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% |
IUPAC Name: Buta-1,3-diyne
The MF of Diacetylene (CAS NO.460-12-8) is C4H2.
The MW of Diacetylene (CAS NO.460-12-8) is 50.05868.
Synonyms of Diacetylene (CAS NO.460-12-8): 1,3-Butadiin ; 1,3-Butadiyne ; Biacetylene ; Biethynyl ; Butadiyne
Stability: Stability Highly flammable
Index of Refraction: 1.436
Boiling Point: 10.3 °C
Melting Point: -10 °C
Density: 0.806 g/ml
Appearance: gas
EINECS: 207-303-9
Diacetylene (CAS NO.460-12-8) is used in organic synthesis.This product is an unsaturated aliphatic hydrocarbons, with a simple asphyxiation and weak narcotic effect.
A dangerous explosive. Polymerizes violently above 0°C. Arsenic pentafluoride catalyzes explosive polymerization. Reaction with silver nitrate forms a very explosive friction-sensitive product. When heated to decomposition it emits acrid smoke and fumes.Safety information of Diacetylene (CAS NO.460-12-8):
RIDADR 3161
HazardClass 2.1
Diacetylene has been identified in the atmosphere of Titan and in the protoplanetary nebula CRL 618 by its characteristic vibrational modes. The molecule is most likely to have formed in Titan's atmosphere by a reaction between acetylene and the ethynyl radical C2H, which is produced when acetylene undergoes photolysis. This radical can in turn attack the triple bond in acetylene and react efficiently even at cold temperatures.
Diacetylene, with the formula C4H2, is a highly unsaturated hydrocarbon that contains one single bond and two triple bonds. It is the first in the series of polyynes.
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