Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

A13547 N,N-Dimethylformamide, 99%

CAS Number
68-12-2
Synonyms
DMF

Stock No. Size Price ($) Quantity Availability
A13547-AK 250ml 20.50
A13547-0F 2500ml 75.60
A13547-0D 10000ml 218.00
Add to Cart Bulk/Specialty Print Quote View Item

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
Storage & Sensitivity
Ambient temperatures.
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: H226-H312-H319-H332-H335-H336-H350-H360D

Flammable liquid and vapour. Harmful in contact with skin. Causes serious eye irritation. Harmful if inhaled. May cause respiratory irritation. May cause drowsiness or dizziness. May cause cancer. May damage the unborn child.

Precautionary Statements: P201-P202-P210-P233-P235-P240-P241-P242-P243-P260-P264b-P271-P280-P281-P303+P361+P353-P304+P340-P305+P351+P338-P308+P313-P312-P337+P313-P363-P370+P378q-P501c

Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. 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 INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or concerned: Get medical advice/attention. Call a POISON CENTER or doctor/physician if you feel unwell. If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

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

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware