Conditions | Yield |
---|---|
With phosphorus pentoxide; silica gel at 140℃; for 1h; | 97% |
Conditions | Yield |
---|---|
With phosphorus pentaoxide | 85% |
With phosphorus pentoxide at 180℃; | 70% |
With phosphorus pentoxide at 120℃; | 61% |
Conditions | Yield |
---|---|
37% |
Conditions | Yield |
---|---|
With phosphorus pentoxide at 100 - 370℃; self-propagating stationary heat wave mode; | A n/a B 33% |
2-amino-4-phenyl-4H-pyran-3,5-dicarbonitrile
A
propiolonitrile
B
(E)-2-cyano-3-phenylacrylamide
Conditions | Yield |
---|---|
In dichloromethane for 1h; Irradiation; | A 22% B 17% C 23% |
α-picoline
A
methane
B
hydrogen cyanide
C
propiolonitrile
D
1,3-cyclopentadiene-1-carbonitrile
E
acetylene
Conditions | Yield |
---|---|
In gas at 1350 - 1500℃; under 10640 - 12160 Torr; Mechanism; Product distribution; single-pulse shock tube experiments; |
Butadiyne
cyanoacetylene cation radical
A
propiolonitrile
B
diacetylene radical cation
C
Hexa-1,3,5-triyne
Conditions | Yield |
---|---|
In various solvent(s) at 23.9℃; under 0.3 Torr; Product distribution; Rate constant; in a Selected-Ion Flow Tube (SIFT) apparatus; |
3,4-Didehydropyridine
A
Butadiyne
B
propiolonitrile
C
acetylene
Conditions | Yield |
---|---|
at -260.2℃; for 0.5h; Irradiation; photolysis, λ>210 nm; |
C3(3)HN
propiolonitrile
Conditions | Yield |
---|---|
With amine buffer; water at 25℃; Rate constant; μ = 0.10 M; |
Conditions | Yield |
---|---|
In gas Product distribution; Irradiation; |
Conditions | Yield |
---|---|
at 876.9 - 1176.9℃; Product distribution; Kinetics; |
cyanoacetylene cation radical
acetylene
A
hydrogen cyanide
B
propiolonitrile
C
diacetylene radical cation
D
acetylene cation radical
Conditions | Yield |
---|---|
In various solvent(s) at 23.9℃; under 0.3 - 0.4 Torr; Product distribution; Rate constant; in a Selected-Ion Flow Tube (SIFT) apparatus; |
acetylene
A
3-buten-1-yne
B
Butadiyne
C
propiolonitrile
D
benzene
Conditions | Yield |
---|---|
With hydrogen cyanide In gas Irradiation; C2H2:HCN = 1 : 5; 37 percent of the light is absorbed by HCN; Further byproducts given; |
pyridine
A
3-buten-1-yne
B
Butadiyne
C
hydrogen cyanide
D
propiolonitrile
E
acrylonitrile
F
acetylene
Conditions | Yield |
---|---|
With sulphur hexafluoride Product distribution; Mechanism; laser pyrolysis (IR LPHP method, 1100-1150 K); 2-, 3-, 4-bromopyridine investigated (at ca. 1000 K); |
PYRIMIDINE
A
hydrogen cyanide
B
propiolonitrile
C
acrylonitrile
D
acetylene
Conditions | Yield |
---|---|
With sulphur hexafluoride Product distribution; Mechanism; laser pyrolysis (IR LPHP method, 1100-1150 K); 5-bromopyrimidine and pyrazine investigated; |
indole
A
Butadiyne
B
propiolonitrile
C
phenylacetonitrile
D
benzonitrile
E
acetonitrile
F
acetylene
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol at 776.9 - 1361.9℃; Product distribution; Rate constant; Mechanism; Arrhenius parameters; |
acrylonitrile
A
hydrogen cyanide
B
propiolonitrile
C
vinylidene biradical
D
vinyl radical
F
acetylene
Conditions | Yield |
---|---|
In gas Mechanism; Irradiation; |
quinoline
A
Butadiyne
B
propiolonitrile
C
benzonitrile
D
phenylacetylene
E
acetylene
F
benzene
Conditions | Yield |
---|---|
In gaseous matrix at 1051.85℃; Product distribution; other temperatures; |
isoquinoline
A
Butadiyne
B
propiolonitrile
C
benzonitrile
D
phenylacetylene
E
acetylene
F
benzene
Conditions | Yield |
---|---|
In gaseous matrix at 1061.85℃; Product distribution; other temperatures; |
α-picoline
A
methane
B
hydrogen cyanide
C
propiolonitrile
D
acrylonitrile
E
acetonitrile
F
acetylene
Conditions | Yield |
---|---|
In gas at 1350 - 1500℃; under 10640 - 12160 Torr; Kinetics; Product distribution; single-pulse shock tube experiments; |
Conditions | Yield |
---|---|
at 1471.9 - 1938.9℃; under 107 - 140 Torr; Product distribution; various temperature and pressure, laser-schlieren densitometry and time-of-flight MS techniques, effect of H2 addition; |
Conditions | Yield |
---|---|
