Production Method 1

96-49-1

935-44-4

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: Polyethylene glycol ;  50 °C; 50 °C → 126 °C; 5 h, 126 °C

Reference

Cyclopropanation of substituted phenylacetonitrile or phenyl acetate

, World Intellectual Property Organization, , ,

Production Method 2

106-93-4

935-44-4

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0 °C; 15 min, 0 °C
1.2 Reagents: Sodium iodide Solvents: Dimethylformamide ;  4 h, 0 °C → 120 °C

Reference

Piperazine compounds as pyruvate kinase M2 modulators and their preparation, compositions and use in the treatment of cancer

, World Intellectual Property Organization, , ,

Production Method 3

6120-95-2

935-44-4

Reaction Conditions

1.1 Reagents: Benzenesulfonamide, N-cyano-N-(4-fluorophenyl)-2-nitro- Catalysts: Iron chloride (FeCl3) Solvents: Toluene ;  24 h, 110 °C

Reference

Fe-Catalyzed Direct Synthesis of Nitriles from Carboxylic Acids with Electron-Deficient N-Cyano-N-aryl-arylsulfonamide

Zhang, Guodong ; Zhang, Chengyu; Tian, Ye; Chen, Feng, Organic Letters, 2023, 25(6), 917-922

Production Method 4

106-93-4

935-44-4

Reaction Conditions

1.1 Reagents: Hexamethylphosphoramide ,  Ethanamine, N-ethyl-, lithium salt

Reference

Addition and substitution reactions of nitrile-stabilized carbanions

Arseniyadis, Simeon; Kyler, Keith S.; Watt, David S., Organic Reactions (Hoboken, 1984, 31,

Production Method 5

106-93-4

935-44-4

Reaction Conditions

1.1 Reagents: Potassium hydroxide Catalysts: Tetrabutylammonium bromide Solvents: Water ;  2 h, 50 °C

Reference

Preparation of boronic acid compound for the treatment of proteasome-borne disease

, World Intellectual Property Organization, , ,

Production Method 6

935-44-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Catalysts: Benzyltriethylammonium chloride Solvents: Water

Reference

Synthesis of 1-arylcyclopropanecarbonitriles under phase-transfer catalytic conditions

Fedorynski, Michal; Jonczyk, Andrzej, Organic Preparations and Procedures International, 1995, 27(3), 355-9

Production Method 7

106-93-4

935-44-4

Reaction Conditions

1.1 Reagents: Potassium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  cooled; 30 min, 0 °C
1.2 Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; overnight, rt

Reference

Preparation of allylhydrazine and hydroxylamine derivatives as inhibitors of semicarbazide-sensitive amine oxidase (SSAO) and vascular adhesion protein 1 (VAP-1)

, World Intellectual Property Organization, , ,

Production Method 8

106-93-4

935-44-4

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0 °C; 40 min, 0 °C
1.2 0 °C; 5 h, 0 °C
1.3 Reagents: Water ;  0 °C

Reference

From Isocyanides to Iminonitriles via Silver-mediated Sequential Insertion of C(sp3)-H Bond

Chi, Huiwen; Li, Hao ; Liu, Bingxin; Ye, Rongxuan; Wang, Haoyang ; et al, iScience, 2019, 21, 650-663

Production Method 9

106-93-4

935-44-4

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  rt; 30 min, rt
1.2 rt; 3 h, rt
1.3 Reagents: Water

Reference

Preparation of 2-oximino-2'-[[[[[ (hetero)arylcyclopropyl]ethylidene]nitrilo]oxy]methyl]benzeneacetates as fungicides and insecticides

, European Patent Organization, , ,

Production Method 10

52370-86-2

935-44-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water

Reference

N-Methyl-N-[trans-2-(1-pyrrolidinyl)cyclohexyl]-1-phenylcyclopropanecarboxylic amides. Analogs of U50488 with much reduced opiate affinity and loss of κ-selectivity

Cheng, C. Y.; Lu, H. Y.; Lee, F. M., European Journal of Medicinal Chemistry, 1991, 26(2), 125-8

Production Method 11

106-93-4

935-44-4

Reaction Conditions

1.1 Reagents: Potassium hydroxide Catalysts: Tetrabutylammonium bromide Solvents: Water ;  50 °C; 30 min, 50 °C

Reference

Phase transfer alkylation of arylacetonitriles revisited

Barbasiewicz, Michal; Marciniak, Karolina; Fedorynski, Michal, Tetrahedron Letters, 2006, 47(23), 3871-3874

Production Method 12

2415284-42-1

935-44-4

Reaction Conditions

1.1 Catalysts: Dichloro[1,2-di(methoxy-κO)ethane]nickel ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Solvents: Dimethylformamide ;  15 min, rt
1.2 Reagents: Lithium bis(trimethylsilyl)amide ;  12 h, rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Nickel-Catalyzed Favorskii-Type Rearrangement of Cyclobutanone Oxime Esters to Cyclopropanecarbonitriles

Shuai, Bin; Fang, Ping; Mei, Tian-Sheng, Synlett, 2021, 32(16), 1637-1641

Production Method 13

5500-21-0

935-44-4

Reaction Conditions

1.1 Reagents: Zincate(1-), dichloro(2,2,6,6-tetramethyl-1-piperidinyl)-, lithium (1:1) Catalysts: (SP-4-4)-[2′-(Amino-κN)[1,1′-biphenyl]-2-yl-κC]chloro[dicyclohexyl[2′,4′,6′-tris… Solvents: Cyclopentyl methyl ether ;  < 27 °C; 20 min, 23 °C; 1 h, 25 °C → 80 °C; 80 °C → 23 °C
1.2 Reagents: Methanol

