227056

N,N-Dimethylformamide

anhydrous, 99.8%

• Synonym(s): DMF, NSC 5356
• Linear Formula: HCON(CH₃)₂
• CAS Number: 68-12-2
• Molecular Weight: 73.09
• Beilstein: 605365
• EC Number: 200-679-5
• MDL number: MFCD00003284
• PubChem Substance ID: 57647999
• NACRES: NA.21

Properties

• grade: anhydrous
• Quality Level: 200
• 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

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

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Legal Information

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

Safety Information

• Pictograms: GHS02,GHS07,GHS08
• Signal Word: Danger
• Hazard Statements: H226 - H312 + H332 - H319 - H360D
• Precautionary Statements: P210 - P280 - P303 + P361 + P353 - P304 + P340 + P312 - P305 + P351 + P338 - P308 + P313
• 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