

3-buten-1-yne

Conditions
ConditionsYield
With zinc; butan-1-ol at 110 - 120℃;
1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

buta-2,3-dienyl-trimethyl-ammonium; chloride

buta-2,3-dienyl-trimethyl-ammonium; chloride

A

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

3-buten-1-yne

B

trimethylamine
75-50-3

trimethylamine

3-butyn-1-yl p-toluenesulfonate
23418-85-1

3-butyn-1-yl p-toluenesulfonate

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

3-buten-1-yne

Conditions
ConditionsYield
With potassium hydroxide
1,2-bis-(4-methoxy-phenyl)-hex-5-en-3-yn-2-ol

1,2-bis-(4-methoxy-phenyl)-hex-5-en-3-yn-2-ol

A

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

3-buten-1-yne

B

1,4-di(4-methoxyphenyl)ethanone
120-44-5

1,4-di(4-methoxyphenyl)ethanone

hexa-N-methyl-N,N'-but-2-enediyl-di-ammonium; dihydroxide
116054-63-8

hexa-N-methyl-N,N'-but-2-enediyl-di-ammonium; dihydroxide

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

3-buten-1-yne

Conditions
ConditionsYield
at 100 - 120℃; under 13 Torr;
buta-1,3-diene
106-99-0

buta-1,3-diene

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

3-buten-1-yne

Conditions
ConditionsYield
durch Crackung;
but-3-yn-2-ol
2028-63-9

but-3-yn-2-ol

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

3-buten-1-yne

Conditions
ConditionsYield
With basic aluminium sulfate at 240 - 260℃;
acetylene
74-86-2

acetylene

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

3-buten-1-yne

Conditions
ConditionsYield
With hydrogenchloride; ammonium chloride; copper(l) chloride at 50 - 75℃; unter Zusatz von Kupferpulver; Ausfuehrung der Reaktion unter Zusatz von Dispersionsmitteln wie Stearoyloxyaethansulfonsaeure;
With CuCl containing solid catalysts
With copper; ammonium chloride; copper(l) chloride Reagens4:Salzsaeure;
acetylene
74-86-2

acetylene

A

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

3-buten-1-yne

B

hexa-1,5-dien-3-yne
821-08-9

hexa-1,5-dien-3-yne

Conditions
ConditionsYield
With water; copper(l) chloride at 25 - 65℃; Gegenwart von Kupfer;
With water; ammonium chloride at 25 - 65℃; Gegenwart von Kupfer;
With hydrogenchloride; water at 25 - 65℃; Gegenwart von Kupfer;
acetylene
74-86-2

acetylene

A

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

3-buten-1-yne

B

benzene
71-43-2

benzene

Conditions
ConditionsYield
at 750℃; bei schnellem Leiten durch ein erhitztes Quarzrohr;
at 661.85℃; under 27 Torr; Kinetics; Further Variations:; Temperatures; Pressures;
(3-chloro-but-2-enyl)-dimethyl-amine
14352-90-0

(3-chloro-but-2-enyl)-dimethyl-amine

1,3-dichloro-2-butene
926-57-8

1,3-dichloro-2-butene

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

3-buten-1-yne

Conditions
ConditionsYield
With water beim anschliessenden Erwaermen mit wss. Natronlauge;
1,3-dichloro-2-butene
926-57-8

1,3-dichloro-2-butene

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

3-buten-1-yne

Conditions
ConditionsYield
With potassium hydroxide; 2-Butoxyethanol; ethylene glycol at 165 - 170℃;
With potassium hydroxide In ethylene glycol tert-buty ether; ethylene glycol at -78℃; for 2h; Inert atmosphere;
n-butane
106-97-8

n-butane

A

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

3-buten-1-yne

B

Butadiyne
460-12-8

Butadiyne

C

but-1-yne
107-00-6

but-1-yne

D

acetylene
74-86-2

acetylene

Conditions
ConditionsYield
bei der Einwirkung von Hochfrequenz-Entladungen;
thiophene
188290-36-0

thiophene

A

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

3-buten-1-yne

B

2,3-butadienthial
100945-80-0

2,3-butadienthial

C

cyclopropene-3-thiocarbaldehyde
86596-77-2

cyclopropene-3-thiocarbaldehyde

D

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
at -263.2℃; Irradiation; Further byproducts given;
thiophene
188290-36-0

thiophene

A

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

3-buten-1-yne

B

cyclopropene-3-thiocarbaldehyde
86596-77-2

cyclopropene-3-thiocarbaldehyde

C

Dewar thiophene
72110-26-0

Dewar thiophene

D

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
at -263.2℃; Irradiation; Further byproducts given;
Isopropylbenzene
98-82-8

