Cas no 931-20-4 (1-Methylpiperidin-2-one)

1-Methylpiperidin-2-one structure
1-Methylpiperidin-2-one structure
Product Name:1-Methylpiperidin-2-one
CAS No:931-20-4
MF:C6H11NO
MW:113.157641649246
CID:804940
PubChem ID:13603
Update Time:2024-10-26

1-Methylpiperidin-2-one Chemical and Physical Properties

Names and Identifiers

    • 1-Methylpiperidin-2-one
    • 1-Methyl-2-piperidone
    • 2-Piperidinone,1-methyl-
    • 1-methyl-2-piperidinon
    • 1-Methyl-2-piperidinone
    • 1-methyl-2-piperidon
    • 1-Methylpiperidin-2-on
    • 1-methyl-piperidinone
    • 2-Piperidone,1-methyl
    • N(1)-methyl-2-piperidone
    • N-Methyl-2-piperidinone
    • N-methyl-2-piperidone
    • N-methylpiperidin-2-one
    • n-methylvalerolactam
    • 1-Methyl-2-piperidinone (ACI)
    • 2-Piperidone, 1-methyl- (6CI, 7CI, 8CI)
    • 1-Methyl-6-oxopiperidine
    • N-Methyl-δ-valerolactam
    • N-Methylpiperidone
    • NSC 67384
    • Inchi: 1S/C6H11NO/c1-7-5-3-2-4-6(7)8/h2-5H2,1H3
    • InChI Key: GGYVTHJIUNGKFZ-UHFFFAOYSA-N
    • SMILES: O=C1CCCCN1C

Computed Properties

  • Exact Mass: 113.08400
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 8
  • Rotatable Bond Count: 0
  • Complexity: 101
  • 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
  • Surface Charge: 0
  • Tautomer Count: 2
  • XLogP3: nothing

Experimental Properties

  • Color/Form: Not determined
  • Density: 0.997?g/mL?at 25?°C(lit.)
  • Boiling Point: 105-106?°C/12?mmHg(lit.)
  • Flash Point: Degrees Fahrenheit:195.8°F
    Degrees Celsius:91°C
  • Refractive Index: n20/D 1.482
  • PSA: 20.31000
  • LogP: 0.56660
  • Solubility: Not determined

1-Methylpiperidin-2-one Security Information

  • Symbol: GHS07
  • Signal Word:Warning
  • Hazard Statement: H315-H319-H335
  • Warning Statement: P261-P305+P351+P338
  • Hazardous Material transportation number:NA 1993 / PGIII
  • WGK Germany:3
  • Hazard Category Code: 36/37/38
  • Safety Instruction: S26; S36
  • FLUKA BRAND F CODES:3-10
  • RTECS:TO0124000
  • Hazardous Material Identification: Xi
  • Risk Phrases:R36/37/38

1-Methylpiperidin-2-one Customs Data

  • HS CODE:2933790090
  • Customs Data:

    China Customs Code:

    2933790090

    Overview:

    2933790090 Other lactams. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:9.0% general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933790090. other lactams. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:9.0%. General tariff:20.0%

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1-Methylpiperidin-2-one Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Sodium hydride ,  18-Crown-6 Solvents: Tetrahydrofuran
Reference
Stereoselective Conjugate Addition of Cyanide
Convine, Nicola Jane, 2005, , ,

Production Method 2

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Acetone ;  20 °C; 20 min, 20 °C
Reference
Synthesis of N-methyl-2-piperidone
Wang, Haiyang; Xu, Haoran; Zang, Na; Wang, Shoukai, Jingxi Huagong Zhongjianti, 2010, 40(1), 52-53

Production Method 3

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Platinum dioxide Solvents: Acetic acid
Reference
Rearrangement of α-aminoketones during Clemmensen reduction. III. Contraction of a seven-membered ring in the monocyclic series
Leonard, Nelson J.; Barthel, Eric Jr., Journal of the American Chemical Society, 1949, 71, 3098-100

Production Method 4

Reaction Conditions
1.1 Reagents: Potassium hydroxide ,  Oxygen Solvents: Diethyl ether ;  90 h, rt
Reference
A novel and efficient oxidation of 1,2-amino alcohols to dialkylamides
Garcia-Valverde, Maria; Pedrosa, Rafael; Vicente, Martina, Synlett, 2002, (12), 2092-2094

Production Method 5

Reaction Conditions
1.1 Reagents: Titanium isopropoxide Solvents: 1,2-Dichloroethane
Reference
Titanium tetraisopropoxide-mediated lactamizations
Mader, Mary; Helquist, Paul, Tetrahedron Letters, 1988, 29(25), 3049-52

Production Method 6

Reaction Conditions
1.1 Reagents: Ethylenediaminetetraacetic acid ,  Mercuric acetate Solvents: Dichloromethane
Reference
Preparation of lactams via oxidation of cyclic, tertiary and secondary amines with mercury(II)-EDTA complex in alkaline medium
Wenkert, Ernest; Angell, E. Charles, Synthetic Communications, 1988, 18(12), 1331-7

