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227056 Sigma-Aldrich

N,N-Dimethylformamide

anhydrous, 99.8%

Synonym: DMF, NSC 5356

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Properties

Related Categories Anhydrous, Anhydrous Solvents, Returnable Containers, Solvent Bottles, Solvent Packaging Options,
grade   anhydrous
vapor density   2.5 (vs air)
vapor pressure   2.7 mmHg ( 20 °C)
InChI Key   ZMXDDKWLCZADIW-UHFFFAOYSA-N
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.)
bp   153 °C(lit.)
mp   −61 °C(lit.)
density   0.944 g/mL(lit.)

Description

Application

Solvent for many hydrophobic organic compounds.

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.

Packaging

1, 6×1, 2, 4×2 L in Sure/Seal™

View returnable container options.

100, 12×100 mL in Sure/Seal™

18, 200 L in Pure-Pac™ 1

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.

Legal Information

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

Price and Availability


LC-MS Grade Solvents and Reagents

Bulk Chemicals
Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2265 3 / PGIII
WGK Germany 
2
RTECS 
LQ2100000
Flash Point(F) 
136.4 °F
Flash Point(C) 
58 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

First cross-coupling reactions on halogenated 1H-1,2,4-triazole nucleosides

C-O activation of mesylates by a palladium catalyst and subsequent cross-coupling with potassium cyclopropyltrifluoroborate have been achieved with high yield. Both electron-enriched and electron- de...
Keywords: Chromatography, Cross couplings

KitAlysis High-Throughput Metal Scavenger Reaction Screening Kit

The screening sets come pre-loaded with 12 scavengers / resins (10mg or 50mg) in each vial according to the following design.
Keywords: Metal scavengers

Palladium-Catalyzed Reaction of Aryl Iodides with ortho- Bromoanilines and Norbornene/Norbornadiene: Unexpected Formation of Dibenzoazepine Derivatives-

The cross-coupling reaction of aryl bromides and iodides with aliphatic and aromatic thiols catalyzed by palladium complexes of the bisphosphine ligand CyPF-tBu (1) is reported. Reactions occur in ex...
Keywords: Catalysis, Chromatography, Column chromatography, Coupling reactions, Cross couplings, Gas chromatography, Ligands, Solvents

Pressure-Temperature Calculator for Solvents

*Calculations provide estimated results based on Antoine's Coefficients and their associated temperature range values. Antoine's Coefficients were obtained from the National Institute of Standards an...

The First Applications of Carbene Ligands in Cross-Couplings of Alkyl Electrophiles: Sonogashira Reactions of Unactivated Alkyl Bromides and Iodides

The synthesis of ?,?-alkynyl esters and amides using air-stable potassium alkynyltrifluoroborates as nucleophilic partners in a mild Suzuki-Miyaura cross-coupling reaction has been achieved. Propargy...
Keywords: Chromatography, Column chromatography, Coupling reactions, Cross couplings

Related Content

Agriculture | Crop Protection Workflow

Pesticides are an essential component in modern agriculture and enable growers to fully realize the yield potential of their seeds. From compound discovery to active ingredient development, our chemi...
Keywords: Agriculture, Pesticides

Pressure-Temperature Nomograph Interactive Tool

The Pressure-Temperature Nomograph tool is an application of the Clausius-Clapeyron Equation, which assumes the heat of vaporization is a constant over a pressure range. Antoine´s Equation gets aroun...
Keywords: Evaporation, Vaporization

Properties of Solvents Table

a. Gant, R., LC/GC 10(7), 515 (1992) 1. At 20 °C 2. At 20 °C +/- 5 °C relative to water at 4 °C 3. At 10mmHg pressure 4. At l=589.32nm
Keywords: Gas chromatography, High performance liquid chromatography

Peer-Reviewed Papers
15

References

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