437573

N,N-Dimethylformamide

ACS reagent, ≥99.8%

• Synonym(s): DMF, NSC 5356
• Linear Formula: HCON(CH₃)₂
• CAS Number: 68-12-2
• Molecular Weight: 73.09
• Beilstein/REAXYS Number: 605365
• EC Number: 200-679-5
• MDL number: MFCD00003284
• UNSPSC Code: 12352111
• PubChem Substance ID: 24867382
• grade: ACS reagent
• assay: ≥99.8%
• technique(s): electrophoresis: suitable
• bp: 153 °C (lit.)
• vapor pressure: 2.7 mmHg ( 20 °C)

Properties

• grade: ACS reagent
• Quality Level: 200
• vapor density: 2.5 (vs air)
• vapor pressure: 2.7 mmHg ( 20 °C)
• assay: ≥99.8%
• form: liquid
• autoignition temp.: 833 °F
• expl. lim.: 15.2 %
• technique(s): electrophoresis: suitable
• impurities: ≤0.0005 meq/g Titr. acid; ≤0.003 meq/g Titr. base; ≤0.15% water
• evapn. residue: ≤0.005%
• color: APHA: ≤15
• refractive index: n20/D 1.430 (lit.)
• pH: 6.7
• bp: 153 °C (lit.)
• mp: −61 °C (lit.)
• solubility: water: miscible
• density: 0.944 g/mL (lit.)
• SMILES string: [H]C(=O)N(C)C
• InChI: 1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
• InChI key: ZMXDDKWLCZADIW-UHFFFAOYSA-N

Description

General description

N,N-Dimethylformamide (DMF) is a polar organic solvent with a wide range of industrial applications.[1] It is a precursor for numerous reactions such as formylation, aminocarbonylation, amination, amidation and cyanation.[2] Along with phosphorus oxychloride, it forms Vilsmeier reagent used in the formylation of reactive aromatic and heteroaromatic substrates.[3] Dielectric relaxation experiments on DMF have been conducted between 238.15K and 338.15K.[4] The thermophysical properties of the molecular interactions between DMF and the ionic liquids, ammonium salts and imidazolium salts have been studied.[5] The characteristics of solute-solvent interactions between ammonium nitrate and DMF have been investigated.[6]

Application

N,N-Dimethylformamide (DMF) may be used in the following processes:

• As a solvent synthesis of gold nanoparticles.[7][8]
• As a solvent in capillary electrophoresis.[9]
• Regioselective synthesis of N,N-dimethylaminopyridzines by reacting with choropyridazines.[10]
• Synthesis of urea-N,N-dimethylformamide, a 3:1 solvate with urea.[11]

Solvent for many hydrophobic organic compounds.

Safety Information

• pictograms: GHS02,GHS08,GHS07
• signalword: Danger
• hcodes: H226,H312 + H332,H319,H360D
• pcodes: P210 - P280 - P303 + P361 + P353 - P304 + P340 + P312 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Eye Irrit. 2 - Flam. Liq. 3 - Repr. 1B
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 2
• flash_point_f: 135.5 °F - closed cup
• flash_point_c: 57.5 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter