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/REAXYS Number:
605365
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

grade

anhydrous

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

<0.005% water

evapn. residue

<0.0005%

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 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.

Application

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.

Packaging

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

Legal Information

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

Signal Word

Danger

hazcat

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

storage_class_code

3 - Flammable liquids

WGK Germany

WGK 2

Flash Point(F)

135.5 °F - closed cup

Flash Point(C)

57.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Reference electrode for anhydrous dimethylformamide.
Marple LW.
Analytical Chemistry, 39(7), 844-846 (1967)
X Wang et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(20), 11081-11084 (1999-09-29)
Chemotherapy is commonly used in the treatment of cancers. However, the mechanism of action of many of these agents is not well understood. We present the synthesis of a two-photon fluorophore (C625) and its biological application when chemically linked to...
A concise and scalable route to L-azidohomoalanine.
Roth S, et al.
Nature Protocols, 5(2), 1967-1973 (2010)
Metabolic labeling of glycans with azido sugars and subsequent glycan-profiling and visualization via Staudinger ligation.
Laughlin ST and Bertozzi CR.
Nature Protocols, 2(11), 2930-2944 (2007)
W P Inskeep et al.
Plant physiology, 77(2), 483-485 (1985-02-01)
We found inconsistencies in the commonly used data for chlorophyll analysis in 80% acetone. Recently developed extinction coefficients for chlorophyll b in N,N-dimethylformamide (DMF) based on values from 80% acetone are low as a result of these inconsistencies. We determined...

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