Product Name

  • Name

    3-CYANOMETHYLBENZOIC ACID METHYL ESTER

  • EINECS
  • CAS No. 68432-92-8
  • Article Data46
  • CAS DataBase
  • Density 1.141 g/cm3
  • Solubility
  • Melting Point
  • Formula C10H9NO2
  • Boiling Point 314.059 °C at 760 mmHg
  • Molecular Weight 175.187
  • Flash Point 146.515 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 68432-92-8 (3-CYANOMETHYLBENZOIC ACID METHYL ESTER)
  • Hazard Symbols
  • Synonyms 3-Cyanomethylbenzoicacid methyl ester;Methyl 3-(cyanomethyl)benzoate;Methylm-(cyanomethyl)benzoate;
  • PSA 50.09000
  • LogP 1.53928

Synthetic route

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

3-methoxycarbonylbenzyl bromide
1129-28-8

3-methoxycarbonylbenzyl bromide

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 60℃; for 15h;98%
With tetrabutyl ammonium fluoride In acetonitrile for 20h; Heating / reflux;43%
potassium cyanide
151-50-8

potassium cyanide

3-methoxycarbonylbenzyl bromide
1129-28-8

3-methoxycarbonylbenzyl bromide

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
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
1129-28-8

3-methoxycarbonylbenzyl bromide

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
In acetonitrile91%
In dimethyl sulfoxide
In N,N-dimethyl-formamide
potassium cyanide

potassium cyanide

3-methoxycarbonylbenzyl bromide
1129-28-8

3-methoxycarbonylbenzyl bromide

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
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
773837-37-9

sodium cyanide

3-methoxycarbonylbenzyl bromide
1129-28-8

3-methoxycarbonylbenzyl bromide

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
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
143-33-9

sodium cyanide

3-methoxycarbonylbenzyl bromide
1129-28-8

3-methoxycarbonylbenzyl bromide

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
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
928664-98-6

4-isoxazoleboronic acid pinacol ester

methyl 3-bromobenzoate
618-89-3

methyl 3-bromobenzoate

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
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
1624363-23-0

3-azido-2-methylbut-3-en-2-ol

3-(methoxycarbonyl)benzenediazonium tetrafluoroborate

3-(methoxycarbonyl)benzenediazonium tetrafluoroborate

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
With 2,6-dimethylpyridine In acetonitrile at 20℃; for 4h;65%
3-bromomethylbenzoyl chloride
54267-06-0

3-bromomethylbenzoyl chloride

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / 18-crown-6 / acetonitrile / 40 h / 20 °C
View Scheme
3-Methylbenzoyl chloride
1711-06-4

3-Methylbenzoyl chloride

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
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
99-36-5

1-methoxycarbonyl-3-methylbenzene

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
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-bromomethylenebenzoate

Methyl-3-bromomethylenebenzoate

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
In methanol; dichloromethane; water; acetonitrile
methyl 3-bromobenzoate
618-89-3

methyl 3-bromobenzoate

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
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
929301-93-9

methyl 3-(2-amino-2-oxoethyl)benzoate

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
With thionyl chloride In chloroform for 8h; Reflux;32 g
m-bromobenzoic acid
585-76-2

m-bromobenzoic acid

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
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
153599-45-2

methyl 3-(2-hydroxylethyl)benzoate

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
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
99-04-7

m-Toluic acid

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
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
773837-37-9

sodium cyanide

1-methoxycarbonyl-3-methylbenzene
99-36-5

1-methoxycarbonyl-3-methylbenzene

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

Conditions
ConditionsYield
In methanol at 40 - 80℃; for 2h;
methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

methyl 3-(2-amino-2-thioxoethyl)benzoate

methyl 3-(2-amino-2-thioxoethyl)benzoate

Conditions
ConditionsYield
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
68432-92-8

methyl 3-cyanomethylbenzoate

2-(3-(hydroxymethyl)phenyl)acetonitrile
177665-49-5

2-(3-(hydroxymethyl)phenyl)acetonitrile

Conditions
ConditionsYield
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
68432-92-8

methyl 3-cyanomethylbenzoate

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

2-<3-(carboxymethyl)phenyl>propionitrile
146257-39-8

2-<3-(carboxymethyl)phenyl>propionitrile

Conditions
ConditionsYield
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
67-56-1

methanol

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

3-methoxycarbonylphenylacetic acid methyl ester
52787-20-9

3-methoxycarbonylphenylacetic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride In methanol at 20℃; for 6h;87%
methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

