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319937

Sigma-Aldrich

N,N-Dimethylformamide

ACS reagent, ≥99.8%

Synonym(s):

DMF, NSC 5356

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About This Item

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
NACRES:
NA.07

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

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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.

Signal Word

Danger

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

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