Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating; | A 98% B 95% |
2-[(Z)-Hydroxyimino]-3-naphthalen-1-yl-propionic acid
naphthalen-1-ylacetonitrile
Conditions | Yield |
---|---|
With 1,1'-carbonyldiimidazole In benzene 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h; | 97% |
Conditions | Yield |
---|---|
With trichloromethyl chloroformate In various solvent(s) 0-5 deg C then heated to 60 deg C, 5 min; | 96% |
With (dimethoxy)methylsilane; copper diacetate; 1,2-bis-(dicyclohexylphosphino)ethane In tetrahydrofuran at 20℃; for 12h; Sealed tube; | 96% |
With phosgene In tetrahydrofuran; toluene at 25℃; for 4h; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
In acetonitrile at 60℃; for 3h; 18-crown-6 polyether; | 96% |
β-(1-naphthyl)nitroethylene
naphthalen-1-ylacetonitrile
Conditions | Yield |
---|---|
With titanium tetrachloride; tetraethylammonium tosylate In N,N-dimethyl-formamide electroreduction - 4 mA/cm2; | 95% |
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(η3-allyl-μ-chloropalladium(II)) In 1,3,5-trimethyl-benzene at 20 - 140℃; for 5.16667h; Inert atmosphere; Sealed tube; chemoselective reaction; | 95% |
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate In 1,4-dioxane; water at 60℃; for 12h; Inert atmosphere; Sealed tube; | 93% |
2-[(Z)-Hydroxyimino]-3-naphthalen-1-yl-propionic acid
naphthalen-1-ylacetonitrile
Conditions | Yield |
---|---|
With 1,1'-oxalyldiimidazole In benzene 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h; | 90% |
naphthalen-1-ylacetonitrile
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 100℃; for 24h; | 90% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 100℃; for 24h; | 90% |
Methylsulfanyl-naphthalen-1-yl-acetonitrile
naphthalen-1-ylacetonitrile
Conditions | Yield |
---|---|
With acetic acid; zinc at 100℃; for 1h; | 89% |
1-naphthylacetaldehyde
naphthalen-1-ylacetonitrile
Conditions | Yield |
---|---|
With HCl·DMPU; hydroxylamine hydrochloride In acetonitrile at 60℃; | 88% |
With ammonia; iodine at 0℃; for 1h; | 74% |
zinc(II) cyanide
1-naphthylmethyl 2,2-dimethylpropanoate
naphthalen-1-ylacetonitrile
Conditions | Yield |
---|---|
Stage #1: zinc(II) cyanide; 1-naphthylmethyl 2,2-dimethylpropanoate With potassium phosphate; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride In N,N-dimethyl-formamide for 0.0166667h; Inert atmosphere; Sealed tube; Stage #2: With diethylzinc In hexane; N,N-dimethyl-formamide at 110℃; for 16h; Inert atmosphere; Sealed tube; | 77% |
Conditions | Yield |
---|---|
Stage #1: bromocyane; 1-naphthalene methanol With triphenylphosphine In dichloromethane at 20℃; Inert atmosphere; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; Cooling with ice; Inert atmosphere; | 69% |
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(η3-allyl-μ-chloropalladium(II)) In 1,3,5-trimethyl-benzene at 20 - 140℃; for 10.1667h; Inert atmosphere; Sealed tube; chemoselective reaction; | 68% |
sodium cyanide
2-(bromomethyl)naphthalene
naphthalen-1-ylacetonitrile
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide In acetonitrile Inert atmosphere; Reflux; | 67% |
1-Naphthylboronic acid
2-aminoacetonitrile hydrochloride
naphthalen-1-ylacetonitrile
Conditions | Yield |
---|---|
With sodium nitrite In water; toluene at 50℃; for 24h; Schlenk technique; | 65% |
[(p-methylphenyl)sulfonylmethyl]isonitrile
