trimethylsilyl cyanide
3-methoxycarbonylbenzyl bromide
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 60℃; for 15h; | 98% |
With tetrabutyl ammonium fluoride In acetonitrile for 20h; Heating / reflux; | 43% |
potassium cyanide
3-methoxycarbonylbenzyl bromide
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
With 18-crown-6 ether In acetonitrile for 24h; Heating / reflux; | 96% |
With 18-crown-6 ether In acetonitrile for 24h; Ambient temperature; | 92% |
With 18-crown-6 ether In acetonitrile at 20℃; for 40h; | 91% |
In ethanol at 60℃; | 68% |
3-methoxycarbonylbenzyl bromide
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
In acetonitrile | 91% |
In dimethyl sulfoxide | |
In N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
With 18-crown-6 ether In acetonitrile at 20℃; for 72h; | 91% |
With 18-crown-6 ether In acetonitrile at 20℃; for 72h; | 91% |
In methanol; water for 5h; Reflux; Inert atmosphere; | 1 g |
sodium cyanide
3-methoxycarbonylbenzyl bromide
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; | 89% |
In N,N-dimethyl-formamide at 20℃; | 89% |
In water; N,N-dimethyl-formamide at 75℃; for 5h; Inert atmosphere; | 85% |
sodium cyanide
3-methoxycarbonylbenzyl bromide
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide at 75℃; for 5h; | 70% |
In water; N,N-dimethyl-formamide at 75℃; for 5h; | 70% |
Stage #1: sodium cyanide; 3-methoxycarbonylbenzyl bromide In water; N,N-dimethyl-formamide at 75℃; for 5h; Stage #2: With water In N,N-dimethyl-formamide | 70% |
4-isoxazoleboronic acid pinacol ester
methyl 3-bromobenzoate
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
With potassium fluoride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl sulfoxide at 130℃; for 18h; Suzuki Coupling; Inert atmosphere; Sealed tube; | 69% |
3-azido-2-methylbut-3-en-2-ol
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In acetonitrile at 20℃; for 4h; | 65% |
3-bromomethylbenzoyl chloride
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 91 percent / 18-crown-6 / acetonitrile / 40 h / 20 °C View Scheme |
3-Methylbenzoyl chloride
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Br2 / 0.5 h / 180 °C 2: 91 percent / 18-crown-6 / acetonitrile / 40 h / 20 °C View Scheme |
1-methoxycarbonyl-3-methylbenzene
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NBS / CCl4 2: dimethylsulfoxide View Scheme | |
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 3 h / Inert atmosphere; Reflux; Irradiation 2: methanol; water / 5 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 2 steps 1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 4 h / 70 °C 2: dimethyl sulfoxide / 3.25 h / 0 - 10 °C 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 |
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
In methanol; dichloromethane; water; acetonitrile |
methyl 3-bromobenzoate
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: magnesium; iodine / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 1.2: 6 h / 0 - 20 °C / Inert atmosphere 2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium bromide; sodium hypochlorite; sodium hydrogencarbonate / acetonitrile / 2 h / 0.5 °C / pH 9-10 3.1: ammonia; thionyl chloride / 70 °C 4.1: thionyl chloride / chloroform / 8 h / Reflux View Scheme |
methyl 3-(2-amino-2-oxoethyl)benzoate
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
With thionyl chloride In chloroform for 8h; Reflux; | 32 g |
m-bromobenzoic acid
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: thionyl chloride / 5 h / 70 °C 1.2: 4 h / 20 °C / Cooling with ice 2.1: magnesium; iodine / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 2.2: 6 h / 0 - 20 °C / Inert atmosphere 3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium bromide; sodium hypochlorite; sodium hydrogencarbonate / acetonitrile / 2 h / 0.5 °C / pH 9-10 4.1: ammonia; thionyl chloride / 70 °C 5.1: thionyl chloride / chloroform / 8 h / Reflux View Scheme |
methyl 3-(2-hydroxylethyl)benzoate
