N-Methylformanilide

Base Information

• Chemical Name: N-Methylformanilide
• CAS No.: 93-61-8
• Molecular Formula: C8H9NO
• Molecular Weight: 135.166
• Hs Code.: 29242995
• European Community (EC) Number: 202-262-3
• NSC Number: 3828
• UNII: 3D8E5U4HSE
• DSSTox Substance ID: DTXSID0059089
• Nikkaji Number: J37.681G
• Wikidata: Q19859377
• Mol file: 93-61-8.mol

Synonyms:N-Methylformanilide;93-61-8;N-Methyl-N-phenylformamide;Formamide, N-methyl-N-phenyl-;N-Formyl-N-methylaniline;Formanilide, N-methyl-;Methylphenylformamide;N-Methyl-N-formylaniline;N-Phenyl-N-methylformamide;methyl(phenyl)formamide;N-methyl formanilide;NSC 3828;AI3-12081;NSC-3828;EINECS 202-262-3;N-Methylformanilid;N-methyl-N-phenyl-formamide;NSC3828;N-methyl-N-formyl-aniline;N-Methylformanilide, 99%;N-methyl-N-phenyl formamide;3D8E5U4HSE;SCHEMBL66606;DTXSID0059089;MFCD00003283;AKOS009157113;AM87443;AS-17245;BB 0258777;FT-0631471;M0552;EN300-39082;W-100237;Q19859377;F0001-2241

Chemical Property of N-Methylformanilide

Chemical Property:

• Appearance/Colour: clear colourless to yellow liquid
• Vapor Pressure: 0.0329mmHg at 25°C
• Melting Point: 8-13 °C(lit.)
• Refractive Index: n20/D 1.561(lit.)
• Boiling Point: 243 °C at 760 mmHg
• PKA: 0.53±0.50(Predicted)
• Flash Point: 126.7 °C
• PSA: 20.31000
• Density: 1.083 g/cm³
• LogP: 1.91510
• Storage Temp.: Store below +30°C.
• Solubility.: 10.3g/l
• Water Solubility.: immiscible
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 135.068413911
• Heavy Atom Count: 10
• Complexity: 108

Purity/Quality:

99% ^*data from raw suppliers

N-Methylformanilide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-43-38
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: CN(C=O)C1=CC=CC=C1
• Uses: Organic synthesis. N-Methylformanilide is used as a formylating reagent for certain organometallics. It is in combination with phosphoryl chloride used for Vilsmeier-Haack reactions and in heterocycle syntheses. Further, it acts as a swelling agent in the dyeing process of meta-aramid fibers.

Technology Process of N-Methylformanilide

There total 162 articles about N-Methylformanilide 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: 85.0%

2-azido-N-(2-iodophenyl)-N-methyltridecanamide (1029963-84-5) → 1-methyl-3-undecyl-2(1H)-quinoxalinone (1029964-01-9) + N-methyl-N-phenylformamide (93-61-8) + undecyl cyanide (2437-25-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 110 ℃;

DOI:10.1021/jo800453z

Reference yield: 78.0%

1-(4-methoxyphenyl)-2-(methyl(phenyl)amino)ethan-1-one (75681-30-0) → 4-methoxybenzoic acid (100-09-4) + N-methyl-N-phenylformamide (93-61-8)

Guidance literature:

With TEMPO; oxygen; In acetonitrile; at 50 ℃; for 10h; under 760.051 Torr;

DOI:10.1002/adsc.201100225

Reference yield: 76.0%

N,N-dimethyl-aniline (121-69-7,77733-26-7) → 3-phenyl-oxazolidine (20503-92-8) + 1-methyl-1-phenylethyl alcohol (617-94-7) + acetophenone (98-86-2) + N-methyl-N-phenylformamide (93-61-8)

Guidance literature:

With chlorhexidine diphosphanilate; In acetonitrile; at 100 ℃; for 48h; Further byproducts given;

DOI:10.1021/jo00157a020

upstream raw materials:

N,N'-dimethyl-N,N'-diphenylethylenediamine

N-phenyl-formimidic acid methyl ester

formamide

acetic acid

Downstream raw materials:

thiophene-2-carbaldehyde

3,4-dimethylthiophene-2-carbaldehyde

5-ethyl-thiophene-2-carbaldehyde

2,4,5-trimethyl-thiophene-3-carbaldehyde

Refernces

• 1、 Benaissa, Idir,Cantat, Thibault,Genre, Caroline,Godou, Timothé,Pinault, Mathieu. "Additive-free selective methylation of secondary amines with formic acid over a Pd/In2O3 catalyst". . p. 57 - 61. Retrieved 2022/01/19.
• 2、 Ji, Shuohan,Luo, Lu,Qin, Shengxiang,Yin, Chunyu,Zhang, Hua. "Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation". supporting information. . Retrieved 2021/12/27.