838-88-0

Basic information

• Product Name: 4,4'-DIAMINO-3,3'-DIMETHYLDIPHENYLMETHANE
• Synonyms: 4,4’-methylenebis(2-methyl-anilin;4,4’-methylenebis(2-methyl-benzenamin;4,4’-methylenebis(2-methylbenzenamine);4,4’-methylenebis[2-methyl-benzenamin;4,4’-methylenedi-o-toluidin;bis(4-amino-3-methylphenyl)-methan;bis(4-amino-3-methylphenyl)methane;bis-4-amino-3-methylfenylmethan
• CAS NO: 838-88-0
• Molecular Formula: C₁₅H₁₈N₂
• Molecular Weight: 226.32
• EINECS: 212-658-8
• Product Categories: Industrial/Fine Chemicals;Diphenylmethanes (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research
• Mol File: 838-88-0.mol

Chemical Properties

• Melting Point: 155-157 °C
• Boiling Point: 357.94°C (rough estimate)
• Flash Point: 238.9 °C
• Appearance: /
• Density: 0.9543 (rough estimate)
• Vapor Pressure: 1.8hPa at 205.5℃
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 5.18±0.25(Predicted)
• Water Solubility: Insoluble in water
• BRN: 398069
• CAS DataBase Reference: 4,4'-DIAMINO-3,3'-DIMETHYLDIPHENYLMETHANE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-DIAMINO-3,3'-DIMETHYLDIPHENYLMETHANE(838-88-0)
• EPA Substance Registry System: 4,4'-DIAMINO-3,3'-DIMETHYLDIPHENYLMETHANE(838-88-0)

Safety Data

• Hazard Codes: T,N
• Statements: 45-22-43-50/53
• Safety Statements: 53-45-60-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• RTECS: BY5300000
• F: 10-23
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 838-88-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder. Soluble in ethanol and hot water.

Uses

Different sources of media describe the Uses of 838-88-0 differently. You can refer to the following data:
1. 4,4′-Methylene-bis(2-methylaniline) has been used as a reference standard for the determination of 4,4′-methylene-bis(2-methylaniline) in plastic multilayer food packaging materials by liquid chromatography (LC)-Orbitrap-full scan-high resolution mass spectrometry (HRMS). It may be used as a reference standard for the analysis of 4,4′-methylene-bis(2-methylaniline) in dyes, cosmetics, finger paints and inks for pens and tattoos by LC-MS.
2. 4,4'-Diamino-3,3'-dimethyldiphenylmethane can be used for preparation polyimide and epoxy resin material.

General Description

4,4′-Methylene-bis(2-methylaniline) belongs to the primary aromatic amines (PAAs) family of compounds which are toxic in nature and are probable human carcinogens.

Safety Profile

Confirmed carcinogen with experimental carcinogenic data. Moderately toxic by ingestion. An eye irritant. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Upstream product

• 54560-77-9 bis(2-methylphenylamino)methane 
• 636-21-5 o-toluidine hydrochloride 
• 50-00-0 formaldehyd 
• 95-53-4 o-toluidine 
• 91-78-1 1,3,5-triphenylhexahydro-1,3,5-triazine 
• 72621-64-8 2-toluidine 
• 5293-94-7 bis(chloromethyl)mercury 
• 71893-15-7 C₄H₇ClHgO 
• 7647-01-0 hydrogenchloride 
• 861612-93-3 bis-(4-amino-3-methyl-phenyl)-acetic acid 
• 67-68-5 dimethyl sulfoxide 
• 108-44-1 1-amino-3-methylbenzene 
• 62001-35-8 N-(1-benzotriazolylmethyl)-2-methylaniline 
• 88919-92-0 Methoxymethyl-o-tolyl-amine 

Downstream Products

• 122240-79-3 bis-(4-diacetylamino-3-methyl-phenyl)-methane 
• 71655-97-5 bis-(4-acetoacetylamino-3'-methyl-phenyl)-methane 
• 139-25-3 bis-(4-isocyanato-3-methyl-phenyl)-methane 
• 104398-64-3 bis-(4-benzoylamino-3-methyl-phenyl)-methane 
• 103396-01-6 bis-(4-acetylamino-3-methyl-phenyl)-methane 
• 64497-21-8 2-methylbis-(4-aminophenyl)methane 
• 63861-54-1 4,4',4-triamino-3,3',3-trimethyl-triphenyl-carbenium-chloride 
• 2467-25-6 bis(4-hydroxy-3-methylphenyl)methane 
• 6864-37-5 bis-(4-amino-3-methylcyclohexyl)-methane 
• 46893-31-6 4,4'-diamino-3,3'-dimethyl-benzophenone 
• 122397-61-9 3,3'-dimethyl-4,4'-bis(salicylideneimino)diphenylmethane 
• 35112-57-3 4,4'-diamino-5,5'-dimethyl-2,2'-dinitrodiphenylmethane 
• 84797-73-9 4,4'-diamino-5,3'-dimethyl-2-nitrodiphenylmethane 
• 84797-74-0 4,4'-diamino-5,3'-dimethyl-2,2'-dinitrodiphenylmethane 

