N,N-Dimethylformamide

• CAS: 68-12-2
• Catalog Number: ACM68122
• Category: Main Products
• Molecular Weight: 73.09 g/mol
• Molecular Formula: C₃H₇NO
• Description: N,n-dimethylformamide appears as a water-white liquid with a faint fishy odor. Flash point 136 °F. Slightly less dense than water. Vapors heavier than air. Toxic by inhalation or skin absorption. May irritate eyes.; N,N-dimethylformamide is a member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups. It has a role as a polar aprotic solvent, a hepatotoxic agent and a geroprotector. It is a volatile organic compound and a member of formamides. It is functionally related to a formamide.
• Synonyms: AKOS BBS-00004259;FORMIC ACID DIMETHYLAMIDE;FORMDIMETHYLAMIDE;FORMYLDIMETHYLAMINE;DIMETHYLFORMAMIDE;DMF;DMFA;N,N-DIMETHYLFORMAMIDE
• IUPAC Name: N,N-dimethylformamide
• SMILES: CN(C)C=O
• InChI: InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
• InChI Key: ZMXDDKWLCZADIW-UHFFFAOYSA-N
• Boiling Point: 153°C(lit.)
• Melting Point: -61°C
• Flash Point: 136°F
• Density: 0.948g/mL at 20°C
• Appearance: colourless liquid
• Complexity: 33.9
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• EC Number: 200-679-5
• Exact Mass: 73.052763847 g/mol
• Formal Charge: 0
• Hazard Statements: T
• Heavy Atom Count: 5
• Hydrogen Bond Acceptor Count: 1
• Hydrogen Bond Donor Count: 0
• Isotope Atom Count: 0
• Monoisotopic Mass: 73.052763847 g/mol
• Packing Group: III
• Rotatable Bond Count: 0
• Safety Description: 53-45
• Supplemental Hazard Statements: H312-H332-H302-H318-H331-H341-H370-H372-H360-H226-H312+H332-H319-H360D
• Symbol: GHS08,GHS02,GHS07,GHS05,GHS06
• Topological Polar Surface Area: 20.3Ų
• Undefined Atom Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• UN Number: 2265
• WGK Germany: 1
• XLogP3: -1

Case Study

Golden Reactions in a DMF Shield - How a Solvent Layer Unlocks Nanocluster Catalysis

Yamamoto, H., et al. Nanoscale 4.14 (2012): 4148-4154.

Ultrafine gold nanoclusters composed of roughly 13 atoms, prepared through a surfactant-free reduction process in N,N-dimethylformamide, exhibit remarkable catalytic efficiency in converting 4-nitrophenol to 4-aminophenol. What makes this system unusual is that the DMF molecules do not merely serve as a passive dispersion medium -- they form a tightly adsorbed protective layer around each cluster, binding through interactions between their formyl groups and the gold surface. This adsorbed DMF shell initially blocks reactant access, creating a pronounced induction period before catalysis begins. The formyl proton signals of surface-bound DMF differ dramatically from those of free solvent molecules, and the adsorbed layer undergoes progressive restructuring during the reaction.
Experimental Protocol: DMF-stabilized gold nanoclusters were synthesized by adding aqueous HAuCl₄ to preheated DMF at 140 degrees Celsius, followed by refluxing and vacuum concentration. Catalytic reduction of 4-nitrophenol was monitored by UV-vis spectroscopy at 410 nm under excess NaBH₄. The pseudo-first-order rate constant reached 3 x 10^-3 s^-1 at 1.0 microM gold concentration.
Performance Evaluation: The activation energy was determined to be 31 kJ mol^-1, comparable to other gold nanoparticle systems. Thermal aging pretreatment at 80 degrees Celsius dramatically shortened the induction time from approximately 3000 seconds to roughly 100 seconds, demonstrating that controlled restructuring of the DMF layer is the key to activation. After repeated reuse, the induction time vanished but the catalytic conversion rate decreased, attributed to product aminophenol binding to active gold sites. Atomically precise glutathione-protected Au₂₅ nanoclusters achieved even higher activity with no induction period, suggesting that certain structural features of thiolate-protected clusters leave active surface facets sterically accessible. This work highlights how the seemingly passive solvent shell around metal clusters can be engineered to control catalytic onset and performance.

