3,4-Dichlorophenylacetonitrile

Base Information

• Chemical Name: 3,4-Dichlorophenylacetonitrile
• CAS No.: 3218-49-3
• Molecular Formula: C8H5Cl2N
• Molecular Weight: 186.04
• Hs Code.: 29269095
• European Community (EC) Number: 221-743-9
• NSC Number: 111725
• DSSTox Substance ID: DTXSID70185959
• Nikkaji Number: J60.901C
• Wikidata: Q72467276
• Mol file: 3218-49-3.mol

Synonyms:3,4-Dichlorophenylacetonitrile;3218-49-3;2-(3,4-dichlorophenyl)acetonitrile;3,4-Dichlorobenzyl cyanide;(3,4-Dichlorophenyl)acetonitrile;Benzeneacetonitrile, 3,4-dichloro-;3,4-dichlorobenzylcyanide;3,4-dichlorobenzeneacetonitrile;EINECS 221-743-9;MFCD00001909;AI3-12074;NSC111725;SCHEMBL2308;3,4-dichloro-phenylacetonitrile;3,4-dichlorophenyl acetonitrile;3,4-dichlorophenyl-acetonitrile;3,4-dichlorophenylaceto-nitrile;DTXSID70185959;(3,4-dichlorophenyl)-acetonitrile;STR03683;(3,4-dichloro-phenyl)-acetonitrile;3,4-Dichlorophenylacetonitrile, 98%;AKOS001141970;AC-2970;CS-W007701;NSC 111725;NSC-111725;PS-4611;AM20061095;D1794;FT-0614240;EN300-21758;A25098;D77685;W-106851;Z111875426;4,4-Dichlorophenylacetonitrile

Chemical Property of 3,4-Dichlorophenylacetonitrile

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.000673mmHg at 25°C
• Melting Point: 39-42 °C(lit.)
• Refractive Index: 1.565
• Boiling Point: 308.6 °C at 760 mmHg
• Flash Point: 125.9 °C
• PSA: 23.79000
• Density: 1.333 g/cm³
• LogP: 3.05948
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 184.9799046
• Heavy Atom Count: 11
• Complexity: 172

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,4-Dichlorophenylacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CC#N)Cl)Cl
• Uses: 3,4-Dichlorophenylacetonitrile was used in the synthesis of:SR 48968, a potent, competitive and selective non-peptide antagonist of the neurokinin A (NK2) receptortachykinin NK3 receptor antagonist SR 142801, (R)-N-[ 1-[3-[ 1-benzoyl-3-(3,4-dichlororphenyl)-3-piperidinyl]propyyl]-4-phenyl-4-piperidinyl-N-methyl acetamideMDL 105,212, a non-peptide tachykinin receptor antagonist

Technology Process of 3,4-Dichlorophenylacetonitrile

There total 11 articles about 3,4-Dichlorophenylacetonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

2-aminoacetonitrile hydrochloride (6011-14-9) + 3,4-dichlophenylboronic acid (151169-75-4) → 3,4-dichloro-benzeneacetonitrile (3218-49-3)

Guidance literature:

With sodium nitrite; In water; toluene; at 50 ℃; for 24h; Schlenk technique;

DOI:10.1002/anie.201406765

Reference yield: 84.0%

3,4-dichlorophenyl acetic acid (5807-30-7) + N-cyano-N-phenyl-p-toluenesulfonamide (55305-43-6) → 3,4-dichloro-benzeneacetonitrile (3218-49-3)

Guidance literature:

3,4-dichlorophenyl acetic acid; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at 0 ℃; for 0.25h; Inert atmosphere;

N-cyano-N-phenyl-p-toluenesulfonamide; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/acs.joc.7b00033

Reference yield: 79.0%

potassium cyanide (151-50-8) + 3,4-dichlorobenzyl bromide (18880-04-1) → 3,4-dichloro-benzeneacetonitrile (3218-49-3)

Guidance literature:

In ethanol; water; for 4h; Heating;

DOI:10.1016/0022-328X(95)05717-4

upstream raw materials:

3,4-Dichlorophenylmethyl chloride

potassium cyanide

3,4-dichlorobenzyl bromide

sodium cyanide

Downstream raw materials:

2-(3,4-dichloro-phenyl)-3-oxo-valeronitrile

2-<3,4-Dichlor-phenyl>-butyronitril

3.4-Dichlor-α-ethoxy-acetylphenylacetonitril

3,4-Dichlor-α-diethoxy-acetyl-phenylacetonitril

Refernces

• 1、 Wu, Guojiao,Deng, Yifan,Wu, Chaoqiang,Zhang, Yan,Wang, Jianbo. "Synthesis of α-aryl esters and nitriles: Deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids". supporting information. p. 10510 - 10514. Retrieved 2016/02/18.
• 2、 Cambie, Richard C.,Clark, George R.,Coombe, Sheryl L.,Coulson, Sally A.,Rutledge, Peter S.,Woodgate, Paul D.. "Towards the synthesis of aminodibenzo[b,e][1,4]dioxin derivatives via cationic ruthenium complexes". . p. 1 - 21. Retrieved 2007/10/03.