Dimethylformamide

Dimethylformamide

Dimethylformamide sample and bottle
Names
IUPAC name N,N-Dimethylformamide
Other names N,N-Dimethylmethanamide DMF
Identifiers
Jmol-3D images	Image
SMILES C[n](C):c:[o] CN(C)C=O
Properties
Chemical formula	C3H7NO
Molar mass	73.10 g/mol
Appearance	Colorless liquid
Odor	None (fresh) Fishy, amoniacal (old)
Density	0.948 g/mL
Melting point	−60.5 °C (−76.9 °F; 212.7 K)
Boiling point	152 to 154 °C (306 to 309 °F; 425 to 427 K)
Solubility in water	Miscible
Solubility	Miscible with ethanol, toluene
Vapor pressure	516 Pa
Thermochemistry
Std enthalpy of formation (ΔfHo298)	−240.6–−238.2 kJ mol−1
Hazards
Safety data sheet	LabChem
Flash point	58 °C
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	1.5 g kg−1 (dermal, rabbit) 2.8 g kg−1 (oral, rat) 3.7 g/kg (mouse, oral) 3.5 g/kg (rat, oral)
LC50 (Median concentration)	3092 ppm (mouse, 2 hr)
Related compounds
Related compounds	Formamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dimethylformamide or N,N-dimethylformamide is an organic compound with the formula (CH₃)₂NC(O)H.

Properties

Chemical

Reaction of dimethylformamide with a strong base like sodium hydroxide or strong acid like hydrochloric acid, yields dimethylamine and dimethylamine hydrochloride respectively:

(CH₃)₂NC(O)H + NaOH → (CH₃)₂NH + HCOONa

(CH₃)₂NC(O)H + HCl → (CH₃)₂NH·HCl + HCOOH

DMF has a tendency to penetrate many types of plastic and causes them to swell.

Physical

Dimethylformamide is an odorless, colorless liquid, miscible with water and most organic liquids. Technical grade or degraded samples often have a fishy smell due to impurities, such as dimethylamine, though obtaining completely 100% odorless DMF is extremely difficult due to dimethylamine's strong odor and is not always done.

Availability

DMF is sold by various chemical suppliers.

Preparation

Dimethylformamide can be synthesized from methyl formate and dimethylamine or by reaction of dimethylamine with carbon monoxide. Another route involves carbon dioxide, hydrogen and dimethylamine, in the presence of CuO/ZnO catalyst.

Projects

• Acyl halide synthesis
• Make cadaverine
• Make dimethylamine and dimethylamine hydrochloride
• Vilsmeier–Haack reaction
• Storage of acetylene

Handling

Safety

DMF has been linked to cancer in humans, and it is thought to cause birth defects.

Storage

DMF should be kept in closed bottles, away from any acidic vapors. DMF will slowly break down to release dimethylamine.

Disposal

DMF should be mixed with a more flammable solvent and safely burned.

References

Relevant Sciencemadness threads

• dimethylformamide