N-Methylcyclohexylamine

Base Information

• Chemical Name: N-Methylcyclohexylamine
• CAS No.: 100-60-7
• Molecular Formula: C7H15N
• Molecular Weight: 113.203
• Hs Code.: 29213099
• European Community (EC) Number: 202-869-3
• NSC Number: 434
• UN Number: 2924
• UNII: YH8PF4C1OW
• DSSTox Substance ID: DTXSID3059216
• Nikkaji Number: J23.469I
• Wikidata: Q23775590
• Metabolomics Workbench ID: 60349
• Mol file: 100-60-7.mol

Synonyms:N-METHYLCYCLOHEXYLAMINE;N-Methylcyclohexanamine;100-60-7;Methylcyclohexylamine;N-Cyclohexylmethylamine;Cyclohexanamine, N-methyl-;Cyclohexylmethylamine;N-Methyl-N-cyclohexylamine;(Methylamino)cyclohexane;Cyclohexylamine, N-methyl-;N-Cyclohexyl-N-methylamine;Cyclohexyl(methyl)amine;C7H15N;NSC 434;1-Methylcyclohexylamine;cyclohexyl-methyl-amine;N-methyl-cyclohexylamine;EINECS 202-869-3;UNII-YH8PF4C1OW;MFCD00003832;YH8PF4C1OW;BRN 1523664;AI3-16733;NSC-434;4-12-00-00017 (Beilstein Handbook Reference);NSC434;cyclohexyl-methylamine;methylcyclohexyl amine;N-methylcylohexylamine;cyclohexyl(methyl)amin;N-Metyhcyclohexylamine;N-methyl cyclohexylamine;2-cyclohexyl-methylamine;SCHEMBL8918;N-methyl-N-cyclo-hexylamine;N-methyl-N-cyclohexyl-amine;N-Methylcyclohexylamine, 99%;SCHEMBL7556380;DTXSID3059216;CHEBI:59018;STR01459;STL183276;AKOS000119082;CS-W016609;AM802809;LS-57643;BB 0218286;FT-0631525;M0202;EN300-18953;F86361;N-Methylcyclohexylamine, purum, >=98.0% (GC);W-108953;Q23775590;F2190-0309;Z102766892

Chemical Property of N-Methylcyclohexylamine

Chemical Property:

• Appearance/Colour: clear colourless to yellow liquid
• Vapor Pressure: 11 mm Hg ( 40 °C)
• Melting Point: -9--7 °C(lit.)
• Refractive Index: n20/D 1.456(lit.)
• Boiling Point: 146.5 °C at 760 mmHg
• PKA: 11.03±0.20(Predicted)
• Flash Point: 29.4 °C
• PSA: 12.03000
• Density: 0.868 g/cm³
• LogP: 1.92940
• Storage Temp.: Flammables area
• Sensitive.: Air Sensitive
• Solubility.: 54g/l
• Water Solubility.: 5.4 g/100 mL (20 ºC)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 113.120449483
• Heavy Atom Count: 8
• Complexity: 55.4
• Transport DOT Label: Flammable Liquid Corrosive

Purity/Quality:

99% ^*data from raw suppliers

N-Methylcyclohexanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 10-21/22-35-20/21/22
• Safety Statements: 16-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1CCCCC1
• Uses: Intermediate, solvent, acid acceptor. N-Methylcyclohexanamine is a chemical reagent used in the synthesis of Mps1 kinase inhibitors used in cancer research. Also used in the synthesis of antituberculosis agents as indole-2-carboxamides. N-Methylcyclohexylamine is used as a component of vulcanization accelerators, but the market size is relatively small.

Technology Process of N-Methylcyclohexylamine

There total 84 articles about N-Methylcyclohexylamine 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: 96.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + dimethyl amine (124-40-3) → N-methylcyclohexylamine (100-60-7) + N,N-dimethyl-cyclohexanamine (98-94-2) + cyclohexanol (108-93-0)

Guidance literature:

With hydrogen; at 160 - 220 ℃; for 100 - 1000h; under 67506.8 - 97509.8 Torr; Product distribution / selectivity;

Reference yield: 75.0%

methanol (67-56-1) + cyclohexylamine (108-91-8,157973-60-9) → N-methylcyclohexylamine (100-60-7)

Guidance literature:

