319937

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: 605365
• EC Number: 200-679-5
• MDL number: MFCD00003284
• UNSPSC Code: 12352111
• PubChem Substance ID: 329753939

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 %
• impurities: ≤0.0005 meq/g Titr. acid; ≤0.003 meq/g Titr. base; ≤0.15% water
• evapn. residue: ≤0.005%
• color: clear; APHA: ≤15
• refractive index: n20/D 1.430 (lit.)
• pH: 7 (20 °C, 200 g/L)
• bp: 153 °C (lit.)
• mp: −61 °C (lit.)
• 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 an organic compound commonly used as a reagent as well as a solvent in organic synthesis. It plays multiple roles in various reactions such as formylating agent, dehydrating agent, reducing agent as well as a catalyst.

Application

DMF can be used as:     

• A formylating agent for organometallic compounds.
• A reactant to prepare Vilsmeier reagent by reacting with phosphorus oxychloride.
• A reagent for amination of aryl chlorides in the presence of potassium t-butoxide.     
• A reducing agent for metal salts to prepare metal colloids.
• A catalyst for the regioselective silylation of unprotected carbohydrates.

DMF can also be used in the following:     

• DMF-Phosgene catalytic system is used to prepare alkyl halides from alcohols.      
• DMF-POCl₃ is used to convert acyclic and cyclic enolizable ketones to β-chloro-α, β-unsaturated aldehydes.
• DMF-POCl₃ is used to synthesize quinoline-3-carbaldehydes from acylanilides.      
• DMF-SOCl₂ combination is used to dehydrate oximes to nitriles.      
• DMF-Ag₂O converts α-bromopropionamides to oxazolidinones.
• DMF is frequently used as a solvent in many chemical reactions, which require a high solvency power.

Solvent for many hydrophobic organic compounds.

Safety Information

• Pictograms: GHS02,GHS07,GHS08
• Signal Word: Danger
• Hazard Statements: H226 - H312 + H332 - H319 - H360D
• Precautionary Statements: 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 Code: 3 - Flammable liquids
• WGK: WGK 2
• Flash Point(F): 135.5 °F - closed cup
• Flash Point(C): 57.5 °C - closed cup