at 1405.9 - 2027.9℃; under 136 - 214 Torr; Product distribution; various temperature and pressure, laser-schlieren densitometry and time-of-flight MS techniques, effect of H2 addition; |
Conditions | Yield |
---|---|
at 1415.9 - 2088.9℃; under 131 - 198 Torr; Product distribution; Thermodynamic data; various temperature and pressure, laser-schlieren densitometry and time-of-flight MS techniques, effect of H2 addition; |
Conditions | Yield |
---|---|
at 976.9 - 1326.9℃; under 9880 - 11400 Torr; Product distribution; Mechanism; |
pyridine
A
3-buten-1-yne
B
Butadiyne
C
methane
D
hydrogen cyanide
E
propiolonitrile
F
acetylene
Conditions | Yield |
---|---|
at 926.9 - 1526.9℃; under 7 - 11 Torr; Kinetics; Mechanism; Product distribution; shock tube pyrolysis in Argon; |
Conditions | Yield |
---|---|
With phosphorus pentoxide at 20 - 370℃; Product distribution; self-propagating stationary heat wave mode, other initial temp., var. initial concentration; | A 0.003 g B n/a |
ethene
cyanoacetylene cation radical
A
propiolonitrile
C
vinyl radical
D
ethylene cation radical
Conditions | Yield |
---|---|
In various solvent(s) at 23.9℃; under 0.3 - 0.4 Torr; Product distribution; Rate constant; in a Selected-Ion Flow Tube (SIFT) apparatus; |
carbon oxide sulfide
cyanoacetylene cation radical
A
propiolonitrile
B
carbon monoxide
C
COS(1+)
Conditions | Yield |
---|---|
In various solvent(s) at 23.9℃; under 0.3 - 0.4 Torr; Product distribution; Rate constant; in a Selected-Ion Flow Tube (SIFT) apparatus; |
Propargylamine
A
propiolonitrile
B
trans-prop-2-ynylideneamine
C
acrylonitrile
D
acetonitrile
Conditions | Yield |
---|---|
With N-chloro-succinimide; potassium tert-butylate 2) 60 deg C, 1 h; Multistep reaction; |
Conditions | Yield |
---|---|
In diethyl ether at 0℃; | 100% |
Conditions | Yield |
---|---|
In diethyl ether at 0℃; | 100% |
Conditions | Yield |
---|---|
20°C, 1 h;; | 100% |
20°C, 1 h;; | 100% |
propiolonitrile
Conditions | Yield |
---|---|
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 60℃; for 2h; Inert atmosphere; Sealed tube; | 99% |
propiolonitrile
(Z)-3-Iodopropenenitrile
Conditions | Yield |
---|---|
With acetic acid; lithium iodide at 70℃; for 24h; | 98% |
Conditions | Yield |
---|---|
With ionic liquid [bmim]BF4 stabilized magnetic cobalt nanoparticles In neat (no solvent) at 20℃; for 0.333333h; Michael Addition; | 98% |
Conditions | Yield |
---|---|
With ionic liquid [bmim]BF4 stabilized magnetic cobalt nanoparticles In neat (no solvent) at 20℃; for 0.416667h; Michael Addition; | 98% |
propiolonitrile
Conditions | Yield |
---|---|
In toluene at 20℃; for 168h; | 97% |
propiolonitrile
Conditions | Yield |
---|---|
With dithionitronium hexafluoroarsenate In liquid sulphur dioxide | 96% |
With dithionitronium hexafluoroarsenate Yield given; |
propiolonitrile
Conditions | Yield |
---|---|
In toluene (N2); added cyanacetylene to a soln. of Ta-complex; evapd. after 1 h; elem. anal.; | 96% |
Conditions | Yield |
---|---|
With ionic liquid [bmim]BF4 stabilized magnetic cobalt nanoparticles In neat (no solvent) at 20℃; for 0.5h; Michael Addition; | 96% |
propiolonitrile
N-methylaniline
3-(methylphenylamino)-2-propenenitrile
Conditions | Yield |
---|---|
With ionic liquid [bmim]BF4 stabilized magnetic cobalt nanoparticles In neat (no solvent) at 20℃; for 0.466667h; Michael Addition; | 96% |
Conditions | Yield |
---|---|
With ionic liquid [bmim]BF4 stabilized magnetic cobalt nanoparticles In neat (no solvent) at 20℃; for 0.416667h; Michael Addition; | 95% |
Conditions | Yield |
---|---|
With ionic liquid [bmim]BF4 stabilized magnetic cobalt nanoparticles In neat (no solvent) at 20℃; for 0.466667h; Michael Addition; | 95% |
Conditions | Yield |
---|---|
In water at 20℃; for 20h; | 94% |
propiolonitrile
5-methyl-4-azahomoadamant-4-ene N-oxide
methyl 5-cyano-3-oxa-2-azatetracyclo<7.3.1.17,11.02,6>tetradec-4-ene
Conditions | Yield |
---|---|
In toluene at 20 - 25℃; for 0.5h; | 93% |
In toluene for 0.5h; Ambient temperature; | 93% |
propiolonitrile
cyclopenta-1,3-diene
