1529-41-5

Basic information

• Product Name: 3-Chlorobenzyl cyanide
• Synonyms: 3-Chlorobenzyl Cyanide m-Chlorobenzyl Cyanide;3-ChlorobenzylCyanide99%;3-Chlorobenzyl;10) META CHLORO BENZYL CYANIDE;m-Chlorobenzyl nitrile;3-Chlorophenylacetonitrilel;3-Chlorobenzyl cyanide ,99.88%;(3-Chlorophenyl)acetonitrile,3-Chlorobenzyl cyanide
• CAS NO: 1529-41-5
• Molecular Formula: C₈H₆ClN
• Molecular Weight: 151.59
• EINECS: 216-213-9
• Product Categories: Aromatic Nitriles
• Mol File: 1529-41-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 11-13 °C(lit.)
• Boiling Point: 134-136 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colourless liquid
• Density: 1.283 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00704mmHg at 25°C
• Refractive Index: n20/D 1.544(lit.)
• Stability: Stable. Incompatible with strong acids, strong bases, strong oxidizing agents, strong reducing agents.
• BRN: 2042965
• CAS DataBase Reference: 3-Chlorobenzyl cyanide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chlorobenzyl cyanide(1529-41-5)
• EPA Substance Registry System: 3-Chlorobenzyl cyanide(1529-41-5)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 36/37/39-45-28B
• RIDADR: UN 3276 6.1/PG 1
• WGK Germany: 3
• RTECS: AL8240000
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 1529-41-5(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

InChI:InChI=1/C8H6ClN/c9-8-3-1-2-7(6-8)4-5-10/h1-3,6H,4H2

Synthetic route

sodium cyanide (143-33-9) + 1-bromomethyl-3-chlorobenzene (766-80-3) → 3-chloro-benzeneacetonitrile (1529-41-5)

Conditions	Yield
In ethanol at 80℃; for 2h;	87%

sodium cyanide (773837-37-9) + 1-Chloro-3-chloromethyl-benzene (620-20-2) → 3-chloro-benzeneacetonitrile (1529-41-5)

Conditions	Yield
With polyethylene glycol functionalized magnetic dicationic ionic liquid In water for 1h; Reflux; Green chemistry;	86%

3-(3-chloro-phenyl)-2-hydroxyimino-propionic acid + acetic anhydride (108-24-7) → 3-chloro-benzeneacetonitrile (1529-41-5)

potassium cyanide (151-50-8) + 1-bromomethyl-3-chlorobenzene (766-80-3) → 3-chloro-benzeneacetonitrile (1529-41-5)

1-Chloro-3-chloromethyl-benzene (620-20-2) → 3-chloro-benzeneacetonitrile (1529-41-5)

1-chloro-3-methylbenzene (108-41-8) + potassium cyanide (151-50-8) → 3-chloro-benzeneacetonitrile (1529-41-5)

Conditions	Yield
(i) Br2, (irradiation), (ii) /BRN= 4652394/, aq. EtOH; Multistep reaction;

C8H5(3)HClN → 3-chloro-benzeneacetonitrile (1529-41-5)

Conditions	Yield
With piperidine In dimethyl sulfoxide at 25℃; Rate constant;

C8H5ClNNa → 3-chloro-benzeneacetonitrile (1529-41-5)

Conditions	Yield
With methanol In dimethyl sulfoxide at 25℃; Equilibrium constant;

3-chlorobenzyl tosylate (14503-42-5) + tetraethylammoniumcyanide (13435-20-6) → 3-chloro-benzeneacetonitrile (1529-41-5)

Conditions	Yield
With 1-methyl-4-nitrobenzene In water; acetonitrile at 0℃; Rate constant; kinetic isotope effect (11C/14C and 1H/2H); other solvent, var. temp.;

tetraethylammoniumcyanide (13435-20-6) + 4-Methoxy-benzenesulfonic acid 3-chloro-benzyl ester (139218-48-7) → 3-chloro-benzeneacetonitrile (1529-41-5)

