N-methyl-N-phenylformamide

• ChemBase ID: 148783
• Molecular Formular: C8H9NO
• Molecular Mass: 135.16316
• Monoisotopic Mass: 135.06841391
• SMILES: CN(C=O)c1ccccc1
• Canonical SMILES: O=CN(c1ccccc1)C
• InChI: InChI=1S/C8H9NO/c1-9(7-10)8-5-3-2-4-6-8/h2-7H,1H3
• InChIKey: JIKUXBYRTXDNIY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-methyl-N-phenylformamide
• IUPAC Traditional name: N-methylformanilide
• Synonyms: N-Methylformanilide; methyl(phenyl)formamide; N-Formyl-N-methylaniline; N-Methyl-N-phenylformamide; N-Methylformanilide; N-甲酰-N-甲基苯胺; N-苯基-N-甲基甲酰胺; N-甲基甲酰苯胺

Database IDs

• CAS Number: 93-61-8
• EC Number: 202-262-3
• MDL Number: MFCD00003283
• Beilstein Number: 636496
• PubChem SID: 24885017; 24896936; 162242958
• PubChem CID: 66737

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.0263236
• LogD (pH = 7.4): 1.0263236
• Log P: 1.0263236
• Molar Refractivity: 39.5464 cm^3
• Polarizability: 15.206059 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 8 - 13°C; 8-13 °C(lit.); 9-13°C
• Boiling Point: 242-244°C; 243-244 °C(lit.)
• Flash Point: 126°C(258°F); 127 °C; 260.6 °F
• Density: 1.095; 1.095 g/mL at 25 °C(lit.)
• Refractive Index: 1.5610; n20/D 1.561; n20/D 1.561(lit.)
• Hydrophobicity(logP): 1.081

Safety Information

• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22-43; 36/37/38
• Safety Statements: 26-37; 36/37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥97.0% (GC); 95%; 97%; 98%; 99%
• Grade: technical
• Linear Formula: HCON(CH3)C6H5

DETAILS

Sigma Aldrich - M46802

Packaging
5, 100, 500 g in glass bottle

REFERENCES

• Has also been used for the conversion of aryllithiums to aldehydes: J. Chem. Soc. (C), 1700 (1969).
• Component of Vilsmeier's original reagent for the formylation of reactive aromatics via the iminium salts: Ber., 60, 119 (1927); much used in earlier work, where N,N-Dimethylformamide, A13547, is often now preferred due to lower cost, greater thermal stability of the iminium salt and easier separation of the by-products (water-soluble in the case of DMF). The N-methylformanilide reagent is still occasionally preferred because of its higher electrophilic potential, although this may be partially offset by its greater steric demand. For examples of its use, see: Org. Synth. Coll., 3, 96 (1955); 4, 915 (1963). Review: Adv. Org. Chem., 9, 225 (1976). Monograph: Synthesis Using Vilsmeier Reagents, C. M. Marson, P. R. Giles, CRC Press, Boca Raton, FL (1994).