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high purity Application:Drug intermediates Materials intermediates and active molecules
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 70 - 75℃; into -78 deg C cooling trap; | 93% |
With potassium hydroxide In tetrahydrofuran; water; dimethyl sulfoxide at 95℃; for 0.25h; | 90% |
With potassium hydroxide Dehydrochlorination; | 50% |
ethynylmagnesium chloride
Butadiyne
Conditions | Yield |
---|---|
With 1,2-dichloro-ethane; manganese(ll) chloride In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; | 67.5% |
Conditions | Yield |
---|---|
Zersetzung durch Ultraschall; |
Conditions | Yield |
---|---|
With calcium hydroxide at 125 - 130℃; | |
With barium dihydroxide at 125 - 130℃; | |
With potassium carbonate at 125 - 130℃; |
Conditions | Yield |
---|---|
bei der Einw. dunkler elektrischer Entladungen; |
Conditions | Yield |
---|---|
at 970 - 1170℃; Pyrolysis; |
methane
Butadiyne
Conditions | Yield |
---|---|
bei der Funkenentladung; |
Conditions | Yield |
---|---|
bei der pyrogenen Spaltung im Lichtbogen; |
Conditions | Yield |
---|---|
With potassium hydroxide |
1,2-dibromo-buta-1,3-diene
Butadiyne
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With potassium permanganate; ammonia |
Conditions | Yield |
---|---|
at 60℃; |
n-butane
A
3-buten-1-yne
B
Butadiyne
C
but-1-yne
D
acetylene
Conditions | Yield |
---|---|
bei der Einwirkung von Hochfrequenz-Entladungen; |
Conditions | Yield |
---|---|
In gas at 426.9 - 1026.9℃; under 76 Torr; Kinetics; |
Conditions | Yield |
---|---|
Irradiation; |
3,4-Didehydropyridine
A
Butadiyne
B
propiolonitrile
C
acetylene
Conditions | Yield |
---|---|
at -260.2℃; for 0.5h; Irradiation; photolysis, λ>210 nm; |
Conditions | Yield |
---|---|
under 0.06 Torr; Mechanism; Product distribution; Irradiation; XeCl-excimerlaser ( 308 nm, 64 mJ, 7.5 ns ); |
Hexafluorobenzene
A
polytetrafluoroethylene
B
Butadiyne
C
Hexafluoroethane
D
Pentafluorobenzene
E
acetylene
Conditions | Yield |
---|---|
With hydrogen Mechanism; Thermodynamic data; Irradiation; ΔH (excit.), various mole fractions of reactants; | A n/a B n/a C n/a D 3 % Chromat. E n/a |
methane
A
Butadiyne
B
ethane
C
ethene
D
1,2-propanediene
E
acetylene
Conditions | Yield |
---|---|
With carbon vapors at -196.1℃; Mechanism; laser carbon evaporation; other temperature; |
ethene
A
Butadiyne
B
naphthalene
C
hexa-1,3,5-triyne
D
octa-1,3,5,7-tetrayne
E
benzene
Conditions | Yield |
---|---|
With oxygen In gas under 30 Torr; Mechanism; flame stabilized diffusion, analysed by MS; |
Conditions | Yield |
---|---|
Rate constant; |
bromoethyne
A
3-buten-1-yne
B
Butadiyne
C
hexa-1,3,5-triyne
D
octa-1,3,5,7-tetrayne
E
acetylene
Conditions | Yield |
---|---|
With sodium at 349.9℃; under 3.8 Torr; Product distribution; Mechanism; Thermodynamic data; also in the presence of ethyne, butadiyne, other temperatures; |
2-methylprop-1-enyl chloride
A
Butadiyne
B
dimethylacetylene
C
1,2-propanediene
D