Conditions	Yield
With 1-methyl-4-nitrobenzene In water; acetonitrile at 0℃; Rate constant; kinetic isotope effect (11C/14C and 1H/2H); other solvent, var. temp.;

tetraethylammoniumcyanide (13435-20-6) + Benzenesulfonic acid 3-chloro-benzyl ester → 3-chloro-benzeneacetonitrile (1529-41-5)

Conditions	Yield
With 1-methyl-4-nitrobenzene In water; acetonitrile at 0℃; Rate constant; kinetic isotope effect (11C/14C and 1H/2H);

tetraethylammoniumcyanide (13435-20-6) + 4-Chloro-benzenesulfonic acid 3-chloro-benzyl ester → 3-chloro-benzeneacetonitrile (1529-41-5)

Conditions	Yield
With 1-methyl-4-nitrobenzene In water; acetonitrile at 0℃; Rate constant; kinetic isotope effect (11C/14C and 1H/2H); other solvent, var. temp.;

diazotized <3-amino-phenyl>-acetonitrile → 3-chloro-benzeneacetonitrile (1529-41-5)

Conditions	Yield
With hydrogenchloride; copper(l) chloride

3-(3-chloro-phenyl)-2-thioxo-propionic acid (860190-02-9) → 3-chloro-benzeneacetonitrile (1529-41-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous ethanol; hydroxylamine View Scheme

sodium cyanide (143-33-9) + 1-Chloro-3-chloromethyl-benzene (620-20-2) → 3-chloro-benzeneacetonitrile (1529-41-5)

Conditions	Yield
With tetrabutylammomium bromide In water; toluene Heating / reflux;

3-chloro-benzeneacetonitrile (1529-41-5) + 1-Bromo-2-chloroethane (107-04-0) → 1-(3-chloro-phenyl)cyclopropanecarbonitrile (124276-32-0)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 50℃;	100%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 40℃; for 2.5h;	80%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 50℃; for 12h;

3-chloro-benzeneacetonitrile (1529-41-5) → (Z)-2-(3-chlorophenyl)-N'-hydroxyacetimidamide (925252-77-3, 175532-13-5)

Conditions	Yield
With hydroxylamine hydrochloride; sodium In methanol	100%
With hydroxylamine hydrochloride; sodium In methanol	100%
With hydroxylamine In ethanol; water at 20℃; for 5h;	99%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol; water for 6h; Reflux;	82%
With hydroxylamine hydrochloride; triethylamine In methanol at 60℃; for 12h; Inert atmosphere;

3-chloro-benzeneacetonitrile (1529-41-5) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 3-(dimethylamino)-2-(3-chlorophenyl)acrylonitrile (62739-01-9)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine for 4h; Reflux;	100%
With N,N,N,N,-tetramethylethylenediamine for 4h; Reflux;	100%
With N,N,N,N,-tetramethylethylenediamine Reflux;	100%
With triethylamine In N,N-dimethyl-formamide at 120℃; for 0.333333h; Microwave irradiation;

3-chloro-benzeneacetonitrile (1529-41-5) → 5-(3'-chlorobenzyl)-1H-tetrazole

Conditions	Yield
With sodium azide; ammonium chloride In N,N-dimethyl-formamide for 24h; Reflux;	99%
With sodium azide; ammonium chloride In N,N-dimethyl-formamide for 24h; Reflux;	99%
With sodium azide In dimethyl sulfoxide at 120℃; for 4h; Catalytic behavior;	91%

3-chloro-benzeneacetonitrile (1529-41-5) + rac-3-bromocyclohexene (1521-51-3) → 2-(3-chlorophenyl)-N-(cyclohex-2-en-1-yl)acetamide

Conditions	Yield
With water; silver trifluoromethanesulfonate at 0℃; for 1h; Ritter Amidation; chemoselective reaction;	99%

2-Aminonicotinaldehyde (7521-41-7) + 3-chloro-benzeneacetonitrile (1529-41-5) → 2-amino-3-(m-chlorophenyl)-1,8-naphthyridine (756500-63-7)