Isopropylbenzene

A

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

3-buten-1-yne

B

styrene
292638-84-7

styrene

C

ethylbenzene
100-41-4

ethylbenzene

D

buta-1,3-diene
106-99-0

buta-1,3-diene

E

acetylene
74-86-2

acetylene

F

isopropenylbenzene
98-83-9

isopropenylbenzene

Conditions
ConditionsYield
With oxygen at 726.9℃; Mechanism; gas phase oxidation in flow reactor at various temperatures;
but-1-yne
107-00-6

but-1-yne

A

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

3-buten-1-yne

B

methane
34557-54-5

methane

C

ethane
74-84-0

ethane

D

ethene
74-85-1

ethene

E

1,2-propanediene
463-49-0

1,2-propanediene

F

acetylene
74-86-2

acetylene

Conditions
ConditionsYield
With bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoyloxymethyl]bis(hydroxymethyl)methane under 10 Torr; Quantum yield; Irradiation; different pressures, different additives, different wavelengths;
dimethylacetylene
503-17-3

dimethylacetylene

A

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

3-buten-1-yne

B

(Z)-2-Butene
590-18-1

(Z)-2-Butene

C

methane
34557-54-5

methane

D

trans-2-Butene
624-64-6

trans-2-Butene

E

prop-1-yne
74-99-7

prop-1-yne

F

acetylene
74-86-2

acetylene

Conditions
ConditionsYield
With bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoyloxymethyl]bis(hydroxymethyl)methane under 1 Torr; Quantum yield; Irradiation; different pressures, different additives, different wavelengths;
3-buten-1-yne
689-97-4

3-buten-1-yne

triphenylstannane
892-20-6

triphenylstannane

Triphenyl-butadien-(1,2)-yl-(1)-zinn
4104-92-1, 4104-91-0

Triphenyl-butadien-(1,2)-yl-(1)-zinn

Conditions
ConditionsYield
In tetrahydrofuran 70°C, 3 h, molar ratio = 5:1, in presence of azobisisobutyronitrile;;100%
In tetrahydrofuran 70°C, 3 h, molar ratio = 5:1, in presence of azobisisobutyronitrile;;100%
With azo-bis-isobutyric acid dinitrile In tetrahydrofuran reaction for 3 h at 70°C in presence of azoisobutyric acid dinitrile;;
3-buten-1-yne
689-97-4

3-buten-1-yne

2,5-dihydro-thiophene
1708-32-3

2,5-dihydro-thiophene

Conditions
ConditionsYield
With sodium hydrogensulfide; water In dimethyl sulfoxide at 90℃; for 4h;97.8%
3-buten-1-yne
689-97-4

3-buten-1-yne

((i)Pr2PC2H4P(i)Pr2)Pd(C2H4)
138234-21-6

((i)Pr2PC2H4P(i)Pr2)Pd(C2H4)

Pd*(((CH3)2CH)2PCH2)2*HCCCHCH2=Pd((((CH3)2CH)2PCH2)2)(HCCCHCH2)
194996-69-5, 194996-76-4

Pd*(((CH3)2CH)2PCH2)2*HCCCHCH2=Pd((((CH3)2CH)2PCH2)2)(HCCCHCH2)

Conditions
ConditionsYield
In pentane Ar-atmosphere, -30°C; crystn. (-78°C, 1 d), washing (pentane), drying (vac., -30°C); elem. anal.;96%
3-buten-1-yne
689-97-4

