| Customization: | Available |
|---|---|
| CAS No.: | 68-12-2; 68-18-2;1968-12-2 |
| Formula: | C3h7no |
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| Name | N,N-Dimethylformamide |
| Synonyms | DMF Dimethylformamide Formdimethylamide Dimethyl Formamide Formyldimethylamine N,N-Dimethylformamide N,N-dimethyl-Formamide dimethylamidkyselinymravenci amide,n,n-dimethyl-formicaci N,N-DIMETHYLFORMAMIDE, 4X25 ML Dimethylamid kyseliny mravenci N,N-DIMETHYLFORMAMIDE, MOLECULARBIOLOGY REAGENT N,N-DIMETHYLFORMAMIDE NEUTRAL MARKER*FOR CAPILLARY |
| CAS | 68-12-2 68-18-2 1968-12-2 |
| EINECS | 200-679-5 |
| InChI | InChI=1/C3H7NO/c1-4(2)3-5/h3H,1-2H3 |
| InChIKey | ZMXDDKWLCZADIW-UHFFFAOYSA-N |
| Molecular Formula | C3H7NO |
| Molar Mass | 73.09 |
| Density | 0.944 g/mL (lit.) |
| Melting Point | -61 °C (lit.) |
| Boling Point | 153 °C (lit.) |
| Specific Rotation(α) | 0.94 º |
| Flash Point | 136°F |
| Water Solubility | soluble |
| Solubility | water: miscible |
| Vapor Presure | 2.7 mm Hg ( 20 °C) |
| Vapor Density | 2.5 (vs air) |
| Appearance | liquid |
| Color | APHA: ≤15 |
| Odor | Faint, ammonia-like odor detectable at 100 ppm |
| Exposure Limit | NIOSH REL: TWA 10 ppm (30 mg/m3), IDLH 500 ppm; OSHA PEL: TWA 10ppm; ACGIH TLV: TWA 10 ppm (adopted). |
| Maximum wavelength(λmax) | λ: 270 nm Amax: 1.00λ: 275 nm Amax: 0.30λ: 295 nm Amax: 0.10λ: 310 nm Amax: 0.05λ: 340-400 nm Amax: |
| Merck | 14,3243 |
| BRN | 605365 |
| pKa | -0.44±0.70(Predicted) |
| PH | 7 (200g/l, H2O, 20ºC) |
| Storage Condition | Store at +5°C to +30°C. |
| Sensitive | Hygroscopic |
| Explosive Limit | 2.2-16%(V) |
| Refractive Index | n20/D 1.430(lit.) |
| Physical and Chemical Properties | Density 0.945 melting point -61°C boiling point 153°C refractive index 1.429-1.432 flash point 58°C specific rotation 0.94 ° water-soluble solution |
| Use | Used as analytical reagents and ethylene resin, acetylene solvent |
| Hazard Symbols | T - Toxic |
| Risk Codes | R61 - May cause harm to the unborn child R20/21 - Harmful by inhalation and in contact with skin. R36 - Irritating to the eyes |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | UN 2265 3/PG 3 |
| WGK Germany | 1 |
| RTECS | LQ2100000 |
| FLUKA BRAND F CODES | 3-10 |
| TSCA | Yes |
| HS Code | 29241990 |
| Hazard Note | Toxic |
| Hazard Class | 3 |
| Packing Group | III |
| Toxicity | LD50 in mice, rats (ml/kg): 6.8, 7.6 orally; 6.2, 4.7 i.p. (Bartsch) |
| Raw Materials | Dimethylamine Methyl alcohol Sodium methoxide Formic acid Methyl formate Ammonia carbon monoxide,cyl. with 10 L (net~3kg) |
| Downstream Products | 5-methylfurfural 2-(Aminomethyl)-1-ethylpyrrolidine Polyurethane cefotaxim sodium salt roxithromycin Sulfadiazine Lomefloxacin hydrochloride Labetalol Bifendate etomidate 1,3,5-Tris(2-hydroxyethyl)cyanuric acid |
| Overview | dimethylformamide (DMF). A compound formed by substitution of a hydroxyl group of formic acid with a dimethylamine group and having the molecular formula HCON(CH3)2. Is a colorless transparent high boiling point liquid, with a light amine flavor, relative density of 0.9445(25 degrees C). Melting Point -61 °c. Boiling point 152.8 °c. Flash point 57.78 °c. The vapor density was 2.51. The vapor pressure was 0.49kpa(3.7mm HG 25 °c). Spontaneous ignition point 445. The explosive limit of the mixture of vapor and air is 2.2 ~ 15.2%. Fire, high heat can cause combustion explosion. It can react with concentrated sulfuric acid, fuming nitric acid and even explosive. Miscible with water and most organic solvents. It is a common solvent for chemical reactions. Pure dimethylformamide is odorless, but industrial-grade or deteriorated dimethylformamide has a fishy odor because it contains impurities of dimethylamine. The name is derived because it is a dimethyl substituent of Formamide (the amide of formic acid) and both methyl groups are located on the N (nitrogen) atom. Dimethylformamide is a polar (hydrophilic) aprotic solvent having a high boiling point, and can promote the progress of the SN2 reaction mechanism. Dimethylformamide is produced using formic acid and dimethylamine. Dimethylformamide is unstable (especially at elevated temperatures) in the presence of a strong base such as sodium hydroxide or a strong acid such as hydrochloric acid or sulfuric acid, and hydrolyzes to formic acid and dimethylamine. It is stable in air and when heated to boiling. When the temperature is higher than 350 ° C, the water is lost, and carbon monoxide and dimethylamine are formed. N,N-dimethylformamide is a good aprotic polar solvent, can dissolve most organic and inorganic matter, and water, alcohols, ethers, aldehydes, ketones, esters, halogenated hydrocarbons and aromatic hydrocarbons can be miscible. The positively charged one end of the N,N-dimethylformamide molecule is surrounded by a methyl group, forming a steric obstruction that makes negative ions inaccessible, and only positive ions are associated. The activity of a naked negative ion is much greater than that of a solvated negative ion. Many ionic reactions proceed more easily in N,N-dimethylformamide than in common protic solvents. For example, carboxylates react with halogenated hydrocarbons in N,N-dimethylformamide at room temperature, it can produce esters with high yield, and is particularly suitable for the synthesis of sterically hindered esters. |
