28049-61-8

Basic information

• Product Name: 1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile
• Synonyms: CYCLOBUTANECARBONITRILE, 1-(4-CHLOROPHENYL);1-CYANO-1-(4-CHLOROPHENYL)CYCLOBUTANE;1-(4-CHLOROPHENYL)-1-CYCLOBUTANECARBONITRILE;1-(4-CHLOROPHENYL)CYCLOBUTANECARBONITRILE;NSC 154613;SIBU-1;CYCLOBUTANECARBONITRILE, 1-(4-CHLOROPHENYL)(INTERMEDIATE OF SIBUTRAMINE);CYCLOBUTANECARBONITRILE, 1-(4-CHLOROPHENYL)/FOR SIBUTRAMINE
• CAS NO: 28049-61-8
• Molecular Formula: C₁₁H₁₀ClN
• Molecular Weight: 191.66
• EINECS: 248-799-7
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;C10 to C27;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 28049-61-8.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 295 °C(lit.)
• Flash Point: >230 °F
• Appearance: colourless oil
• Density: 1.137 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000351mmHg at 25°C
• Refractive Index: n20/D 1.548(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: 1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile(28049-61-8)
• EPA Substance Registry System: 1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile(28049-61-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 36-36/37/39-26
• RIDADR: UN3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 28049-61-8(Hazardous Substances Data)

Usage

Description

1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile, also known as 1-(4-chlorophenyl)-1-cyanocyclobutane, is a colorless oil with chemical properties that make it a valuable intermediate in the synthesis of various compounds.

Uses

Used in Pharmaceutical Industry:
1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile is used as an intermediate in the preparation of Sibutramine and its respective metabolites. Sibutramine is an anti-obesity drug that has been used to aid in weight loss and maintenance.
Additionally, 1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile can be used in the synthesis of pharmacologically active metabolites of Sibutramine, which may have potential applications in the treatment of obesity and related health conditions.

InChI:InChI=1/C11H10ClN/c12-10-4-2-9(3-5-10)11(8-13)6-1-7-11/h2-5H,1,6-7H2

Upstream product

• 109-64-8 1,3-dibromo-propane 
• 140-53-4 p-chlorobenzyl cyanide 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 4426-11-3 cyclobutanecarbonitrile 
• 84467-19-6 1-(3,4-dichlorophenyl)-1-cyclobutanecarbonitrile 
• 106-39-8 bromochlorobenzene 

Downstream Products

• 29786-47-8 1-(4-chlorophenyl)cyclobutane-1-carboxamide 
• 63010-09-3 C-[1-(4-chlorophenyl)cyclobutyl]methylamine 
• 50921-39-6 1-(4-chlorophenyl)cyclobutane-1-carboxylic acid 
• 186521-85-7 1-[1-(4-chloro-phenyl)cyclobutyl]-3-methyl-butan-1-one 
• 106650-56-0 didesmethylsibutramine 
• 421558-88-5 1-[1-(4-chloro-phenyl)-cyclobutyl]-3-methyl-butylideneamine 
• 106079-12-3 1-(4-chlorophenyl)-cyclobutanecarboxaldehyde 
• 229639-56-9 (R)-N-{1-[1-(4-Chlorophenyl)cyclobutyl]-3-methylbutyl}amine 
• 229639-57-0 (S)-(-)-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine 
• 858645-29-1 (R)-N-(1-(4-chlorophenyl)cyclobutanemethylene)-t-butanesulfinamide 
• 84467-85-6 N-{1-[1-(4-chlorophenylcyclobutyl)]-3-methylbuty}formamide 
• 84467-94-7 (+/-)-Desmethylsibutramine hydrochloride 
• 84467-94-7 (+)-Desmethylsibutramine hydrochloride 
• 84467-94-7 (-)-Desmethylsibutramine hydrochloride 

Relevant articles and documents

Iridium-Catalyzed Enantioselective C(sp3)–H Borylation of Cyclobutanes

We herein report the first example of iridium-catalyzed enantioselective C(sp3)–H borylation of cyclobutanes using benzoxazoline as the directing group. The combination of a chiral bidentate boryl ligand and an iridium precursor has found to effectively catalyze C(sp3)–H borylation to afford a variety of cyclobutylboronates with good to excellent enantioselectivities. We also demonstrate the synthetic utility of the current method by converting the stereogenic C—B bond to other functionalities.

Identification of A Novel Small-Molecule Binding Site of the Fat Mass and Obesity Associated Protein (FTO)

N-(5-Chloro-2,4-dihydroxyphenyl)-1-phenylcyclobutanecarboxamide (N-CDPCB, 1a) is found to be an inhibitor of the fat mass and obesity associated protein (FTO). The crystal structure of human FTO with 1a reveals a novel binding site for the FTO inhibitor and defines the molecular basis for recognition by FTO of the inhibitor. The identification of the new binding site offers new opportunities for further development of selective and potent inhibitors of FTO, which is expected to provide information concerning novel therapeutic targets for treatment of obesity or obesity-associated diseases.

SYNTHESIS, METHODS OF USING, AND COMPOSITIONS OF CYCLOALKYLMETHYLAMINES

The present invention provides novel cycloalkylmethylamine analogs, and methods of preparing cycloalkylmethylamine analogs. The present invention also provides methods of using cycloalkylmethylamine analogs and compositions of cycloalkylmethylamine analogs. The pharmaceutical compositions of the compounds of the present invention can be advantageously used for treating and/or preventing obesity and obesity related co-morbid indications.