3085-54-9

Basic information

• Product Name: 4-METHYLFORMANILIDE
• Synonyms: 4'-METHYLFORMANILIDE;4-METHYLFORMANILIDE;4-METHYLPHENYLFORMAMIDE;N-FORMYL-P-TOLUIDINE;N-(P-TOLYL)FORMAMIDE;N-(4-TOLYL)FORMAMIDE;Formamide, N-(4-methylphenyl)-;p-Formotoluidide
• CAS NO: 3085-54-9
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.16
• EINECS: 221-400-3
• Product Categories: Amides;Carbonyl Compounds;Organic Building Blocks;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 3085-54-9.mol
• Article Data: 188

Chemical Properties

• Melting Point: 51-55 °C(lit.)
• Boiling Point: 293.5°Cat760mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.103g/cm³
• Vapor Pressure: 0.00172mmHg at 25°C
• Refractive Index: 1.581
• Solubility: soluble in Methanol
• PKA: 15.01±0.70(Predicted)
• BRN: 2205371
• CAS DataBase Reference: 4-METHYLFORMANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYLFORMANILIDE(3085-54-9)
• EPA Substance Registry System: 4-METHYLFORMANILIDE(3085-54-9)

Safety Data

• Statements: 20/21/22
• Safety Statements: 22-24/25
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 3085-54-9(Hazardous Substances Data)

Usage

General Description

4-Methylformanilide, also known as N-formyl-4-methylaniline or N-Methyl-p-Toluidide, is an organic compound and a derivative of aniline. It is widely used as an intermediate in the synthesis of various pharmaceuticals and dyes. 4-Methylformanilide is a colorless to pale yellow liquid with a faint odor, and it is soluble in organic solvents. It is also used as a solvent in organic synthesis and as a reagent in the chemical industry. The compound is known to be a skin and eye irritant and has been found to be toxic to aquatic organisms, making it important to handle and dispose of it properly.

InChI:InChI=1/C8H9NO/c1-7-2-4-8(5-3-7)9-6-10/h2-6H,1H3,(H,9,10)

Upstream product

• 106-49-0 p-toluidine 
• 134965-38-1 Hex-1-en-2-yl formate 
• 201230-82-2 carbon monoxide 
• 111333-97-2 formic acid pentafluorophenyl ester 
• 32978-00-0 Isopropenyl formate 
• 18197-22-3 N-formylformamide 
• 7175-47-5 4-methylphenyl isocyanide 
• 5469-72-7 1-deoxy-1-p-toluidino-D-fructose 
• 622-52-6 p-methylphenylthiourea 
• 99-99-0 1-methyl-4-nitrobenzene 
• 109-99-9 tetrahydrofuran 
• 2101-86-2 p-methylazidobenzene 
• 77287-34-4 formamide 
• 64-19-7 acetic acid 

Downstream Products

• 621-00-1 1,3-di-p-tolylurea 
• 16596-03-5 N,N'-di-p-tolylformamidine 
• 623-08-5 N-methyl-p-toluidine 
• 106-49-0 p-toluidine 
• 99-97-8 Dimethyl-p-toluidine 
• 104-85-8 para-methylbenzonitrile 
• 620-93-9 di-p-tolylamine 
• 123324-87-8 4-tert-butyl-N-(4-methylphenyl)aniline 
• 52753-44-3 (2-nitrophenyl)-p-tolylamine 
• 77486-44-3 N'-(4-methylphenyl)-N-(3-dimethylaminopropyl)formamidine 
• 77486-43-2 N'-(4-methylphenyl)-N-propylformamidine 
• 95475-02-8 2H-2-(4-methylphenyl)benzo[d]-1,2,3-triazole 1-oxide 
• 67519-76-0 N-(Chloro-dimethyl-silanylmethyl)-N-p-tolyl-formamide 
• 2739-04-0 N-methyl-N-(4-methylphenyl)formamide 

Relevant articles and documents

Metal-Free, Rapid, and Highly Chemoselective Reduction of Aromatic Nitro Compounds at Room Temperature

In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4′-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.

Facile N-Formylation of Amines on Magnetic Fe3O4?CuO Nanocomposites

A facile, eco-friendly, efficient, and recyclable heterogeneous catalyst is synthesized by immobilizing copper impregnated on mesoporous magnetic nanoparticles. The surface chemistry analysis of Fe3O4?CuO nanocomposites (NCs) by XRD and XPS demonstrates the synergistic effect between Fe3O4 and CuO nanoparticles, providing mass-transfer channels for the catalytic reaction. TEM images clearly indicate the impregnation of CuO onto mesoporous Fe3O4. This hydrothermally synthesized eco-friendly and highly efficient Fe3O4?CuO NCs are applied as a magnetically retrievable heterogeneous catalyst for the N-formylation of wide range of aliphatic, aromatic, polyaromatic and heteroaromatic amines using formic acid as a formylating agent at room temperature. The catalytic activity of the NCs for N-formylation is attributable to the synergistic effect between Fe3O4 and CuO nanoparticles. The N-formylated product is further employed for the synthesis of biologically active quinolone moieties.

Catalyst freeN-formylation of aromatic and aliphatic amines exploiting reductive formylation of CO2using NaBH4

Herein, we report a sustainable approach forN-formylation of aromatic as well as aliphatic amines using sodium borohydride and carbon dioxide gas. The developed approach is catalyst free, and does not need pressure or a specialized reaction assembly. The reductive formylation of CO2with sodium borohydride generates formoxy borohydride speciesin situ, as confirmed by1H and11B NMR spectroscopy. Thein situformation of formoxy borohydride species is prominent in formamide based solvents and is critical for the success of theN-formylation reactions. The formoxy borohydride is also found to promote transamidation reactions as a competitive pathway along with reductive functionalization of CO2with amine leading toN-formylation of amines.