buta-1,3-diene
Conditions | Yield |
---|---|
under 4 - 5 Torr; Product distribution; Irradiation; various added gases; |
Conditions | Yield |
---|---|
In gas at 426.9 - 1026.9℃; under 76 Torr; Kinetics; |
1,4-dichloro-1-butyne
Butadiyne
Conditions | Yield |
---|---|
With potassium hydroxide In 1,4-dioxane |
toluene
A
Butadiyne
B
phenyl radical
C
benzyl radical
D
acetylene
Conditions | Yield |
---|---|
under 152 - 380 Torr; Product distribution; Kinetics; Thermodynamic data; thermal decomposition at 1550-2200 K by shock tube techniques; products were detected by MS; Ea; |
Butadiyne
Conditions | Yield |
---|---|
In gas at 426.9 - 1026.9℃; under 76 Torr; Kinetics; |
Hexafluorobenzene
acetylene
A
Butadiyne
B
fluoroethyne
C
3,3,3-trifluoroprop-1-yne
D
Pentafluorobenzene
E
2,3,4,5,6-pentafluorophenylacetylene
Conditions | Yield |
---|---|
Mechanism; Irradiation; |
Conditions | Yield |
---|---|
at 19.9℃; under 30 Torr; Rate constant; He; or 5 Torr; | |
Rate constant; | |
at -130.1 - 85.9℃; Kinetics; Irradiation; |
Conditions | Yield |
---|---|
Mechanism; pyrolysis; | |
In solid matrix at -263.2℃; Irradiation; |
Conditions | Yield |
---|---|
In diethylamine at 20℃; for 2.5h; | 100% |
In ammonium hydroxide at 5 - 20℃; for 5.5h; Product distribution; other solvents, other reaction temperature, other time; | 63% |
In methylamine at -25 - 20℃; for 3.5h; Product distribution; other solvents, other reaction time, other temperature; | 52% |
With potassium hydroxide |
Conditions | Yield |
---|---|
In ammonia between -15 and +10°C, density of aq.NH3: 0.92-0.96 g/ml; | 99% |
In ammonia aq. ammonia=NH3; between -15 and +10°C, density of aq.NH3: 0.92-0.96 g/ml; | 99% |
Butadiyne
rac-3-sulfanylpropane-1,2-diol
1-(2,3-dihydroxypropylthio)-1-buten-3-yne
Conditions | Yield |
---|---|
In ammonia at -33℃; | 98% |
Conditions | Yield |
---|---|
With ammonia at -33℃; | 97% |
Butadiyne
trans-(C6F5)(Ph2P(CH2)4O(CH2)2CH=CH2)2PtCl
trans-(C6F5)(Ph2P(CH2)4O(CH2)2CH=CH2)2Pt(CC)2H
Conditions | Yield |
---|---|
With HN(C2H5)2; copper(l) iodide In not given Pt complex treated with butadiyne/HNEt2 in the presence of CuI; | 97% |
With HNEt2; copper(l) iodide In tetrahydrofuran a Schlenk flask was charged with Pt-contg. compd. (0.269 mmol), CuI (0.149 mmol), and HNEt2 with stirring, and cooled to -45°C; then H(CC)2H (15.3 mmol) in THF was added via syringe; after 3 h, the cold bath was removed; after 1 h, solvent was removed by oil pump vac.; the residue was extd. with toluene-ethyl acetate (50:50 v/v); the ext. was chromd. on an alumina column (50:50 hexanes-ethyl acetate); solvent was removed by oil pump vac.; elem. anal.; | 97% |
Butadiyne
trimethylsilanyl-methanethiol
1-trimethylsilylmethylthio-1-buten-3-yne
Conditions | Yield |
---|---|
In ammonia at -33℃; | 96% |
Butadiyne
[platinum(II)dichloride(1,2-bis(diphenylphosphino)ethane)]
cis-[Pt(CCCCH)2(1,2-bis(diphenylphosphino)ethane)]
Conditions | Yield |
---|---|
