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N,N-dimethylformamide

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N,N-dimethylformamide

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Also known as Dimethyl formamide, DMF, N-Formyldimethylamine, Dimethylformamide, Dwumetyloformamid, N,N- Dimethylformamide, N,N- Dimethyl formamide

Dimethylformamide, DMF is an organic compound with the chemical formula . Its structure is . Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Dimethylformamide is odorless, but technical-grade or degraded samples often have a fishy smell due to impurity of dimethylamine. Dimethylamine degradation impurities can be removed by sparging samples with an inert gas such as argon or by sonicating the samples

OverviewAI-generated

N,N-dimethylformamide is a chemical compound with the formula C₃H₇NO. It has a molecular mass of 73.053 and a density of 0.95. The substance features a melting point ranging from -78 to -60.43 and a boiling point of 307. Its vapor pressure is 3, and it possesses an electric dipole moment of 3.82. The ionization energy is 9.13.

Safety data indicates a flash point of 136, with a lower flammable limit of 2.2 and an upper flammable limit of 15.2. The time-weighted average exposure limit is 30, while the immediately dangerous to life or health concentration is 1495. The compound has a charge of 0, with one hydrogen bond acceptor and no hydrogen bond donors. Its xlogp value is -1, and the topological polar surface area is 20.3.

Synthesized by Vinony from 31 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula
C3H7NO
Molecular weight
73.09 g/mol
IUPAC name
N,N-dimethylformamide
SMILES
CN(C)C=O
InChIKey
ZMXDDKWLCZADIW-UHFFFAOYSA-N
XLogP
-1
Polar surface area
20.3 Ų
H-bond donors
0
H-bond acceptors
1
Formal charge
0

via PubChem

Wikidata facts

Subclass of
amides
Has part
hydrogen
Mass
73.053
Show 18 more facts
NIOSH Pocket Guide ID
0226
density
0.95
canonical SMILES
CN(C)C=O
ionization energy
9.13
chemical formula
C₃H₇NO
flash point
136
lower flammable limit
2.2
immediately dangerous to life or health
1495
melting point
-60.43
boiling point
153
vapor pressure
3
upper flammable limit
15.2
time-weighted average exposure limit
30
MCN code
2924.19.22
Commons category
Dimethylformamide
found in taxon
Nicotiana tabacum
subject has role
carcinogen
electric dipole moment
3.82
Sources (5)

via Wikidata · CC0

~7 min read

Encyclopedic overview

8 sections
Contents
  • Structure and properties
  • Reactions
  • History and synthesis
  • Applications
  • Safety
  • Toxicity
  • References
  • External links

Dimethylformamide, DMF is an organic compound with the chemical formula . Its structure is . Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Dimethylformamide is odorless, but technical-grade or degraded samples often have a fishy smell due to impurity of dimethylamine. Dimethylamine degradation impurities can be removed by sparging samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, it is structurally related to formamide, having two methyl groups in the place of the two hydrogens. 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.

Excerpted from Wikipedia’s “N,N-dimethylformamide” article, available under the CC BY-SA 4.0 licence.

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