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76469-88-0

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76469-88-0 Usage

Uses

The key intermediate of Fexofenadine (F322490).

Check Digit Verification of cas no

The CAS Registry Mumber 76469-88-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,6,4,6 and 9 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 76469-88:
(7*7)+(6*6)+(5*4)+(4*6)+(3*9)+(2*8)+(1*8)=180
180 % 10 = 0
So 76469-88-0 is a valid CAS Registry Number.
InChI:InChI=1/C10H9NO2/c1-13-10(12)9-4-2-8(3-5-9)6-7-11/h2-5H,6H2,1H3

76469-88-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl 4-(cyanomethyl)benzoate

1.2 Other means of identification

Product number -
Other names Methyl |A-Cyano-p-toluate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:76469-88-0 SDS

76469-88-0Synthetic 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%
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.;
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%
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%
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%

76469-88-0Relevant articles and documents

Preparation method of aryl acetonitrile derivative

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Paragraph 0044-0062, (2021/10/20)

The invention relates to a continuous nucleophilic addition and beta-fluorine elimination reaction method of 2,2-difluoroolefin and ammonia water in a catalyst-free and additive-free system. The method comprises the following steps: adding a 2,2-difluoroolefin compound, ammonia water and a solvent into a Schlenk reaction flask, and conducting stirring and reacting at a certain temperature in an air atmosphere to obtain the product aryl acetonitrile derivative.

Spiroindoline-Capped Selective HDAC6 Inhibitors: Design, Synthesis, Structural Analysis, and Biological Evaluation

Saraswati, A. Prasanth,Relitti, Nicola,Brindisi, Margherita,Osko, Jeremy D.,Chemi, Giulia,Federico, Stefano,Grillo, Alessandro,Brogi, Simone,McCabe, Niamh H.,Turkington, Richard C.,Ibrahim, Ola,O'Sullivan, Jeffrey,Lamponi, Stefania,Ghanim, Magda,Kelly, Vincent P.,Zisterer, Daniela,Amet, Rebecca,Hannon Barroeta, Patricia,Vanni, Francesca,Ulivieri, Cristina,Herp, Daniel,Sarno, Federica,Di Costanzo, Antonella,Saccoccia, Fulvio,Ruberti, Giovina,Jung, Manfred,Altucci, Lucia,Gemma, Sandra,Butini, Stefania,Christianson, David W.,Campiani, Giuseppe

supporting information, p. 2268 - 2276 (2020/12/17)

Histone deacetylase inhibitors (HDACi) have emerged as promising therapeutics for the treatment of neurodegeneration, cancer, and rare disorders. Herein, we report the development of a series of spiroindoline-based HDAC6 isoform-selective inhibitors based on the X-ray crystal studies of the hit 6a. We identified compound 6j as the most potent and selective hHDAC6 inhibitor of the series. Biological investigation of compounds 6b, 6h, and 6j demonstrated their antiproliferative activity against several cancer cell lines. Western blotting studies indicated that they were able to increase tubulin acetylation, without significant variation in histone acetylation state, and induced PARP cleavage indicating their apoptotic potential at the molecular level. 6j induced HDAC6-dependent pSTAT3 inhibition.

Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

Das, Riki,Kapur, Manmohan

, p. 1114 - 1126 (2018/06/18)

A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.

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