copper(l) iodide In tetrahydrofuran; diethylamine; N,N-dimethyl-formamide (N2); CuI and soln. of diyne in THF were added sequentially to soln. of Pt complex in DMF/NHEt2; mixt. was stirred for 15 min; solvent removed (vac.); residue stirred with water; washed (water; methanol; Et2O); extd. (CH2Cl2); concd.; filtered through celite into stirredhexane; filtered; washed (cold hexane); dried in air; elem. anal.; | 96% |
With diethylamine; copper(l) iodide In tetrahydrofuran byproducts: (H2NEt2)Cl; | 94% |
Butadiyne
P(C6H5)3NP(C6H5)3(1+)*Au(C4H)2(1-)=P(C6H5)3NP(C6H5)3Au(C4H)2
Conditions | Yield |
---|---|
In tetrahydrofuran; dichloromethane; diethylamine soln. of ligand in THF was added to soln. of Au-complex in NHEt2-CH2Cl2,stirred at room temp. for 1 h under N2; solvent was removed, filtered, extd. with CH2Cl2, cold Et2O was added; elem. anal.; | 96% |
Conditions | Yield |
---|---|
In ammonia at -33℃; for 5h; | 95% |
Conditions | Yield |
---|---|
In ammonia at -33℃; | 95% |
Butadiyne
dichloro{bis(dicyclohexylphosphino)ethane}platinum(II)
1,2-bis(dicyclohexylphosphino)ethane platinum dibutadiyne
Conditions | Yield |
---|---|
copper(l) iodide In diethyl ether; diethylamine bubbling butadiyne into suspn. of Pt-complex (-20°C, 1 h); stirring (room temp., 20 min); | 95% |
Butadiyne
[1,3-bis(diphenylphosphino)propane]dichloroplatinum(II)
cis-[Pt(CCCCH)2(1,3-bis(diphenylphosphino)propane)]
Conditions | Yield |
---|---|
With Et2NH; copper(l) iodide In tetrahydrofuran (Ar); CuI was added to suspn. of Pt complex in THF/Et2NH; mixt. was maintained at 0°C; cold soln. of butadyine in THF was added; mixt. was stirred at 0°C for 2 h; solvent removed (vac.); residue dissolved in CH2Cl2; washed (H2O); org. phase dried (MgSO4); filtered; filtrate passed through alumina; solvent removed; crystd. (CH2Cl2/ether); dried (vac.); elem. anal.; | 95% |
copper(l) iodide In tetrahydrofuran; diethylamine; N,N-dimethyl-formamide (N2); CuI and soln. of diyne in THF were added sequentially to soln. of Pt complex in DMF/NHEt2; mixt. was stirred for 30 min; concd.; H2O added; recrystd. (CH2Cl2/hexane); elem. anal.; | 80% |
Butadiyne
trans-(C6F5)(Ph2P(CH2)8CH=CH2)2PtCl
trans-(C6F5)(Ph2P(CH2)8CH=CH2)2Pt(C2)2H
Conditions | Yield |
---|---|
With HN(C2H5)2; copper(l) iodide In tetrahydrofuran; dichloromethane diyne, HN(C2H5)2, CuI (cat.); | 95% |
Butadiyne
trans-[(C6F5)(Ph2P(CH2)7CH=CH2)2PtCl]
trans-(C6F5)(Ph2P(CH2)7CH=CH2)2Pt(C2)2H
Conditions | Yield |
---|---|
With HN(C2H5)2; copper(l) iodide In tetrahydrofuran; dichloromethane diyne, HN(C2H5)2, CuI (cat.); | 95% |
Butadiyne
1-[(2S)-oxiran-2-yl]-(1S)-octan-1-ol
(6S,7S)-6,7-dihydroxytetradeca-1,3-diyne
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane at -30℃; for 2h; | 94.1% |
Butadiyne
(mercaptomethyl)trimethoxysilane
1-trimethoxysilylmethylthio-1-buten-3-yne
Conditions | Yield |
---|---|
In ammonia at -33℃; | 94% |
Butadiyne
piperidinium piperidyldithiocarbamate
1-buten-3-ynyl pentamethylenedithiocarbamate
Conditions | Yield |
---|---|