bicyclo[2.2.1]hepta-2,5-diene-2-carbonitrile
Conditions | Yield |
---|---|
In dichloromethane for 12h; Ambient temperature; | 90% |
propiolonitrile
2-(9,10-Dihydro-10-oxo-9-anthracenylio)-3,5-dioxo-4-phenyl-1,2,4-triazolidin-1-id
Conditions | Yield |
---|---|
In benzene at 20℃; Cycloaddition; | 90% |
Conditions | Yield |
---|---|
25°C, 1 h;; | 90% |
25°C, 1 h;; | 90% |
propiolonitrile
tri-n-butyl-tin hydride
α-Tri-n-butyl-stannyl-acrylnitril
Conditions | Yield |
---|---|
0°C;; | 90% |
0°C;; | 90% |
In methanol 65°C, 15 h;; | 38% |
In methanol 65°C, 15 h;; | 38% |
Conditions | Yield |
---|---|
With C38H47N4P In toluene at -78℃; for 3h; Michael Addition; enantioselective reaction; | 88% |
nido-decaborane
propiolonitrile
bis(triphenylphosphine)iminium chloride
Conditions | Yield |
---|---|
With KH In tetrahydrofuran to the borane and KH THF is vacuum destilled at -196°C; warming to room temp.; filtn. (N2); cyanoacetylene (THF) is added at 0°C; stirred for 14 h at 0°C; PPNCl is added; stirred at room temp. for 1 h; THF is vacuum evaporated; CH2Cl2 is added; filtered; diethyl ether is added; filtered again; heptane is addded slowly with stirring; slow evapn. of solvent; elem. anal.; | 87.1% |
propiolonitrile
cyclohexa-1,3-diene
2-cyanobicyclo<2.2.2>octa-2,5-diene
Conditions | Yield |
---|---|
In dichloromethane at 50℃; under 7050560 Torr; for 24h; | 87% |
Conditions | Yield |
---|---|
In diethyl ether | 87% |
propiolonitrile
Conditions | Yield |
---|---|
In water at 60℃; for 24h; | 87% |
propiolonitrile
4-iso-butyl-2-(4-methoxyphenyl)-5-oxo-4,5-dihydrooxazole
Conditions | Yield |
---|---|
With C38H47N4P In toluene at -78℃; for 22h; Michael Addition; enantioselective reaction; | 87% |
propiolonitrile
4-benzyl-2-(4-methoxyphenyl)-5-oxo-4,5-dihydrooxazole
Conditions | Yield |
---|---|
With C38H47N4P In toluene at -78℃; for 4h; Michael Addition; enantioselective reaction; | 87% |
propiolonitrile
(Z)-3-Bromopropenenitrile
Conditions | Yield |
---|---|
With acetic acid; lithium bromide at 70℃; for 24h; | 86% |
The Cyanoacetylene, with the CAS registry number 1070-71-9, is also known as Propynenitrile. It belongs to the product category of Pharmaceutical Intermediates. This chemical's molecular formula is C3HN and molecular weight is 51.05. What's more, its IUPAC name is prop-2-ynenitrile. It is sensitive to air and light. It is used as pharmaceutical intermediates. It is the simplest cyanopolyyne. It has been detected by spectroscopic methods in interstellar clouds and in the atmosphere of Saturn's moon Titan. It is one of the molecules that was produced in the Miller-Urey experiment.
Physical properties of Cyanoacetylene are: (1)ACD/LogP: 0.66; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.66; (4)ACD/BCF (pH 5.5): 1.87; (5)ACD/KOC (pH 5.5): 54.5; (6)#H bond acceptors: 1; (7)#H bond donors: 0; (8)#Freely Rotating Bonds: 0; (9)Polar Surface Area: 23.79 Å2; (10)Index of Refraction: 1.41; (11)Molar Refractivity: 13.68 cm3; (12)Molar Volume: 55.2 cm3; (13)Surface Tension: 39.9 dyne/cm; (14)Density: 0.924 g/cm3; (15)Enthalpy of Vaporization: 28.67 kJ/mol; (16)Boiling Point: 42.5 °C at 760 mmHg; (17)Vapour Pressure: 391 mmHg at 25°C.
Preparation: this chemical can be prepared by propynoic acid amide at the temperature of 180 °C. This reaction will need reagent P2O5. The yield is about 70%.
Uses of Cyanoacetylene: it can be used to produce 2-cyanonorbornadiene at the ambient temperature. It will need solvent CH2Cl2 with the reaction time of 12 hours. The yield is about 90%.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C#CC#N
(2)InChI: InChI=1S/C3HN/c1-2-3-4/h1H
(3)InChIKey: LNDJVIYUJOJFSO-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LDLo | subcutaneous | 48mg/kg (48mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 152, Pg. 1707, 1911. |
rabbit | LDLo | intravenous | 15mg/kg (15mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 152, Pg. 1707, 1911. |
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