6306-60-1

Basic information

• Product Name: 2,4-Dichlorophenylacetonitrile
• Synonyms: 2,4-DICHLOROPHENYLACETONITRILE;2,4-DICHLOROBENZYL CYANIDE;2,4-DCCN;2-(2,4-Dichlorophenyl)acetonitrile;2,4-Dichlorobenzeneacetonitrile;Acetonitrile, (2,4-dichlorophenyl)-;2,4-dichloro cyanobenzene;2,4-Dichlorophenylacetonitrile,98%
• CAS NO: 6306-60-1
• Molecular Formula: C₈H₅Cl₂N
• Molecular Weight: 186.04
• EINECS: 228-621-4
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;Nitrile;Building Blocks;C8 to C9;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 6306-60-1.mol

Chemical Properties

• Melting Point: 58-61 °C(lit.)
• Boiling Point: 306.06°C (rough estimate)
• Flash Point: 176 °C
• Appearance: white to light yellow crystal powder
• Density: 1.4274 (rough estimate)
• Vapor Pressure: 0.00299mmHg at 25°C
• Refractive Index: 1.5690 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• BRN: 2047688
• CAS DataBase Reference: 2,4-Dichlorophenylacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichlorophenylacetonitrile(6306-60-1)
• EPA Substance Registry System: 2,4-Dichlorophenylacetonitrile(6306-60-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36/37/39
• RIDADR: 3276
• WGK Germany: 1
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 6306-60-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dichlorophenylacetonitrile is used as a key intermediate in the synthesis of 2,4-dichloromandelic acid, which is an important compound in the pharmaceutical industry. The synthesis of 2,4-dichloromandelic acid from 2,4-Dichlorophenylacetonitrile is crucial for the development of certain pharmaceutical products, highlighting its significance in this application.

InChI:InChI=1/C8H5Cl2N/c9-7-1-2-8(10)6(5-7)3-4-11/h1-2,5H,3H2

Synthetic route

sodium cyanide (773837-37-9) + 2,4-Dichlorobenzyl chloride (94-99-5) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
With tetrabutylammomium bromide In water; 1,2-dichloro-ethane at 70℃; for 5h;	88.1%
With sodium iodide In methanol for 6h; Finkelstein reaction; Reflux;	87%
With polyethylene glycol functionalized magnetic dicationic ionic liquid In water for 1.25h; Reflux; Green chemistry;	84%

2,4-dichloro-1-(methoxymethoxy)methyl benzene (877468-98-9) + tetra-n-butylammonium cyanide (10442-39-4) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
With phosphotungstic acid at 130 - 142℃; for 0.05h; Microwave irradiation; Ionic liquid; chemoselective reaction;	89%
With 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0916667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;	82%
With 1-methyl-3H-imidazolium nitrate at 135 - 140℃; for 0.075h; Microwave irradiation;	82%

2,4-dichlorophenylacetic acid (19719-28-9) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
With sodium azide; TEA; triethylphosphine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane; dimethyl sulfoxide at 0℃; for 30h;	92%

sodium cyanide (773837-37-9) + 2,4-dichlorobenzyl bromide (20443-99-6) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
In ethanol; water	93%
With silica-coated Fe3O4 nanoparticles-functionalized polycalix[4]resorcinarene In water at 90℃; for 0.333333h; Green chemistry;	80%

2,4-dichloro-1-[(ethoxymethoxy)methyl]benzene (1058649-24-3) + tetra-n-butylammonium cyanide (10442-39-4) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
With 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0916667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;	80%

potassium cyanide (151-50-8) + 2,4-Dichlorobenzyl chloride (94-99-5) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
With ethanol

sodium cyanide (143-33-9) + 2,4-Dichlorobenzyl chloride (94-99-5) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
In dimethyl sulfoxide at 40 - 50℃; for 5h; Yield given;

→ 2,4-Dichlorophenylacetonitrile

Conditions	Yield
Multi-step reaction with 2 steps 1: PBr3 / CH2Cl2 View Scheme
Multi-step reaction with 2 steps 1: phosphorus tribromide / dichloromethane; N,N-dimethyl-formamide / 80 °C 2: ethanol; water View Scheme
Multi-step reaction with 3 steps 1: diethylamino-sulfur trifluoride / dichloromethane / 1 h / -78 - 20 °C 2: tris(pentafluorophenyl)borate / 1,2-dichloro-ethane / 0.08 h / 20 °C / Glovebox; Schlenk technique 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C View Scheme

sodium cyanide (773837-37-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h;

→ 2,4-Dichlorophenylacetonitrile

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2, (PhCO)2O2 View Scheme
Multi-step reaction with 2 steps 1: 2,2'-azobis(isobutyronitrile); chlorine / 3 h / 110 °C 2: tetrabutylammomium bromide / 1,2-dichloro-ethane; water / 5 h / 70 °C View Scheme

2,4-dichlorobenzylnitrile → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / 2 h / 125 - 130 °C 2: sodium bis(2-methoxyethoxy)aluminium dihydride / diethyl ether / 1 h / 20 °C 3: phosphorus tribromide / dichloromethane; N,N-dimethyl-formamide / 80 °C 4: ethanol; water View Scheme

2,4 dichlorobenzoic acid (50-84-0) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium bis(2-methoxyethoxy)aluminium dihydride / diethyl ether / 1 h / 20 °C 2: phosphorus tribromide / dichloromethane; N,N-dimethyl-formamide / 80 °C 3: ethanol; water View Scheme