Conditions	Yield
With potassium hydroxide for 0.0333333h; microwave irradiation;	98%
With piperidine In neat (no solvent) Milling; Green chemistry;

3,4-dimethylbenzaldehyde (5973-71-7) + 3-chloro-benzeneacetonitrile (1529-41-5) → (2E)-2-(3-chlorophenyl)-3-(3,4-dimethylphenyl)acrylonitrile (1379649-36-1)

Conditions	Yield
With sodium methylate In methanol at 20℃; for 2h;	98%
With sodium methylate In ethanol at 20℃; for 2h;	98%

3-chloro-benzeneacetonitrile (1529-41-5) → 3-chlorophenylacetic acid (1878-65-5)

Conditions	Yield
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 1.4h; Green chemistry;	95%
With sulfuric acid; acetic acid
With potassium hydroxide
(saponification);
With hydrogenchloride; water for 24h; Reflux;

3-chloro-benzeneacetonitrile (1529-41-5) + Phenyl azide (622-37-7) → 5-(3-Chloro-phenyl)-3-phenyl-3H-[1,2,3]triazol-4-ylamine (126158-50-7)

Conditions	Yield
With sodium ethanolate In methanol; ethanol Heating;	95%

3-chloro-benzeneacetonitrile (1529-41-5) + 2-(1,3-benzothiazol-2-yl)-2-(tetrahydro-2-furanyliden)acetonitrile (654064-80-9) → 2-(3-chlorophenyl)-3-(3-hydroxypropyl)-1-imino-1H-pyrido[2,1-b][1,3]benzothiazole-4-carbonitrile (1549536-42-6)

Conditions	Yield
Stage #1: 3-chloro-benzeneacetonitrile With sodium hydride In 1,4-dioxane at 20℃; for 0.5h; Stage #2: 2-(1,3-benzothiazol-2-yl)-2-(tetrahydro-2-furanyliden)acetonitrile In 1,4-dioxane at 20℃; for 3h; Michael Addition;	94%

ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (4506-71-2) + 3-chloro-benzeneacetonitrile (1529-41-5) → 2-(3-chlorobenzyl)-5,6,7,8-tetrahydrothieno[2,3-d]pyrimidin-4(3H)-one

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 20℃; for 18h;	93%

3-chloro-benzeneacetonitrile (1529-41-5) + methyl iodide (74-88-4) → 2-(3-chloro-phenyl)-2-methyl-propionitrile (64798-33-0)

Conditions	Yield
Stage #1: 3-chloro-benzeneacetonitrile With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃;	92%
Stage #1: 3-chloro-benzeneacetonitrile With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran at 0℃; for 2h;	92%
Stage #1: 3-chloro-benzeneacetonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.666667h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃;	90%

3-chloro-benzeneacetonitrile (1529-41-5) + 4-methoxy-benzaldehyde (123-11-5) → 2-(3-chlorophenyl)-3-(4-methoxyphenyl)acrylonitrile (280140-89-8)

Conditions	Yield
With 20percent deep eutectic solvents(DES) of choline chloride and urea at 20℃; for 0.75h; Knoevenagel Condensation;	92%
With ionic tagged amine supported on magneticnanoparticle In water at 20℃; for 5h; Knoevenagel Condensation;	82%

benzoic acid tert-butyl ester (774-65-2) + 3-chloro-benzeneacetonitrile (1529-41-5) → N-(tert-butyl)-2-(3-chlorophenyl) acetamide

Conditions	Yield
With zinc perchlorate In neat (no solvent) at 50℃; for 5h; Ritter Amidation;	91%

3-chloro-benzeneacetonitrile (1529-41-5) + formic acid ethyl ester (109-94-4) → 2-(3-Chlorophenyl)-3-oxopropanenitrile (66154-58-3)

Conditions	Yield
Stage #1: 3-chloro-benzeneacetonitrile With lithium diisopropyl amide In tetrahydrofuran for 0.166667h; Stage #2: formic acid ethyl ester In tetrahydrofuran at -78 - 20℃; for 16.5h; Stage #3: With hydrogenchloride; water In tetrahydrofuran pH=~ 3;	90%
With sodium hydride 1.) toluene, tert-amyl alcohol, 70 deg C, 2.) toluene, tert-amyl alcohol, from 70 to 80 deg C, 6 h; Yield given. Multistep reaction;
With ethanol; sodium for 16h; Reflux;

