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93-61-8 - N-Methylformanilide, 99% - A11829 - Alfa Aesar

A11829 N-Methylformanilide, 99%

CAS Number
93-61-8
Synonyms

Size Price ($) Quantity Availability
250g 37.90
500g 53.73
2500g 242.55
10000g 924.94
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N-Methylformanilide, 99%

MDL
MFCD00003283
EINECS
202-262-3

Chemical Properties

Formula
C8H9NO
Formula Weight
135.17
Melting point
9-13°
Boiling Point
242-244°
Flash Point
126°(258°F)
Density
1.095
Refractive Index
1.5610
Solubility
Immisible with water.

Applications

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.

Notes

Incompatible with oxidizing agents.

Literature References

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).

Has also been used for the conversion of aryllithiums to aldehydes: J. Chem. Soc. (C), 1700 (1969).

Islam, M. T.; Aimone, F.; Ferri, A.; Rovero, G. Use of N-methylformanilide as swelling agent for meta-aramid fibers dyeing: Kinetics and equilibrium adsorption of Basic Blue 41. Dyes Pigm. 2015, 113, 554-561.

Zhang, J.; Wang, Y.; Luo, N.; Chen, Z.; Wu, K.; Yin, G. Redox inactive metal ion triggered N-dealkylation by an iron catalyst with dioxygen activation: a lesson from lipoxygenases. Dalton Trans. 2015, 44 (21), 9847-9859.

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H317

Harmful if swallowed. May cause an allergic skin reaction.

Precautionary Statements: P261-P280-P264-P270-P301+P312-P363-P321-P333+P313-P302+P352-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Wash thoroughly after handling. Do not eat, drink or smoke when using this product. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Wash contaminated clothing before reuse. Specific treatment (see label). If skin irritation or rash occurs: Get medical advice/attention. IF ON SKIN: Wash with plenty of soap and water. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
636496
Harmonized Tariff Code
2924.29
TSCA
Yes

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