N-Cyclohexylaniline

Base Information

• Chemical Name: N-Cyclohexylaniline
• CAS No.: 1821-36-9
• Molecular Formula: C12H17N
• Molecular Weight: 175.274
• Hs Code.: 29214900
• European Community (EC) Number: 217-344-4
• NSC Number: 27510
• UNII: 949TFM4PMV
• DSSTox Substance ID: DTXSID6061997
• Nikkaji Number: J68.528C
• Wikidata: Q81989785
• Mol file: 1821-36-9.mol

Synonyms:N-Cyclohexylaniline;1821-36-9;Benzenamine, N-cyclohexyl-;N-Phenylcyclohexylamine;Aniline, N-cyclohexyl-;Cyclohexylamine, N-phenyl-;Cyclohexylphenylamine;Cyclohexanamine, N-phenyl-;Diphenylamine, ar-hexahydro-;N-Cyclohexylbenzenamine;cyclohexyl-phenyl-amine;NSC 27510;949TFM4PMV;EINECS 217-344-4;MFCD00014284;NSC-27510;NSC27510;Phenylcyclohexylamine;n-cyclohexyl aniline;Maybridge3_006295;UNII-949TFM4PMV;Oprea1_273099;BIDD:GT0417;N-Cyclohexyl-N-phenylamine #;SCHEMBL285479;DTXSID6061997;BENZENAMINE,N-CYCLOHEXYL-;STR05327;AKOS000121357;PS-8600;IDI1_017682;SY101001;N-Cyclohexylaniline, >=98.0% (GC/NT);CS-0015900;FT-0629703;EN300-16626;H12007;A880927;J-011657;Z56347230;Aniline,N-cyclohexyl;Diphenylamine,ar-hexahydro;N-cyclohexyl-aniline

Chemical Property of N-Cyclohexylaniline

Chemical Property:

• Appearance/Colour: dark brown liquid
• Vapor Pressure: 0.00178mmHg at 25°C
• Melting Point: 14-15 °C
• Refractive Index: n20/D 1.560
• Boiling Point: 292.9 °C at 760 mmHg
• PKA: 5.46±0.20(Predicted)
• Flash Point: 135.5 °C
• PSA: 12.03000
• Density: 1.022 g/cm³
• LogP: 3.50420
• Storage Temp.: Store below +30°C.
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 175.136099547
• Heavy Atom Count: 13
• Complexity: 132

Purity/Quality:

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

N-Cyclohexylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 23-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC(CC1)NC2=CC=CC=C2
• Uses: N-Cyclohexylaniline has been used as reagent in palladium-catalyzed amination of aromatic bromides.

Technology Process of N-Cyclohexylaniline

There total 225 articles about N-Cyclohexylaniline 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: 99.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + aniline (62-53-3) → N-phenyl-2-cyclohexylamine (1821-36-9)

Guidance literature:

With Bu₂SnClH-HMPA; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1055/s-1998-1895

Reference yield: 98.0%

bromobenzene (108-86-1,52753-63-6) + cyclohexylamine (108-91-8,157973-60-9) → N-phenyl-2-cyclohexylamine (1821-36-9)

Guidance literature:

With dichloro{1,10-[di-2,3,4,5,6-pentamethylbenzyl]-3,3'-o-xylyldibenzimidazolidin-2,2'-diylidene}palladium (II); potassium tert-butylate; In 1,2-dimethoxyethane; at 80 ℃; for 15h; Inert atmosphere;

DOI:10.1016/j.poly.2010.10.015

Reference yield: 98.0%

aniline (62-53-3) + cyclohexanol (108-93-0) → N-phenyl-2-cyclohexylamine (1821-36-9)

Guidance literature:

With NiCuFeO(x); In 5,5-dimethyl-1,3-cyclohexadiene; for 24h; Inert atmosphere; Sealed tube; Reflux;

DOI:10.1002/chem.201203417

upstream raw materials:

N-cyclohexyl-N-nitrosoaniline

N-cyclohexylidenebenzenamine

cyclohexanone

nitrobenzene

Downstream raw materials:

cyclohexene

N-cyclohexyl-N-ethylaniline

N-cyclohexyl-N-phenylaniline

N-cyclohexyl-4-phenylazo-aniline

Refernces

• 1、 Minato, Makoto,Fujiwara, Yutaka,Ito, Takashi. "Reduction of imines to amines through use of Cp2MoH2 and protonic acid system". . p. 647 - 648. Retrieved 1995.
• 2、 Kawakami, Takayo,Sugimoto, Takayuki,Shibata, Ikuya,Baba, Akio,Matsuda, Haruo,Sonoda, Noboru. "Highly Coordinated Tin Hydrides: A Novel Synthesis of Tertiary Amines via Hydrostannation of Imines". . p. 2677 - 2682. Retrieved 1995.
• 3、 Karaca, Emine ?zge,Gürbüz, Nevin,?ahin, Onur,Büyükgüng?r, Orhan,?zdemir, ?smail. "Synthesis of palladium complexes derived from imidazolidin-2-ylidene ligands and used for catalytic amination reactions". . p. 1050 - 1055. Retrieved 2016.
• 4、 Tomkins, Patrick,Valgaeren, Carlot,Adriaensen, Koen,Cuypers, Thomas,De Vos, Dirk E.. "The impact of the nature of amine reactants in the palladium catalyzed conversion of phenol to N-substituted anilines". . p. 207 - 213. Retrieved 2019.
• 5、 Kamal, Mohammad M.,Liu, Zhizhou,Vidovi?, Dragoslav,Zhai, Siyuan. "Imine reduction with me2s-bh3". . . Retrieved 2021/09/13.
• 6、 Agbossou-Niedercorn, Francine,Corre, Yann,Dongare, Mohan K.,Kemnitz, Erhard,Kokane, Reshma,Michon, Christophe,Umbarkar, Shubhangi B.. "Palladium supported on magnesium hydroxyl fluoride: An effective acid catalyst for the hydrogenation of imines and N-heterocycles". supporting information. p. 19572 - 19583. Retrieved 2021/11/04.