1-(4-Methylphenyl)-1-cyclopropanecarbonitrile

Base Information

• Chemical Name: 1-(4-Methylphenyl)-1-cyclopropanecarbonitrile
• CAS No.: 71172-78-6
• Molecular Formula: C11H11N
• Molecular Weight: 157.215
• Hs Code.: 2926909090
• European Community (EC) Number: 275-240-4
• NSC Number: 155168
• UNII: J2Y3R9QBH4
• DSSTox Substance ID: DTXSID50221369
• Nikkaji Number: J267.425D
• Wikidata: Q72494764
• Mol file: 71172-78-6.mol

Synonyms:71172-78-6;1-(4-METHYLPHENYL)-1-CYCLOPROPANECARBONITRILE;1-(4-methylphenyl)cyclopropanecarbonitrile;1-(p-Tolyl)cyclopropanecarbonitrile;1-p-tolylcyclopropanecarbonitrile;1-(4-methylphenyl)cyclopropane-1-carbonitrile;J2Y3R9QBH4;EINECS 275-240-4;MFCD00065228;NSC-155168;NSC155168;UNII-J2Y3R9QBH4;SCHEMBL1020434;AMY6312;DTXSID50221369;WCA17278;1-p-tolylcyclopropane-1-carbonitrile;AKOS009375018;AB02616;NSC 155168;SY225596;TS-02097;CS-0088473;FT-0605870;A866486;CYCLOPROPANECARBONITRILE, 1-(4-METHYLPHENYL)-

Chemical Property of 1-(4-Methylphenyl)-1-cyclopropanecarbonitrile

Chemical Property:

• Appearance/Colour: clear yellow liquid
• Vapor Pressure: 0.00178mmHg at 25°C
• Refractive Index: 1.5333-1.5353
• Boiling Point: 293 °C at 760 mmHg
• Flash Point: 107.2 °C
• PSA: 23.79000
• Density: 1.06 g/cm³
• LogP: 2.55018
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 157.089149355
• Heavy Atom Count: 12
• Complexity: 210

Purity/Quality:

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

1-(P-TOLYL)-1-CYCLOPROPANECARBONITRILE AldrichCPR ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C2(CC2)C#N

Technology Process of 1-(4-Methylphenyl)-1-cyclopropanecarbonitrile

There total 8 articles about 1-(4-Methylphenyl)-1-cyclopropanecarbonitrile 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: 82.0%

(Z)-2-(p-tolyl)cyclobutan-1-one O-(4-(trifluoromethyl)benzoyl)oxime → 1-(p-tolyl)cyclopropane-1-carbonitrile (71172-78-6)

Guidance literature:

(Z)-2-(p-tolyl)cyclobutan-1-one O-(4-(trifluoromethyl)benzoyl)oxime; With (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h; Glovebox;

With lithium hexamethyldisilazane; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1055/s-0039-1690872

Reference yield: 77.0%

benzaldehyde dimethyl acetal (1125-88-8) + 1-(4-bromophenyl)cyclopropanecarbonitrile (124276-67-1) → 1-(p-tolyl)cyclopropane-1-carbonitrile (71172-78-6)

Guidance literature:

With nickel(II) bromide dimethoxyethane; potassium phosphate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine; In acetonitrile; benzene; for 24h; Glovebox; Sealed tube; Irradiation;

DOI:10.1021/jacs.1c12203

Reference yield: 47.0%

(4-methylphenyl)acetonitrile (2947-61-7) + 1-Bromo-2-chloroethane (107-04-0) → 1-(p-tolyl)cyclopropane-1-carbonitrile (71172-78-6)

Guidance literature:

With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; at 50 ℃; for 17h;

upstream raw materials:

(4-methylphenyl)acetonitrile

1-Bromo-2-chloroethane

[1,3]-dioxolan-2-one

ethylene dibromide

Downstream raw materials:

1-(p-tolyl)cyclopropane-1-carbaldehyde

C₁₁H₁₄O

methyl 1-(p-tolyl)cyclopropanecarboxylate

1-(4-methylphenyl)cyclopropanecarboxylic acid

Refernces

• 1、 Fang, Ping,Mei, Tian-Sheng,Shuai, Bin. "Nickel-Catalyzed Favorskii-Type Rearrangement of Cyclobutanone Oxime Esters to Cyclopropanecarbonitriles". supporting information. p. 1637 - 1641. Retrieved 2021/10/02.
• 2、 Gieuw, Matthew H.,Leung, Vincent Ming-Yau,Ke, Zhihai,Yeung, Ying-Yeung. "Electrophilic Bromolactonization of Cyclopropyl Diesters Using Lewis Basic Chalcogenide Catalysts". supporting information. p. 4306 - 4311. Retrieved 2018/10/02.