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68-12-2 - N,N-Dimethylformamide, 99% - DMF - A13547 - Alfa Aesar

A13547 N,N-Dimethylformamide, 99%

CAS Number
68-12-2
Synonyms
DMF

Size Price ($) Quantity Availability
250ml 19.36
2500ml 68.60
10000ml 197.76
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N,N-Dimethylformamide, 99%

MDL
MFCD00003284
EINECS
200-679-5

Chemical Properties

Formula
HCON(CH3)2
Formula Weight
73.09
Melting point
-61°
Boiling Point
153°
Flash Point
57°(135°F)
Density
0.944
Refractive Index
1.4310
Solubility
Miscible with water and most organic solvents.

Applications

N, N-Dimethylformamide is commonly used as a solvent. It is used as a reagent in Bouveault aldehyde synthesis and also in Vilsmeier-Haack reaction. It acts as a catalyst in the synthesis of acyl chlorides. It is used for separating and refining crude from olefin gas. DMF along with methylene chloride acts as a remover of varnish or lacquers. It is also used in the manufacture of adhesives, fibers and films.

Notes

Reaction with sodium hydride gives exothermic decomposition at low temperatures. Keep container tightly closed in a dry and well-ventilated place.

Literature References

Dipolar aprotic solvent, in which anions have enhanced nucleophilicity, compare Dimethyl­ sulfoxide, A13280. Effective solvent for a vast range of reactions.

CAUTION! Thermal runaway reactions can occur with NaH; see Sodium hydride, 13431.

In combination with POCl3, (COCl)2, etc., generates an iminium chloride intermediate for the formylation of reactive aromatic nuclei by the Vilsmeier reaction:

Compare also N-Methyl­formanilide, A11829, and preformed Vilsmeier reagent (Chloromethyl­ene)­dimethyl­ammonium chloride, B24172. Monograph: Synthesis Using Vilsmeier Reagents, C. M. Marson, P. R. Giles, CRC Press, Boca Raton, FL (1994). Formylation can be extended to less active substrates, e.g. acenaphthene or mesitylene, with the DMF-triflic anhydride reagent: J. Chem. Soc., Chem. Commun., 1571 (1990). Under Vilsmeier conditions, electron-rich alkenes can be converted to ɑß-unsaturated aldehydes; see, e.g.: Synthesis, 752 (1976); and ketones to ß-chloroenals: Synthesis, 496 (1985); Org. Synth. Coll., 5, 215 (1973).

Vilsmeier conditions also promote dehydrations, e.g. in cyclodehydration of hydroxyphenols to give cyclic ethers, as an efficient alternative to the Mitsunobu reaction: J. Chem. Soc., Perkin 1, 2249 (1996); J. Org. Chem., 59, 4346 (1994):

DMF can also be used for formylation with alkyllithium or Grignard reagents: Synthesis, 228 (1984).

In aqueous DMF, tosylate esters undergo formolysis to formate esters: Synth. Commun., 26, 1031 (1996).

For the free-radical formylation of perfluoroalkyl iodides, see Zinc-copper couple, L09811.

Mahendra, N. R.; Pritam D.; Partha S. S. Physicochemical study of solution behaviour of alkali metal perchlorates prevailing in N,N-Dimethyl Formamide with the manifestation of ion Salvation consequences. J. Mol. Liq. 2015, 204, 243-247.

Wang, F.; Guo-zhu, J. The hydrogen bonding dynamics and cooperative Interactions in aqueous N,N-dimethyl formamide solution Studied by dielectric relaxation spectroscopy. Physica A 2014, 404, 315-322.

GHS Hazard and Precautionary Statements

Hazard Statements: H360-H226-H312-H332-H319

May damage fertility or the unborn child. Flammable liquid and vapour. Harmful in contact with skin. Harmful if inhaled. Causes serious eye irritation.

Precautionary Statements: P210-P201-P261-P280-P281-P303+P361+P353-P305+P351+P338-P304+P340-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Obtain special instructions before use. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Use personal protective equipment as required. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,3243
Beilstein
605365
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2924.19
TSCA
Yes
RTECS
LQ2100000

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