Product Name

  • Name

    Methyl 4-(cyanomethyl)benzoate

  • EINECS
  • CAS No. 76469-88-0
  • Article Data35
  • CAS DataBase
  • Density 1.141g/cm3
  • Solubility
  • Melting Point 64 ºC
  • Formula C10H9 N O2
  • Boiling Point 110 °C0.2 mm Hg(lit.)
  • Molecular Weight 175.187
  • Flash Point 145.9°C
  • Transport Information
  • Appearance
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 76469-88-0 (Methyl 4-(cyanomethyl)benzoate)
  • Hazard Symbols
  • Synonyms p-Toluicacid, a-cyano-, methyl ester (7CI);4-Cyanomethylbenzoic acid methyl ester; Methyl 4-cyanomethylbenzoate; Methylp-(cyanomethyl)benzoate; Methyl a-cyano-p-toluate; [p-(Methoxycarbonyl)phenyl]acetonitrile
  • PSA 50.09000
  • LogP 1.53928

Synthetic route

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

4-methoxycarbonylphenylboronic acid
99768-12-4

4-methoxycarbonylphenylboronic acid

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
With sodium nitrite In water; 1,2-dichloro-ethane at 100℃; for 24h; Schlenk technique;90%
chloroacetonitrile
107-14-2

chloroacetonitrile

4-methoxycarbonylphenylboronic acid
99768-12-4

4-methoxycarbonylphenylboronic acid

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
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;87%
With nickel(II) nitrate hexahydrate; potassium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine; sodium iodide In 1,4-dioxane at 80℃; for 12h; Suzuki Coupling; Inert atmosphere; Sealed tube;80%
4-(methoxycarbonyl)benzyl alcohol
6908-41-4

4-(methoxycarbonyl)benzyl alcohol

potassium cyanide
151-50-8

potassium cyanide

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
Stage #1: 4-(methoxycarbonyl)benzyl alcohol With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 15h;
Stage #2: potassium cyanide With 18-crown-6 ether In acetonitrile at 20℃; for 40h;		86%
Methyl 4-(bromomethyl)benzoate
2417-72-3

Methyl 4-(bromomethyl)benzoate

potassium cyanide
151-50-8

potassium cyanide

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
In ethanol Substitution; Heating;81%
In ethanol for 24h; Heating;76%
In ethanol; water for 3h; Heating;74%
In ethanol; water for 3.25h; Heating / reflux;
diethyl ether
60-29-7

diethyl ether

p-methyloxycarbonylbenzyl chloride
34040-64-7

p-methyloxycarbonylbenzyl chloride

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
In ethanol; water80%
p-methyloxycarbonylbenzyl chloride
34040-64-7

p-methyloxycarbonylbenzyl chloride

sodium cyanide
143-33-9

sodium cyanide

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 3h;79%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

Methyl 4-(bromomethyl)benzoate
2417-72-3

Methyl 4-(bromomethyl)benzoate

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
Stage #1: trimethylsilyl cyanide With tetrabutyl ammonium fluoride for 1h;
Stage #2: Methyl 4-(bromomethyl)benzoate In acetonitrile at 80℃; for 1h;		68.7%
With tetrabutyl ammonium fluoride In acetonitrile at 25℃; for 12h;
sodium cyanide
773837-37-9

sodium cyanide

Methyl 4-(bromomethyl)benzoate
2417-72-3

Methyl 4-(bromomethyl)benzoate

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide In acetonitrile Inert atmosphere; Reflux;65%
In methanol; water for 1.25h; Kolbe nitrile synthesis; Reflux;60%
With N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

lithium methanolate
865-34-9

lithium methanolate

p-chlorobenzyl cyanide
140-53-4

p-chlorobenzyl cyanide

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; 5 mol% Pd/C; sodium fluoride In 1,4-dioxane at 150℃; Inert atmosphere;64%
...Expand
potassium cyanide

potassium cyanide

Methyl 4-(bromomethyl)benzoate
2417-72-3

Methyl 4-(bromomethyl)benzoate

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
In methanol; water for 5h; Reflux;58.6%
In methanol; water for 5h; Reflux; Inert atmosphere;
In methanol; water for 5h; Inert atmosphere; Reflux;
Methyl 4-(bromomethyl)benzoate
2417-72-3

