3-Chloro-3-(4-chlorophenyl)acrylonitrile

Base Information

• Chemical Name: 3-Chloro-3-(4-chlorophenyl)acrylonitrile
• CAS No.: 78583-86-5
• Molecular Formula: C9H5 Cl2 N
• Molecular Weight: 198.051
• Hs Code.: 2926909090
• European Community (EC) Number: 673-945-5
• DSSTox Substance ID: DTXSID00420769
• Nikkaji Number: J267.448C,J2.493.647C
• Wikidata: Q76310728
• Mol file: 78583-86-5.mol

Synonyms:3-Chloro-3-(4-chlorophenyl)acrylonitrile;78583-86-5;(Z)-3-chloro-3-(4-chlorophenyl)prop-2-enenitrile;(2z)-3-chloro-3-(4-chlorophenyl)prop-2-enenitrile;DTXSID00420769;MFCD00052456;AKOS009158039;3-Chloro-3-(4-chlorophenyl)propenenitrile;(Z)-3-(4-Chlorophenyl)-3-chloroacrylonitrile;A839451;(Z)-3-chloro-3-(4-chlorophenyl)-2-propenenitrile;(Z)-3-Chloro-3-(4-chlorophenyl)acrylonitrile, AldrichCPR

Chemical Property of 3-Chloro-3-(4-chlorophenyl)acrylonitrile

Chemical Property:

• Vapor Pressure: 0.000379mmHg at 25°C
• Melting Point: 80-85°C
• Boiling Point: 317.7°C at 760 mmHg
• Flash Point: 140°C
• PSA: 23.79000
• Density: 1.316g/cm³
• LogP: 3.44328
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 196.9799046
• Heavy Atom Count: 12
• Complexity: 218

Purity/Quality:

99% ^*data from raw suppliers

3-Chloro-3-(4-chlorophenyl)acrylonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=CC#N)Cl)Cl
• Isomeric SMILES: C1=CC(=CC=C1/C(=C/C#N)/Cl)Cl

Technology Process of 3-Chloro-3-(4-chlorophenyl)acrylonitrile

There total 6 articles about 3-Chloro-3-(4-chlorophenyl)acrylonitrile 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: 59.0%

(Z)-3-Chloro-3-(4-chloro-phenyl)-propenal oxime (88534-53-6) → (E)-3-Chloro-3-(4-chloro-phenyl)-acrylonitrile (78583-86-5)

Guidance literature:

With acetic anhydride; for 4h; Heating;

Reference yield:

para-chloroacetophenone (99-91-2) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → (E)-3-Chloro-3-(4-chloro-phenyl)-acrylonitrile (78583-86-5)

Guidance literature:

With hydroxylamine hydrochloride; trichlorophosphate; Yield given. Multistep reaction; 1) 30 min, RT, 2) 30 min, 210 deg C;

Reference yield:

3‐chloro‐3‐(4‐chlorophenyl)acrylaldehyde (14063-77-5) → (E)-3-Chloro-3-(4-chloro-phenyl)-acrylonitrile (78583-86-5)

Guidance literature:

With ammonium hydroxide; iodine; In dichloromethane; water; at 20 ℃; for 0.75h;

DOI:10.1080/00397911.2021.1910846

upstream raw materials:

para-chloroacetophenone

N,N-dimethyl-formamide

(Z)-3-Chloro-3-(4-chloro-phenyl)-propenal oxime

[3-chloro-3-(4-chloro-phenyl)-allylidene]-dimethyl-ammonium; perchlorate

Downstream raw materials:

3-(4-chlorophenyl)-1H-pyrazol-5-amine

N-[5-(4-Chloro-phenyl)-1-methyl-1H-pyrazol-3-yl]-4-methyl-benzenesulfonamide

N-[5-(4-Chloro-phenyl)-2-methyl-2H-pyrazol-3-yl]-4-methyl-benzenesulfonamide

2-Ethoxycarbonyl-3-(4-dimethylaminophenylazo)-5-(4-chlorophenyl)-thiophene

Refernces

• 1、 Sharma, Pawan K.,Kumar, Rajiv,Ram, Sita,Chandak, Navneet. "Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions". supporting information. p. 1847 - 1856. Retrieved 2021/04/26.
• 2、 Romagnoli, Romeo,Prencipe, Filippo,Oliva, Paola,Baraldi, Stefania,Baraldi, Pier Giovanni,Schiaffino Ortega, Santiago,Chayah, Mariem,Kimatrai Salvador, Maria,Lopez-Cara, Luisa Carlota,Brancale, Andrea,Ferla, Salvatore,Hamel, Ernest,Ronca, Roberto,Bortolozzi, Roberta,Mariotto, Elena,Mattiuzzo, Elena,Viola, Giampietro. "Design, Synthesis, and Biological Evaluation of 6-Substituted Thieno[3,2- d]pyrimidine Analogues as Dual Epidermal Growth Factor Receptor Kinase and Microtubule Inhibitors". supporting information. p. 1274 - 1290. Retrieved 2019/01/30.