N-[(4-chlorophenyl)methyl]pyridin-2-amine

Base Information

• Chemical Name: N-[(4-chlorophenyl)methyl]pyridin-2-amine
• CAS No.: 22881-33-0
• Molecular Formula: C12H11 Cl N2
• Molecular Weight: 218.686
• Hs Code.: 2933399090
• European Community (EC) Number: 245-283-3
• NSC Number: 118980
• DSSTox Substance ID: DTXSID30945556
• Nikkaji Number: J286.336G
• Wikidata: Q82922937
• ChEMBL ID: CHEMBL1310074
• Mol file: 22881-33-0.mol

Synonyms:22881-33-0;N-[(4-chlorophenyl)methyl]pyridin-2-amine;N-(4-chlorobenzyl)pyridin-2-amine;2-pyridinamine, n-[(4-chlorophenyl)methyl]-;(4-Chloro-benzyl)-pyridin-2-yl-amine;2-[(p-chlorobenzyl)amino]-pyridine;EINECS 245-283-3;N-((4-Chlorophenyl)methyl)pyridin-2-amine;2-Pyridinamine, N-((4-chlorophenyl)methyl)-;NSC118980;N-[(4-Chlorophenyl)methyl]-2-pyridinamine;chlorobenzyl-a-amino pyridin;Oprea1_580436;MLS000708380;2-(p-chlorobenzyl)aminopyridine;4-Chlorobenzyl 2-pyridinylamine;CHEMBL1310074;SCHEMBL14980562;DTXSID30945556;HMS1687B11;HMS2735F08;XAA88133;STK134945;AKOS000505700;NSC 118980;NSC-118980;SB79000;NCGC00245410-01;SMR000287847;CS-0262220;EN300-817901;W-110554

Chemical Property of N-[(4-chlorophenyl)methyl]pyridin-2-amine

Chemical Property:

• Vapor Pressure: 4.04E-05mmHg at 25°C
• Melting Point: 96-98.5 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• Boiling Point: 351.7°Cat760mmHg
• PKA: 6.14±0.10(Predicted)
• Flash Point: 166.5°C
• PSA: 24.92000
• Density: 1.251g/cm³
• LogP: 3.42010
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 218.0610761
• Heavy Atom Count: 15
• Complexity: 179

Purity/Quality:

99% ^*data from raw suppliers

2-[(p-chlorobenzyl)amino]-pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=NC(=C1)NCC2=CC=C(C=C2)Cl
• Uses: 2-[(p-chlorobenzyl)amino]-pyridine is a useful synthetic intermediate. It can be prepared via selective iridium-catalyzed alkylation of (hetero)aromatic amines.

Technology Process of N-[(4-chlorophenyl)methyl]pyridin-2-amine

There total 16 articles about N-[(4-chlorophenyl)methyl]pyridin-2-amine 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%

2-aminopyridine (504-29-0) + para-Chlorobenzyl alcohol (873-76-7) → N-[(4-chlorophenyl)methyl]pyridin-2-amine (22881-33-0)

Guidance literature:

With iron(II,III) oxide; potassium tert-butylate; In 1,4-dioxane; at 90 ℃; for 168h; Inert atmosphere;

DOI:10.1039/b901929d

Reference yield: 90.0%

pyridin-3-ylamine (462-08-8) + para-Chlorobenzyl alcohol (873-76-7) → N-[(4-chlorophenyl)methyl]pyridin-2-amine (22881-33-0)

Guidance literature:

With [(η5-pentamethylcyclopentadienyl)Ir^IIIbis-(κC-1,3-dimethylimidazol-2-ylidene)Cl]BF₄; potassium tert-butylate; In toluene; at 80 ℃; for 12h;

DOI:10.1016/j.poly.2021.115289

Reference yield: 90.0%

2-aminopyridine (504-29-0) + para-Chlorobenzyl alcohol (873-76-7) → N-benzylpyridin-2-amine (6935-27-9) + N-[(4-chlorophenyl)methyl]pyridin-2-amine (22881-33-0)

Guidance literature:

With potassium tert-butylate; copper diacetate; In 1,4-dioxane; at 130 ℃; for 24h;

DOI:10.1016/j.tetlet.2009.11.009

upstream raw materials:

2-aminopyridine

4-chlorobenzaldehyde

2-<(p-chlorobenzylidene)amino>pyridine

para-Chlorobenzyl alcohol

Downstream raw materials:

QKE₂₃

chloropyramine

Refernces

• 1、 Huang, Ming,Li, Yinwu,Lan, Xiao-Bing,Liu, Jiahao,Zhao, Cunyuan,Liu, Yan,Ke, Zhuofeng. "Ruthenium(ii) complexes with N-heterocyclic carbene-phosphine ligands for theN-alkylation of amines with alcohols". supporting information. p. 3451 - 3461. Retrieved 2021/05/03.
• 2、 Wei, Dongyue,Yang, Peng,Yu, Chuanman,Zhao, Fengkai,Wang, Yilei,Peng, Zhihua. "N-Alkylation of Amines with Alcohols Catalyzed by Manganese(II) Chloride or Bromopentacarbonylmanganese(I)". . p. 2254 - 2263. Retrieved 2021/02/26.