Methyl 4-(bromomethyl)benzoate

sodium cyanide
143-33-9

sodium cyanide

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
In dimethyl sulfoxide at 40℃; for 1.5h;55%
In dimethyl sulfoxide at 40℃; for 1.5h;55%
In dimethyl sulfoxide at 40℃; for 2h;54%
In dimethyl sulfoxide
Methyl 4-(bromomethyl)benzoate
2417-72-3

Methyl 4-(bromomethyl)benzoate

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
With sodium cyanide
In tetrahydrofuran; water; N,N-dimethyl-formamide6.7 g (76%)
In tetrahydrofuran; water; N,N-dimethyl-formamide6.7 g (76%)
4-(cyanomethyl)benzoic acid
50685-26-2

4-(cyanomethyl)benzoic acid

sodium methylate
124-41-4

sodium methylate

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
In dimethyl sulfoxide
4-Bromophenylacetonitrile
16532-79-9

4-Bromophenylacetonitrile

carbon monoxide
201230-82-2

carbon monoxide

sodium methylate
124-41-4

sodium methylate

A

methyl 4-(2-methoxy-2-oxoethyl)benzoate
52787-14-1

methyl 4-(2-methoxy-2-oxoethyl)benzoate

B

(4-bromo-phenyl)-acetic acid methyl ester
41841-16-1

(4-bromo-phenyl)-acetic acid methyl ester

C

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
With dicobalt octacarbonyl In methanol at 50℃; Product distribution; Mechanism; Irradiation; other p-halogenobenzyl cyanides, var. time and initial concn.;
...Expand
4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Cp2Ti(Cl)CH2Al(CH3)2

Cp2Ti(Cl)CH2Al(CH3)2

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NBS / CCl4
2: dimethylsulfoxide
View Scheme
Multi-step reaction with 2 steps
1: 86 percent / Br2 / benzene / 2 h / Irradiation
2: 74 percent / ethanol; H2O / 3 h / Heating
View Scheme
4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

CO2 anion radical

CO2 anion radical

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / N-bromosuccinimide, dibenzoyl-peroxide / CCl4 / 2.5 h / Heating
2: 54 percent / dimethylsulfoxide / 2 h / 40 °C
View Scheme
4-bromomethylbenzoic Acid
6232-88-8

4-bromomethylbenzoic Acid

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol. H2SO4
2: NaCN
View Scheme
para-bromotoluene
106-38-7

para-bromotoluene

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 195 °C / Erhitzen des Reaktionsgemisches mit wss. H2SO4 auf 150grad
2: nitrobenzene; bromine
3: methanol. H2SO4
4: NaCN
View Scheme
p-Toluic acid
99-94-5

p-Toluic acid

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: nitrobenzene; bromine
2: methanol. H2SO4
3: NaCN
View Scheme
4-(methoxycarbonyl)benzyl alcohol
6908-41-4

4-(methoxycarbonyl)benzyl alcohol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
With triethylamine In dichloromethane; acetonitrile
With triethylamine In dichloromethane; acetonitrile
4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
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: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 1 h
2: N-benzyl-N,N,N-triethylammonium chloride / dichloromethane; water
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
4-Bromophenylacetonitrile
16532-79-9

