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689-97-4

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689-97-4 Usage

General Description

A colorless gas or liquid. Derived by the dimerization of acetylene. Used in the synthesis of neoprene and for other organic syntheses.

Air & Water Reactions

Highly flammable. Oxidizes in air to form unstable peroxides that may explode spontaneously.

Reactivity Profile

1-BUTEN-3-YNE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions. Forms an explosive salt with silver nitrate. Thermally unstable, under pressure, in combination with 1,3-butadiene [Loss Prev., 1971, 5, 67].

Check Digit Verification of cas no

The CAS Registry Mumber 689-97-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,8 and 9 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 689-97:
(5*6)+(4*8)+(3*9)+(2*9)+(1*7)=114
114 % 10 = 4
So 689-97-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H4/c1-3-4-2/h1,4H,2H2

689-97-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name butenyne

1.2 Other means of identification

Product number -
Other names 1-Butenyne

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:689-97-4 SDS

689-97-4Synthetic 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%

689-97-4Relevant articles and documents

Fraser et al.

, p. 1456,1457 (1975)

The i.r., Raman and microwave spectra of 1-butene-3-yne (vinylacetylene) and 1-butene-3-yne-4d

Torneng, E.,Nielsen, C. J.,Klaeboe, P.,Hopf, H.,Priebe, H.

, p. 975 - 988 (1980)

The i.r. spectra of 1-butene-3-yne and 1-butene-3-yne-4d in the vapour phase and as crystalline solids at 90 K were recorded in the region 5000-100 cm-1.Raman spectra, including semiquantitative polarization data, of the neat liquid and of the solid were obtained at 90 K.Microwave spectra of the compounds were recorded in the region 8-40 GHz at ambient temperature.Rotational transitions of the vibrational ground state and of the two lowest vibrational excited states ν13(a') and ν18(a'') were measured.The fundamental frequencies of both compounds were assigned in excellent agreement with the results of normal coordinate calculations.Rotational fine structure was observed for several bands and interpreted as the Q-sub-branches of the perpendicular bands (in the symmetrical top approximation).For six bands the Q-sub-branches were assigned to the proper K-values.The Coriolis coupling constant ξa13,18 was derived from the i.r. and from the microwave spectra.

Reaction Mechanism of the Homogeneous Thermal Decomposition of Acetylene

Tanzawa, T.,Gardiner, W. C.

, p. 236 - 239 (1980)

A modeling study is reported in which experiments on the rate of and product distribution from C2H2 pyrolysis from 625 to 3400 K are described with a single mechanism.The essential primary mechanism at low temperatures proves to consist of an H-atom, vinyl radical chain H + C2H2 -> C2H3, C2H3 + C2H2 -> C4H4+ H producing vinyl acetylene at early times.At high temperatures this is replaced by the ethynyl chain H + C2H2 -> C2H + H2, C2H + C2H2 + H producing diacetylene.By considering a variety of studies simulteneusly it was possible to assign rate constant expressions to the key elementary reactions.While all of the basic observations on the primary decomposition are accounted for by final mechanism, uncertainties still remain in the rates of secondary reactions and in the magnitudes of the fallof corrections required for the unimolecular reactions involved.

A novel risedronic acid-modified Nieuwland catalyst for acetylene dimerization

Zhang, Qixia,Li, Congcong,Luo, Juan,Xie, Jianwei,Zhang, Jinli,Dai, Bin

, (2020)

Nieuwland catalyst (NC) was modified with different phosphonic acids (Px) and evaluated for their acetylene dimerization activity in monovinyl acetylene (MVA) production. Nearly 49.2% of acetylene conversion and 80.3% of MVA selectivity were obtained in 5 mol% risedronic acid (P2)-modified NC under an acetylene-gas space velocity of 105 h?1 at 80 °C, which was 17.8% higher than the yield of the control NC. The characterization results of NC and P2–NC indicated that the addition of P2 effectively enhanced the stability of the Cu ions and inhibited oxidation of the active component Cu+, improving their catalytic activity and long-term stability.

Zelikoff,Aschenbrand

, p. 1034 (1956)

Hedaya et al.

, p. 6880 (1969)

-

Hennion et al.

, p. 5160 (1954)

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