1-(4-Chlorophenyl)cyclobutanecarbonitrile

Base Information

• Chemical Name: 1-(4-Chlorophenyl)cyclobutanecarbonitrile
• CAS No.: 28049-61-8
• Molecular Formula: C11H10ClN
• Molecular Weight: 191.66
• Hs Code.: 29269095
• European Community (EC) Number: 248-799-7
• NSC Number: 154613
• UNII: 35U5QL7HSY
• DSSTox Substance ID: DTXSID30182328
• Nikkaji Number: J250.638F
• Wikidata: Q72456665
• Mol file: 28049-61-8.mol

Synonyms:1-(4-Chlorophenyl)cyclobutanecarbonitrile;28049-61-8;1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile;1-(4-chlorophenyl)cyclobutane-1-carbonitrile;1-(4-Chlorophenyl)cyclobutane Carbonitrile;Cyclobutanecarbonitrile, 1-(4-chlorophenyl)-;EINECS 248-799-7;NSC-154613;1-(4-Chlorophenyl)cyclobutane-d6Carbonitrile;NSC154613;CCBC;NSC 154613;1-(p-Chlorophenyl)cyclobutanecarbonitrile;1-(4-Chlorophenyl)-cyclobutanecarbonitrile;SCHEMBL2218;35U5QL7HSY;DTXSID30182328;AMY40876;MFCD00065239;1-(4-chlorophenyl)cyclobutane nitrile;AKOS005216180;CS-W010718;1--(4-chlorophenyl)cyclobutane nitrile;1-(4-chlorophenyl)cylcobutanecarbonitrile;AC-19028;AS-66135;1-(4-Chlorophenyl)cyclobutane-carbonitrile;1-(4-chloro-phenyl)-cyclobutanecarbonitrile;A5366;C3161;Cyclobutanecarbonitrile, 1-(p-chlorophenyl)-;FT-0605678;FT-0638749;1-(4-chlorophenyl)-1-cyclobutane carbonitrile;D70099;1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile, 97%;W-107079

Chemical Property of 1-(4-Chlorophenyl)cyclobutanecarbonitrile

Chemical Property:

• Appearance/Colour: colourless oil
• Vapor Pressure: 0.000351mmHg at 25°C
• Refractive Index: n20/D 1.548(lit.)
• Boiling Point: 318.884 °C at 760 mmHg
• Flash Point: 136.351 °C
• PSA: 23.79000
• Density: 1.207 g/cm³
• LogP: 3.28528
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 191.0501770
• Heavy Atom Count: 13
• Complexity: 228

Purity/Quality:

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

1-(4-Chlorophenyl)cyclobutaneCarbonitrile ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C1)(C#N)C2=CC=C(C=C2)Cl
• Uses: An intermediate in the preparation of Sibutramine and respective metabolites 1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile (1-(4-chlorophenyl)-1-cyanocyclobutane) can be used in the synthesis of pharmacologically active metabolites of the anti-obesity drug-sibutramine.

Technology Process of 1-(4-Chlorophenyl)cyclobutanecarbonitrile

There total 8 articles about 1-(4-Chlorophenyl)cyclobutanecarbonitrile 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: 96.0%

bromochlorobenzene (106-39-8) + cyclobutanecarbonitrile (4426-11-3) → 1-(4-chlorophenyl)cyclobutanecarbonitrile (28049-61-8)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium hexamethyldisilazane; In tetrahydrofuran; at 80 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol5030426

Reference yield: 90.0%

1-Chloro-4-fluorobenzene (352-33-0) + cyclobutanecarbonitrile (4426-11-3) → 1-(4-chlorophenyl)cyclobutanecarbonitrile (28049-61-8)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)00297-6

Reference yield: 79.0%

1,3-dibromo-propane (109-64-8) + p-chlorobenzyl cyanide (140-53-4) → 1-(4-chlorophenyl)cyclobutanecarbonitrile (28049-61-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 12h;

upstream raw materials:

1,3-dibromo-propane

p-chlorobenzyl cyanide

1-Chloro-4-fluorobenzene

cyclobutanecarbonitrile

Downstream raw materials:

sibutramine hydrochloride

1-[1-(4-chloro-phenyl)cyclobutyl]-3-methyl-butan-1-one

{3-[1-(4-chloro-phenyl)-cyclobutyl]-[1,2,4]oxadiazol-5-ylmethyl}-{2-[4-(2-methoxy-phenyl)-piperidin-1-yl]-ethyl}-amine hydrochloride

{3-[1-(4-chloro-phenyl)-cyclobutyl]-[1,2,4]oxadiazol-5-ylmethyl}-{2-[4-(2-methoxy-phenyl)-piperidin-1-yl]-ethyl}-amine

Refernces

• 1、 -. "Oxadiazole Amine Derivative Compounds as Histone Deacetylase 6 Inhibitor, and the Pharmaceutical Composition Comprising the same". Paragraph 0484-0487. . Retrieved 2017/07/18.
• 2、 McCabe Dunn, Jamie M.,Kuethe, Jeffrey T.,Orr, Robert K.,Tudge, Matthew,Campeau, Louis-Charles. "Development of a palladium-catalyzed α-arylation of cyclopropyl nitriles". supporting information. p. 6314 - 6317. Retrieved 2015/02/19.