4-Bromophenylacetonitrile

methyl chloroformate
79-22-1

methyl chloroformate

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Conditions
ConditionsYield
With 2,6-dimethylpyridine; (1,2-dimethoxyethane)dichloronickel(II); tris(triethylsilyl)silane; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine In 1,2-dimethoxyethane at 25℃; for 8h; Inert atmosphere; Sealed tube; Irradiation;24 %Spectr.
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

benzaldehyde
100-52-7

benzaldehyde

4-(1-cyano-2-phenylvinyl)benzoic acid methyl ester

4-(1-cyano-2-phenylvinyl)benzoic acid methyl ester

Conditions
ConditionsYield
With L-proline In dimethyl sulfoxide at 25℃; for 71h;99%
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

methyl 4-(2-oxo-2H-chromen-3-yl)benzoate

methyl 4-(2-oxo-2H-chromen-3-yl)benzoate

Conditions
ConditionsYield
With potassium fluoride at 80℃; for 5.5h; Inert atmosphere;99%
...Expand
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

methyl 4-(2-amino-2-(hydroxyimino)ethyl)benzoate

methyl 4-(2-amino-2-(hydroxyimino)ethyl)benzoate

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol at 65℃; for 18h;99%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol at 65℃; for 18h;99%
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

dimethyl sulfate
77-78-1

dimethyl sulfate

methyl 4-(1-cyano-1-methylethyl)-benzoate

methyl 4-(1-cyano-1-methylethyl)-benzoate

Conditions
ConditionsYield
Stage #1: methyl 4-(cyanomethyl)benzoate With tetrabutylammomium bromide; sodium hydroxide In water at 20℃; Large scale reaction;
Stage #2: dimethyl sulfate In water at 0 - 3℃; for 4h;		96%
C-phenyl-N-methylnitrone
3376-23-6, 7372-59-0, 59862-60-1

C-phenyl-N-methylnitrone

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

Triethylsilyl trifluoromethanesulfonate
79271-56-0

Triethylsilyl trifluoromethanesulfonate

methyl 4-(1-cyano-2-(methyl((triethylsilyl)oxy)amino)-2-phenylethyl)benzoate

methyl 4-(1-cyano-2-(methyl((triethylsilyl)oxy)amino)-2-phenylethyl)benzoate

Conditions
ConditionsYield
With triethylamine In 1,2-dichloro-ethane at -30℃; for 0.5h; Inert atmosphere;96%
...Expand
2-formyl-5,10,15,20-tetrakis-(3,5-dimethylphenyl)porphyrin

2-formyl-5,10,15,20-tetrakis-(3,5-dimethylphenyl)porphyrin

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

C63H53N5O2

C63H53N5O2

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 23℃; for 1h; Knoevenagel Condensation; Inert atmosphere;93%
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

4-(cyanomethyl)benzoic acid
50685-26-2

4-(cyanomethyl)benzoic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol at 80℃; for 3h;92.2%
With sodium hydroxide In methanol for 3h; Reflux;92.2%
Stage #1: methyl 4-(cyanomethyl)benzoate With water; lithium hydroxide In tetrahydrofuran at 20℃; for 16h;
Stage #2: With hydrogenchloride In water		86%
Stage #1: methyl 4-(cyanomethyl)benzoate With water; lithium hydroxide In tetrahydrofuran at 20℃; for 16h;
Stage #2: With hydrogenchloride In water		86%
With potassium hydroxide In water at 0 - 20℃; for 2h;26%
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

4-(2-amino-ethyl)-benzoic acid methyl ester
77265-67-9

4-(2-amino-ethyl)-benzoic acid methyl ester

Conditions
ConditionsYield
90%
With ammonia; hydrogen In methanol at 55℃;66%
With hydrogen; palladium on activated charcoal
With borane-THF In tetrahydrofuran for 15h;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate
177736-04-8

methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate

Conditions
ConditionsYield
With triethylamine; platinum (IV) oxide In methanol; dichloromethane; chloroform88%
With triethylamine; platinum (IV) oxide In methanol; dichloromethane; chloroform88%
Stage #1: methyl 4-(cyanomethyl)benzoate With hydrogen; platinum(IV) oxide In methanol; chloroform at 20℃; for 3h;
Stage #2: di-tert-butyl dicarbonate With triethylamine In dichloromethane at 0 - 20℃; for 13h;		88%
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

