| Dimethylformamide | |
|---|---|
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| IUPAC name | N,N-dimethylmethanamide |
| Other names | DMF, dimethylformide, N,N-dimethylformide, DMFA |
| Identifiers | |
| CAS number | [68-12-2] |
| RTECS number | LQ2100000 |
| SMILES | O=CN(C)C |
| Properties | |
| Molecular formula | C3H7NO |
| Molar mass | 73. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 09 g/mol |
| Appearance | Clear liquid |
| Density | 0. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 944 g/cm3, liquid |
| Melting point |
-61 °C (212 K) |
| Boiling point |
153 °C (426 K) |
| Solubility in water | Miscible |
| Refractive index (nD) | 1. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. The refractive index (or index of Refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves is reduced inside the medium 4305 (20 °C), εr = 36. Measurement The relative static permittivity εr can be measured for static Electric fields as follows first the Capacitance of a test 71 (25°C) |
| Viscosity | 0. Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. 92 cP at 20 °C |
| Structure | |
| Dipole moment | 3. The poise (symbol P pwɑːz is the unit of dynamic Viscosity in the Centimetre gram second system of units. In physics there are two kinds of dipoles ( Hellènic: di(s- = two- and pòla = pivot hinge An electric dipole is a 86 D D (25 °C) |
| Hazards | |
| MSDS | ScienceLab.com |
| Main hazards | flammable |
| R-phrases | 61-20/21-36 |
| S-phrases | 53-45 |
| Flash point | 58 °C |
| Related compounds | |
| Related amides | Acetamide, Formamide, hexamethylphosphoramide |
| Related compounds | Dimethyl sulfoxide, acetonitrile |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Dimethylformamide is the organic compound with the formula (CH3)2NC(O)H. The debye (symbol D) is a non- SI, CGS unit of electrical dipole moment. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance Occupational safety and health is a cross-disciplinary area concerned with protecting the Safety, Health and welfare of people engaged in R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air In Chemistry, an amide is one of three kinds of Compounds (sometimes called acid amide the organic Functional group characterized Acetamide (or acetic acid amide or ethanamide) CH3CONH2 the Amide of Acetic acid, is a white crystalline solid in Formamide, also known as methanamide is an Amide derived from Formic acid. Hexamethylphosphoramide (abbreviated HMPA is a colorless organic liquid with the formula 3PO Dimethyl sulfoxide (DMSO is the Chemical compound with the formula (CH32SO Acetonitrile (ACN is the Chemical compound with formula CH3CN In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly An organic compound is any member of a large class of Chemical compounds whose Molecules contain Carbon. A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes In Chemistry, a methyl group is a Hydrophobic Alkyl Functional group named after Methane (4 Commonly abbreviated DMF, this colourless liquid is miscible with water and the majority of organic liquids. Water ( H2[[oxygen O]] H OH) is the most abundant Molecule on Earth 's surface composing of about 70% of the Earth's surface as DMF is a common solvent for chemical reactions. A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. A chemical reaction is a process that always results in the interconversion of Chemical substances The substance or substances initially involved in a chemical reaction are called Pure dimethylformamide is odorless whereas technical grade or degraded dimethylformamide often has a fishy smell due to impurity of dimethylamine. Dimethylamine is an Organic compound with the formula (CH32NH Its name is derived from the fact that it is a derivative of formamide, the amide of formic acid. Formamide, also known as methanamide is an Amide derived from Formic acid. In Chemistry, an amide is one of three kinds of Compounds (sometimes called acid amide the organic Functional group characterized Formic acid (systematically called methanoic acid) is the simplest Carboxylic acid.
Dimethylformamide is a polar (hydrophilic) aprotic solvent with a high boiling point. "Polar molecule" and "Non-polar" redirect here Hydrophile, from the Greek (hydros "water" and φιλια (philia "friendship" refers to a physical property of a Molecule It facilitates reactions that follow polar mechanisms, such as SN2 reactions. The SN2 reaction (also known as bimolecular nucleophilic substitution) is a type of Nucleophilic substitution, where a lone pair from a Nucleophile Dimethylformamide can be synthesized from methyl formate and dimethyl amine or reaction of dimethyl amine and carbon monoxide. Methyl formate, also called methyl methanoate, is the methyl Ester of Formic acid. Dimethylamine is an Organic compound with the formula (CH32NH Dimethylamine is an Organic compound with the formula (CH32NH Carbon monoxide, with the chemical formula CO is a colorless odorless tasteless yet highly toxic Gas. [1] Dimethylformamide is not stable in the presence of strong bases like sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid and is hydrolyzed back into formic acid and dimethylamine, especially at elevated temperatures. Sodium hydroxide ( Na[[hydroxide OH]]) also known as Lye, caustic soda and (incorrectly according to IUPAC nomenclature Hydrochloric acid is the Solution of Hydrogen chloride ( H[[Chlorine Cl]] in water Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid. Hydrolysis is a Chemical reaction during which one or more water molecules are split into hydrogen and hydroxide ions which may go on to participate in further reactions
Contents |
Structure and properties
