100-62-9

Basic information

• Product Name: N-methyleneaniline
• Synonyms: N-methyleneaniline;N-Methylenebenzenamine;N-Phenylmethanimine;methylene(phenyl)amine
• CAS NO: 100-62-9
• Molecular Formula: C7H7N
• Molecular Weight: 105.13718
• EINECS: 202-871-4
• Mol File: 100-62-9.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 169.8°C at 760 mmHg
• Flash Point: 47.7°C
• Appearance: /
• Density: 0.87g/cm³
• Vapor Pressure: 2.01mmHg at 25°C
• Refractive Index: 1.496
• CAS DataBase Reference: N-methyleneaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-methyleneaniline(100-62-9)
• EPA Substance Registry System: N-methyleneaniline(100-62-9)

Safety Data

• Hazardous Substances Data: 100-62-9(Hazardous Substances Data)

Usage

General Description

N-methyleneaniline, also known as N-methylaniline or NMA, is an aromatic amine with the chemical formula C7H9N. It is a colorless to pale yellow liquid with a fishy odor and is commonly used as an intermediate in the production of dyes, pharmaceuticals, and other organic compounds. N-methyleneaniline is considered a hazardous chemical, as it is toxic if swallowed, inhaled, or comes into contact with skin and eyes. Exposure to N-methyleneaniline can cause irritation to the skin, eyes, and respiratory system, as well as potential damage to the liver and kidneys. It is important to handle and store N-methyleneaniline with proper safety measures and equipment to prevent any adverse health effects.

InChI:InChI=1/C7H7N/c1-8-7-5-3-2-4-6-7/h2-6H,1H2

Upstream product

• 6628-07-5 N-allyl-N-methylaniline 
• 622-14-0 N,N'-diphenylmethylenediamine 
• 18158-72-0 N-ethyl-N-phenyl-N-propargylamine 
• 35673-10-0 bis(3-(trifluoromethyl)benzenesulfonyl) peroxide 
• 100-46-9 benzylamine 
• 91-78-1 1,3,5-triphenylhexahydro-1,3,5-triazine 
• 75-09-2 dichloromethane 
• 62-53-3 aniline 
• 16078-91-4 N-allyl-N-ethylaniline 
• 103-01-5 N-Phenylglycine 
• 106-51-4 p-benzoquinone 
• 88933-19-1 methoxymethylphenylamine 
• 91-78-1 1,3,5-triphenyl-hexahydro-sym-triazine 
• 67-56-1 methanol 

Downstream Products

• 861086-73-9 2-((phenylamino)methyl)naphthalen-1-ol 
• 6638-95-5 1-(phenylaminomethyl)naphthalen-2-ol 
• 2655-27-8 N-pentylaniline 
• 2563-99-7 N-phenyl-2,2-dichloroacetamide 
• 134126-50-4 4,5-bis(dichloromethylene)-1,3-diphenylimidazolidin-2-one 
• 50-00-0 formaldehyd 
• 62-53-3 aniline 
• 3376-52-1 pentaphenylcyclopentaphosphane 
• 137180-90-6 [(Formyl-phenyl-amino)-methyl]-phosphonic acid dimethyl ester 
• 56195-80-3 2-Anilino-N,1,2,2-tetraphenyl-ethan-1-imin 
• 1601484-13-2 (E)-1-(1,3,5-triphenylimidazolidin-4-ylidene)propan-2-one 
• 1601483-85-5 (E)-methyl 2-(1,3-diphenylimidazolidin-4-ylidene)acetate 
• 1601483-94-6 (E)-ethyl 2-(1,3-diphenylimidazolidin-4-ylidene)acetate 
• 1601483-96-8 (E)-1-(1,3-diphenylimidazolidin-4-ylidene)propan-2-one 

Relevant articles and documents

Synthesis of imines from nitrobenzene and TiO2 particles suspended in alcohols via semiconductor photocatalysis type B

UV irradiation on a non-aqueous suspension of titanium dioxide with nitrobenzene and different alcohols in deaerated conditions produces imines and aniline as main products. The conversion of nitrobenzene and the corresponding selectivity of imines or aniline depend on the type of alcohol used. A low conversion (3-12%) and selectivity close to 100% to imines were obtained with methyl, ethyl, or propyl alcohol. Otherwise, using i-propanol only aniline was detected with a conversion of 13%. Finally, a mixture of aniline and imines was formed employing n-butyl, n-amyl, and i-amyl alcohols with the higher conversion (～50%).

Cyclocondensation of lower aliphatic aldehydes with arylamines and cyclopentadiene

Three-component condensation of lower aliphatic aldehydes (C 1-C3) with arylamines and cyclopentadiene (the Povarov reaction) gave 3a,4,5,9b-tetrahydro-3H-cyclopenta[c]-quinolines. Ozonization of their N-trifluoroacetyl derivatives a

Carbonylation of nitrobenzene in methanol with palladium bidentate phosphane complexes: An unexpectedly complex network of catalytic reactions, centred around a Pd-imido intermediate

The reactivity of palladium complexes of bidentate diaryl phosphane ligands (P2) was studied in the reaction of nitrobenzene with CO in methanol. Careful analysis of the reaction mixtures revealed that, besides the frequently reported reduction products of nitrobenzene [methyl phenyl carbamate (MPC), N,N′-diphenylurea (DPU), aniline, azobenzene (Azo) and azoxybenzene (Azoxy)], large quantities of oxidation products of methanol were co-produced (dimethyl carbonate (DMC), dimethyl oxalate (DMO), methyl formate (MF), H 2O, and CO). From these observations, it is concluded that several catalytic processes operate simultaneously, and are coupled via common catalytic intermediates. Starting from a P2Pd0 compound formed in situ, oxidation to a palladium imido compound P2PdII=NPh, can be achieved by de-oxygenation of nitrobenzene 1) with two molecules of CO, 2) with two molecules of CO and the acidic protons of two methanol molecules, or 3) with all four hydrogen atoms of one methanol molecule. Reduction of P 2PdII=NPh to P2Pd0 makes the overall process catalytic, while at the same time forming Azo(xy), MPC, DPU and aniline. It is proposed that the Pd-imido species is the central key intermediate that can link together all reduction products of nitrobenzene and all oxidation products of methanol in one unified mechanistic scheme. The relative occurrence of the various catalytic processes is shown to be dependent on the characteristics of the catalysts, as imposed by the ligand structure.

Sulfated polyborate: A dual catalyst for the reductive amination of aldehydes and ketones by NaBH4

An efficient, quick, and environment-friendly one-pot reductive amination of aldehydes or ketones was developed. In ethanol at 70 °C, a imination catalyzed by sulfated polyborate and further reduced by sodium borohydride yields various amines. The present method has many significant benefits, including a shorter reaction time, excellent yields, and a hassle-free, straightforward experimental process. The reaction has a wide range of applications due to its flexibility, including secondary amine for reductive amination.

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

The iron-catalyzed α-C-H alkylation of N-methylanilines without any directing group by cross-dehydrogenative coupling between unactivated C(sp3)-H and C(sp3)-H bonds has been established for the first time, which provides a good complement to C(sp3)-H activation reactions and expands the field of Fe-catalyzed C-H functionalizations. Many different C(sp3)-H bonds in cyclic alkanes, cyclic ethers, and toluene derivatives can be used as coupling partners. Mechanistic investigations including the radical reaction process, the main role of various reagents, and the kinetic isotope effect experiment were also described.