2,2'-Methylenedianiline

Base Information

• Chemical Name: 2,2'-Methylenedianiline
• CAS No.: 6582-52-1
• Molecular Formula: C13H14N2
• Molecular Weight: 198.268
• Hs Code.: 2921590090
• European Community (EC) Number: 229-512-4
• DSSTox Substance ID: DTXSID5064413
• Nikkaji Number: J81.242K
• Wikidata: Q81976976
• Mol file: 6582-52-1.mol

Synonyms:2,2'-Methylenedianiline;6582-52-1;2-[(2-aminophenyl)methyl]aniline;Benzenamine, 2,2'-methylenebis-;2,2'methylenedianiline;Aniline, 2,2'-methylenedi-;2,2'-Diaminodiphenylmethane;2,2'-Methylenebis(benzeneamine);EINECS 229-512-4;MFCD01109641;2,2-methylenedianiline;2,2' methylenedianiline;2,2'- methylenedianiline;Oprea1_274500;SCHEMBL36019;2,2'-diamino-diphenylmethane;DTXSID5064413;AKOS004900765;DS-19352;CS-0156658;FT-0699796;2,2 inverted exclamation mark methylenedianiline;EN300-1264348

Chemical Property of 2,2'-Methylenedianiline

Chemical Property:

• Melting Point: 134-135 °C
• Boiling Point: 390.2°Cat760mmHg
• PKA: 4.27±0.10(Predicted)
• Flash Point: 226.8°C
• PSA: 52.04000
• Density: 1.143g/cm³
• LogP: 3.60420
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 198.115698455
• Heavy Atom Count: 15
• Complexity: 173

Purity/Quality:

98% ^*data from raw suppliers

2,2'-Methylenedianiline 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CC2=CC=CC=C2N)N
• Uses: 2,2''-Methylenedianiline is used in the production of rigid polyurethane foams.

Technology Process of 2,2'-Methylenedianiline

There total 19 articles about 2,2'-Methylenedianiline 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: 52.0%

1-nitro-2-[(2-nitrophenyl)methyl]benzene (21540-57-8) → 2,2'-methylenedianiline (6582-52-1)

Guidance literature:

With hydrogenchloride; tin; In ethanol; for 1h; Heating;

Reference yield: 44.5%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + aniline (62-53-3) → polyamines + 2,4'-diaminodiphenylmethane (1208-52-2) + 2,2'-methylenedianiline (6582-52-1) + 4,4'-diamino diphenyl methane (101-77-9)

Guidance literature:

formaldehyd; aniline; In water; at 25 - 80 ℃;

hydrogenchloride; In water; at 45 - 140 ℃; for 2.5 - 2.83333h; under 750.075 - 3750.38 Torr;

With sodium hydroxide; In water; at 100 ℃; Product distribution / selectivity;

Reference yield:

N,N'-diphenylmethylenediamine (622-14-0) → 2,4'-diaminodiphenylmethane (1208-52-2) + 2,2'-methylenedianiline (6582-52-1) + N-(2-aminobenzyl)aniline (20887-06-3) + N-(4-aminobenzyl)aniline (24007-66-7) + 4,4'-diamino diphenyl methane (101-77-9)

Guidance literature:

With Fe_1.3 loaded silica catalyst; at 150 ℃; for 24h; Concentration; Catalytic behavior; Sealed tube; Inert atmosphere;

DOI:10.1016/j.jcat.2021.05.031

upstream raw materials:

1-nitro-2-[(2-nitrophenyl)methyl]benzene

1,2-dihydrodibenzo--diazepine

2,4'-diaminodiphenylmethane

4,4'-diamino diphenyl methane

Downstream raw materials:

C₄₉H₄₀N₂P₂

2,4'-methylene-dicyclohexyldiamine

N-methyl-4,4'-diaminodicyclohexylmethane

4,4'-diaminodicyclohexylmethane

Refernces

• 1、 -. "HETEROGENEOUS SYNTHESIS OF METHYLENE DIANILINE". Page/Page column 33-35. . Retrieved 2021/06/22.
• 2、 Botella,Corma,Carr, Robert H.,Mitchell, Christopher J.. "Towards an industrial synthesis of diamino diphenyl methane (DADPM) using novel delaminated materials: A breakthrough step in the production of isocyanates for polyurethanes". experimental part. p. 143 - 149. Retrieved 2012/02/13.