2,4-dichlorobenzyl fluoride → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: tris(pentafluorophenyl)borate / 1,2-dichloro-ethane / 0.08 h / 20 °C / Glovebox; Schlenk technique 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C View Scheme

potassium cyanide (151-50-8) + 2,4-dichlorobenzyl bromide (20443-99-6) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

2,4-Dichlorophenylacetonitrile (6306-60-1) + cyclopentanone (120-92-3) → 2,4-bis(2,4-dichlorobenzyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine

Conditions	Yield
With trifluoromethylsulfonic anhydride In chloroform for 47h; Heating;	99%

2,4-Dichlorophenylacetonitrile (6306-60-1) + 1-(4'-methylbenzenesulfonyl)-1H-benzo[d][1.2.3]triazole (1028-19-9) → (2,4-dichlorophenyl)(toluene-4-sulfonyl)acetonitrile

Conditions	Yield
Stage #1: 2,4-Dichlorophenylacetonitrile With potassium tert-butylate In dimethyl sulfoxide for 0.166667h; cooling; Stage #2: 1-(4'-methylbenzenesulfonyl)-1H-benzo[d][1.2.3]triazole In dimethyl sulfoxide at 20℃; for 8h;	97%

sodium cyanide (773837-37-9) + 2,4-dichlorobenzyl bromide (20443-99-6) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
In ethanol; water	93%
With silica-coated Fe3O4 nanoparticles-functionalized polycalix[4]resorcinarene In water at 90℃; for 0.333333h; Green chemistry;	80%

2,4-dichlorophenylacetic acid (19719-28-9) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
With sodium azide; TEA; triethylphosphine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane; dimethyl sulfoxide at 0℃; for 30h;	92%

2,4-dichloro-1-(methoxymethoxy)methyl benzene (877468-98-9) + tetra-n-butylammonium cyanide (10442-39-4) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
With phosphotungstic acid at 130 - 142℃; for 0.05h; Microwave irradiation; Ionic liquid; chemoselective reaction;	89%
With 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0916667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;	82%
With 1-methyl-3H-imidazolium nitrate at 135 - 140℃; for 0.075h; Microwave irradiation;	82%

sodium cyanide (773837-37-9) + 2,4-Dichlorobenzyl chloride (94-99-5) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
With tetrabutylammomium bromide In water; 1,2-dichloro-ethane at 70℃; for 5h;	88.1%
With sodium iodide In methanol for 6h; Finkelstein reaction; Reflux;	87%
With polyethylene glycol functionalized magnetic dicationic ionic liquid In water for 1.25h; Reflux; Green chemistry;	84%

2,4-dichloro-1-[(ethoxymethoxy)methyl]benzene (1058649-24-3) + tetra-n-butylammonium cyanide (10442-39-4) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
With 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0916667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;	80%

potassium cyanide (151-50-8) + 2,4-Dichlorobenzyl chloride (94-99-5) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
With ethanol

sodium cyanide (143-33-9) + 2,4-Dichlorobenzyl chloride (94-99-5) → 2,4-Dichlorophenylacetonitrile (6306-60-1)

Conditions	Yield
In dimethyl sulfoxide at 40 - 50℃; for 5h; Yield given;

Upstream product

• 151-50-8 potassium cyanide 
• 94-99-5 2,4-Dichlorobenzyl chloride 
• 143-33-9 sodium cyanide 
• 20443-99-6 2,4-dichlorobenzyl bromide 
• 1777-82-8 (2,4-dichlorophenyl)methanol 
• 95-73-8 2,4-dichlorotoluene 
• 19719-28-9 2,4-dichlorophenylacetic acid 
• 877468-98-9 2,4-dichloro-1-(methoxymethoxy)methyl benzene 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 1058649-24-3 2,4-dichloro-1-[(ethoxymethoxy)methyl]benzene 
• 773837-37-9 sodium cyanide 
• 6574-98-7 2,4-dichlorobenzylnitrile 
• 50-84-0 2,4 dichlorobenzoic acid 
• 60211-56-5 2,4-dichlorobenzyl fluoride 

Downstream Products

• 96461-91-5 (2,4-dichloro-phenyl)-[2]pyridyl-acetonitrile 
• 131410-42-9 3c-benzo[1,3]dioxol-5-yl-2-(2,4-dichloro-phenyl)-acrylonitrile 
• 19719-28-9 2,4-dichlorophenylacetic acid 
• 52516-13-9 2-(2,4-dichloro-phenyl)-ethylamine 
• 18970-83-7 Bis-[2-(2,4-dichloro-phenyl)-ethyl]-amine 
• 65619-23-0 4-(2,4-Dichlorphenyl)-4-cyanopimelinsaeuredimethylester 
• 76574-78-2 6-(2,4-Dichloro-phenyl)-2-methyl-pyrido[2,3-d]pyrimidin-7-ylamine 
• 26923-38-6 2-(2,4-Dichloro-phenyl)-acrylonitrile 
• 132205-69-7 3-Cyano-3-(2,4-dichloro-phenyl)-propionic acid tert-butyl ester 
• 874-42-0 2,4-dichlorobenzaldeyhde 
• 68284-72-0 2-(2,4-Dichloro-phenyl)-4-diisopropylamino-butyronitrile 
• 128862-86-2 1-phenyl-4-(2,4-dichlorophenyl)-5,6,8-tribenzoyl-2-oxabicyclo<2.2.2>octan-3-one 
• 64009-24-1 2-(2.4-Dichlorphenyl)-5-phenoxyvaleronitril 
• 64009-26-3 5-(4-Chloro-phenoxy)-2-(2,4-dichloro-phenyl)-pentanenitrile 

Relevant articles and documents

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