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

• 64-18-6 formic acid 
• 106-49-0 p-toluidine 
• 77287-34-4 formamide 
• 64-19-7 acetic acid 
• 109-99-9 tetrahydrofuran 
• 2101-86-2 p-methylazidobenzene 
• 18197-22-3 N-formylformamide 
• 32978-00-0 Isopropenyl formate 
• 16954-74-8 (1,3-dioxoindan-2-ylidene)propanedinitrile 
• 16596-03-5 N,N'-di-p-tolylformamidine 
• 105-36-2 ethyl bromoacetate 
• 110-86-1 pyridine 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 135523-42-1 1-(p-methylphenylamino)-3-(p-methylphenylimino)-1-butene 

Downstream Products

• 16596-03-5 N,N'-di-p-tolylformamidine 
• 80535-18-8 4-(4-methylphenyl)-4H-1,2,4-triazole 
• 105971-45-7 N-(4-methylphenyl)-2-methyltetrahydropyrrole 
• 22071-69-8 formic acid-(N-nitroso-p-toluidide) 
• 621-00-1 1,3-di-p-tolylurea 
• 26060-31-1 N-(4-methylphenyl)thioformamide 
• 877-43-0 2,6-dimethylquinoline 
• 93663-20-8 formic acid-(N-bromo-p-toluidide) 
• 7175-47-5 4-methylphenyl isocyanide 
• 104-85-8 para-methylbenzonitrile 
• 89-62-3 4-methyl-2-nitroaniline 
• 622-57-1 N-ethyl-p-tolylamine 
• 104175-33-9 2,6-dimethylquinoline-4-carboxylic acid 
• 79643-58-6 9-methyl-julolidine 

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.

Supported CuII Single-Ion Catalyst for Total Carbon Utilization of C2 and C3 Biomass-Based Platform Molecules in the N-Formylation of Amines

The shift from fossil carbon sources to renewable ones is vital for developing sustainable chemical processes to produce valuable chemicals. In this work, value-added formamides were synthesized in good yields by the reaction of amines with C2 and C3 biomass-based platform molecules such as glycolic acid, 1,3-dihydroxyacetone and glyceraldehyde. These feedstocks were selectively converted by catalysts based on Cu-containing zeolite 5A through the in situ formation of carbonyl-containing intermediates. To the best of our knowledge, this is the first example in which all the carbon atoms in biomass-based feedstocks could be amidated to produce formamide. Combined catalyst characterization results revealed preferably single CuII sites on the surface of Cu/5A, some of which form small clusters, but without direct linking via oxygen bridges. By combining the results of electron paramagnetic resonance (EPR) spin-trapping, operando attenuated total reflection (ATR) IR spectroscopy and control experiments, it was found that the formation of formamides might involve a HCOOH-like intermediate and .NHPh radicals, in which the selective formation of .OOH radicals might play a key role.

Solvent-free, Efficient Transamidation of Carboxamides with Amines Catalyzed by Recyclable Sulfated Polyborate Catalyst

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