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium bromide; sodium hypochlorite; sodium hydrogencarbonate / acetonitrile / 2 h / 0.5 °C / pH 9-10 2: ammonia; thionyl chloride / 70 °C 3: thionyl chloride / chloroform / 8 h / Reflux View Scheme |
m-Toluic acid
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: thionyl chloride / 4 h / Reflux 1.2: 100 °C 2.1: 40 °C 3.1: methanol / 2 h / 40 - 80 °C View Scheme |
sodium cyanide
1-methoxycarbonyl-3-methylbenzene
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
In methanol at 40 - 80℃; for 2h; |
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
With sodium hydrogen sulfide; hydrogen sulfide; acetamidine hydrochloride In water at 70℃; under 3750.38 Torr; for 4h; pH=10; Reagent/catalyst; pH-value; Pressure; Temperature; Autoclave; | 98.6% |
With sodium hydrogen sulfide; triethylamine hydrochloride In methanol at 70℃; for 7h; Concentration; Reagent/catalyst; | 95.8% |
methyl 3-cyanomethylbenzoate
2-(3-(hydroxymethyl)phenyl)acetonitrile
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 10℃; for 16.25h; | 95% |
With lithium borohydride In tetrahydrofuran for 4h; Heating / reflux; | 41% |
methyl 3-cyanomethylbenzoate
carbonic acid dimethyl ester
2-<3-(carboxymethyl)phenyl>propionitrile
Conditions | Yield |
---|---|
With potassium carbonate at 180℃; for 8h; Product distribution; Mechanism; the course of reaction according various periods of time; | 91% |
With potassium carbonate at 180℃; for 8h; | 91% |
With potassium carbonate at 180℃; for 8h; | 91% |
methanol
methyl 3-cyanomethylbenzoate
3-methoxycarbonylphenylacetic acid methyl ester
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 20℃; for 6h; | 87% |
methyl 3-cyanomethylbenzoate
(3-(2-aminoethyl)phenyl)methanol
Conditions | Yield |
---|---|
With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 20℃; Inert atmosphere; | 83% |
Stage #1: methyl 3-cyanomethylbenzoate With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 20℃; Inert atmosphere; Stage #2: With sulfuric acid; water In tetrahydrofuran; diethyl ether | |
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / tetrahydrofuran; methanol / 16.25 h / 0 - 10 °C 2: hydrogen; ammonia / Raney-Ni / methanol / 3 h / 10 °C View Scheme |
methyl 3-cyanomethylbenzoate
3-(cyanomethyl)benzoic acid
Conditions | Yield |
---|---|
With lithium hydroxide; water In tetrahydrofuran at 20 - 50℃; | 79% |
methyl 3-cyanomethylbenzoate
methyl iodide
methyl 3-(1-cyano-1-methylethyl)benzoate
Conditions | Yield |
---|---|
In dimethyl sulfoxide | 79% |
Stage #1: methyl 3-cyanomethylbenzoate With sodium hydride In dimethyl sulfoxide; mineral oil at 20 - 25℃; Stage #2: methyl iodide In dimethyl sulfoxide; mineral oil at 20℃; for 16h; | 79% |
Stage #1: methyl 3-cyanomethylbenzoate With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 0.333333h; Cooling with ice; Stage #2: methyl iodide In dimethyl sulfoxide; mineral oil at 20℃; for 16h; | 79% |
methyl 3-cyanomethylbenzoate
3-(2-Amino-ethyl)-benzoic acid methyl ester
Conditions | Yield |
---|---|
With hydrogenchloride; palladium 10% on activated carbon In methanol; water at 20℃; for 2h; Inert atmosphere; | 78% |
With sodium tetrahydroborate; trifluoroacetic acid In tetrahydrofuran for 4h; Ambient temperature; | |
With hydrogen; palladium on activated charcoal |
methyl 3-cyanomethylbenzoate
ethylene dibromide
methyl 3-(1-cyanocyclopropyl)benzoate
Conditions | Yield |
---|---|
With dimethyl sulfoxide | 76% |
Stage #1: methyl 3-cyanomethylbenzoate With sodium hydride In dimethyl sulfoxide; mineral oil at 20 - 25℃; Stage #2: ethylene dibromide In dimethyl sulfoxide; mineral oil at 20℃; for 10h; | 76% |
Stage #1: methyl 3-cyanomethylbenzoate With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 0.333333h; Cooling with ice; Stage #2: ethylene dibromide In dimethyl sulfoxide; mineral oil at 20℃; for 16h; | 76% |
Stage #1: methyl 3-cyanomethylbenzoate With sodium hydride In dimethyl sulfoxide; mineral oil at 20 - 25℃; for 0.5h; Stage #2: ethylene dibromide In dimethyl sulfoxide; mineral oil at 20℃; for 16h; |