(3-(2-aminoethyl)phenyl)methanol
743384-09-0

(3-(2-aminoethyl)phenyl)methanol

Conditions
ConditionsYield
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
68432-92-8

methyl 3-cyanomethylbenzoate

3-(cyanomethyl)benzoic acid
5689-33-8

3-(cyanomethyl)benzoic acid

Conditions
ConditionsYield
With lithium hydroxide; water In tetrahydrofuran at 20 - 50℃;79%
methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

methyl iodide
74-88-4

methyl iodide

methyl 3-(1-cyano-1-methylethyl)benzoate
872091-85-5

methyl 3-(1-cyano-1-methylethyl)benzoate

Conditions
ConditionsYield
In dimethyl sulfoxide79%
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
68432-92-8

methyl 3-cyanomethylbenzoate

3-(2-Amino-ethyl)-benzoic acid methyl ester
179003-00-0

3-(2-Amino-ethyl)-benzoic acid methyl ester

Conditions
ConditionsYield
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
68432-92-8

methyl 3-cyanomethylbenzoate

ethylene dibromide
106-93-4

ethylene dibromide

methyl 3-(1-cyanocyclopropyl)benzoate
884000-93-5

methyl 3-(1-cyanocyclopropyl)benzoate

Conditions
ConditionsYield
With dimethyl sulfoxide76%
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
68432-92-8

methyl 3-cyanomethylbenzoate

methyl 3-(2-amino-2-oxoethyl)benzoate
929301-93-9

methyl 3-(2-amino-2-oxoethyl)benzoate

Conditions
ConditionsYield
Stage #1: methyl 3-cyanomethylbenzoate With hydrogenchloride In tetrahydrofuran; water
Stage #2: With sodium hydroxide In tetrahydrofuran; water		70%
1,5-dibromo-pentane
111-24-0

1,5-dibromo-pentane

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

methyl 3-(1-cyanocyclohexyl)benzoate
1005788-17-9

methyl 3-(1-cyanocyclohexyl)benzoate

Conditions
ConditionsYield
With dimethyl sulfoxide68%
methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

1-Bromo-2-chloroethane
107-04-0

1-Bromo-2-chloroethane

methyl 3-(1-cyanocyclopropyl)benzoate
884000-93-5

methyl 3-(1-cyanocyclopropyl)benzoate

Conditions
ConditionsYield
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
68432-92-8

methyl 3-cyanomethylbenzoate

3-carboxymethyl-benzoic acid
2084-13-1

3-carboxymethyl-benzoic acid

Conditions
ConditionsYield
With sulfuric acid; water at 160℃; for 3h;68%
methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

methyl 3-(1-cyano-1-methylethyl)benzoate
872091-85-5

methyl 3-(1-cyano-1-methylethyl)benzoate

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide at 0 - 25℃; for 12h;66%
methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

[2-(3-methoxycarbonylphenyl)ethyl]ammonium chloride

[2-(3-methoxycarbonylphenyl)ethyl]ammonium chloride

Conditions
ConditionsYield
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol; water63%
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
68432-92-8

methyl 3-cyanomethylbenzoate

4-bromo-3-(cyanomethyl)benzoic acid methyl ester

4-bromo-3-(cyanomethyl)benzoic acid methyl ester

Conditions
ConditionsYield
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)
5414-19-7

1,1'-oxybis(2-bromo-ethane)

methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoate
884000-92-4

methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoate

Conditions
ConditionsYield
With dimethyl sulfoxide46%
methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

methyl 3-(1-cyanocyclobutyl)benzoate
884000-91-3

methyl 3-(1-cyanocyclobutyl)benzoate

Conditions
ConditionsYield
With dimethyl sulfoxide42%
methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

2-(3-((2,4-dichlorophenoxy)methyl)phenyl)acetic acid

2-(3-((2,4-dichlorophenoxy)methyl)phenyl)acetic acid

Conditions
ConditionsYield
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
68432-92-8

methyl 3-cyanomethylbenzoate

3-carbamimidoylmethyl-benzoic acid methyl ester hydrochloride

3-carbamimidoylmethyl-benzoic acid methyl ester hydrochloride

Conditions
ConditionsYield
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
methyl 3-cyanomethylbenzoate
68432-92-8

methyl 3-cyanomethylbenzoate

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

C18H21NO6

C18H21NO6

Conditions
ConditionsYield
With N-benzyl-trimethylammonium hydroxide In acetonitrile Michael reaction; Heating;

Benzoicacid, 3-(cyanomethyl)-, methyl ester Specification

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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