• USA Home
  • 227056 - N,N-Dimethylformamide

EMAIL THIS PAGE TO A FRIEND
227056 Sigma-Aldrich

N,N-Dimethylformamide

anhydrous, 99.8%

Synonym: DMF, NSC 5356

  • CAS Number 68-12-2

  • Linear Formula HCON(CH3)2

  • Molecular Weight 73.09

  •  Beilstein/REAXYS Number 605365

  •  EC Number 200-679-5

  •  MDL number MFCD00003284

  •  PubChem Substance ID 57647999

  •  NACRES NA.21

Purchase

Properties

Related Categories Anhydrous, Anhydrous Solvents, Returnable Containers, Solvent Bottles, Solvent Packaging Options,
Quality Level   200
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.)
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

Description

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

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

Legal Information

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

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 2265 3 / PGIII
WGK Germany 
WGK 2
RTECS 
LQ2100000
Flash Point(F) 
135.5 °F - closed cup
Flash Point(C) 
57.5 °C - closed cup

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number

Certificate of Origin (COO)

Please Enter a Lot Number

Dispensette™ S
Protocols & Articles

Articles

Anhydrous Solvents for Coupling Reactions

Due to the sensitivity to air and moisture, coupling reactions often require relatively low air and water conditions to initiate the reaction. Therefore, the use of anhydrous solvents is highly recom...
Keywords: Coupling reactions, Cross couplings, Negishi Coupling, Solvents

Anhydrous Solvents for Organic and Organometallic Chemistry

Many well-known reactions require water-free conditions to initiate or complete the reaction. Failure to include anhydrous solvents can result in low product yield or reaction failure. As the market ...
Keywords: Acylations, Alkylations, Electrophilic aromatic substitution, Formylations, Grignard Reaction, Solvents, Substitutions, Vilsmeier-Haack reaction

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, Building blocks, Gas chromatography, Gas chromatography mass spectrometry, High performance liquid chromatography, Liquid chromatography mass spectrometry, Mass spectrometry, Organic synthesis, Pesticides, Polymerase chain reaction - quantitative, Purification, Solvents

Lab Chemicals

We are a leading global supplier and manufacturer of high-quality, stockroom and basic research products including solvents, acids and inorganics. We specialize in providing the most comprehensive pr...
Keywords: Solvents

Peer-Reviewed Papers
15

References

Related Products

also commonly purchased with this product

Product #

Description

Add to Cart

Z124656 Suba-Seal® septa, red rubber, Suba Seal, 45, fits neck I.D., 22 mm, for use with 24/40 joints
270997 Dichloromethane, anhydrous, ≥99.8%, contains 40-150 ppm amylene as stabilizer
186562 Tetrahydrofuran, anhydrous, contains 250 ppm BHT as inhibitor, ≥99.9%
401757 Tetrahydrofuran, anhydrous, ≥99.9%, inhibitor-free

recommended

Product #

Description

Add to Cart

Z108812 Zerostat anti-static instrument, keeps film, glass, and plasticware dust and lint-free

related product

Product #

Description

Add to Cart

Z568058 PureSolv Micro 100 Liter solvent purification system, with activated molecular sieves, joint Joint: ST/NS 24/40
Z568082 PureSolv Micro replacement purification column, activated molecular sieves

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?