3-buten-1-yne

2,2,5-trimethyl-4-hexenal
1000-30-2

2,2,5-trimethyl-4-hexenal

6,6,9-trimethyldeca-1,8-dien-3-yn-5-ol

6,6,9-trimethyldeca-1,8-dien-3-yn-5-ol

Conditions
ConditionsYield
Stage #1: 3-buten-1-yne With n-butyllithium In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 2,2,5-trimethyl-4-hexenal In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at -78℃; for 3h; Inert atmosphere;
96%
3-buten-1-yne
689-97-4

3-buten-1-yne

2,2,3,3-tetramethylpent-4-enal
993-67-9

2,2,3,3-tetramethylpent-4-enal

6,6,7,7-tetramethylnona-1,8-dien-3-yn-5-ol

6,6,7,7-tetramethylnona-1,8-dien-3-yn-5-ol

Conditions
ConditionsYield
Stage #1: 3-buten-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: 2,2,3,3-tetramethylpent-4-enal In tetrahydrofuran; hexane at -78℃; for 3h; Inert atmosphere;
94%
3-buten-1-yne
689-97-4

3-buten-1-yne

6-Methyl-hept-5-en-2-on
110-93-0

6-Methyl-hept-5-en-2-on

5,9-dimethyldeca-1,8-dien-3-yn-5-ol
116851-03-7

5,9-dimethyldeca-1,8-dien-3-yn-5-ol

Conditions
ConditionsYield
Stage #1: 3-buten-1-yne With n-butyllithium In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78℃; Inert atmosphere;
Stage #2: 6-Methyl-hept-5-en-2-on In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78 - 20℃; for 5h; Inert atmosphere;
92%
3-buten-1-yne
689-97-4

3-buten-1-yne

5-cyclopentylidenepentan-2-one
97764-12-0

5-cyclopentylidenepentan-2-one

1-cyclopentylidene-4-methyloct-7-en-5-yn-4-ol

1-cyclopentylidene-4-methyloct-7-en-5-yn-4-ol

Conditions
ConditionsYield
Stage #1: 3-buten-1-yne With n-butyllithium In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78℃; Inert atmosphere;
Stage #2: 5-cyclopentylidenepentan-2-one In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78 - 20℃; for 5h; Inert atmosphere;
92%
3-buten-1-yne
689-97-4

3-buten-1-yne

formaldehyd
50-00-0

formaldehyd

4-hydroxy-4-phenylpiperidin
40807-61-2

4-hydroxy-4-phenylpiperidin

1-(pentyn-2'-en-4'-yl)-4-phenylpiperidin-4-ol
94769-52-5

1-(pentyn-2'-en-4'-yl)-4-phenylpiperidin-4-ol

Conditions
ConditionsYield
With copper(I) chloride In 1,4-dioxane at 110 - 115℃; for 14.5h;91.8%
3-buten-1-yne
689-97-4

3-buten-1-yne

(but-3-en-1-yne)Co2(CO)6

(but-3-en-1-yne)Co2(CO)6

Conditions
ConditionsYield
In diethyl ether byproducts: CO; under Ar; Co2(CO)8 added to vinylacetylene in ether, stirred for 40 min; filtration through silica gel, evapn., residue dissolved in hexane, filtration, evapn.;91%
3-buten-1-yne
689-97-4

3-buten-1-yne

(E)-5-methylhept-5-en-2-one
25524-99-6

(E)-5-methylhept-5-en-2-one

(E)-5,8-dimethyldeca-1,8-dien-3-yn-5-ol

(E)-5,8-dimethyldeca-1,8-dien-3-yn-5-ol

Conditions
ConditionsYield
Stage #1: 3-buten-1-yne With n-butyllithium In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78℃; Inert atmosphere;
Stage #2: (E)-5-methylhept-5-en-2-one In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78 - 20℃; for 5h; Inert atmosphere;
89%
3-buten-1-yne
689-97-4