1-naphthaldehyde
naphthalen-1-ylacetonitrile
Conditions | Yield |
---|---|
With potassium tert-butylate In 1,2-dimethoxyethane at -55℃; for 1h; | 62% |
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran at 20 - 80℃; for 1.5h; Inert atmosphere; Schlenk technique; Sealed tube; | 53% |
Conditions | Yield |
---|---|
Stage #1: ethyl 2-cyanoacetate; 1-Chloronaphthalene With N-(2-methylnaphthalen-1-yl)-N’-(pyridin-2-ylmethyl)oxalamide; copper(I) bromide; sodium t-butanolate In isopropyl alcohol at 105℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With water In isopropyl alcohol at 105℃; for 12h; Schlenk technique; Inert atmosphere; Cooling; | 51% |
1-Iodonaphthalene
ethyl 2-cyanoacetate
A
naphthalen-1-ylacetonitrile
B
ethyl 2-cyano-2-(naphthalen-1-yl)acetate
Conditions | Yield |
---|---|
With potassium carbonate; copper(l) iodide In dimethyl sulfoxide at 120℃; for 9h; | A 27% B 47% |
With potassium carbonate; copper(l) iodide In dimethyl sulfoxide at 120℃; for 9h; | A 27% B 27% |
methyl thiocyanate
1-naphthaldehyde
A
naphthalen-1-ylacetonitrile
B
[1]thionaphthoic acid S-methyl ester
Conditions | Yield |
---|---|
With tributylphosphine 1.) 1h, 0 deg C, 2.) 2h, ambient temperature; | A 32% B 15% |
With tributylphosphine 1.) 0 deg C, 1 h, 2.) room temperature, 2 h; | A 32% B 15% |
(+)-(1R)-1-exo-Cyano-1a,7b-dihydro-1H-cyclopropanaphthalene
A
naphthalen-1-ylacetonitrile
B
6-Cyano-2,3-benzonorcaradien
C
(1S)-1-endo-Cyano-1a,7b-dihydro-1H-cyclopropanaphthalene
D
(1R)-1-endo-Cyano-1a,7b-dihydro-1H-cyclopropanaphthalene
E
(1S)-1-exo-Cyano-1a,7b-dihydro-1H-cyclopropanaphthalene
Conditions | Yield |
---|---|
In benzene for 0.5h; Product distribution; Irradiation; | A 19% B 14% C n/a D n/a E n/a |
Conditions | Yield |
---|---|
With iron(III) chloride at 175℃; | |
With iron(III) oxide; potassium bromide |
Conditions | Yield |
---|---|
With cyanogen chloride at 650℃; | |
Multi-step reaction with 2 steps 1: N-bromosuccinimide / CCl4 / 4 h / 80 °C / Irradiation 2: 18-crown-6 / dimethylsulfoxide / 20 h View Scheme | |
Multi-step reaction with 2 steps 1: bromine / 190 - 230 °C / UV-Licht 2: sodium cyanide; potassium cyanide; aqueous methanol View Scheme | |
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / Inert atmosphere; Reflux 2: tetra-(n-butyl)ammonium iodide / acetonitrile / Inert atmosphere; Reflux View Scheme | |
With cyanogen chloride at 650℃; |
Conditions | Yield |
---|---|
With methanol; potassium cyanide; sodium cyanide | |
With potassium cyanide; sodium cyanide; ethanol | |
With sodium cyanide; water |
Conditions | Yield |
---|---|
With ethanol |
Conditions | Yield |
---|---|
With potassium cyanide; sodium cyanide; ethanol | |
With methanol; potassium cyanide; sodium cyanide |
Conditions | Yield |
---|---|
In ethanol |
naphthalene
chloroacetonitrile
A
naphthalen-1-ylacetonitrile
B
2-naphthaleneacetonitrile
Conditions | Yield |
---|---|
In acetonitrile for 22h; Kinetics; Irradiation; |
potassium cyanide
2-(bromomethyl)naphthalene
naphthalen-1-ylacetonitrile
Conditions | Yield |
---|---|
18-crown-6 ether In dimethyl sulfoxide for 20h; |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; aluminium trichloride | 100% |
With nickel dichloride; diborane In tetrahydrofuran; methanol for 1h; Ambient temperature; | 80% |
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol at 20℃; under 1810.02 Torr; for 2.5h; | 60% |
