File:Dimethylformamide-2D-skeletal.svg · Wikimedia Commons · See Wikimedia Commons
N,N-dimethylformamide
Sign in to saveAlso 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
Research
3,327 papers- The deleterious effects of N,N-dimethylformamide on liver: A mini-review.Chemico-biological interactions · 2019
- The potential health risks of N,N-dimethylformamide: An updated review.Journal of applied toxicology : JAT · 2024
- N,N-Dimethylformamide-Protected Single-Sized Metal Nanoparticles and Their Use as Catalysts for Organic Transformations.ACS omega · 2020
- Recent Uses of N,N-Dimethylformamide and N,N-Dimethylacetamide as Reagents.Molecules (Basel, Switzerland) · 2018
- N,N-dimethylformamide: a multipurpose building block.Angewandte Chemie (International ed. in English) · 2012
via PubMed
Wikidata facts
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
via Wikidata · CC0
~7 min read
Encyclopedic overview
8 sectionsContents
- 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.