Relevant articles and documents

Synthesis of 3,3′-dimethyl-4,4′-diaminodiphenylmethane catalyzed by zeolites replacing mineral acids

Synthesis of 3,3′-dimethyl-4,4′-diaminodiphenylmethane (MDT) from o-tolylamine and formaldehyde over zeolites was investigated. Among the three tested zeolites, Hβ showed higher catalytic activity than HY and HZSM-5 for MDT synthesis. In the case of Hβ as a catalyst, the effects of feed composition, reaction time and temperature on the yield and selectivity of product MDT were further examined to optimize process conditions. In an o-tolylamine:formaldehyde = 8:1 molar ratio, the two-step reaction running at 413 K for 0.5 h and then 433 K for 0.5 h gave the MDT yield of 87.5%.

By using micro-reactor preparation 4, 4' - diamino diphenylmethane derivatives (by machine translation)

The invention discloses the use of micro-reactor for preparing the 4, 4 '- diamino diphenylmethane derivatives, water, inorganic acid of the reaction liquid and the formaldehyde solution respectively through the advection pump conveying to the micro-reactor in the two inlets, in micro-contacting in a reactor, mixing and reaction, then cooling, sodium hydroxide aqueous solution, a white precipitate is separated out, filtering, drying, to obtain 4, 4' - diamino diphenylmethane derivatives (MDA, MDT or MOCA) crude, recrystallized with ethanol, filtering, drying, to get the pure product. The invention adopts the micro-reactor technology to achieve a 4, 4' - diamino diphenylmethane derivatives of continuous preparation, easy large-scale production; the reaction speed, reaction time is greatly shortened. (by machine translation)

Continuous preparation of solid acid catalysis 4, the 4 [...] -diamino diphenylmethane derivatives (by machine translation)

The invention discloses a continuous preparation of solid acid catalysis 4, the 4 [...] -diaminodiphenylmethane derivative method, the method to aniline derivatives as raw materials with formaldehyde, in one stage or two stage fixed-bed reactor to conduct the condensation reaction of the solid acid catalysis of the reaction, the reaction liquid airspeed is 2-9h -1, obtain 4, the 4 [...] -diamino diphenylmethane derivatives (MDA, MDT, MOCA). The invention uses a solid acid Hβ, HY, HZSM-5 molecular sieve to replace the hydrochloric acid, the traditional inorganic acid catalyst such as sulfuric acid, the reaction is carried out continuously, the method of the invention process is simple, short reaction time, the productivity is high, high yield, no corrosion to equipment, environmental protection, especially suitable for continuous industrial production. (by machine translation)

Highly regioselective para-methylthiolation/bridging methylenation of arylamines promoted by NH4I

Aryl methyl thioethers and methylene-bridged arylamines were synthesized via highly regioselective para-methylthiolation/bridging methylenation of arylamines using DMSO as the methylthio or methylene source in the presence of NH4I under metal-free conditions. For the substrates with both electron-donating and electron-withdrawing substituents, the reaction proceeded smoothly and gave moderate to good yields.

Insight into the mechanism of 3,3′-dimethyl-4,4′-diaminodiphenylmethane synthesis over Hβ zeolite

Heterogeneous synthesis of 3,3′-dimethyl-4,4′-diaminodiphenylmethane (MDT) from o-tolylamine and formaldehyde on acidic zeolites HY, HZSM-5, Hβ and TS-1 was investigated. Hβ zeolite with strong Bronsted acidity and proper textural property demonstrated be

Salt suitable for an acid generator and a chemically amplified positive resist composition containing the same

