4-Chloro-n-methylideneaniline

Base Information

• Chemical Name: 4-Chloro-n-methylideneaniline
• CAS No.: 32328-78-2
• Molecular Formula: C7H6ClN
• Molecular Weight: 139.5822
• NSC Number: 99332
• DSSTox Substance ID: DTXSID30295023
• Nikkaji Number: J1.258.923I
• Wikidata: Q82034684
• Mol file: 32328-78-2.mol

Synonyms:32328-78-2;4-chloro-n-methylideneaniline;NSC99332;SCHEMBL13354662;DTXSID30295023;NSC-99332

Chemical Property of 4-Chloro-n-methylideneaniline

Chemical Property:

• Vapor Pressure: 0.181mmHg at 25°C
• Boiling Point: 218.9°Cat760mmHg
• Flash Point: 86.2°C
• Density: 1.07g/cm³
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 139.0188769
• Heavy Atom Count: 9
• Complexity: 95.1

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=NC1=CC=C(C=C1)Cl

Technology Process of 4-Chloro-n-methylideneaniline

There total 4 articles about 4-Chloro-n-methylideneaniline 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: 95.0%

methanol (67-56-1) + 4-chloro-aniline (106-47-8) → N-methyl(p-chloroaniline) (932-96-7) + 4-chloro-N,N-dimethylaniline (698-69-1) + N,N-bis(methoxymethyl)-N-(p-chlorophenyl)amine (1451094-78-2) + 4-chloro-N-methylen-aniline (32328-78-2) + 4-methyl-N-(methoxymethyl)-N-methylaniline (146303-58-4)

Guidance literature:

With Cu₁-Mo₁/TiO₂; In neat liquid; at 20 ℃; for 21h; Reagent/catalyst; Time; Catalytic behavior; Mechanism; Inert atmosphere; UV-irradiation;

DOI:10.1039/c5cy00316d

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-chloro-aniline (106-47-8) → 4-chloro-N-methylen-aniline (32328-78-2)

Guidance literature:

With 1-ethyl-3-methylimidazolium (S)-2-pyrrolidinecarboxylic acid salt; In dichloromethane; water; at 20 ℃;

DOI:10.1016/j.catcom.2009.12.021

Reference yield:

4-chlorobenzonitrile (100-00-5) → 4-chloro-N-methylen-aniline (32328-78-2)

Guidance literature:

Multi-step reaction with 2 steps

1: rhodium(III) chloride hydrate; potassium tert-butylate; methanol / 60 h / 150 °C / Sealed tube; High pressure

2: rhodium(III) chloride hydrate; potassium tert-butylate / toluene / 24 h / 130 °C / Sealed tube; High pressure

With methanol; rhodium(III) chloride hydrate; potassium tert-butylate; In toluene;

DOI:10.1002/cctc.202001937

upstream raw materials:

hexahydro-1,3,5-(4-chlorophenyl)-1,3,5-triazine

formaldehyd

4-chloro-aniline

methanol

Downstream raw materials:

N-methyl(p-chloroaniline)

(E)-methyl 2-(3-(4-chlorophenyl)-1,5-diphenylimidazolidin-4-ylidene)acetate

(E)-1-(1,3-bis(4-chlorophenyl)imidazolidin-4-ylidene)propan-2-one

(E)-methyl 2-(1,3-bis(4-chlorophenyl)imidazolidin-4-ylidene)acetate

Refernces

• 1、 Li, Ze-Lin,Sun, Kang-Kang,Wu, Peng-Yu,Cai, Chun. "Iron-Catalyzed Regioselective α-C-H Alkylation of N-Methylanilines: Cross-Dehydrogenative Coupling between Unactivated C(sp3)-H and C(sp3)-H Bonds via a Radical Process". . p. 6830 - 6839. Retrieved 2019/06/14.
• 2、 Kikue, Nobutaka,Takahashi, Tetsuya,Nishino, Hiroshi. "Mn(III)-based oxidative cyclization of N-aryl-3-oxobutanamides. facile synthesis and transformation of substituted oxindoles". . p. 540 - 562. Retrieved 2015/03/04.