3-Chlorobenzoylacetonitrile

Base Information

• Chemical Name: 3-Chlorobenzoylacetonitrile
• CAS No.: 21667-62-9
• Molecular Formula: C9H6 Cl N O
• Molecular Weight: 179.606
• Hs Code.: 29269090
• European Community (EC) Number: 626-892-7
• NSC Number: 31892
• DSSTox Substance ID: DTXSID20176054
• Nikkaji Number: J243.015K
• Wikidata: Q83046388
• ChEMBL ID: CHEMBL228247
• Mol file: 21667-62-9.mol

Synonyms:3-Chlorobenzoylacetonitrile;21667-62-9;3-(3-chlorophenyl)-3-oxopropanenitrile;3-Chlorophenacylcyanide;MFCD00067891;(3-chlorobenzoyl)acetonitrile;3-CHLOROBENZOYLACETONITIRLE;NSC31892;beta-ketonitrile 5b;OLEYLACETATE;3-(3-chlorophenyl)-3-oxo-propanenitrile;Maybridge1_004670;SCHEMBL134693;3'-Chloro-2-cyanoacetophenone;CHEMBL228247;2-(3-Chlorobenzoyl)acetonitrile;BDBM16185;HMS554M06;DTXSID20176054;3-Chlorobenzoylacetonitrile, 97%;?3-CHLOROBENZOYLACETONITRILE;CL8860;NSC 31892;NSC-31892;Benzenepropanenitrile,3-chloro-b-oxo-;AKOS000206305;AA-0866;CS-W019269;3-(3-chlorophenyl)-3-oxo-propionitrile;SY037741;A4657;AM20061107;Benzenepropanenitrile, 3-chloro-.beta.-oxo-;C2581;FT-0604210;EN300-24692;W-206666;Z199507038

Chemical Property of 3-Chlorobenzoylacetonitrile

Chemical Property:

• Vapor Pressure: 5.49E-05mmHg at 25°C
• Melting Point: 78 °C
• Boiling Point: 347.1°Cat760mmHg
• PKA: 7.12±0.10(Predicted)
• Flash Point: 163.7°C
• PSA: 40.86000
• Density: 1.257g/cm³
• LogP: 2.43638
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 179.0137915
• Heavy Atom Count: 12
• Complexity: 218

Purity/Quality:

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

3-(3-Chlorophenyl)-3-oxopropanenitrile ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)Cl)C(=O)CC#N

Technology Process of 3-Chlorobenzoylacetonitrile

There total 18 articles about 3-Chlorobenzoylacetonitrile 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%

3-chloro-benzoic acid ethyl ester (1128-76-3) + acetonitrile (75-05-8,26809-02-9) → 3-chlorobenzoylacetonitrile (21667-62-9)

Guidance literature:

With naphthalene; potassium; In toluene; at 5 - 10 ℃; for 1.5h; ultrasonic irradiation;

DOI:10.1080/00304940109356599

Reference yield: 83.0%

m-chlorobenzyl alcohol (873-63-2) + acetonitrile (75-05-8,26809-02-9) → 3-chlorobenzoylacetonitrile (21667-62-9)

Guidance literature:

With oxygen; potassium hydroxide; copper dichloride; In N,N-dimethyl acetamide; at 20 ℃; for 12h; Green chemistry;

DOI:10.1021/ol403555n

Reference yield: 81.0%

diazoacetonitrile (13138-21-1) + m-Chlorobenzaldehyde (587-04-2) → 3-chlorobenzoylacetonitrile (21667-62-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃;

DOI:10.1002/ejoc.201402901

upstream raw materials:

3-amino-3-(3-chlorophenyl)acrylonitrile

methyl 3-chlorobenzoate

acetonitrile

3-chloro-benzoic acid ethyl ester

Downstream raw materials:

α-(3-Chlorobenzoyl)acetamide

1-(3-chlorophenyl)-2-cyanovinyl 4-methylbenzenesulfonate

(R)-3-hydroxy-3-(3’-chlorophenyl)-propanenitrile

C₁₄H₇ClN₄O₂S

Refernces

• 1、 Liu, Chong,Yuan, Jing,Zhang, Zhenfeng,Gridnev, Ilya D.,Zhang, Wanbin. "Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C3-Chirogenic Center". supporting information. p. 8997 - 9002. Retrieved 2021/03/16.
• 2、 Sharma, Pawan K.,Kumar, Rajiv,Ram, Sita,Chandak, Navneet. "Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions". . p. 1847 - 1856. Retrieved 2021/04/26.