4,4'-Methylenedianiline

Base Information

• Chemical Name: 4,4'-Methylenedianiline
• CAS No.: 101-77-9
• Deprecated CAS: 28602-61-1,83712-44-1,120859-32-7,136601-30-4,148263-71-2,120859-32-7,148263-71-2,83712-44-1
• Molecular Formula: C13H14N2
• Molecular Weight: 198.268
• Hs Code.: 29215900
• European Community (EC) Number: 202-974-4,236-934-2,663-410-4
• ICSC Number: 1111
• NSC Number: 4709
• UN Number: 2651
• UNII: GG5LL7OBZC
• DSSTox Substance ID: DTXSID6022422
• Nikkaji Number: J4.995F
• Wikipedia: 4,4%27-Methylenedianiline,4'-Methylenedianiline
• Wikidata: Q229848
• NCI Thesaurus Code: C44320
• Metabolomics Workbench ID: 49551
• ChEMBL ID: CHEMBL85728
• Mol file: 101-77-9.mol

Synonyms:4,4'-diaminodiphenylmethane;4,4'-diaminodiphenylmethane dihydrochloride;4,4'-diaminodiphenylmethane, sodium chloride (3:1);4,4'-MDA;4,4'-methylene dianiline;4,4'-methylenebisaniline;4,4'-methylenedianiline;di(4-aminophenyl)methane;p,p'-diaminodiphenylmethane;Tonox

Chemical Property of 4,4'-Methylenedianiline

Chemical Property:

• Appearance/Colour: white to yellow or beige flakes or crystals
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 89-91 °C(lit.)
• Refractive Index: 1.5014 (estimate)
• Boiling Point: 398 °C at 760 mmHg
• PKA: 5.32±0.25(Predicted)
• Flash Point: 226.3 °C
• PSA: 52.04000
• Density: 1.143 g/cm³
• LogP: 3.60420
• Solubility.: water: soluble
• Water Solubility.: Slightly soluble.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 198.115698455
• Heavy Atom Count: 15
• Complexity: 157
• Transport DOT Label: Poison

Purity/Quality:

99.9% ^*data from raw suppliers

4,4''-Methylenedianiline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 45-39/23/24/25-43-48/20/21/22-51/53-68
• Safety Statements: 53-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Polyaromatic
• Canonical SMILES: C1=CC(=CC=C1CC2=CC=C(C=C2)N)N
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance may cause effects on the liver. This may result in liver impairment.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the liver. This substance is possibly carcinogenic to humans.
• Uses: 4,4'-Methylenedianiline is used in the production of polyurethane foams and epoxy resins. Potential contributor in pulmonary arterial hypertension (PAH) in rats through alteration of the serotenergic transport system. Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants. Dyes and metabolites, Environmental Testing. 4,4'-methylenedianiline be used as organic intermediates. Mainly used for the synthesis of polyimide and as curing agent of epoxy resin. As chemical intermediate in production of isocyanates and polyisocyantes for preparation of polyurethane foams, Spandex fibers; as curing agent for epoxy resins and urethane elastomers; in production of polyamides; in the determination of tungsten and sulfates; in preparation of azo dyes; as corrosion inhibitor. 4,4'-Diaminodiphenyl-methane is used in the determination of tungsten and sulfates; in the preparation of azo dyes; cross-linking agent for epoxy resins; in the preparation of isocyanates and polyisocyanates; in the rubber industry as a curative for neoprene, as an anti-frosting agent (antioxidant) in footwear; raw material in preparation of poly(amide-imide) resins (used in magnet-wire enamels); curing agent for epoxy res ins and urethane elastomers; corrosion inhibitor; rubber additive (accelerator, antidegradant, retarder) in tires and heavy rubber products; in adhesives and glues, laminates, paints and inks, PVC products, handbags, eyeglass frames, plastic jewelry, electric encapsulators, surface coatings, spandex clothing, hairnets, eyelash curlers, earphones, balls, shoe soles, face masks.
• Description: 4,4'-Methylenedianiline is an industrial chemical that is not known to occur naturally. It is also commonly known as diaminodiphenylmethane or MDA. It occurs as a colorless to pale yellow solid and has a faint odor. 4,4'-Methylenedianiline is used mainly for making polyurethane foams, which have a variety of uses, such as insulating materials in mailing containers. It is also used for making coating materials, glues, Spandex? fiber, dyes, and rubber. 4,4'-Methylenedianiline is also a by-product of azo dyes. It is also possibly formed by hydrolysis of diphenylmethane-4A'-diisocyanate.

Technology Process of 4,4'-Methylenedianiline

There total 89 articles about 4,4'-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: 93.0%

bis(4-nitrophenyl)methane (1817-74-9) → 4,4'-diamino diphenyl methane (101-77-9)

Guidance literature:

With potassium fluoride; polymethylhydrosiloxane; palladium diacetate; In tetrahydrofuran; water; at 20 ℃; for 0.5h;

DOI:10.1021/ol052120n

Reference yield: 73.0%

α-chloromethylmercuriopropiophenone (73269-50-8) + aniline (62-53-3) → 4,4'-diamino diphenyl methane (101-77-9) + 1-phenyl-propan-1-one (93-55-0)

Guidance literature:

at 20 ℃; for 1h;

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;

upstream raw materials:

Dimethoxymethane

aniline hydrochloride

bis(4-nitrophenyl)methane

4-aminobenzenemethanol

Downstream raw materials:

bis-(4-acetoacetylamino-phenyl)-methane

1,1'-(methylenedi-4,1-phenylene)bismaleimide

bis-[4-(4,6-diamino-[1,3,5]triazin-2-ylamino)-phenyl]-methane

bis-(4-propionylamino-phenyl)-methane

Refernces

• 1、 Candu, Natalia,Ciobanu, Madalina,Filip, Petru,Haskouri, Jamal El,Guillem, Carmen,Amoros, Pedro,Beltran, Daniel,Coman, Simona M.,Parvulescu, Vasile I.. "Efficient Sc triflate mesoporous-based catalysts for the synthesis of 4,4′-methylenedianiline from aniline and 4-aminobenzylalcohol". . p. 76 - 85. Retrieved 2012.
• 2、 Fedotova et al.. "-". . p. 1600,1601. Retrieved 1963.
• 3、 Baghbanian, Seyed Meysam,Farhang, Maryam,Vahdat, Seyed Mohammad,Tajbakhsh, Mahmood. "Hydrogenation of arenes, nitroarenes, and alkenes catalyzed by rhodium nanoparticles supported on natural nanozeolite clinoptilolite". . p. 128 - 136. Retrieved 2015.
• 4、 Salzinger, Michael,Lercher, Johannes A.. "Reaction network and mechanism of the synthesis of methylenedianiline over dealuminated Y-type zeolites". . p. 149 - 155. Retrieved 2011.
• 5、 Fischer,O.. "". . p. 1341. Retrieved 1895.
• 6、 -. "HETEROGENEOUS SYNTHESIS OF METHYLENE DIANILINE". Page/Page column 33-35. . Retrieved 2021/06/22.
• 7、 -. "METHOD OF PRODUCING DIAMINES AND POLYAMINES OF THE DIPHENYLMETHANE SERIES". Paragraph 0136-0167. . Retrieved 2020/05/02.