Cas no 91054-33-0 (2-Acetylbenzonitrile)

2-Acetylbenzonitrile structure
2-Acetylbenzonitrile structure
Product Name:2-Acetylbenzonitrile
CAS No:91054-33-0
MF:C9H7NO
MW:145.157982110977
MDL:MFCD00272571
CID:61470
PubChem ID:2763539
Update Time:2024-10-26

2-Acetylbenzonitrile Chemical and Physical Properties

Names and Identifiers

    • 2-Acetylbenzonitrile
    • 2-Acetyl benzene carbonitrile
    • 2-acetylbenzenecarbonitrile
    • Benzonitrile, acetyl-
    • C9H7NO
    • o-cyanoacetophenone
    • 2'-cyanoacetophenone
    • 2-Acetyl-benzonitrile
    • PubChem19789
    • 2-ethanoylbenzenecarbonitrile
    • KSC481E1D
    • UZSGWJQJDLCCFN-UHFFFAOYSA-N
    • SBB086403
    • VZ23489
    • 2-acetylbenzenecarbonitrile, AldrichCPR
    • ST2409438
    • AB0027519
    • 2-Acetylbenzonitrile (ACI)
    • Benzonitrile, o-acetyl- (6CI, 7CI)
    • 2′-Cyanoacetophenone
    • 91054-33-0
    • SB39827
    • CS-W005120
    • DTXSID70919993
    • 1T-0269
    • EN300-93628
    • MFCD00272571
    • SY012002
    • AKOS005069845
    • J-507710
    • DB-020345
    • Z1201620078
    • SCHEMBL180961
    • AE-562/43459667
    • 2-Acetylbenzene carbonitrile
    • MDL: MFCD00272571
    • Inchi: 1S/C9H7NO/c1-7(11)9-5-3-2-4-8(9)6-10/h2-5H,1H3
    • InChI Key: UZSGWJQJDLCCFN-UHFFFAOYSA-N
    • SMILES: N#CC1C(C(C)=O)=CC=CC=1

Computed Properties

  • Exact Mass: 145.05300
  • Monoisotopic Mass: 145.053
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 201
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.2
  • Topological Polar Surface Area: 40.9

Experimental Properties

  • Color/Form: No data avaiable
  • Density: 1.1555 (rough estimate)
  • Melting Point: 46-48 oC
  • Boiling Point: 285.1°C at 760 mmHg
  • Flash Point: 126.2±22.6 °C
  • Refractive Index: 1.4500 (estimate)
  • PSA: 40.86000
  • LogP: 1.76088
  • Vapor Pressure: 0.0±0.6 mmHg at 25°C

2-Acetylbenzonitrile Security Information

2-Acetylbenzonitrile Customs Data

  • HS CODE:2926909090
  • Customs Data:

    China Customs Code:

    2926909090

    Overview:

    2926909090 Other nitrile based compounds. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:6.5% general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    HS:2926909090 other nitrile-function compounds VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

2-Acetylbenzonitrile Pricemore >>

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2-Acetylbenzonitrile Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Potassium carbonate ,  Oxygen Catalysts: Nickel ferrite Solvents: Dimethylformamide ;  70 h, 100 °C
Reference
Highly active recyclable heterogeneous nanonickel ferrite catalyst for cyanation of aryl and heteroaryl halides
Matloubi Moghaddam, Firouz; Tavakoli, Ghazal; Rezvani, Hamid Reza, Applied Organometallic Chemistry, 2014, 28(10), 750-755

Production Method 2

Reaction Conditions
1.1 Reagents: Sodium bicarbonate Catalysts: Tricyclohexylphosphine ,  Manganese ,  Nickel bromide Solvents: Toluene ;  22 h, 150 °C
Reference
Nickel-catalyzed cyanation reaction of aryl/alkenyl halides with alkyl isocyanides
Zhang, Yanling; Zhang, Zhiguo; Hu, Yuanyuan; Liu, Yunkui; Jin, Hongwei; et al, Organic & Biomolecular Chemistry, 2022, 20(41), 8049-8053