DMF Sets the Electrochemical Stage - First Estimates of Oxygen and CO₂ Reduction Benchmarks in Organic Media

Pegis, Michael L., et al. Inorganic chemistry 54.24 (2015): 11883-11888.

The standard reduction potentials of dioxygen and carbon dioxide represent fundamental thermodynamic references that govern the efficiency of energy conversion catalysts. While these values are well established in water, their counterparts in organic solvents had remained unknown. This study delivers the first estimates of the O₂/H₂O couple in acetonitrile and N,N-dimethylformamide by constructing thermochemical cycles that relate organic-solvent potentials back to the known aqueous standard of +1.229 V versus the standard hydrogen electrode.
Experimental Protocol: The H⁺/H₂ standard potential in DMF was measured directly via open-circuit potential readings at a platinum wire electrode as a function of protonated-DMF concentration, yielding a value of -0.662 V against the ferrocenium/ferrocene (Fc^+/0) reference. The free energy of water transfer from aqueous solution to each organic solvent was derived from vapor pressure data, giving -0.43 kcal mol^-1 for acetonitrile and -1.47 kcal mol^-1 for DMF. These experimental inputs were combined algebraically to calculate the O₂/H₂O standard potentials without relying on extra-thermodynamic assumptions about single-ion solvation energies.
Performance Evaluation: The resulting O₂/H₂O standard potentials are +1.21 V in acetonitrile and +0.60 V in DMF, both versus Fc^+/0. The substantial 0.61 V difference between solvents stems primarily from the much higher basicity of DMF, which stabilizes protons and shifts the equilibrium potential more negative. Extending the same methodology to carbon dioxide couples gave CO₂/CO potentials of -0.12 V (acetonitrile) and -0.73 V (DMF), and CO₂/CH₄ values of +0.15 V and -0.48 V, respectively. These thermodynamic benchmarks now enable researchers to quantify overpotentials for electrocatalytic oxygen evolution, oxygen reduction, and CO₂ conversion in nonaqueous media.

One Precursor, Triple Payoff - DMF Crafts Nitrogen-Doped Porous Carbon Nitride for Solar Hydrogen

Guo, Feng, et al. Inorganic Chemistry Frontiers 7.8 (2020): 1770-1779.

Graphitic carbon nitride (g-C₃N₄) has attracted widespread attention as a metal-free visible-light photocatalyst, yet its practical performance remains constrained by rapid charge recombination and limited light absorption. This investigation demonstrates that N,N-dimethylformamide, when co-thermally condensed with urea, simultaneously addresses three limitations through a single-step synthetic strategy. During calcination at 550 degrees Celsius, DMF serves as a nitrogen dopant substituting carbon atoms in the triazine framework, releases dimethylamine gas that creates a porous nanosheet architecture, and promotes the formation of a two-dimensional layered morphology - a triple-function precursor.
Experimental Protocol: Urea (10 g) was mixed with varying volumes of DMF (5-20 mL) and calcined in a covered crucible at 550 degrees Celsius for 3 hours. Photocatalytic hydrogen production was conducted under visible light irradiation (wavelength greater than 400 nm) using triethanolamine as a sacrificial agent and platinum as a co-catalyst. Structural characterization employed XRD, FT-IR, XPS, solid-state ¹³C NMR, Raman spectroscopy, and electron microscopy.
Performance Evaluation: The optimal sample, prepared with 10 mL of DMF, achieved a hydrogen evolution rate of 263.4 micromol h^-1, representing a 14-fold enhancement over pristine g-C₃N₄ nanosheets. Apparent quantum efficiencies at 420, 535, and 630 nm were 11.4%, 4.4%, and 1.5%, respectively. The nitrogen-doped material displayed a narrowed band gap of 2.71 eV, enhanced visible-light absorption, and a substantially shorter fluorescence lifetime of 0.960 ns compared to 2.443 ns for the undoped counterpart, confirming suppressed electron-hole recombination. Electrochemical impedance spectroscopy revealed a much smaller charge-transfer resistance, and surface photovoltage measurements indicated more efficient photogenerated carrier separation. The catalyst retained its activity without significant degradation across four consecutive reaction cycles totaling 16 hours. Excessive DMF addition proved counterproductive, causing disruption of the conjugated carbon nitride network and reduced performance.