The present invention provides a salt represented by the formula (I): wherein P1, P2 and P3 each independently represent a C1-C30 alkyl group which may be substituted with at least one selected from a hydroxyl group, a C3-C12 cyclic hydrocarbon group and a C1-C12 alkoxy group, or a C3-C30 cyclic hydrocarbon group which may be substituted with at least one selected from a hydroxyl group and a C1-C12 alkoxy group, provided that all of P1, P2 and P3 are not simultaneously phenyl groups which may be substituted, Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, and R represents a group represented by the formula: wherein A1 represents —OH or —Y1—OH, n represents an integer of 1 to 9, and Y1 represents a divalent C1-C6 saturated aliphatic hydrocarbon group; a group represented by the formula: wherein ring X1 represents a C3-C30 monocyclic or polycyclic hydrocarbon group in which one —CH2— group is substituted with —CO—, and at least one hydrogen atom in the monocyclic or polycyclic hydrocarbon group may be substituted with a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C4 perfluoroalkyl group, a C1-C6 hydroxyalkyl group, a hydroxyl group or a cyano group; a group represented by the formula: wherein ring X2 represents a C3-C30 monocyclic or polycyclic hydrocarbon group in which a hydrogen atom of one —CH2— group is substituted with a hydroxyl group, and at least one hydrogen atom in the monocyclic or polycyclic hydrocarbon group may be substituted with a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C4 perfluoroalkyl group, a C1-C6 hydroxyalkyl group, a hydroxyl group or a cyano group; a group represented by the formula: wherein ring X3 represents a C3-C30 monocyclic or polycyclic hydrocarbon group in which one —CH2— group is substituted with —COO—, and at least one hydrogen atom in the monocyclic or polycyclic hydrocarbon group may be substituted with a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C4 perfluoroalkyl group, a C1-C6 hydroxyalkyl group, a hydroxyl group or a cyano group, and m represents an integer of 0 to 12; or a group represented by the formula: wherein ring X4 represents a C6-C30 polycyclic hydrocarbon group having tricycle or more, and at least one hydrogen atom in the polycyclic hydrocarbon group may be substituted with a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C4 perfluoroalkyl group, a C1-C6 hydroxyalkyl group or a cyano group, and l represents an integer of 1 to 12. The present invention further provides a chemically amplified resist composition comprising the salt represented by the above-mentioned formula (I).

Functionalized Photoreactive Compounds

The present invention concerns functionalized photoreactive compounds of formula (I), that are particularly useful in materials for the alignment of liquid crystals. Due to the adjunction of an electron withdrawing group to specific molecular systems bearing an unsaturation directly attached to two unsaturated ring systems, exceptionally high photosensitivities, excellent alignment properties as well as good mechanical robustness could be achieved in materials comprising said functionalized photoreactive compounds of the invention.

Synthesis and properties of new poly(imide-amide)s

New aromatic poly(imide-amide)s have been synthesized by solution polycondensation of various aromatic diamines with diacid chlorides containing dimethylsillane or hexafluoroisopropylidene units. These polymers are easily soluble in polar amidic solvents such as N-methylpyrrolidinone (NMP) or dimethylformamide (DMF) and can be cast into thin flexible films or coatings from such solutions. They show high thermal stability, with initial decomposition temperature above 400°C and glass transition temperature in the range of 265-324°C. Very thin polymer films deposited by the spin-coating technique onto silicon wafers showed a smooth, pinhole-free surface in Atomic Force Microscopy investigations.

Process for the preparation of 4,4'-diaminoditolylmethane

Gegenstand der Erfindung ist ein Verfahren zur Herstellung von 4,4'-Diaminoditolylmethan durch Umsetzung von o-Toluidin mit Formaldehyd in Gegenwart eines sauren Katalysators, wobei das Molverh?ltnis des sauren Katalysators zu o-Toluidin von 0,8 bis 1,2 ?quivalenten des sauren Katalysators pro Mol o-Toluidin betr?gt.Das Molverh?ltnis o-Toluidin zu Formaldehyd betr?gt vorzugsweise von 1,5:1 bis 10:1. Der saure Katalysator ist bevorzugt Salzs?ure.

Benzotriazole Mediated Synthesis of Methylenebisanilines

Methylenebisanilines and methylenebis(N,N-dialkylaniline)s are prepared by the reactions of 1-hydroxymethylbenzotriazole with anilines and with N,N-dialkylanilines under acidic conditions.Isolation of the intermediate 4-(benzotriazol-1-ylmethyl)anilines and the N,N-dialkyl analogues and their reactions with anilines allow the efficient preparation of both symmetrical and unsymmetrical members of both product classes.