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D158550

Sigma-Aldrich

N,N-Dimethylformamide

ReagentPlus®, ≥99%

Synonym(s):
DMF, NSC 5356
Linear Formula:
HCON(CH3)2
CAS Number:
Molecular Weight:
73.09
Beilstein:
605365
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

vapor density

2.5 (vs air)

vapor pressure

2.7 mmHg ( 20 °C)

product line

ReagentPlus®

assay

≥99%

form

liquid

autoignition temp.

833 °F

expl. lim.

15.2 %

impurities

≤0.1% Water (Karl Fischer)

refractive index

n20/D 1.430 (lit.)

pH

6.7

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

Application

N,N-Dimethylformamide has been used in the to prepare pure polyurethane as well as nanocomposite solutions.
It may be used in the following processes:
  • Synthesis of gold nanoparticles.
  • Capillary electrophoresis.
  • Regioselective synthesis of N,N-dimethylaminopyridzines.
  • Synthesis of urea-N,N-dimethylformamide, a 3:1 solvate with urea.
Solvent for many hydrophobic organic compounds.

Packaging

1, 4 L in glass bottle
18 L in steel drum
5 L in poly drum

Other Notes

A Greener alternative is available for many DMF applications, Cyrene (807796)

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

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

Certificate of Analysis

Certificate of Origin

Reaction of chloropyridazines with N,N -dimethylformamide.
Lee WS, et al.
Journal of Heterocyclic Chemistry, 37(6), 1591-1591 (2000)
Urea-N,N-dimethylformamide (3/1).
Fernandes P, et al.
Acta Crystallographica Section E, Structure Reports Online, 63(12), 4861-4861 (2007)
Capillary electrophoresis in N,N-dimethylformamide.
Porras SP and Kenndler E.
Electrophoresis, 26(17), 3279-3291 (2005)
Review article on Vilsmeier Haack reaction and its Applications.
Beniwal M and Jain N.
European Journal of Biomedical AND Pharmaceutical sciences, 2(3), 1340-1374 (2015)
N,N-dimethylformamide as a reaction medium for metal nanoparticle synthesis.
Pastoriza-Santos I and Liz-Marzan LM.
Advances in Functional Materials, 19(5), 679-688 (2009)

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