227056
N,N-Dimethylformamide
anhydrous, 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
UNSPSC Code:
12352111
NACRES:
NA.21
PubChem Substance ID:
EC Number:
200-679-5
Beilstein/REAXYS Number:
605365
MDL number:
eCl@ss:
39031202
Assay:
99.8%
Form:
liquid
grade
anhydrous
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 %
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
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
Legal Information
FLAG is a registered trademark of Merck KGaA, Darmstadt, Germany
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Danger
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Eye Irrit. 2 - Flam. Liq. 3 - Repr. 1B
Storage Class
3 - Flammable liquids
flash_point_f
135.5 °F - closed cup
flash_point_c
57.5 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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A concise and scalable route to L-azidohomoalanine.
Roth S, et al.
Nature Protocols, 5(2), 1967-1973 (2010)
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