3-buten-1-yne

1-(3-methylbut-2-en-1-yl)cyclopentane-1-carbaldehyde
2228-92-4

1-(3-methylbut-2-en-1-yl)cyclopentane-1-carbaldehyde

1-(1-(3-methylbut-2-en-1-yl)cyclopentyl)pent-4-en-2-yn-1-ol

1-(1-(3-methylbut-2-en-1-yl)cyclopentyl)pent-4-en-2-yn-1-ol

Conditions
ConditionsYield
Stage #1: 3-buten-1-yne With n-butyllithium In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78℃; Inert atmosphere;
Stage #2: 1-(3-methylbut-2-en-1-yl)cyclopentane-1-carbaldehyde In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78 - 20℃; for 5h; Inert atmosphere;
89%
3-buten-1-yne
689-97-4

3-buten-1-yne

4-(benzo[b]furan-2-yl)butan-2-one

4-(benzo[b]furan-2-yl)butan-2-one

1-(benzofuran-2-yl)-3-methylhept-6-en-4-yn-3-ol

1-(benzofuran-2-yl)-3-methylhept-6-en-4-yn-3-ol

Conditions
ConditionsYield
Stage #1: 3-buten-1-yne With n-butyllithium In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78℃; Inert atmosphere;
Stage #2: 4-(benzo[b]furan-2-yl)butan-2-one In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78 - 20℃; for 5h; Inert atmosphere;
88%
3-buten-1-yne
689-97-4

3-buten-1-yne

diphenylphosphane
829-85-6

diphenylphosphane

1,4-bis(diphenylphosphino)-2-butene
73892-35-0

1,4-bis(diphenylphosphino)-2-butene

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide for 1h; Ambient temperature;87.7%
3-buten-1-yne
689-97-4

3-buten-1-yne

2-isopropenyl-5-methyl-4-hexenal
58191-81-4

2-isopropenyl-5-methyl-4-hexenal

6-isopropyl-9-methyldeca-1,8-dien-3-yn-5-ol

6-isopropyl-9-methyldeca-1,8-dien-3-yn-5-ol

Conditions
ConditionsYield
Stage #1: 3-buten-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: 2-isopropenyl-5-methyl-4-hexenal In tetrahydrofuran; hexane at -78℃; for 3h; Inert atmosphere;
87%
3-buten-1-yne
689-97-4

3-buten-1-yne

(E)-1-phenylhept-4-en-1-one
56305-41-0

(E)-1-phenylhept-4-en-1-one

(E)-5-phenylundeca-1,8-dien-3-yn-5-ol

(E)-5-phenylundeca-1,8-dien-3-yn-5-ol

Conditions
ConditionsYield
Stage #1: 3-buten-1-yne With n-butyllithium In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: (E)-1-phenylhept-4-en-1-one In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78 - 20℃; for 5h; Inert atmosphere;
87%
3-buten-1-yne
689-97-4

3-buten-1-yne

cyclohexanone
108-94-1

cyclohexanone

1-vinylethynyl-1-cyclohexanol
2696-22-2

1-vinylethynyl-1-cyclohexanol

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide for 2h; Ambient temperature;85%
With potassium hydroxide; diethyl ether
With potassium hydroxide; xylene
With diethyl ether; sodium amide
(i) EtMgBr, (ii) /BRN= 385735/; Multistep reaction;
3-buten-1-yne
689-97-4

3-buten-1-yne

tributyltin methoxide
1067-52-3

tributyltin methoxide

but-3-en-1-yn-1-yltributylstannane
994-80-9

but-3-en-1-yn-1-yltributylstannane

Conditions
ConditionsYield
85%
85%
3-buten-1-yne
689-97-4

3-buten-1-yne

triethylmethoxystannane
1067-21-6

triethylmethoxystannane

1-triethylstannylbut-3-ene-1-yne
994-98-9

1-triethylstannylbut-3-ene-1-yne

Conditions
ConditionsYield
room temp., 3-4 h;;85%
room temp., 3-4 h;;85%
3-buten-1-yne
689-97-4

3-buten-1-yne

5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

(E)-3-(1H-indol-5-yl)acrylonitrile

(E)-3-(1H-indol-5-yl)acrylonitrile

Conditions
ConditionsYield
With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; sodium tetrachloropalladate; sodium carbonate In water; acetonitrile at 80℃; for 1h; Heck Reaction; Inert atmosphere; Microwave irradiation;85%
3-buten-1-yne
689-97-4