3-chloro-benzeneacetonitrile (1529-41-5) + benzaldehyde (100-52-7) → 2-(3-chlorophenyl)-3-phenylacrylonitrile (95065-61-5)

Conditions	Yield
With 20percent deep eutectic solvents(DES) of choline chloride and urea at 20℃; for 0.75h; Knoevenagel Condensation;	90%
With 6C4H12N(1+)*6H2O*Nb10O28(6-) In methanol at 69.84℃; for 24h; Knoevenagel Condensation;	39%

3-chloro-benzeneacetonitrile (1529-41-5) + 3-(hydroxymethyl)-2-(trifluoromethyl)-2H-chromen-2-ol → 2-(3-chlorophenyl)-N-((2-hydroxy-2-(trifluoromethyl)-2H-chromen-3-yl)methyl)acetamide

Conditions	Yield
With tetrafluoroboric acid diethyl ether complex at 20℃; for 0.25h; Ritter Amidation;	90%

N-methyl-bis(chloro-ethyl)amine monohydrochloride + 3-chloro-benzeneacetonitrile (1529-41-5) + cetyltributylphosphonium bromide (14937-45-2) → 1-methyl-4-(3-chlorophenyl)-4-piperidinecarbonitrile (126555-97-3)

Conditions	Yield
With sodium hydroxide In water	88%
With sodium hydroxide In water	88%

3-chloro-benzeneacetonitrile (1529-41-5) + acrylic acid methyl ester (292638-85-8) → C15H14ClNO3

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 25℃; for 1h;	87%

3-chloro-benzeneacetonitrile (1529-41-5) + 2-(4-Chlorophenyl)-2-(4-nitrophenyl)-1,3-dioxolane (190898-64-7) → 3-(3-chlorophenyl)-5-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]-2,1-benzisoxazole (190898-77-2)

Conditions	Yield
With sodium hydroxide In methanol at 60℃; for 1h;	86%
With sodium hydroxide In methanol	47.3 g (70%)

3-chloro-benzeneacetonitrile (1529-41-5) + 6-bromo-3-(hydroxymethyl)-2-(trifluoromethyl)-2H-chromen-2-ol → N-((6-bromo-2-hydroxy-2-(trifluoromethyl)-2H-chromen-3-yl)methyl)-2-(3-chlorophenyl)acetamide

Conditions	Yield
With tetrafluoroboric acid diethyl ether complex at 20℃; for 0.25h; Ritter Amidation;	86%

3-chloro-benzeneacetonitrile (1529-41-5) + Diethyl carbonate (105-58-8) → ethyl α-(3-chlorophenyl)-α-cyanoacetate (92847-34-2)

Conditions	Yield
Stage #1: 3-chloro-benzeneacetonitrile With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Stage #2: Diethyl carbonate In tetrahydrofuran; mineral oil for 0.5h;	85%
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 26h; Heating / reflux;	68%
(i) NaH, Et2O, (ii) /BRN= 956591/; Multistep reaction;
Stage #1: 3-chloro-benzeneacetonitrile With n-butyllithium In tetrahydrofuran; hexane for 2h; Reflux; Stage #2: Diethyl carbonate In tetrahydrofuran; hexane for 5h; Reflux;

3-chloro-benzeneacetonitrile (1529-41-5) → 2-(3-chlorophenyl)acetamide (58357-84-9)

Conditions	Yield
With hydrogenchloride at 65 - 70℃; for 2h;	85%
With hydrogenchloride In water at 65 - 70℃; for 2h; Inert atmosphere;	61%
With water; sodium hydroxide for 1h; Reflux;

3-chloro-benzeneacetonitrile (1529-41-5) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → tert-butyl 4-[(3-chlorophenyl)(cyano)methylidene]piperidine-1-carboxylate (1207438-38-7)

