4,4'-Methylene bis(2-chloroaniline)

Base Information

• Chemical Name: 4,4'-Methylene bis(2-chloroaniline)
• CAS No.: 101-14-4
• Deprecated CAS: 126699-69-2,29371-14-0,51065-07-7,78642-65-6,142661-36-7,913092-91-8,1899048-27-1,1951406-44-2,142661-36-7,1899048-27-1,1951406-44-2,29371-14-0,78642-65-6,913092-91-8
• Molecular Formula: C13H12Cl2N2
• Molecular Weight: 267.158
• Hs Code.: 2921.59
• European Community (EC) Number: 202-918-9
• ICSC Number: 0508
• NSC Number: 52954
• UN Number: 3077
• UNII: 3L2W5VTT2A
• DSSTox Substance ID: DTXSID5020865
• Nikkaji Number: J3.595E
• Wikipedia: 4,4%27-Methylenebis(2-chloroaniline),4'-Methylenebis(2-chloroaniline)
• Wikidata: Q2257591
• NCI Thesaurus Code: C44319
• Metabolomics Workbench ID: 67547
• ChEMBL ID: CHEMBL82846
• Mol file: 101-14-4.mol

Synonyms:Aniline,4,4'-methylenebis[2-chloro- (6CI,8CI);2,2'-Dichloro-4,4'-methylenedianiline;3,3'-Dichloro-4,4'-diaminodiphenylmethane;4,4'-Methylenebis(2-chloraniline);4,4'-Methylenebis(2-chlorobenzenamine);4,4'-Methylenebis[2-chloroaniline];4,4'-Methylenebis[o-chloroaniline];Bis(3-chloro-4-aminophenyl)methane;Bis(4-amino-3-chlorophenyl)methane;Bisamine A;Bisamine S;MOCA (curing agent);Methylenebis(3-chloro-4-aminobenzene);Methylenebis(chloraniline);Millionate M;NSC 52954;Pandex E;Pandex M 3202;Quodorole;SL 4037;

Chemical Property of 4,4'-Methylene bis(2-chloroaniline)

Chemical Property:

• Appearance/Colour: off-white powder with slight odor
• Vapor Pressure: 0.001Pa at 20℃
• Melting Point: 102-107 °C(lit.)
• Refractive Index: 1.6710 (estimate)
• Boiling Point: 412 °C at 760 mmHg
• PKA: 3.33±0.25(Predicted)
• Flash Point: 203 °C
• PSA: 52.04000
• Density: 1.354 g/cm³
• LogP: 4.91100
• Water Solubility.: <0.1 g/100 mL at 25 oC
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 266.0377538
• Heavy Atom Count: 17
• Complexity: 226
• Transport DOT Label: Class 9

Purity/Quality:

99% ^*data from raw suppliers

4,4''-Methylenebis(2-chloroaniline)(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 45-22-50/53-53-50-68
• Safety Statements: 53-45-60-61-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Plastics & Rubber -> Curing Agents (Aromatic)
• Canonical SMILES: C1=CC(=C(C=C1CC2=CC(=C(C=C2)N)Cl)Cl)N
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance may cause effects on the blood.
• Effects of Long Term Exposure: This substance is carcinogenic to humans.
• Uses: MOCA is widely used in machinery, automobile, aircraft manufacturing, mining, industrial and sports facilities (such as plastic track and plastic floor) can be used for curing and waterproof coatings such as epoxy resin, which can be given to polyester and polyether elastomer most good physical and mechanical properties and the results. Curing agent for polyurethanes and epoxy resins

Technology Process of 4,4'-Methylene bis(2-chloroaniline)

There total 10 articles about 4,4'-Methylene bis(2-chloroaniline) 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: 85.0%

→ 4,4'-methylenebis-(2-chloroaniline) (101-14-4,78642-65-6)

Guidance literature:

With hydrogenchloride; In water; for 0.5h; Microwave irradiation;

In water; at 40 ℃; Microwave irradiation;

Reference yield: 80.1%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + o-chloroaniline (95-51-2) → 4,4'-methylenebis-(2-chloroaniline) (101-14-4,78642-65-6)

Guidance literature:

With phosphotungstic acid; In water; at 160 ℃; for 0.5h;

Reference yield: 56.0%

dimethyl sulfoxide (67-68-5,8070-53-9) + o-chloroaniline (95-51-2) → 4,4'-methylenebis-(2-chloroaniline) (101-14-4,78642-65-6)

Guidance literature:

With ammonium iodide; In water; at 140 ℃; for 16h; regioselective reaction; Sealed tube;

DOI:10.1039/c5ob01679g

upstream raw materials:

N,N'-bis-(2-chlorophenyl)methanediamine

o-chloroaniline

2-chloroaniline hydrochloride

N-benzotriazol-1-ylmethyl-2-chloro-aniline

Downstream raw materials:

4-(4-amino-3-chlorobenzyl)-2-azido-6-chloroaniline

N,N'-[methylenebis(2-chloro-4,1-phenylene)]bis(2-bromoacetamide)

N,N'-[methylenebis(2-chloro-4,1-phenylene)]bis[2-(1-pyrrolidinyl)acetamide]

3,3'-dichloro-4,4'-bis(salicylideneimino)diphenylmethane

Refernces

• 1、 -. "Continuous synthesis process of 3, 3'-dichloro-4, 4'-diaminodiphenyl methane". Paragraph 0032-0051. . Retrieved 2021/05/01.
• 2、 -. "By using micro-reactor preparation 4, 4' - diamino diphenylmethane derivatives (by machine translation)". Paragraph 0048; 0049; 0050; 0051-0055; 0068; 0069. . Retrieved 2017/08/31.