| purification and water removal method | DMF can be mixed with most organic solvents and water at will, the solubility of organic and inorganic compounds is better. N,N-dimethylformamide contains a small amount of water. Some decomposition of atmospheric distillation, produce dimethylamine and carbon monoxide. Decomposition is accelerated in the presence of acid or base. Therefore, the addition of solid potassium hydroxide (sodium) was partially decomposed after several hours at room temperature. Thus, most commonly, calcium sulfate, magnesium sulfate, barium oxide, silica gel or molecular sieves are dried and then distilled under reduced pressure to collect a fraction of 76 °c/4800PA (36mm Hg). When there is more water, 1/10 volume of benzene may be added, distilled off water and benzene at normal pressure and below 80 ° C., then dried with anhydrous magnesium sulfate or barium oxide, and finally distilled under reduced pressure. The purified N,N-dimethylformamide was stored in the dark. If free amine is present in N,N-dimethylformamide, it can be checked by color generation of 2,4 dinitrofluorobenzene. |
| Use of dimethylformamide | dimethylformamide is a good solvent for a variety of high polymers such as polyethylene, polyvinyl chloride, polyacrylonitrile, polyamide, etc, it can be used for wet spinning of synthetic fibers such as polyacrylonitrile fibers, synthesis of polyurethane; For plastic film; Can also be used as paint remover to remove paint; It can also dissolve some low solubility pigments, so that the pigment with the characteristics of dyes. Dimethylformamide is used in aromatic extraction and in the separation and recovery of butadiene from the C4 fraction and isoprene from the C5 fraction. It is also useful as an effective reagent for the separation of non-hydrocarbon components from paraffin. It has good selectivity to the solubility of isophthalic acid and terephthalic acid: the solubility of isophthalic acid in dimethylformamide is greater than that of terephthalic acid, and the two can be separated by solvent extraction or partial crystallization in formamide. In the petrochemical industry, dimethylformamide can be used as a gas absorbent for the separation and purification of gases. As a washing curing agent in the polyurethane industry, it is mainly used in the production of wet synthetic leather; As a solvent in the acrylic fiber industry, it is mainly used in the dry spinning production of acrylic fiber; in the electronics industry as the quenching of tin-plated parts and circuit board cleaning; Other industries including carriers of dangerous gases, pharmaceutical crystallization solvents, adhesives, etc. In organic reactions, dimethylformamide is not only widely used as a reaction solvent, but also an important intermediate in organic synthesis. Pesticide industry can be used to produce chlordimeform; Pharmaceutical industry can be used for the synthesis of iodoamine pyrimidine, doxycycline, cortisone, vitamin B6, iodin, quetiapine, thiopyrimidine, N-formyl soluble sarcoma, anti-tumor amino acid, methoxyaryl mustard, bianmustard, cyclohexylisourea, fuflurouracil, haemostatic cyclic acid, trimethoprim, megestrol, vitamin A, chlorpheniramine, production of sulfonamides. Dimethylformamide in The hydrogenation, dehydrogenation, dehydration and dehydrohalogenation reaction has a catalytic effect, so that the reaction temperature is reduced, and the purity of the product is improved. |
| universal solvent-dimethylformamide | dimethylformamide is mainly used as a low volatility solvent. Dimethylformamide is used in the manufacture of acrylic fibers and plastics. In the pharmaceutical industry, it is also used in the manufacture of pesticides, adhesives, artificial leather, fiber, film and surface coating. Dimethylformamide is a reagent for the bouveult aldehyde synthesis reaction and the Vilsmeier-Haack reaction, another useful aldehyde synthesis reaction. In the nuclear magnetic resonance spectrum, the protons on the methyl group of dimethylformamide form two single peaks because the rotation rate of the carbonyl carbon-nitrogen bond is very slow in the time scale of nuclear magnetic resonance. The degree of the carbon-nitrogen bond of the carbonyl group is greater than one, and the degree of the carbon-oxygen bond of the amide is less than two. In the infrared spectrum of the amide, the C = O band pass is often less than 1700cm − 1, because its C = O bond is weakened by the electron density of oxygen supplied from nitrogen. Dimethylformamide is commonly used as one of the components of paint scavengers because it penetrates most plastics and expands them. Dimethylformamide has also been used as a "universal solvent", but also has its limitations. High boiling point, 154 ° C, as a solvent for many polymer materials is more appropriate, in organic synthesis should be carefully selected, often encounter solvent removal is not net. In addition, it can be miscible with water, and the simple method of recovering the solvent is difficult to dehydrate. At the cost, it can be washed out with water, and the feasibility of mass production should be considered in the small test. Cost and wastewater treatment options need to be accounted. |
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