Production Method 7

Reaction Conditions
1.1 Reagents: Iodosylbenzene Solvents: Water
Reference
Hypervalent iodine oxidation of amines using iodosobenzene: synthesis of nitriles, ketones and lactams
Moriarty, Robert M.; Vaid, Radhe K.; Duncan, Michael P.; Ochiai, Masahito; Inenaga, Minako; et al, Tetrahedron Letters, 1988, 29(52), 6913-16

Production Method 8

Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran
Reference
Reactions of silyllithium reagents with tertiary amides
Mack, Stephen R., 1997, , ,

Production Method 9

Reaction Conditions
1.1 Reagents: Triethylamine ,  Hydrogen Catalysts: Ruthenium Solvents: Methanol ,  Water
Reference
Preparation of lactams
, Japan, , ,

Production Method 10

Reaction Conditions
1.1 Reagents: Potassium hydroxide Catalysts: Tetrabutylammonium bromide Solvents: Toluene ;  24 h, rt
Reference
Asymmetric synthesis and evaluation of α-quaternary chiral lactam derivatives as novel anticancer agents
Lee, Hwanhyuk; Hwang, Su Jung; Jung, Jisung; Hong, Suckchang; Lee, Myungmo; et al, Archives of Pharmacal Research, 2014, 37(10), 1264-1270

Production Method 11

Reaction Conditions
1.1 Reagents: Water Solvents: Water
Reference
Ruthenium-catalyzed amidation of nitriles with amines. A novel, facile route to amides and polyamides
Murahashi, Shunichi; Naota, Takeshi; Saito, Eiichiro, Journal of the American Chemical Society, 1986, 108(24), 7846-7

Production Method 12

Reaction Conditions
1.1 Reagents: Oxygen Catalysts: Gold ,  Silica Solvents: 1,4-Dioxane ,  Water ;  1 min, rt; rt → 100 °C; 4 h, 100 °C
Reference
Aerobic Oxidation of Cyclic Amines to Lactams Catalyzed by Ceria-Supported Nanogold
Dairo, Taiwo O.; Nelson, Nicholas C.; Slowing, Igor I.; Angelici, Robert J.; Woo, L. Keith, Catalysis Letters, 2016, 146(11), 2278-2291

Production Method 13

Reaction Conditions
1.1 Reagents: Oxygen Catalysts: Alumina ,  Gold Solvents: Water ;  24 h, 80 °C
Reference
Supported Gold Nanoparticles for Efficient α-Oxygenation of Secondary and Tertiary Amines into Amides
Jin, Xiongjie; Kataoka, Kengo; Yatabe, Takafumi; Yamaguchi, Kazuya; Mizuno, Noritaka, Angewandte Chemie, 2016, 55(25), 7212-7217

Production Method 14

Reaction Conditions
1.1 Reagents: Ammonium chloride
Reference
N-Alkylation of amines and amides catalyzed by ammonium halides
Kashiwagi, Hiroshi; Enomoto, Saburo, Nippon Kagaku Kaishi, 1980, (2), 279-81

Production Method 15

Reaction Conditions
1.1 Reagents: 4-Phenyl-3-buten-2-one Catalysts: Dihydrotetrakis(triphenylphosphine)ruthenium Solvents: 1,2-Dimethoxyethane
Reference
Ruthenium-catalyzed transformations of amino alcohols to lactams
Naota, Takeshi; Murahashi, Shunichi, Synlett, 1991, (10), 693-4

Production Method 16

Reaction Conditions
1.1 Solvents: Toluene ;  12 h, 100 °C; 100 °C → rt
Reference
Selective Methylation of Amides, N-Heterocycles, Thiols, and Alcohols with Tetramethylammonium Fluoride
Cheng, Hong-Gang; Pu, Maoping; Kundu, Gourab; Schoenebeck, Franziska, Organic Letters, 2020, 22(1), 331-334

Production Method 17

Reaction Conditions
1.1 Reagents: p-Toluenesulfonic acid ,  Triethyl orthoformate Solvents: Ethanol
1.2 -
1.3 Reagents: Sodium iodide Solvents: Acetonitrile
Reference
A simple, one-flask transformation of ketones to N-methyllactams
Hoffman, Robert V.; Salvador, James M., Tetrahedron Letters, 1991, 32(22), 2429-32

Production Method 18

Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane
Reference
Fluorination studies using difluoroiodotoluene
Greaney, Michael Francis, 1999, , ,

Production Method 19

Reaction Conditions
1.1 Reagents: Chlorodimethylsilane ,  Trimethylsilyl triflate
Reference
N-methylation of lactams with the use of silicon-containing reagents
Shipov, A. G.; Kramarova, E. P.; Artamkina, O. B.; Baukov, Yu. I., Zhurnal Obshchei Khimii, 1989, 59(11), 2629-30

Production Method 20

Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  0 °C → 25 °C; 30 min, 25 °C; 25 °C → 0 °C
1.2 0 °C; 0 °C → 25 °C; 16 h, 25 °C
Reference
Origin of High Diastereoselectivity in Reactions of Seven-Membered-Ring Enolates
Lavinda, Olga; Witt, Collin H. ; Woerpel, K. A., Angewandte Chemie, 2022, 61(14),

1-Methylpiperidin-2-one Raw materials

1-Methylpiperidin-2-one Preparation Products

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