Conditions	Yield
With sodium methylate In methanol for 2h; Reflux;	85%

3-chloro-benzeneacetonitrile (1529-41-5) + 4-methoxy-benzaldehyde (123-11-5) → C16H12ClNO

Conditions	Yield
With amine functionalized silica coated Fe3O4 nanoparticles In water at 20℃; for 1h; Knoevenagel Condensation; Sonication; Green chemistry;	85%

3-chloro-benzeneacetonitrile (1529-41-5) + 2-amino-4-(N,N-dimethylamino)benzaldehyde (56669-96-6) → 3-(3-chlorophenyl)-N7,N7-dimethylquinoline-2,7-diamine

Conditions	Yield
Stage #1: 3-chloro-benzeneacetonitrile With potassium tert-butylate In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: 2-amino-4-(N,N-dimethylamino)benzaldehyde In N,N-dimethyl-formamide at 0 - 90℃;	85%

3-chloro-benzeneacetonitrile (1529-41-5) + 2,3,4-trimethoxybenzaldehyde (2103-57-3) → 3-(2,3,4-trimethoxyphenyl)-2-(3-chlorophenyl)acrylonitrile

Conditions	Yield
Stage #1: 3-chloro-benzeneacetonitrile; 2,3,4-trimethoxybenzaldehyde In ethanol at 70℃; for 0.5h; Knoevenagel Condensation; Stage #2: With sodium hydroxide In ethanol at 70℃;	85%

3-chloro-benzeneacetonitrile (1529-41-5) + N-(4-formylphenyl)carbazole (110677-45-7) → (Z)-3-(-4-(9H-carbazol-9-yl)phenyl)-2-(3-chlorophenyl)acrylonitrile

Conditions	Yield
With sodium methylate In methanol at 60℃; for 3h;	85%

Upstream product

• 108-41-8 1-chloro-3-methylbenzene 
• 151-50-8 potassium cyanide 
• 14503-42-5 3-chlorobenzyl tosylate 
• 13435-20-6 tetraethylammoniumcyanide 
• 41904-40-9 2-(3-chlorophenyl)acetaldehyde 
• 84750-91-4 1-chloro-3-(2,2-difluorovinyl)benzene 
• 773837-37-9 sodium cyanide 
• 620-20-2 1-Chloro-3-chloromethyl-benzene 
• 143-33-9 sodium cyanide 
• 860190-02-9 3-(3-chloro-phenyl)-2-thioxo-propionic acid 
• 766-80-3 1-bromomethyl-3-chlorobenzene 
• 139218-48-7 4-Methoxy-benzenesulfonic acid 3-chloro-benzyl ester 
• 108-24-7 acetic anhydride 

Downstream Products

• 106595-22-6 2,3c-bis-(3-chloro-phenyl)-acrylonitrile 
• 19450-55-6 2-(3-Chloro-phenyl)-N-(octahydro-naphthalen-4a-yl)-acetamide 
• 122376-68-5 (3-chlorophenyl)(2-pyridyl)acetonitrile 
• 58357-84-9 2-(3-chlorophenyl)acetamide 
• 90775-14-7 Bromo-(3-chloro-phenyl)-acetonitrile 
• 925252-77-3 2-(3-chloro-phenyl)-N-hydroxy-acetamidine 
• 13078-79-0 2-(3-chlorophenyl)ethylamine 
• 99726-59-7 2-(3-chlorophenyl)malononitrile 
• 126158-50-7 5-(3-Chloro-phenyl)-3-phenyl-3H-[1,2,3]triazol-4-ylamine 
• 73742-07-1 (3-chlorophenyl)(pyridin-2-yl)methanone 
• 834861-72-2 2-(3-chlorophenyl)ethanethioamide 
• 77186-53-9 3-chloro-α-propionylphenylacetonitrile 
• 1026014-49-2 2-(3-chloro-phenyl)-3-oxo-6-phenyl-hexanenitrile 
• 1026090-42-5 2-(3-chloro-phenyl)-6-(4-methoxy-phenyl)-3-oxo-hexanenitrile 

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