Production Method 3

Reaction Conditions
1.1 Reagents: Potassium carbonate ,  Diethyl azodicarboxylate Catalysts: Bis[2-[[bis(phenylmethyl)amino-κN]methyl]phenyl-κC]di-μ-bromodipalladium Solvents: Dimethylformamide ;  1 min, 130 °C; 20 min, 130 °C; 130 °C → rt
Reference
Microwave-enhanced synthesis of aryl nitriles using dimeric orthopalladated complex of tribenzylamine and K4[Fe(CN)6]
Hajipour, Abdol Reza; Rafiee, Fatemeh; Ruoho, Arnold E., Tetrahedron Letters, 2012, 53(5), 526-529

Production Method 4

Reaction Conditions
1.1 Reagents: Acetic acid ,  Hydrochloric acid Solvents: Water ;  rt; 5 min, reflux; reflux → 0 °C
1.2 Reagents: Sodium nitrite Solvents: Water ;  0 °C; 0 °C → rt; 2 h, rt
1.3 Reagents: Cuprous cyanide Solvents: Toluene ,  Water ;  rt; 1 h, 65 °C; 2 h, rt
Reference
Highly Stereoselective Chemoenzymatic Synthesis of the 3H-Isobenzofuran Skeleton. Access to Enantiopure 3-Methylphthalides
Mangas-Sanchez, Juan; Busto, Eduardo; Gotor-Fernandez, Vicente; Gotor, Vicente, Organic Letters, 2012, 14(6), 1444-1447

Production Method 5

Reaction Conditions
1.1 Reagents: Potassium carbonate Catalysts: Palladium(1+), [2-[(amino-κN)methyl]phenyl-κC][1-(4-methoxyphenyl)-2-(triphenylp… Solvents: Dimethylformamide ;  30 min, 130 °C; 130 °C → rt
Reference
An efficient palladium catalytic system for microwave assisted cyanation of aryl halides
Hajipour, Abdol R.; Karami, Kazem; Tavakoli, Ghazal; Pirisedigh, Azade, Journal of Organometallic Chemistry, 2011, 696(4), 819-824

Production Method 6

Reaction Conditions
1.1 Reagents: Cesium carbonate Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Toluene ;  24 h, 100 °C
Reference
Synthesis and organocatalytic asymmetric nitro-aldol initiated cascade reactions of 2-acylbenzonitriles leading to 3,3-disubstituted isoindolinones
Romano, Fabio; Di Mola, Antonia; Palombi, Laura; Tiffner, Maximilian; Waser, Mario; et al, Catalysts, 2019, 9(4), 327/1-327/11

Production Method 7

Reaction Conditions
1.1 Reagents: Copper ,  Sulfuric acid ,  Copper sulfate Solvents: Water ;  2 h, reflux
1.2 Reagents: Sodium nitrite Solvents: Water ;  80 - 90 °C
Reference
Candida tenuis xylose reductase catalyzed reduction of acetophenones: the effect of ring-substituents on catalytic efficiency
Vogl, Michael; Kratzer, Regina; Nidetzky, Bernd; Brecker, Lothar, Organic & Biomolecular Chemistry, 2011, 9(16), 5863-5870

Production Method 8

Reaction Conditions
Reference
Direct formation of organocopper compounds by oxidative addition of zerovalent copper to organic halides
Ebert, Greg; Rieke, Reuben D., Journal of Organic Chemistry, 1984, 49(26), 5280-2

Production Method 9

Reaction Conditions
1.1 Reagents: Triethylamine Catalysts: Triphenylphosphine ,  Palladium diacetate Solvents: Dimethyl sulfoxide ,  Dimethylformamide ;  rt; 2 h, 100 °C
Reference
Microwave-assisted one-step synthesis of acetophenones via palladium-catalyzed regioselective arylation of vinyloxytrimethylsilane
Qian, Wangke; Zhang, Lei; Sun, Haifeng; Jiang, Hualiang; Liu, Hong, Advanced Synthesis & Catalysis, 2012, 354(17), 3231-3236

