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D158550

Sigma-Aldrich

N,N-Dimethylformamide

ReagentPlus®, ≥99%

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/REAXYS Number:
605365
EC Number:
200-679-5
MDL number:
MFCD00003284
UNSPSC Code:
12352111
PubChem Substance ID:
329798705
NACRES:
NA.21

vapor density

2.5 (vs air)

Quality Level

100

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.

Other Notes

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

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Eye Irrit. 2 - Flam. Liq. 3 - Repr. 1B

wgk_germany

WGK 2

flash_point_f

135.5 °F

flash_point_c

57.5 °C

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Reaction of chloropyridazines with N,N -dimethylformamide.
Lee WS, et al.
Journal of Heterocyclic Chemistry, 37(6), 1591-1591 (2000)
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)
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)
Volumetric properties of ammonium nitrate in N,N-dimethylformamide.
Vranes M, et al.
The Journal of Chemical Thermodynamics, 54, 245-249 (2012)
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