Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
at 800 - 850℃; under 0.01 Torr; | 67% |
at 850℃; for 3h; | 67% |
benzoic 2-methyl-3-furoic anhydride
A
3-buten-1-yne
B
4-methylene-2-cyclobuten-1-one
C
benzoic acid
Conditions | Yield |
---|---|
at 550℃; under 0.01 Torr; Pyrolysis; neat (no solvent); | A 55% B 17% C n/a |
benzoic 3-methyl-2-furoic anhydride
A
3-buten-1-yne
B
4-methylene-2-cyclobuten-1-one
C
benzoic acid
Conditions | Yield |
---|---|
at 550℃; under 0.01 Torr; Pyrolysis; neat (no solvent); | A 50% B 15% C n/a |
Z-piperylene
A
3-buten-1-yne
B
1-methylbuta-1,3-diene
C
4-methyl-2-pentene
D
cyclopenta-1,3-diene
E
buta-1,3-diene
F
acetylene
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
bei der Einw. dunkler elektrischer Entladungen; |
Conditions | Yield |
---|---|
With potassium hydroxide at 105 - 110℃; |
methane
3-buten-1-yne
Conditions | Yield |
---|---|
With potassium hydroxide at 120℃; |
Conditions | Yield |
---|---|
at 530℃; im Quarzrohr; |
3,4-dichlorobut-1-ene
3-buten-1-yne
Conditions | Yield |
---|---|
With ammonia; sodium amide |
4-bromo-3-ethoxy-but-1-yne
3-buten-1-yne
Conditions | Yield |
---|---|
With zinc; butan-1-ol at 110 - 120℃; |
3-butyn-1-yl p-toluenesulfonate
3-buten-1-yne
Conditions | Yield |
---|---|
With potassium hydroxide |
hexa-N-methyl-N,N'-but-2-enediyl-di-ammonium; dihydroxide
3-buten-1-yne
Conditions | Yield |
---|---|
at 100 - 120℃; under 13 Torr; |
Conditions | Yield |
---|---|
durch Crackung; |
Conditions | Yield |
---|---|
With basic aluminium sulfate at 240 - 260℃; |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
1,3-dichloro-2-butene
3-buten-1-yne
Conditions | Yield |
---|---|
With water beim anschliessenden Erwaermen mit wss. Natronlauge; |
Conditions | Yield |
---|---|
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
A
3-buten-1-yne
B
Butadiyne
C
but-1-yne
D
acetylene
Conditions | Yield |
---|---|
bei der Einwirkung von Hochfrequenz-Entladungen; |
thiophene
A
3-buten-1-yne
B
2,3-butadienthial
C
cyclopropene-3-thiocarbaldehyde
D
prop-1-yne
Conditions | Yield |
---|---|
at -263.2℃; Irradiation; Further byproducts given; |
thiophene
A
3-buten-1-yne
B
cyclopropene-3-thiocarbaldehyde
C
Dewar thiophene
D
prop-1-yne
Conditions | Yield |
---|---|
at -263.2℃; Irradiation; Further byproducts given; |
Isopropylbenzene
A
3-buten-1-yne
B
styrene
C
ethylbenzene
D
buta-1,3-diene
E
acetylene
F
isopropenylbenzene
Conditions | Yield |
---|---|
With oxygen at 726.9℃; Mechanism; gas phase oxidation in flow reactor at various temperatures; |
but-1-yne
A
3-buten-1-yne
B
methane
C
ethane
D
ethene
E
1,2-propanediene
F
acetylene
Conditions | Yield |
---|---|
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
A
3-buten-1-yne
B
(Z)-2-Butene
C
methane
D
trans-2-Butene
E
prop-1-yne
F
acetylene
Conditions | Yield |
---|---|
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
triphenylstannane
Triphenyl-butadien-(1,2)-yl-(1)-zinn
Conditions | Yield |
---|---|
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;; |
Conditions | Yield |
---|---|
With sodium hydrogensulfide; water In dimethyl sulfoxide at 90℃; for 4h; | 97.8% |
3-buten-1-yne
((i)Pr2PC2H4P(i)Pr2)Pd(C2H4)
Pd*(((CH3)2CH)2PCH2)2*HCCCHCH2=Pd((((CH3)2CH)2PCH2)2)(HCCCHCH2)
Conditions | Yield |
---|---|
In pentane Ar-atmosphere, -30°C; crystn. (-78°C, 1 d), washing (pentane), drying (vac., -30°C); elem. anal.; | 96% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
6-Methyl-hept-5-en-2-on
5,9-dimethyldeca-1,8-dien-3-yn-5-ol
Conditions | Yield |
---|---|
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
5-cyclopentylidenepentan-2-one
Conditions | Yield |
---|---|
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
formaldehyd
4-hydroxy-4-phenylpiperidin
1-(pentyn-2'-en-4'-yl)-4-phenylpiperidin-4-ol
Conditions | Yield |
---|---|
With copper(I) chloride In 1,4-dioxane at 110 - 115℃; for 14.5h; | 91.8% |
3-buten-1-yne
dicobalt octacarbonyl
Conditions | Yield |
---|---|
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
(E)-5-methylhept-5-en-2-one
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide for 1h; Ambient temperature; | 87.7% |
3-buten-1-yne
2-isopropenyl-5-methyl-4-hexenal
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
85% | |
85% |
Conditions | Yield |
---|---|
room temp., 3-4 h;; | 85% |
room temp., 3-4 h;; | 85% |
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Triallylborane
3-vinyl-1,5-diallyl-1-bora-2-cyclohexene
Conditions | Yield |
---|---|
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
9-iodo-m-carborane
ethylmagnesium bromide
C2H2B10H9(CH2CHCC)
Conditions | Yield |
---|---|
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
2-ethyl-5-methylhex-4-enal
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
Triallylborane
1-methoxy-5-allyl-3-vinyl-1-bora-2-cyclohexene
Conditions | Yield |
---|---|
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
(Z)-10-Iodo-1-(2-tetrahydropyranyloxy)-9-decene
2-(tetradeca-9,13-dien-11-yn-1-yloxy)tetrahydro-2H-pyran
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In pyrrolidine at 0 - 20℃; for 3h; Sonogashira coupling; Inert atmosphere; | 81% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With potassium hydroxide In diethyl ether at 20℃; for 6h; | 80% |
3-buten-1-yne
(Mo(C5H5)(CO)2)2(HCCCHCH2)
Conditions | Yield |
---|---|
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% |
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 (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. |
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