Reference

Highly Diastereoselective α-Arylation of Cyclic Nitriles

Dalziel, Michael E. ; Chen, Penghao; Carrera, Diane E.; Zhang, Haiming ; Gosselin, Francis, Organic Letters, 2017, 19(13), 3446-3449

Production Method 14

106-93-4

935-44-4

Reaction Conditions

1.1 Reagents: Potassium hydroxide Catalysts: Tetrabutylammonium bromide Solvents: Water ;  50 °C; 1 h, 50 °C

Reference

N-Oxazolidinylmethyl thiophenecarboxamide derivatives as antithrombotic agents and their preparation and use for the treatment of diseases

, India, , ,

Production Method 15

6120-95-2

935-44-4

Reaction Conditions

1.1 Reagents: N-Cyano-4-methyl-N-phenylbenzenesulfonamide Catalysts: Iron chloride (FeCl3) Solvents: 1,2-Dichloroethane ;  24 h, 100 °C

Reference

Iron-Catalyzed Deoxynitrogenation of Carboxylic Acids with Cyanamides to Access Nitriles

Li, Mengsheng; Zhang, Jing, Chemistry - A European Journal, 2023, 29(31),

Production Method 16

19158-51-1

6120-95-2

935-44-4

Reaction Conditions

1.1 Catalysts: Silver hexafluoroantimonate Solvents: Toluene ;  48 h, 120 °C

Reference

Silver-Catalyzed Synthesis of Nitriles from Carboxylic Acids and Cyanamides

Li, Mingsheng; Zi, Lingjian; Chen, Xinqaing; Zhang, Jing, Synlett, 2023, 34(15), 1824-1828

Production Method 17

106-93-4

935-44-4

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0 °C; 15 min, 0 °C
1.2 Solvents: Dimethylformamide ;  24 h, rt

Reference

Lewis Basic Sulfide Catalyzed Electrophilic Bromocyclization of Cyclopropylmethyl Amide

Wong, Ying-Chieh; Ke, Zhihai; Yeung, Ying-Yeung, Organic Letters, 2015, 17(20), 4944-4947

Production Method 18

106-93-4

935-44-4

Reaction Conditions

1.1 Reagents: Potassium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  cooled; 30 min, 0 °C
1.2 Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; overnight, rt

Reference

Preparation of phenylallyl compounds as inhibitors of semicarbazide-sensitive amine oxidase and VAP-1 mediated adhesion

, World Intellectual Property Organization, , ,

1-Phenylcyclopropanecarbonitrile Raw materials

• Ethylene Carbonate
• Cyclopropanecarbonitrile
• 1,2-Dibromoethane
• (1Z)-2-Phenylcyclobutanone O-[4-(trifluoromethyl)benzoyl]oxime
• Benzeneacetic acid, α-(2-chloroethyl)-α-cyano-, ethyl ester
• p-Toluenesulfonyl cyanide
• 1-phenylcyclopropane-1-carboxylic acid

1-Phenylcyclopropanecarbonitrile Preparation Products

• 1-Phenylcyclopropanecarbonitrile (935-44-4)

• 1. Emulsion technologies for multicellular tumour spheroid radiation assays?
  Kay S. McMillan,Anthony G. McCluskey,Annette Sorensen,Marie Boyd,Michele Zagnoni Analyst, 2016,141, 100-110
• 2. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 3. Enabling high-throughput single-animal gene-expression studies with molecular and micro-scale technologies
  Jason Wan Lab Chip, 2020,20, 4528-4538
• 4. Enabling stable MnO2 matrix for aqueous zinc-ion battery cathodes?
  Yiding Jiao,Liqun Kang,Jasper Berry-Gair,Kit McColl,Jianwei Li,Haobo Dong,Hao Jiang,Ryan Wang,Furio Corà,Dan J. L. Brett,Ivan P. Parkin J. Mater. Chem. A, 2020,8, 22075-22082
• 5. Evolution of dealloying induced strain in nanoporous gold crystals?
  Ross Harder,David C. Dunand,Ian McNulty Nanoscale, 2017,9, 5686-5693

• Solvents and Organic Chemicals Organic Compounds cyanides/Cyanides

• 61066-89-5(2-Cyclopropyl-2-phenylacetonitrile)
• 110327-48-5(Cyclopropanecarbonitrile, 2-methyl-1-phenyl-, cis-)
• 87421-62-3(Cyclopropanecarbonitrile, 1,2-diphenyl-, (1R,2S)-rel-)
• 646995-51-9(Cyclopropanecarbonitrile, 2,2-dimethyl-3-phenyl-, (1R,3R)-)
• 99647-68-4(Cyclopropanecarbonitrile, 2,2-dimethyl-3-phenyl-, trans-)
• 71172-78-6(1-(4-Methylphenyl)-1-cyclopropanecarbonitrile)
• 103012-04-0(Cyclopropanecarbonitrile, 2,2-dimethyl-3-(4-methylphenyl)-, cis-)
• 110327-49-6(Cyclopropanecarbonitrile, 2-methyl-1-phenyl-, (1R,2R)-rel-)
• 10224-14-3(Cyclopropanecarbonitrile,1,2-diphenyl-)
• 103012-06-2(Cyclopropanecarbonitrile, 2,2-dimethyl-3-(4-methylphenyl)-, trans-)