Dimethylformamide

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Dimethylformamide
Skeletal formula of dimethylformamide with one explicit hydrogen added
Ball and stick model of dimethylformamide
Spacefill model of dimethylformamide
Names
IUPAC name
N,N-Dimethylformamide[2]
Other names
N,N-Dimethylmethanamide,[1] DMF
Identifiers
68-12-2 YesY
3DMet B00545
605365
ChEBI CHEBI:17741 YesY
ChEMBL ChEMBL268291 YesY
ChemSpider 5993 YesY
DrugBank DB01844 YesY
EC Number 200-679-5
Jmol 3D model Interactive image
Interactive image
KEGG C03134 YesY
MeSH Dimethylformamide
PubChem 6228
RTECS number LQ2100000
UNII 8696NH0Y2X YesY
UN number 2265
  • InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3 YesY
    Key: ZMXDDKWLCZADIW-UHFFFAOYSA-N YesY
  • C[n](C):c:[o]
  • CN(C)C=O
Properties
C3H7NO
Molar mass 73.10 g·mol−1
Appearance Colourless liquid
Odor fishy, ammoniacal
Density 0.948 g mL−1
Melting point −60.5 °C; −76.8 °F; 212.7 K
Boiling point 152 to 154 °C; 305 to 309 °F; 425 to 427 K
Miscible
log P −0.829
Vapor pressure 516 Pa
UV-vismax) 270 nm
Absorbance 1.00
1.4305 (at 20 °C)
Viscosity 0.92 mPa s (at 20 °C)
Structure
3.86 D
Thermochemistry
146.05 J K−1 mol−1
−240.6–−238.2 kJ mol−1
−1.9428–−1.9404 MJ mol−1
Vapor pressure {{{value}}}
Related compounds
Related alkanamides
Related compounds
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
YesY verify (what is YesYN ?)
Infobox references

Dimethylformamide is an organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated as DMF (although this acronym is sometimes used for dimethylfuran), this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Dimethylformamide is odorless whereas technical grade or degraded samples often have a fishy smell due to impurity of dimethylamine. As its name indicates, it is a derivative of formamide, the amide of formic acid. DMF is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions.

Structure and properties

As for most amides, the spectroscopic evidence indicates partial double bond character for the C-N and C-O bonds. Thus, the infrared spectrum shows a C=O stretching frequency at only 1675 cm−1, whereas a ketone would absorb near 1700 cm-1.[3] The methyl groups are inequivalent on the NMR time scale, giving rise to two singlets of 3 protons each at δ 2.97 and 2.88 in the proton NMR spectrum.[3]

DMF is miscible with water.[4] The vapour pressure at 20 °C is 3.5hPa.[5] A Henry's law constant of 7.47×10−5 hPa·m3/mol can be deduced from an experimentally determined equilibrium constant at 25 °C.[6] The partition coefficient logPOW is measured to −0.85.[7] Since the density of DMF (0.95 g/cm3 at 20 °C[4]) is very similar to that of water, significant flotation or stratification in surface waters in case of accidental losses is not expected.

The two resonance forms of DMF

DMF is hydrolyzed by strong acids and bases, especially at elevated temperatures. With sodium hydroxide, DMF converts to formate and dimethylamine.

Production

DMF is prepared by combining methyl formate and dimethylamine or by reaction of dimethylamine with carbon monoxide.[8]

Academic research

DMF can also be prepared from supercritical carbon dioxide using ruthenium-based catalysts.[9]

Applications

The primary use of DMF is as a solvent with low evaporation rate. DMF is used in the production of acrylic fibers and plastics. It is also used as a solvent in peptide coupling for pharmaceuticals, in the development and production of pesticides, and in the manufacture of adhesives, synthetic leathers, fibers, films, and surface coatings.[4]

Niche uses

As a common and cheap reagent, DMF has many uses in the research laboratory.

Safety

Reactions including the use of sodium hydride in DMF as a solvent are somewhat hazardous; exothermic decompositions have been reported at temperatures as low as 26 °C. On a laboratory scale any thermal runaway is (usually) quickly noticed and brought under control with an ice bath and this remains a popular combination of reagents. On a pilot plant scale, on the other hand, several accidents have been reported.[13]

Toxicity

The potential toxicity DMF has received considerable attention.[14] It is not classifiable as human carcinogen (A4), but it is thought to cause birth defects.[15] In some sectors of industry, women are banned from working with DMF. For many reactions, it can be replaced with dimethyl sulfoxide. Most manufacturers of DMF list 'Life' or 'Chronic' as a health hazard in their MSDS since DMF is not readily disposed of by the body. According to IARC, DMF is not classifiable as to its carcinogenicity to humans,[16] and the United States Environmental Protection Agency does not consider it a cancer risk.[citation needed]

References

  1. N,N-Dimethylmethanamide, NIST web thermo tables
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  5. IPCS (International Programme on Chemical Safety) (1991). Environmental Health Criteria 114 “Dimethylformamide” United Nations Environment Programme, International Labour Organisation, World Health Organization; 1–124.
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  7. (BASF AG, department of analytical, unpublished data, J-No. 124659/08, 27.11.1987)
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  11. Ansell, M. F. in "The Chemistry of Acyl Halides"; S. Patai, Ed.; John Wiley and Sons: London, 1972; pp 35–68.
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  13. UK Chemical Reaction Hazards Forum and references cited therein
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  15. Hazardous substance fact sheet for Dimethylformamide
  16. [1]

External links