With rhodium(III) chloride hydrate; potassium tert-butylate; at 130 ℃; for 48h; Sealed tube; High pressure;

DOI:10.1002/cctc.202001937

Reference yield: 5.0%

cyclohexylamine (108-91-8,157973-60-9) + carbonic acid dimethyl ester (616-38-6) → N-methylcyclohexylamine (100-60-7) + N,N-dimethyl-cyclohexanamine (98-94-2)

Guidance literature:

With binder-free NaY zeolite; Heating;

DOI:10.1134/S1070428018040231

upstream raw materials:

diazomethane

cyclohexylamine

N-(cyanomethyl)cyclohexylamine

N-Methylformamide

Downstream raw materials:

C₂₀H₂₃Cl₂N₃

N-[2,2,2-Trichloro-1-(cyclohexyl-methyl-amino)-ethyl]-formamide

2-cyano-N-cyclohexyl-N-methyl-acetamide

1-Cyclohexyl-1,3-dimethyl-urea

Refernces

• 1、 Guyon, Carole,Duclos, Marie-Christine,Métay, Estelle,Lemaire, Marc. "Reductive N-methylation of amines with calcium hydride and Pd/C catalyst". . p. 3002 - 3005. Retrieved 2016.
• 2、 da Silva, Renato A.,Bieber, Lothar W.. "Zinc-promoted, iridium catalyzed reductive alkylation of primary amines with aliphatic ketones in aqueous medium". . p. 689 - 691. Retrieved 2010.
• 3、 Firouzabadi, Habib,Iranpoor, Nasser,Alinezhad, Heshmatollah. "Dichlorobis(1,4-diazabicyclo[2.2.2]octane)(tetrahydroborato)zirco- nium(IV), [Zr(BH4)2Cl2(dabco)2](ZrBDC), as a new, stable, and versatile bench top reducing agent: Reduction of imines and enamines, reductive amination of aldehydes and ketones and reductive methylation of amines". . p. 143 - 151. Retrieved 2003.
• 4、 Cao, Yanwei,Zheng, Huan,Zhu, Gangli,Wu, Haihong,He, Lin. "Ceria supported Ru0-Ruδ+ clusters as efficient catalyst for arenes hydrogenation". . p. 770 - 774. Retrieved 2021.
• 5、 Alper, Howard,Vampollo, Guiseppe. "Catalytic reduction of the arene ring, and other functionalities, of organic substrates using formic acid and palladium on carbon". . p. 7477 - 7480. Retrieved 1992.
• 6、 Sarki, Naina,Goyal, Vishakha,Tyagi, Nitin Kumar,Puttaswamy,Narani, Anand,Ray, Anjan,Natte, Kishore. "Simple RuCl3-catalyzed N-Methylation of Amines and Transfer Hydrogenation of Nitroarenes using Methanol". . p. 1722 - 1729. Retrieved 2021.
• 7、 Baciocchi, Enrico,Del Giacco, Tiziana,Lapi, Andrea. "Quenching of singlet oxygen by tertiary aliphatic amines. Structural effects on rates and products". . p. 2273 - 2280. Retrieved 2006.
• 8、 Toyao, Takashi,Siddiki,Morita, Yoshitsugu,Kamachi, Takashi,Touchy, Abeda S.,Onodera, Wataru,Kon, Kenichi,Furukawa, Shinya,Ariga, Hiroko,Asakura, Kiyotaka,Yoshizawa, Kazunari,Shimizu, Ken-Ichi. "Rhenium-Loaded TiO2: A Highly Versatile and Chemoselective Catalyst for the Hydrogenation of Carboxylic Acid Derivatives and the N-Methylation of Amines Using H2 and CO2". . p. 14848 - 14859. Retrieved 2017.
• 9、 Montgomery, Sarah L.,Mangas-Sanchez, Juan,Thompson, Matthew P.,Aleku, Godwin A.,Dominguez, Beatriz,Turner, Nicholas J.. "Direct Alkylation of Amines with Primary and Secondary Alcohols through Biocatalytic Hydrogen Borrowing". . p. 10491 - 10494. Retrieved 2017.
• 10、 Al Shaik,Oelschlager. "Convenient synthesis of pure N-methylalkanamines by reduction with Zn/hydrochloric acid of 1,3,5-trialkyl(hexahydro)1,3,5-triazines". . p. 214 - 219. Retrieved 1984.