3-buten-1-yne

1-(3-methylbut-2-en-1-yl)cyclohexane-1-carbaldehyde

1-(3-methylbut-2-en-1-yl)cyclohexane-1-carbaldehyde

1-(1-(3-methylbut-2-en-1-yl)cyclohexyl)pent-4-en-2-yn-1-ol

1-(1-(3-methylbut-2-en-1-yl)cyclohexyl)pent-4-en-2-yn-1-ol

Conditions
ConditionsYield
Stage #1: 3-buten-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: 1-(3-methylbut-2-en-1-yl)cyclohexane-1-carbaldehyde In tetrahydrofuran; hexane at -78℃; for 3h; Inert atmosphere;
84%
3-buten-1-yne
689-97-4

3-buten-1-yne

3-vinyl-1,5-diallyl-1-bora-2-cyclohexene
55951-37-6

3-vinyl-1,5-diallyl-1-bora-2-cyclohexene

Conditions
ConditionsYield
In neat (no solvent) (Ar), mixed, cooled to 30-50°C, heated at 50-60°C for 1,5h; distd., elem. anal., IR, NMR;83.5%
3-buten-1-yne
689-97-4

3-buten-1-yne

9-iodo-m-carborane
17157-02-7

9-iodo-m-carborane

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

C2H2B10H9(CH2CHCC)
98420-23-6

C2H2B10H9(CH2CHCC)

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; diethyl ether addn. of EtMgBr in ether to a soln. of acetylenic derivate in absolute dioxane (N2), heating for 1 h at 40°C, cooling, addn. of carborane and Pd-catalyst in dioxane, heating for 30 h at 60°C (stirring), monitoring of react. by GLC; pouring into a ca. 18% soln. of HCl, extn. by ether, washing with H2O, drying (MgSO4), distn. of solvents in vac., column chromy. of residue (silica gel), benzene-petroleum ether (bp 40-70°C) as eluent; elem.anal.;82%
3-buten-1-yne
689-97-4

3-buten-1-yne

2-ethyl-5-methylhex-4-enal
18370-33-7

2-ethyl-5-methylhex-4-enal

6-ethyl-9-methyldeca-1,8-dien-3-yn-5-ol

6-ethyl-9-methyldeca-1,8-dien-3-yn-5-ol

Conditions
ConditionsYield
Stage #1: 3-buten-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: 2-ethyl-5-methylhex-4-enal In tetrahydrofuran; hexane at -78℃; for 3h; Inert atmosphere;
82%
3-buten-1-yne
689-97-4

3-buten-1-yne

hexaethyldistannoxane
1112-63-6

hexaethyldistannoxane

1-triethylstannylbut-3-ene-1-yne
994-98-9

1-triethylstannylbut-3-ene-1-yne

Conditions
ConditionsYield
room temp., 3-5 h;;81.6%
room temp., 3-5 h;;81.6%
In diethyl ether byproducts: (C2H5)3SnCCC6H5; room temp., 8 h, in presence of NaCCC6H5;;39%
In diethyl ether byproducts: (C2H5)3SnCCC6H5; room temp., 8 h, in presence of NaCCC6H5;;39%
3-buten-1-yne
689-97-4

3-buten-1-yne

1-methoxy-5-allyl-3-vinyl-1-bora-2-cyclohexene
55951-42-3

1-methoxy-5-allyl-3-vinyl-1-bora-2-cyclohexene

Conditions
ConditionsYield
With methanol In neat (no solvent) byproducts: C3H6; (Ar), mixed at 50-60°C, heated at 55°C for 1 h, treated with CH3OH; distd., elem. anal.;81%
3-buten-1-yne
689-97-4

