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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:
Molecular Weight:
73.09
Beilstein:
605365
EC Number:
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.07
grade:
ACS reagent
bp:
153 °C (lit.)
vapor pressure:
2.7 mmHg ( 20 °C)

grade

ACS reagent

Quality Level

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 %

dilution

(for analytical testing)

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.
Our premium ACS solvents are ideal for routine chemical synthesis, drying, purification, and critical labware cleaning. They meet or exceed the rigorous standards of the American Chemical Society (ACS), ensuring high-quality results for your research needs.

Premium ACS Solvents: Our solvents meet or exceed the stringent standards set by the American Chemical Society, ensuring high quality and reliability for your laboratory applications.

Replicable and Publishable Results: Designed for consistency, our solvents deliver results that can be reliably reproduced, making them ideal for research that requires publication.

Versatile Applications: Suitable for routine chemical synthesis, drying, purification, and critical labware cleaning, our solvents cater to a wide range of research needs in the laboratory.

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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