naphthalen-1-ylacetonitrile
2-chlorobenzylthiocyanate
2-(naphthalen-1-yl)malononitrile
Conditions | Yield |
---|---|
With lithium diisopropyl amide In benzene at 5℃; for 1h; | 100% |
With hydrogenchloride; lithium diisopropyl amide In benzene | 32% |
naphthalen-1-ylacetonitrile
5-(1-Naphthylmethyl)-1H-tetrazole
Conditions | Yield |
---|---|
With sodium azide; triethylamine hydrochloride In toluene at 110℃; for 16h; Inert atmosphere; | 97% |
With sodium azide; cerium(III) chloride heptahydrate In water; isopropyl alcohol at 160℃; for 4h; Microwave irradiation; | 94% |
With sodium azide; acetic acid; isopropyl alcohol |
naphthalen-1-ylacetonitrile
methyl iodide
2-methyl-2-(naphthalen-1-yl)propanenitrile
Conditions | Yield |
---|---|
Stage #1: naphthalen-1-ylacetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: methyl iodide In tetrahydrofuran at -78 - 20℃; for 10h; | 96% |
With lithium diisopropyl amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃; | 83% |
Stage #1: naphthalen-1-ylacetonitrile With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Metallation; Stage #2: methyl iodide In N,N-dimethyl-formamide for 1h; Methylation; | 78% |
naphthalen-1-ylacetonitrile
Cysteamine
2-(1-naphthylmethyl)-4,5-dihydrothiazole
Conditions | Yield |
---|---|
In ethanol Heating; | 95% |
naphthalen-1-ylacetonitrile
allyl bromide
2-allyl-2-(1-naphthyl)pent-4-enenitrile
Conditions | Yield |
---|---|
Stage #1: naphthalen-1-ylacetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: allyl bromide In tetrahydrofuran at -78 - 20℃; for 10h; | 95% |
naphthalen-1-ylacetonitrile
C-phenyl-N-methylnitrone
Triethylsilyl trifluoromethanesulfonate
Conditions | Yield |
---|---|
With triethylamine In 1,2-dichloro-ethane at -30℃; for 0.5h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
Stage #1: naphthalen-1-ylacetonitrile; 1-methyl-3,4,dihydroisoquinoline With manganese; chloro-trimethyl-silane; bis(cyclopentadienyl)titanium(IV) diphenoxide; triethylamine hydrochloride In tetrahydrofuran at 60℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether; dichloromethane Cooling; regioselective reaction; | 95% |
Conditions | Yield |
---|---|
With water; 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 40h; Green chemistry; diastereoselective reaction; | 95% |
Conditions | Yield |
---|---|
With water; potassium carbonate In isopropyl alcohol at 150℃; for 0.25h; Microwave irradiation; | 94% |
With hydrogenchloride | |
With sulfuric acid; water at 120 - 125℃; |
naphthalen-1-ylacetonitrile
phenylmethanethiol
(Z)-2-(naphthalen-1-yl)-3-phenylacrylonitrile
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; potassium tert-butylate In toluene at 120℃; for 24h; | 94% |
naphthalen-1-ylacetonitrile
2-furoyl-1H-1,2,3-benzotriazole
3-(2-furyl)-2-(1-naphthyl)-3-oxopropanenitrile
Conditions | Yield |
---|---|
Stage #1: naphthalen-1-ylacetonitrile With potassium tert-butylate In dimethyl sulfoxide at 10℃; for 0.166667h; Stage #2: 2-furoyl-1H-1,2,3-benzotriazole In dimethyl sulfoxide at 25℃; for 12h; | 92% |
1-bromo-butane
naphthalen-1-ylacetonitrile
α,α-Dibutyl-(1-naphthyl)-acetonitril
Conditions | Yield |
---|---|
Stage #1: naphthalen-1-ylacetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: 1-bromo-butane In tetrahydrofuran at -78 - 20℃; for 10h; | 92% |
Conditions | Yield |
---|---|
