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
Beilstein:
605365
EC Number:
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.21
Recommended Products
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
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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
Legal Information
FLAG is a registered trademark of Merck KGaA, Darmstadt, Germany
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suggested gloves for splash protection
Signal Word
Danger
Hazard Statements
Precautionary Statements
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
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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)
Reference electrode for anhydrous dimethylformamide.
Marple LW.
Analytical Chemistry, 39(7), 844-846 (1967)
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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