Due to the contribution of the two possible resonance structures of an amide, the bond order of the carbonyl C=O bond is reduced, while that of the carbon-nitrogen bond is increased. In Organic chemistry, a carbonyl group is a Functional group composed of a Carbon Atom double-bonded to an Oxygen A carbon-nitrogen bond is a Covalent bond between Carbon and Nitrogen and one of the most abundant in Organic chemistry and Biochemistry Thus the infrared spectrum of DMF shows a lower C=O stretching frequency at 1675 cm-1[2] than an unsubstituted C=O bond. Infrared spectroscopy (IR spectroscopy is the subset of Spectroscopy that deals with the Infrared region of the Electromagnetic spectrum. Also, because of the partial double bond character, the rotation about the C-N axis is slow, making the two methyl groups inequivalent on the NMR time scale, giving rise to two singlets of 3 protons each at δ 2. 97 and 2. 88,[2] instead of one singlet of 6 protons in the proton NMR spectrum. Proton NMR (also Hydrogen-1 NMR, or 1HNMR) is the application of Nuclear magnetic resonance in NMR spectroscopy
Applications
The primary use of dimethylformamide is as a solvent with low evaporation rate. Dimethylformamide is used in the production of acrylic fibers and plastics. Acrylic fibers are Synthetic fibers made from a polymer ( Polyacrylonitrile) with an average molecular weight of ~100000 Plastic is the general common term for a wide range of synthetic or semisynthetic organic solid materials suitable for the manufacture of industrial products It is also used as a solvent in peptide coupling for pharmaceuticals, in the development and production of pesticides, and in the manufacture of adhesives, synthetic leathers, fibers, films, and surface coatings. A pesticide is a substance or mixture of substances used to kill a pest. Glue or adhesive is a compound that adheres or bonds two items together Leather is a material created through the Tanning of hides and Skins of Animals primarily Cattlehide The Tanning process [3]
It is used as a reagent in the Bouveault aldehyde synthesis and in the Vilsmeier-Haack reaction, another useful method of forming aldehydes. The Bouveault aldehyde synthesis is a one-pot Chemical reaction that converts a primary Alkyl halide to an Aldehyde one carbon longer The Vilsmeier-Haack reaction (also called the Vilsmeier reaction) is the Chemical reaction of a substituted Amide ( 1) with Phosphorus oxychloride An aldehyde is an organic compound containing a terminal Carbonyl group.
DMF penetrates most plastics and makes them swell. Plastic is the general common term for a wide range of synthetic or semisynthetic organic solid materials suitable for the manufacture of industrial products It therefore frequently occurs as a component of paint strippers. Paint stripper, or paint remover, is the generic name given to Solvent mixtures designed to remove Paint and other finishes and also to clean the underlying
It is also used in the manufacturing of solvent dyes as an important raw material. It is consumed during reaction.
Production
Dimethyl formamide is produced either with catalyzed reaction of dimethyl amine and carbon monoxide in methanol or the reaction of methyl formate with dimethyl amine. Dimethylamine is an Organic compound with the formula (CH32NH Carbon monoxide, with the chemical formula CO is a colorless odorless tasteless yet highly toxic Gas. Methyl formate, also called methyl methanoate, is the methyl Ester of Formic acid. [1] It may also be prepared on a laboratory scale by reacting dimethylamine with formic acid.
Precautions
Reaction with sodium hydride in DMF as a solvent are somewhat hazardous; exothermic decomposition has been reported at temperatures as low as 26 °C. Sodium hydride is the Chemical compound with the formula NaH It is primarily used as a strong base in Organic synthesis. On a laboratory scale any thermal runaway is (usually) quickly noticed and brought under control with an ice bath and this remains a popular combination of reagents. On a pilot plant scale, on the other hand, several accidents have been reported. A pilot plant is a small chemical processing system which is operated to generate information about the behavior of the system for use in Design of larger facilities
Toxicity
DMF has been linked to cancer in humans, and it is thought to cause birth defects. Cancer (medical term Malignant Neoplasm) is a class of Diseases in which a group of cells display uncontrolled A congenital disorder is a disease or disorder that is present at birth In some sectors of industry women are banned from working with DMF. For many reactions, it can be replaced with dimethyl sulfoxide. Dimethyl sulfoxide (DMSO is the Chemical compound with the formula (CH32SO Most manufacturers of DMF list (Life) or (Chronic) as a health hazard in their MSDS since DMF is not readily disposed of by the body. According to IARC, DMF is a possible carcinogen, although EPA does not consider it a cancer risk. The International Agency for Research on Cancer ( IARC, or CIRC in its French Acronym) is an intergovernmental agency forming part of the World Health The term carcinogen refers to any substance Radionuclide or radiation that is an agent directly involved in the promotion of Cancer or in the fatation of its propagation
References
- ^ a b Klaus Weissermel, Hans-Jürgen Arpe. Industrial Organic Chemistry: Important Raw Materials and Intermediates, 45-46. ISBN 3527305785.
- ^ a b Spectral Database for Organic Compounds, Dimethylformamide, accessed 27 Jan 2007.
- ^ Redlich, C; Beckett, W. S. ; Sparer, J. ; Barwick, K. W. ; Riely, C. A. ; Miller, H. ; Sigal, S. L. ; Shalat, S. L. ; and Cullen, M. R. ; 1988. Year 1988 ( MCMLXXXVIII) was a Leap year starting on Friday (link displays 1988 Gregorian calendar) Liver disease associated with occupational exposure to the solvent dimethylformamide. Ann. Intern. Med. 108:680-686. PMID 3358569
External links
- International Chemical Safety Card 0457
- NIOSH Pocket Guide to Chemical Hazards 0226
- Dimethylformamide usage on Organic Syntheses
- Concise International Chemical Assessment Document 31: N,N-Dimethylformamide
- Material Safety Data Sheet for DMF
- DMF Chronic Toxicity Summary (PDF)
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