4-Chlorobenzyl cyanide

Base Information

• Chemical Name: 4-Chlorobenzyl cyanide
• CAS No.: 140-53-4
• Molecular Formula: C8H6ClN
• Molecular Weight: 151.595
• Hs Code.: 29269095
• European Community (EC) Number: 205-418-9
• NSC Number: 49108
• UNII: K2K7AKZ2Z7
• DSSTox Substance ID: DTXSID8051708
• Nikkaji Number: J38.178K
• Wikidata: Q27102330
• Metabolomics Workbench ID: 50874
• Mol file: 140-53-4.mol

Synonyms:4-Chlorobenzyl cyanide;140-53-4;(4-Chlorophenyl)acetonitrile;4-Chlorophenylacetonitrile;2-(4-Chlorophenyl)acetonitrile;p-Chlorobenzyl cyanide;Benzeneacetonitrile, 4-chloro-;4-Chlorobenzeneacetonitrile;(p-Chlorophenyl)acetonitrile;Acetonitrile, (p-chlorophenyl)-;p-Chlorophenylacetonitrile;4-Chlorobenzylcyanide;4-Chlor-benzyl-cyanid;MFCD00001918;NSC 49108;CCRIS 9100;4-Chlor-benzyl-cyanid [German];EINECS 205-418-9;BRN 0971171;4-Chlorobenzyl--d4 Cyanide;K2K7AKZ2Z7;AI3-05596;DTXSID8051708;2-(4-chlorophenyl)-acetonitrile;NSC-49108;4-09-00-01676 (Beilstein Handbook Reference);4-CHLORO-BENZENEACETONITRILE;4-chloro-benzylcyanide;p-chlorphenylacetonitrile;4-chlorophenyacetonitrile;4-chlorophenylacetonitriie;p-chlorophenyl-acetonitrile;P-CHLORBENZYLNITRILE;4-chlorophenyl acetonitrile;4-chlorophenyl-acetonitrile;UNII-K2K7AKZ2Z7;4-chlorobenzene-acetonitrile;p-Chloro phenyl acetonitrile;SCHEMBL38192;(p-Chlorophenyl)-acetonitrile;(4-chlorophenyl)-acetonitrile;4-CHLOROBENZYL NITRILE;CHLOROBENZYL CYANIDE, P-;DTXCID8030263;2-(4-chlorophenyl) acetonitrile;CHEBI:17346;2-(4-chloro-phenyl)-acetonitrile;NSC49108;(4-Chlorophenyl)acetonitrile, 96%;Tox21_303864;STK202113;P-CHLORO-.ALPHA.-CYANOTOLUENE;AKOS000119502;AC-4376;AM10673;CS-W018106;PB48045;PS-5408;NCGC00357129-01;CAS-140-53-4;ACETIC ACID,(4-CHLOROPHENYL),NITRILE;FT-0618248;EN300-18340;PYRIMETHAMINE IMPURITY C [EP IMPURITY];A23320;C03679;D70879;W-108204;Q27102330;Z57131037;F0001-0482

Chemical Property of 4-Chlorobenzyl cyanide

Chemical Property:

• Appearance/Colour: clear colorless to yellowish liquid after melting
• Vapor Pressure: 0.00887mmHg at 25°C
• Melting Point: 25-28 °C(lit.)
• Refractive Index: n20/D 1.543
• Boiling Point: 266 °C at 760 mmHg
• Flash Point: 107.7 °C
• PSA: 23.79000
• Density: 1.188 g/cm³
• LogP: 2.40608
• Storage Temp.: Store below +30°C.
• Solubility.: 0.3g/l
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 151.0188769
• Heavy Atom Count: 10
• Complexity: 139

Purity/Quality:

≥99% ^*data from raw suppliers

4-Chlorobenzyl Cyanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 23/24/25-36/37/38
• Safety Statements: 26-36/37/39-45-28B

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C1=CC(=CC=C1CC#N)Cl
• Uses: 4-Chlorobenzyl cyanide is an intermediate for the preparation of 3-methyl-2-(4-chlorophenyl)butyric acid, which can be used to prepare pyrethroid insecticides such as fenvalerate and deltamethrin, and can be used in medicine Industrial preparation of pyrimethamine.

Technology Process of 4-Chlorobenzyl cyanide

There total 56 articles about 4-Chlorobenzyl cyanide 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: 99.0%

1-Chloro-4-(chloromethyl)benzene (104-83-6) → p-chlorobenzyl cyanide (140-53-4)

Guidance literature:

With benzyl alcohol; ethanol; N-benzyl-N,N,N-triethylammonium chloride; at 80 ℃; for 2h;

Reference yield: 99.0%

4-Chlorophenylboronic acid (1679-18-1) + 2-aminoacetonitrile hydrochloride (6011-14-9) → p-chlorobenzyl cyanide (140-53-4)

Guidance literature:

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

DOI:10.1002/anie.201406765

Reference yield: 94.0%

3-(4-chloro-phenyl)-2-hydroxyimino-propionic acid (139109-51-6) → p-chlorobenzyl cyanide (140-53-4)

Guidance literature:

With 1,1'-carbonyldiimidazole; In benzene; 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h;

DOI:10.1248/cpb.39.3030

upstream raw materials:

2-(4-chloro-phenyl)-3-oxo-3-phenyl-propionitrile

4-aminobenzyl cyanide hydrochloride

3-(4-chloro-phenyl)-2-hydroxyimino-propionic acid

acetic anhydride

Downstream raw materials:

(Z)-2-(4-chlorophenyl)-3-(pyridin-2-yl)acrylonitrile

2-(4-chloro-phenyl)-3c-[3]pyridyl-acrylonitrile

(Z)-α-(p-chlorophenyl)-β-(2-furyl)acrylonitrile

4-(4-chloro-phenyl)-4-[2]pyridyl-butan-2-one

Refernces

• 1、 Kim, Kunsoon,Lee, Seulchan,Hong, Soon Hyeok. "Direct C(sp3)-H Cyanation Enabled by a Highly Active Decatungstate Photocatalyst". supporting information. p. 5501 - 5505. Retrieved 2021/07/26.
• 2、 Wong, Jeff Y. F.,Lewandowska, Agnieszka,Trowse, Benjamin R.,Barker, Graeme. "Lithiation Substitution of Unprotected Benzyltetrazoles". . p. 7069 - 7072. Retrieved 2019/09/30.