14377-68-5

Basic information

• Product Name: 1-Phenylcyclobutanecarbonitrile
• Synonyms: 1-PHENYLCYCLOBUTANECARBONITRILE;1-PHENYLCYCLOBUTANECARBONITRILE 95%;1-Phenylcyclobutane-1-carbonitrile;1-Phenylcyclobutanecarbonitrile,95%;1-Phenylcyclobutanecarbonitrile, 95% 25GR;1-Phenylcyclobutanecarbonitrile, 95% 5GR;Cyclobutanecarbonitrile, 1-phenyl-
• CAS NO: 14377-68-5
• Molecular Formula: C₁₁H₁₁N
• Molecular Weight: 157.21
• EINECS: 238-351-9
• Product Categories: Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 14377-68-5.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 85°C/0.3mmHg(lit.)
• Flash Point: 106.3 °C
• Appearance: Clear light yellow/Liquid
• Density: 1.03
• Vapor Pressure: 0.00201mmHg at 25°C
• Refractive Index: 1.5313-1.5333
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-Phenylcyclobutanecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenylcyclobutanecarbonitrile(14377-68-5)
• EPA Substance Registry System: 1-Phenylcyclobutanecarbonitrile(14377-68-5)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26
• Hazardous Substances Data: 14377-68-5(Hazardous Substances Data)

Usage

Description

1-Phenylcyclobutanecarbonitrile is an organic compound characterized by its clear light yellow liquid appearance. It is a derivative of cyclobutane with a phenyl group attached and a carbonitrile functional group, which contributes to its unique chemical properties and potential applications in various industries.

Uses

1. Used in Pharmaceutical Industry:
1-Phenylcyclobutanecarbonitrile is used as a reactant for the preparation of a novel diacylglycerol acyltransferase-1 (DGAT-1) inhibitor. DGAT-1 is an enzyme involved in the synthesis of triglycerides, and its inhibition can potentially lead to the development of treatments for obesity and related metabolic disorders.
2. Used in Chemical Synthesis:
1-Phenylcyclobutanecarbonitrile, due to its unique chemical structure, can be employed as an intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its carbonitrile group can be further functionalized to introduce different functional groups, making it a versatile building block in organic synthesis.
3. Used in Material Science:
The compound's chemical properties may also find applications in the development of new materials with specific properties, such as polymers with tailored characteristics for use in coatings, adhesives, or plastics.

InChI:InChI=1/C11H11N/c12-9-11(7-4-8-11)10-5-2-1-3-6-10/h1-3,5-6H,4,7-8H2

Upstream product

• 140-29-4 phenylacetonitrile 
• 109-64-8 1,3-dibromo-propane 
• 142-28-9 1,3-Dichloropropane 

Downstream Products

• 1469-83-6 1-phenyl-1-cyclobutane-carbaldehyde 
• 106650-56-0 didesmethylsibutramine 
• 1198-34-1 2-Phenylcyclopentanone 
• 811803-25-5 1-(4-aminophenyl)cyclobutanecarbonitrile 
• 1236409-70-3 ethyl 3-(4-(1-cyanocyclobutyl)phenylamino)propanoate 
• 1236410-58-4 ethyl 3-(2-cyano-N-(4-(1-cyanocyclobutyl)phenyl)acetamido)propanoate 
• 1236409-72-5 1-(4-(1-cyanocyclobutyl)phenyl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile 
• 1492906-24-7 C₁₇H₁₄ClN₃O 
• 1236409-75-8 1-(4-(1-cyanocyclobutyl)phenyl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile 
• 1492906-25-8 C₁₈H₁₅N₅O 
• 1236408-39-1 1-(4-(4-amino-2-methoxy-5-oxo-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-phenyl)cyclobutanecarbonitrile 
• 61492-32-8 (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(1-phenyl-cyclobutanecarbonyl)-amino]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 1007-70-1 Methyl(1-phenylcyclobutyl)ether 
• 7306-20-9 1,1'-Diphenyl-1,1'-bicyclobutyl 

Relevant articles and documents

Phase transfer alkylation of arylacetonitriles revisited

Phase transfer alkylations of phenylacetonitrile derivatives carried out in the presence of 60-75% aqueous KOH, instead of the typical 50% NaOH, provide substantial improvements in the overall yields and purity of products. Reactions with simple secondary alkyl halides, as well as cycloalkylations with 1,2- and 1,3-dihaloalkanes proceed with good yields. Increasing the concentration of base diminishes the formation of by-products from competitive β-elimination processes.

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.