methyl 3-cyanomethylbenzoate
methyl 3-(2-amino-2-oxoethyl)benzoate
Conditions | Yield |
---|---|
Stage #1: methyl 3-cyanomethylbenzoate With hydrogenchloride In tetrahydrofuran; water Stage #2: With sodium hydroxide In tetrahydrofuran; water | 70% |
1,5-dibromo-pentane
methyl 3-cyanomethylbenzoate
methyl 3-(1-cyanocyclohexyl)benzoate
Conditions | Yield |
---|---|
With dimethyl sulfoxide | 68% |
methyl 3-cyanomethylbenzoate
1-Bromo-2-chloroethane
methyl 3-(1-cyanocyclopropyl)benzoate
Conditions | Yield |
---|---|
Stage #1: methyl 3-cyanomethylbenzoate With sodium hydride In dimethyl sulfoxide; mineral oil Stage #2: 1-Bromo-2-chloroethane In dimethyl sulfoxide; mineral oil at 0 - 25℃; for 18h; | 68% |
With sodium hydride In dimethyl sulfoxide; mineral oil at 0 - 25℃; for 18h; | 68% |
methyl 3-cyanomethylbenzoate
3-carboxymethyl-benzoic acid
Conditions | Yield |
---|---|
With sulfuric acid; water at 160℃; for 3h; | 68% |
methyl 3-cyanomethylbenzoate
methyl 3-(1-cyano-1-methylethyl)benzoate
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide at 0 - 25℃; for 12h; | 66% |
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol; water | 63% |
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In methanol; dichloromethane; water at 20℃; under 2585.81 Torr; for 10h; | |
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In methanol; dichloromethane; water at 20℃; under 2585.81 Torr; for 10h; |
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
With N-Bromosuccinimide; palladium diacetate; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane Inert atmosphere; Sealed tube; regioselective reaction; | 52% |
1,1'-oxybis(2-bromo-ethane)
methyl 3-cyanomethylbenzoate
methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoate
Conditions | Yield |
---|---|
With dimethyl sulfoxide | 46% |
methyl 3-cyanomethylbenzoate
1,3-dibromo-propane
methyl 3-(1-cyanocyclobutyl)benzoate
Conditions | Yield |
---|---|
With dimethyl sulfoxide | 42% |
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
Stage #1: methyl 3-cyanomethylbenzoate With sodium tetrahydroborate In tetrahydrofuran at 80℃; Stage #2: With methanol In tetrahydrofuran at 20 - 80℃; for 16.5h; | 40% |
methyl 3-cyanomethylbenzoate
Conditions | Yield |
---|---|
With hydrogenchloride; ethanol; ammonia 1.) CH2Cl2, EtOH, 0 deg C, 6 days, 2.) MeOH, 50 deg C, 18 h; Multistep reaction; | |
With ammonia In methanol; ethanol; dichloromethane |
Conditions | Yield |
---|---|
With N-benzyl-trimethylammonium hydroxide In acetonitrile Michael reaction; Heating; |
The CAS register number of Benzoicacid, 3-(cyanomethyl)-, methyl ester is 68432-92-8. It also can be called as Methylm-(cyanomethyl)benzoate and the systematic name about this chemical is methyl 3-(cyanomethyl)benzoate. The molecular formula about this chemical is C10H9NO2 and the molecular weight is 175.18. It belongs to the following product categorie which include Aromatic Esters.
Physical properties about Benzoicacid, 3-(cyanomethyl)-, methyl ester are: (1)ACD/LogP: 1.34; (2)ACD/LogD (pH 5.5): 1; (3)ACD/LogD (pH 7.4): 1; (4)ACD/BCF (pH 5.5): 7; (5)ACD/BCF (pH 7.4): 7; (6)ACD/KOC (pH 5.5): 142; (7)ACD/KOC (pH 7.4): 142; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 50.09 Å2; (11)Index of Refraction: 1.531; (12)Molar Refractivity: 47.489 cm3; (13)Molar Volume: 153.527 cm3; (14)Polarizability: 18.826x10-24cm3; (15)Surface Tension: 44.719 dyne/cm; (16)Density: 1.141 g/cm3; (17)Flash Point: 146.515 °C; (18)Enthalpy of Vaporization: 55.519 kJ/mol; (19)Boiling Point: 314.059 °C at 760 mmHg.
You can still convert the following datas into molecular structure:
(1)SMILES: N#CCc1cc(ccc1)C(=O)OC
(2)InChI: InChI=1/C10H9NO2/c1-13-10(12)9-4-2-3-8(7-9)5-6-11/h2-4,7H,5H2,1H3
(3)InChIKey: XSNUGLQVCGENEM-UHFFFAOYAA
(4)Std. InChI: InChI=1S/C10H9NO2/c1-13-10(12)9-4-2-3-8(7-9)5-6-11/h2-4,7H,5H2,1H3
(5)Std. InChIKey: XSNUGLQVCGENEM-UHFFFAOYSA-N
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