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227056

Sigma-Aldrich

N,N-Dimethylformamide

anhydrous, 99.8%

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

Nivel de calidad

300

grado

anhydrous

densidad de vapor

2.5 (vs air)

presión de vapor

2.7 mmHg ( 20 °C)

ensayo

99.8%

formulario

liquid

temp. de autoignición

833 °F

lim. expl.

15.2 %

impurezas

<0.005% water

residuo de evap.

<0.0005%

índice de refracción

n20/D 1.430 (lit.)

pH

7 (20 °C, 200 g/L)

bp

153 °C (lit.)

mp

−61 °C (lit.)

densidad

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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Descripción general

N,N-Dimethylformamide (DMF) is the commonly employed solvent for chemical reactions. DMF is a useful solvent employed for the isolation of chlorophyll from plant tissues. It is widely employed reagent in organic synthesis. It plays multiple roles in various reactions such as solvent, dehydrating agent, reducing agent as well as catalyst. It is a multipurpose building block for the synthesis of compounds containing O, -CO, -NMe2, -CONMe2, -Me, -CHO as functional groups.
N,N-Dimethylformamide is a polar solvent commonly used in organic synthesis. It also acts as a multipurpose precursor for formylation, amination, aminocarbonylation, amidation and cyanation reactions.

Aplicación

N,N-Dimethylformamide (anhydrous) has been used as solvent for the synthesis of cytotoxic luteinizing hormone-releasing hormone (LH-RH) conjugate AN-152 (a chemotherapeutic drug) and fluorophore C625 [4-(N,N-diphenylamino)-4′-(6-O-hemiglutarate)hexylsulfinyl stilbene]. It may be employed as solvent medium for the various organic reduction reactions.
DMF has been used as a solvent in the following processes:
  • Multi-step synthesis of L-azidohomoalanine (L-Aha) during the substitution of the mesylate by sodium azide.
  • Synthesis of phosphine-FLAG®, a detection reagent for metabolic labeling of glycans.
  • Synthesis of per-O-acetylated 6-azidofucose, a per-O-acetylated azido sugar.
Solvent for many hydrophobic organic compounds.

Envase

18, 200 L in Pure-Pac™ 1
1, 6×1, 2, 4×2 L in Sure/Seal™
100, 12×100 mL in Sure/Seal™

Información legal

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

Palabra de señalización

Danger

Clasificaciones de peligro

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

Código de clase de almacenamiento

3 - Flammable liquids

WGK

WGK 2

Punto de inflamabilidad F

135.5 °F - closed cup

Punto de inflamabilidad C

57.5 °C - closed cup

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificate of Analysis

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Certificate of Origin

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Articles

Greener Chemistry: Methods and Products for Amide Bond Formation

Amide bonds are ubiquitous in both nature and industrial applications. They are vital to the structure and function of biological macromolecules and polymers. The importance of this functionality has resulted in numerous approaches to its formation, ranging from stoichiometric activation of carboxylic acids to more recent advances in catalytic amide bond formation.

Solvent Miscibility Table

Substances are said to be miscible in one another if they dissolve to form a uniform solution. Bookmark or download our miscibility table for common lab solvents.

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