Production Method 10

Reaction Conditions
1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Acetonitrile ,  Water ;  3.5 h, 80 °C
Reference
Synthesis of 2-Acetylbenzonitriles and Their Reactivity in Tandem Reactions with Carbon and Hetero Nucleophiles: Easy Access to 3,3-Disubstituted Isoindolinones
Di Mola, Antonia; Di Martino, Miriam; Capaccio, Vito; Pierri, Giovanni; Palombi, Laura; et al, European Journal of Organic Chemistry, 2018, 2018(14), 1699-1708

Production Method 11

Reaction Conditions
1.1 Reagents: Potassium hydroxide Catalysts: Samarium Solvents: Dimethyl sulfoxide ;  12 h, 110 °C
Reference
A ligand and Palladium-free Avenue for Cyanation of Aryl Halides: The Art of Samarium Powder in C-C Coupling Reaction
Moghaddam, Firouz Matloubi ; Pourkaveh, Raheleh; Gholamtajari, Milad; Karimi, Ashkan, ChemistrySelect, 2019, 4(33), 9618-9621

Production Method 12

Reaction Conditions
1.1 Reagents: 4-(Dimethylamino)pyridine Catalysts: Zinc ,  Nickel dichloride ,  1,1-Bis(diphenylphosphino)ferrocene Solvents: Acetonitrile ;  6 h, 80 °C; 80 °C → rt
Reference
General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP
Zhang, Xingjie; Xia, Aiyou; Chen, Haoyi; Liu, Yuanhong, Organic Letters, 2017, 19(8), 2118-2121

Production Method 13

Reaction Conditions
1.1 Catalysts: Tetrabutylammonium iodide Solvents: Dimethylformamide ,  tert-Butanol ,  Water ;  24 h, 110 °C
Reference
A Serendipitous One-Pot Cyanation/Hydrolysis/Enamide Formation: Direct Access to 3-Methyleneisoindolin-1-ones
Banik, Trisha; Kaliappan, Krishna P., Chemistry - A European Journal, 2021, 27(2), 628-633

Production Method 14

Reaction Conditions
1.1 Solvents: Dimethylformamide ;  12 h, 150 °C
Reference
An Unprecedented, Lewis Acid-Mediated, Metal-Free Iodoannulation Strategy to Aromatic Iodides
Banik, Trisha; Betkekar, Vipul V.; Kaliappan, Krishna P., Chemistry - An Asian Journal, 2018, 13(23), 3676-3680

Production Method 15

Reaction Conditions
1.1 Solvents: 1,2-Dimethoxyethane
Reference
Preparation of aryl, alkynyl, and vinyl organocopper compounds by the oxidative addition of zerovalent copper to carbon-halogen bonds
Ebert, Greg W.; Rieke, Reuben D., Journal of Organic Chemistry, 1988, 53(19), 4482-8

Production Method 16

Reaction Conditions
1.1 Catalysts: Cobalt dibromide Solvents: Acetonitrile ;  rt
Reference
A convenient method for the preparation of aromatic ketones from acyl chlorides and arylzinc bromides using a cobalt catalysis
Fillon, Hyacinthe; Gosmini, Corinne; Perichon, Jacques, Tetrahedron, 2003, 59(41), 8199-8202

Production Method 17

Reaction Conditions
1.1 Reagents: Potassium carbonate Catalysts: Bis[2-[2-(amino-κN)ethyl]-3-methoxyphenyl-κC]di-μ-bromodipalladium Solvents: Dimethylformamide ;  20 min, 130 °C
Reference
Microwave-enhanced cyanation of aryl halides with a dimeric ortho-palladated complex catalyst
Hajipour, Abdol-Reza; Abrisham, Fatemeh; Tavakoli, Ghazal, Transition Metal Chemistry (Dordrecht, 2011, 36(7), 725-730

Production Method 18

Reaction Conditions
Reference
Product class 4: organometallic complexes of copper
Heaney, H.; Christie, S., Science of Synthesis, 2004, 3, 305-662

2-Acetylbenzonitrile Raw materials

2-Acetylbenzonitrile Preparation Products

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