methyl 4-(1H-tetrazol-5-ylmethyl)benzoate
1246251-02-4

methyl 4-(1H-tetrazol-5-ylmethyl)benzoate

Conditions
ConditionsYield
With sodium azide; N,N-diethylethanamine hydrochloride In toluene at 100℃; for 24h; Inert atmosphere;88%
With sodium azide; triethylamine hydrochloride In toluene at 100℃; for 24h; Inert atmosphere;88%
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

4-(carboxymethyl)benzoic acid
501-89-3

4-(carboxymethyl)benzoic acid

Conditions
ConditionsYield
With sulfuric acid In water at 5℃;87%
With sodium hydroxide In methanol at 90℃;70%
With sodium hydroxide
With sulfuric acid; water at 125℃;
With water; sodium hydroxide In methanol at 90℃; for 12h;
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

C41H43N3O3S2

C41H43N3O3S2

C51H50N4O4S2

C51H50N4O4S2

Conditions
ConditionsYield
With piperidine In tetrahydrofuran; acetonitrile Inert atmosphere; Reflux;87%
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

4-(2-aminoethyl)-benzyl alcohol
64353-30-6

4-(2-aminoethyl)-benzyl alcohol

Conditions
ConditionsYield
With diborane In tetrahydrofuran for 10h; Heating;85%
Stage #1: methyl 4-(cyanomethyl)benzoate 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		78%
With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 20℃; Inert atmosphere;78%
triethylsilane
617-86-7

triethylsilane

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

2-(4’-methylcarboxylate)-N,N-bis(triethylsilyl)phenethylamine

2-(4’-methylcarboxylate)-N,N-bis(triethylsilyl)phenethylamine

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 8h;84%
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

12-formyl-5,10,15,20-tetraphenyl-21H,23H-porphine

12-formyl-5,10,15,20-tetraphenyl-21H,23H-porphine

C55H37N5O2

C55H37N5O2

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 23℃; for 0.5h; Knoevenagel Condensation; Inert atmosphere;84%
10-ethyl-10H-phenothiazine-3-carbaldehyde
18413-61-1

10-ethyl-10H-phenothiazine-3-carbaldehyde

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

methyl (Z)-4-(1-cyano-2-(10-ethyl-10H-phenothiazin-3-yl)vinyl)benzoate

methyl (Z)-4-(1-cyano-2-(10-ethyl-10H-phenothiazin-3-yl)vinyl)benzoate

Conditions
ConditionsYield
Stage #1: 10-ethyl-10H-phenothiazine-3-carbaldehyde; methyl 4-(cyanomethyl)benzoate In ethanol for 0.166667h; Reflux;
Stage #2: With pyrrolidine In ethanol for 2h; Reflux;		84%
4-methylphenyl isocyanide
7175-47-5

4-methylphenyl isocyanide

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

methyl (Z)-4-(1-cyano-2-(p-tolylamino)vinyl)benzoate

methyl (Z)-4-(1-cyano-2-(p-tolylamino)vinyl)benzoate

Conditions
ConditionsYield
With copper(l) iodide; potassium tert-butylate In 1,2-dimethoxyethane at 55 - 60℃; for 16h; Inert atmosphere;83%
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

C14H15ClN2O4

C14H15ClN2O4

methyl 4-((1-(benzyloxy)-3-(ethoxymethyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)(cyano)methyl)benzoate

methyl 4-((1-(benzyloxy)-3-(ethoxymethyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)(cyano)methyl)benzoate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;83%
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

methyl iodide
74-88-4

methyl iodide

4-(1-cyano-1-methylethyl)benzoic acid
129488-74-0

4-(1-cyano-1-methylethyl)benzoic acid

Conditions
ConditionsYield
Stage #1: methyl 4-(cyanomethyl)benzoate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran at 0 - 25℃; for 12h;
Stage #3: With hydrogenchloride In water		83%
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

