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
• Article Data: 16

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

Description

2,4-Dichlorophenylacetonitrile is an organic compound that exists as a white to light yellow crystal powder. It is a synthetic chemical with a specific molecular structure, which makes it a valuable intermediate in the production of various chemical compounds.

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 
• 76574-78-2 6-(2,4-Dichloro-phenyl)-2-methyl-pyrido[2,3-d]pyrimidin-7-ylamine 
• 64009-16-1 2-(2,4-Dichlorphenyl)-4-phenoxybutyronitril 
• 2184-86-3 2-(2,4-dichlorophenyl)valeronitrile 
• 58844-44-3 2-(2,4-Dichloro-phenyl)-3-methyl-pentanenitrile 
• 64008-45-3 2-(2,4-Dichloro-phenyl)-4-phenyl-butyric acid methyl ester 
• 64008-66-8 2-(2,4-Dichlorphenyl)-4-phenylbutanol 
• 59666-80-7 α-phenethyl-2,4-dichlorobenzyl cyanide 
• 59666-96-5 2,3-bis(2,4-dichlorophenyl)propanenitrile 
• 59667-02-6 α-(2,4-dichlorophenyl)benzenepropanenitrile 
• 59666-95-4 3-(p-chlorophenyl)-2-(2,4-dichlorophenyl)propionitrile 
• 59666-90-9 2-chloro-α-(2,4-dichlorophenyl)benzenepropanenitrile 
• 59666-94-3 2-(2,4-dichlorophenyl)-3-(2,6-dichlorophenyl)propionitrile 
• 64008-46-4 4-(4-Chloro-phenyl)-2-(2,4-dichloro-phenyl)-butyric acid methyl ester 

Relevant articles and documents

Industrial preparation method of 2,4,5-trifluorophenylacetic acid

The invention relates to the technical field of preparation of chemical drug intermediates, and particularly discloses an industrial preparation method of 2,4,5-trifluorophenylacetic acid. The preparation method comprises the following steps: carrying out a nitration reaction, a fluorination reaction, a hydrogenation reduction reaction, a diazotization reaction, a halogenation reaction, a cyaniding reaction, a thermal decomposition reaction and a hydrolysis reaction on 2,4-dichlorotoluene to prepare the 2,4,5-trifluorophenylacetic acid. The method has the advantages of low preparation cost andhigh product yield.

Design and synthesis of a magnetic hierarchical porous organic polymer: A new platform in heterogeneous phase-transfer catalysis

Recyclable phase transfer catalysts containing magnetic nanoparticles (MNPs) have been known as a major trend towards sustainable catalysts. In this study, a novel class of magnetic porous polymer on the basis of calix[4]resorcinarene was synthesized starting from silica-coated Fe3O4 core-shell nanoparticles. This compound was found as an efficient phase transfer catalyst to the conversion of benzyl halides into benzyl azides and cyanides in good yields. The catalyst could be used at least for five consecutive cycles without appreciable loss in the catalytic activity.

Technological method for preparing halogenated-3,4-dihydro-1H-2-naphthalenone

The invention relates to a technological preparation method of halogenated-3,4-dihydro-1H-2-naphthalenone as shown in a formula (I). (As shown in the description). According to the method disclosed by the invention, through a cheap raw material namely 2,4-dihalogeno-benzene carbonitrile, and an intermediate namely 2,4-dihalogeno-benzene acetic acid is synthesized, and through a reusable trifluoroacetic anhydride/acid system catalyst, a target product namely the halogenated-3,4-dihydro-1H-2-naphthalenone is synthesized. According to the method disclosed by the invention, a large quantity of catalysts such as aluminumtrichloride, and costly catalysts such as Rh, are not needed, and the reaction route can be shortened, so that a large quantity of reagents and time can be saved, and the industrial economic benefits can be greatly increased.