Dimethylformamide
Dimethylformamide (DMF) is an organic compound with the chemical formula HCON(CH3)2[1][2]. It is a colorless, odorless liquid that is miscible with water and most organic liquids[2]. DMF is a polar aprotic solvent with a high boiling point, making it a common solvent for chemical reactions, particularly those that follow polar mechanisms such as S N2 reactions[2].
Structure and Properties
DMF's structure is characterized by partial double bond character for the C-N and C-O bonds, as indicated by spectroscopic evidence[2]. It is a fluxional molecule, meaning that its molecular structure is not fixed and can change over time[2]. The compound's infrared spectrum shows a C=O stretching frequency at 1675 cm-1, which is lower than that of a ketone[2]. DMF is miscible with water and has a vapor pressure of 3.5 hPa at 20°C[2].
Safety and Toxicity
DMF vapor exposure has been linked to reduced alcohol tolerance and skin irritation in some cases[2]. The acute LD50 (oral, rats and mice) is 2.2-7.55 g/kg, indicating its toxicity[2]. The National Institute for Occupational Safety and Health (NIOSH) has highlighted the risks of DMF exposure, including liver damage and skin problems, and has requested assistance in reducing the health risks to workers exposed to the solvent[3].
Applications
DMF is widely used as a solvent, reagent, and catalyst in various industries, including the production of acrylic fibers, polyurethane-based coatings, and pharmaceuticals[4]. It is also used in the petrochemical industry for the purification of acetylene and butadiene, and in the production of high voltage capacitors[4]. Additionally, DMF is used as a carrier for inks and dyes in various printing and fiber-dying applications[4].
Availability and Pricing
DMF is available from various suppliers, including Sigma-Aldrich, Eastman, and Honeywell Research Chemicals, with prices ranging from $5.89565 for anhydrous DMF (≥99.8%) to $1,348.59 for ACS general use solvents[1][4][5].
Citations:
[1] https://www.sigmaaldrich.com/US/en/substance/nndimethylformamide730968122
[2] https://en.wikipedia.org/wiki/Dimethylformamide
[3] https://www.cdc.gov/niosh/docs/90-105/default.html
[4] https://www.eastman.com/en/products/product-detail/71103587/dimethylformamide-dmf
[5] https://lab.honeywell.com/shop/n-n-dimethylformamide-lp076