4-(2-aminoethyl)-benzoic acid methyl ester-hydrochloride
56161-89-8

4-(2-aminoethyl)-benzoic acid methyl ester-hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol at 20℃; for 48h; Catalytic hydrogenation;81%
With hydrogenchloride; hydrogen; 5%-palladium/activated carbon In tetrahydrofuran; methanol for 2h;57.87%
methanol
67-56-1

methanol

methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

methyl 4-(2-methoxy-2-oxoethyl)benzoate
52787-14-1

methyl 4-(2-methoxy-2-oxoethyl)benzoate

Conditions
ConditionsYield
With hydrogenchloride for 2h; Reflux;81%
With hydrogenchloride at 20℃; for 32h; Heating / reflux;
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

10-ethyl-10H-phenothiazine-3,7-dicarboxaldehyde
204977-17-3

10-ethyl-10H-phenothiazine-3,7-dicarboxaldehyde

dimethyl 4,4′-((1Z,1′Z)-(10-ethyl-10H-phenothiazine-3,7-diyl)bis1-cyanoethene-2,1-diyl)dibenzoate

dimethyl 4,4′-((1Z,1′Z)-(10-ethyl-10H-phenothiazine-3,7-diyl)bis1-cyanoethene-2,1-diyl)dibenzoate

Conditions
ConditionsYield
Stage #1: methyl 4-(cyanomethyl)benzoate; 10-ethyl-10H-phenothiazine-3,7-dicarboxaldehyde In ethanol for 0.166667h; Reflux;
Stage #2: With pyrrolidine In ethanol for 2h; Reflux;		81%
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

C20H19NO3
1300627-55-7

C20H19NO3

Conditions
ConditionsYield
With pyrrolidine In dichloromethane at 20℃; for 40h; Michael addition;77%
methyl 4-(cyanomethyl)benzoate
76469-88-0

methyl 4-(cyanomethyl)benzoate

C15H17NO3

C15H17NO3

C25H24N2O4

C25H24N2O4

Conditions
ConditionsYield
With potassium hydroxide In methanol; water at 60℃; for 6h; pH=Ca. 10;75%

Methyl 4-(cyanomethyl)benzoate Chemical Properties

Molecular Structure of Methyl 4-(cyanomethyl)benzoate (76469-88-0):

Systematic Name: Methyl 4-(cyanomethyl)benzoate
Molecular Formula: C10H9NO2
Molecular Weight: 175.184
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 3
SMILES: N#CCc1ccc(cc1)C(=O)OC
InChI: InChI=1/C10H9NO2/c1-13-10(12)9-4-2-8(3-5-9)6-7-11/h2-5H,6H2,1H3
InChIKey: XRZGMNGGCZTNGE-UHFFFAOYAO
Index of Refraction: 1.53
Molar Refractivity: 47.48 cm3
Molar Volume: 153.5 cm3
Surface Tension: 44.7 dyne/cm
Density: 1.141 g/cm3
Flash Point: 145.9
Melting Point: 55-58 °C(lit.)
Boiling Point: 312.9 °C at 760 mmHg
Enthalpy of Vaporization: 55.39 kJ/mol
Vapour Pressure: 0.000513 mmHg at 25 °C
Water Solubility: 2021 mg/L at 25 °C

Methyl 4-(cyanomethyl)benzoate Safety Profile

Safety Information of Methyl 4-(cyanomethyl)benzoate (76469-88-0):
Hazard Codes: Xi
Risk Statements: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
WGK Germany: 3

Methyl 4-(cyanomethyl)benzoate Specification

  Methyl 4-(cyanomethyl)benzoate (76469-88-0) is also called for 4-(Cyanomethyl)benzoic acid methyl ester , used as organic intermediate raw material.

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