3-buten-1-yne

(Z)-10-Iodo-1-(2-tetrahydropyranyloxy)-9-decene
85416-29-1

(Z)-10-Iodo-1-(2-tetrahydropyranyloxy)-9-decene

2-(tetradeca-9,13-dien-11-yn-1-yloxy)tetrahydro-2H-pyran
1218999-61-1

2-(tetradeca-9,13-dien-11-yn-1-yloxy)tetrahydro-2H-pyran

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In pyrrolidine at 0 - 20℃; for 3h; Sonogashira coupling; Inert atmosphere;81%
3-buten-1-yne
689-97-4

3-buten-1-yne

(Z)-1-phenylhept-4-en-1-one

(Z)-1-phenylhept-4-en-1-one

(Z)-5-phenylundeca-1,8-dien-3-yn-5-ol

(Z)-5-phenylundeca-1,8-dien-3-yn-5-ol

Conditions
ConditionsYield
Stage #1: 3-buten-1-yne With n-butyllithium In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: (Z)-1-phenylhept-4-en-1-one In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78 - 20℃; for 5h; Inert atmosphere;
81%
3-buten-1-yne
689-97-4

3-buten-1-yne

2,10-dimethyl-2,9-undecadien-6-one
2520-57-2

2,10-dimethyl-2,9-undecadien-6-one

6-(but-3-en-1-yn-1-yl)-2,10-dimethylundeca-2,9-dien-6-ol

6-(but-3-en-1-yn-1-yl)-2,10-dimethylundeca-2,9-dien-6-ol

Conditions
ConditionsYield
Stage #1: 3-buten-1-yne With n-butyllithium In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78℃; Inert atmosphere;
Stage #2: 2,10-dimethyl-2,9-undecadien-6-one In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; hexane at -78 - 20℃; for 5h; Inert atmosphere;
81%
3-buten-1-yne
689-97-4

3-buten-1-yne

cyclododecanone
830-13-7

cyclododecanone

1-(3-buten-1-ynyl)-1-cyclododecanol
75279-83-3

1-(3-buten-1-ynyl)-1-cyclododecanol

Conditions
ConditionsYield
With potassium hydroxide In diethyl ether at 20℃; for 6h;80%
3-buten-1-yne
689-97-4

3-buten-1-yne

tetracarbonyldicyclopentadienyldimolybdenum

tetracarbonyldicyclopentadienyldimolybdenum

(Mo(C5H5)(CO)2)2(HCCCHCH2)
137966-85-9

(Mo(C5H5)(CO)2)2(HCCCHCH2)

Conditions
ConditionsYield
In toluene addn. of cold soln. of ligand to soln. of Mo-complex at -40°C; stirring for 18h at room temp. (N2); evapn. (vac.); extgn. complex (hexane); removing hexane; elem. anal.;80%

BUTEN-3-YNE Chemical Properties

Details of  BUTEN-3-YNE (689-97-4).
Molecular Formula: C4H4
Molecular Weight: 52.08
Properties: Gas with acetylene-like odor.  Flash p: <-5°C, lel: 2%, uel: 100% d: 0.68 @ 1.7 atm, vap d: 1.8, bp: 2–3°C.
Water Solubility: 1790mg/L
Boiling Point: 5.1°C
Molecular Structure:

BUTEN-3-YNE Toxicity Data With Reference

BUTEN-3-YNE (689-97-4) has the toxicity.
1.   mouse    LC50     inhalation    97200mg/m3/2H (97200mg/m3)    "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 119, 1982.

2.   

ihl-mus LC50:97,200 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,1982,119. 

BUTEN-3-YNE Consensus Reports

Reported in EPA TSCA Inventory.

BUTEN-3-YNE Safety Profile

Low toxicity by inhalation. Forms explosive peroxides with air or oxygen. Very exothermic decomposition when heated. Reacts explosively when heated with 1,3-BUTADIENE or oxygen. Reacts with SILVER nitrate to form the explosive SILVER buten-3-ynide. When heated to decomposition it emits acrid smoke and irritating fumes. See also ACETYLENE COMPOUNDS and ALKYNES.

BUTEN-3-YNE Specification

Storage Features OF BUTEN-3-YNE (689-97-4).
Treasury ventilated low-temperature drying; closed storage; with oxidants, acids separate; easy storage a long time to prevent the peroxide generated.
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