In ammonia at -33℃; for 3h; | 94% |
In tetrahydrofuran at 50℃; for 2h; Product distribution; other solvents, other temperatures, other time, other concentrations; | 67% |
Butadiyne
thiophene
Conditions | Yield |
---|---|
With sodium sulfide; potassium hydroxide In dimethyl sulfoxide at 55℃; for 1.25h; diacetylene passed through solution of Na2S and KOH; | 94% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol for 0.25h; Heating; | 93% |
Butadiyne
trans-((C6H5)3P)2Pt(C6H4CH3)(CCCCH)
Conditions | Yield |
---|---|
copper(l) iodide In tetrahydrofuran; diethylamine under N2 using Schlenk techniques; (Ph3P)2PtCl(C6H4Me), HNEt2, CuI cooled to -45°C; HCCCCH in THF added; stirred for 1.5 h; after 1 h solvent evapd.; residue extd. (benzene); extracts filtered.; solvent evapd.; EtOH added; ppt. filtered; dried (vac.); elem. anal.; | 93% |
Butadiyne
((i)Pr2PC2H4P(i)Pr2)Pd(C2H4)
(iPr2PCH2CH2PiPr2)Pd(η(2)-HCCCH)
Conditions | Yield |
---|---|
In pentane Ar-atmosphere; -30°C; crystn. (-78°C), washing (pentane), drying (vac., -30°C); elem. anal.; | 93% |
Butadiyne
2-mercaptoethyl(trimethoxysilane)
1-trimethoxysilylethylthio-1-buten-3-yne
Conditions | Yield |
---|---|
In ammonia at -33℃; | 92% |
Butadiyne
diethylammonium diethyldithiocarbamate
1,4-bis(diethylthiocarbamoylthio)-1,3-butadiene
Conditions | Yield |
---|---|
In methanol at 40℃; for 2h; | 92% |
Butadiyne
(bis(diisopropylphosphino)ethane)Ni(COD)
(iPr2PCH2CH2PiPr2)Ni(η(2)-HCCCH)
Conditions | Yield |
---|---|
In pentane treatment of solns. of Ni-complex and butadiene (molar ratio 1:1, -78°C), warming (to -30°C), pptn. on cooling (-78°C); washing (cold pentane), drying (-30°C, vacuum); elem. anal.; | 92% |
Butadiyne
(C8H12)Ni((C3H7)2PCH2CH2CH2P(C3H7)2)
(HCCCCH)Ni((C3H7)2PCH2CH2CH2P(C3H7)2)
Conditions | Yield |
---|---|
In pentane mixt. of solns. of Ni-complex and butadiyne (molar ratio 1:1, -78°C), warming (to -30°C), pptn.; washing (cold ether), drying (-30°C, vacuum); elem. anal.; | 92% |
Conditions | Yield |
---|---|
In 1,2-dichloro-benzene (Ar); Ru and Sb complexes suspended in o-dichlorobenzene, excess HC4H added, stirred for 45 min, amine added, reacted for 2 d; filtered, evapd. (vac.), stirred with ether and hexanes, dried (vac.); elem. anal.; | 92% |
Butadiyne
(triethylsilyl)methanethiol
1-triethylsilylmethylthio-1-buten-3-yne
Conditions | Yield |
---|---|
In ammonia at -33℃; | 91% |
Conditions | Yield |
---|---|
Stage #1: Butadiyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: Dipropyl disulfide In tetrahydrofuran; hexane at 25℃; for 3h; | 91% |
N-Methylpyrrole
silver tetrafluoroborate
Butadiyne
chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II)
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether (N2); addn. of the Ru complex to AgBF4 in THF, filtration into a soln. of buta-1,3-diyne in Et2O and N-methylpyrrole in THF, reacting 15 min; evapn., extn. (CH2Cl2), chromy. (alumina; Et2O/CH2Cl2); elem. anal.; | 91% |
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