With potassium phosphate buffer at 30℃; for 96h; Rhodococcus sp. AJ270 cells; | 91.3% |
Stage #1: naphthalen-1-ylacetonitrile With sodium hydroxide In water for 3h; Reflux; Stage #2: With hydrogenchloride In water pH=2; Time; | 74.8% |
With sulfuric acid; acetic acid |
Conditions | Yield |
---|---|
With sodium hydroxide; 5,11,17,23,29,35-hexakis-37,38,39,40,41,42-hexamethoxycalix<6>arene In di-isopropyl ether at 70℃; for 5h; Product distribution; Further Variations:; Catalysts; | 91% |
With sodium hydroxide; calix[8]arene with trimethylammoniomethyl groups In various solvent(s) at 70℃; for 2h; Alkylation; | 78% |
naphthalen-1-ylacetonitrile
acetyl chloride
methyl-2-(1-naphthalenyl)acetimidate hydrochloride
Conditions | Yield |
---|---|
In methanol | 91% |
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In tetrahydrofuran at 60℃; under 760.051 Torr; for 6h; Inert atmosphere; Sealed tube; | 90% |
Conditions | Yield |
---|---|
With ruthenium-grafted hydrotalcite at 180℃; for 20h; | 89% |
ruthenium-grafted hydrotalcite at 180℃; for 20h; | 89% |
naphthalen-1-ylacetonitrile
3-methyl-4,4-bis(methylthio)but-3-en-2-one
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; | 89% |
Conditions | Yield |
---|---|
With lithium tert-butoxide In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; regioselective reaction; | 89% |
Product Name: 1-Naphthyl acetonitrile (CAS NO.132-75-2)
Molecular Formula: C12H9N
Molecular Weight: 167.21g/mol
Mol File: 132-75-2.mol
EINECS: 205-078-1
Appearance: White to yellow solid or melt
Melting Point: 33-35 °C(lit.)
Boiling point: 323.9 °C at 760 mmHg
Flash Point: 180.3 °C
Density: 1.116 g/cm3
Refractive index: n20/D 1.6192(lit.)
Index of Refraction: 1.634
Molar Refractivity: 53.55 cm3
Molar Volume: 149.7 cm3
Surface Tension: 48.8 dyne/cm
Enthalpy of Vaporization: 58 kJ/mol
Vapour Pressure: 0.000255 mmHg at 25°C
XLogP3-AA: 2.9
H-Bond Donor: 0
H-Bond Acceptor: 1
Structure Descriptors of 1-Naphthyl acetonitrile (CAS NO.132-75-2):
IUPAC Name: 2-naphthalen-1-ylacetonitrile
Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2CC#N
InChI: InChI=1S/C12H9N/c13-9-8-11-6-3-5-10-4-1-2-7-12(10)11/h1-7H,8H2
InChIKey: OQRMWUNUKVUHQO-UHFFFAOYSA-N
Product Categories: Intermediates of Dyes and Pigments; Aromatic Nitriles
1-Naphthyl acetonitrile (CAS NO.132-75-2) is used in organic synthesis.
1. | ivn-mus LD50:180 mg/kg | CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#03835 . |
Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.
Poison by intravenous route. When heated to decomposition it emits toxic fumes of NOx and CN−. See also NITRILES.
Safety Information of 1-Naphthyl acetonitrile (CAS NO.132-75-2):
Hazard Codes: Xn
Risk Statements: 20/21/22-36/37/38-22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
R22:Harmful if swallowed.
Safety Statements: 26-37/39-24/25-37-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
S24/25:Avoid contact with skin and eyes.
S37:Wear suitable gloves.
S36:Wear suitable protective clothing.
RIDADR: 3276
WGK Germany: 3
RTECS: AM1240000
HazardClass: 6.1
PackingGroup: III
1-Naphthyl acetonitrile , its CAS NO. is 132-75-2, the synonyms are Acetonitrile, (1-naphthyl)- ; alpha-(1-Naphthyl)acetonitrile ; alpha-Naphthyl acetonitrile ; alpha-Naphthylacetonitrile ; 1-Naphthaleneacetonitrile ; 1-Naphthylacetonitrile .
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