Dose Decides Destiny - DMF's Opposing Faces in Breast Cancer Cell Proliferation and Apoptosis

Zhang, Jihong, et al. Dose-Response 15.4 (2017): 1559325817744450.

N,N-dimethylformamide is an industrial solvent with demonstrated biological activity against various cancer types, yet its role in breast cancer had not been systematically characterized. This study reveals a striking dose-dependent duality: DMF at low concentration promotes breast cancer cell growth while at high concentration it becomes a potent antiproliferative agent. Using MCF-7 adenocarcinoma cells alongside non-tumorous MCF-12A mammary epithelial cells as a control, the researchers mapped the full dose-response landscape across concentrations ranging from 0.1 to 500 mM over 24 to 72 hours.
Experimental Protocol: Both cell lines were exposed to graded DMF concentrations. Cell viability was assessed by trypan blue dye exclusion and WST-1 proliferation assays. Cell cycle distribution was analyzed by flow cytometry with propidium iodide staining. Apoptosis was quantified through annexin-V/FITC and propidium iodide dual staining. Protein expression of cyclin D1, cyclin E1, caspase-9, caspase-8, Bcl-xL, and Bax was measured by Western blot analysis.
Performance Evaluation: In MCF-12A normal cells, DMF exhibited straightforward dose-dependent cytotoxicity at all tested concentrations. In MCF-7 cancer cells, however, low-dose DMF (1 mM) significantly increased cell proliferation and upregulated cyclin D1 and cyclin E1 expression, indicating accelerated cell cycle progression. Simultaneously, low-dose treatment reduced early apoptotic cell populations. High-dose DMF (100 mM) produced the opposite effects: it suppressed proliferation, decreased cyclin protein levels, and caused cell cycle arrest at the G₀/G₁ phase. Apoptosis was induced through the intrinsic mitochondrial pathway, as evidenced by increased cleaved caspase-9 without activation of caspase-8, coupled with elevated proapoptotic Bax and reduced antiapoptotic Bcl-xL protein expression. The Bcl-xL/Bax ratio decreased significantly. These findings constitute the first demonstration that DMF exerts concentration-dependent opposing effects on breast cancer cell fate and underscore the necessity of precise dose determination for any potential therapeutic application.

Custom Q&A

What is the molecular formula of N,N-Dimethylformamide?

The molecular formula of N,N-Dimethylformamide is C3H7NOHCON(CH3)2.

What is the molecular weight of N,N-Dimethylformamide?

The molecular weight of N,N-Dimethylformamide is 73.09 g/mol.

What is the synonyms of N,N-Dimethylformamide?

The synonyms of N,N-Dimethylformamide include Dimethylformamide, 68-12-2, Dimethyl formamide, and N,N-Dimethylmethanamide.

What is the description of N,N-Dimethylformamide?

N,N-Dimethylformamide appears as a water-white liquid with a faint fishy odor. It has a flash point of 136 °F. It is slightly less dense than water and its vapors are heavier than air. It is toxic by inhalation or skin absorption and may irritate the eyes.

What is the role of N,N-Dimethylformamide as mentioned in CAMEO Chemicals?

N,N-Dimethylformamide has a role as a polar aprotic solvent, a hepatotoxic agent, and a geroprotector. It is also mentioned as a volatile organic compound and a member of formamides.

How is N,N-Dimethylformamide used industrially?

N,N-Dimethylformamide is used as an industrial solvent and in the production of fibers, films, and surface coatings.

What are the acute symptoms of N,N-Dimethylformamide exposure in humans?

Acute exposure to N,N-Dimethylformamide in humans can cause abdominal pain, nausea, vomiting, jaundice, alcohol intolerance, and rashes.

What are the potential health effects of chronic occupational exposure to N,N-Dimethylformamide?

Chronic occupational exposure to N,N-Dimethylformamide by inhalation can result in liver damage and digestive disturbances in workers.

What was the initial association suggested between N,N-Dimethylformamide exposure and a specific type of cancer?

Initial human studies suggested a possible association between N,N-Dimethylformamide exposure and testicular cancer.

How is N,N-Dimethylformamide classified regarding its carcinogenicity according to the EPA?

The EPA has not classified N,N-Dimethylformamide with respect to its carcinogenicity.