出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/01/22 23:51:20」(JST)
Formamide | |
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IUPAC name
Methanamide |
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Other names
Carbamaldehyde |
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Identifiers | |
CAS number | 75-12-7 Y |
PubChem | 713 |
ChemSpider | 693 Y |
KEGG | C00488 Y |
ChEBI | CHEBI:48431 Y |
ChEMBL | CHEMBL266160 Y |
Jmol-3D images | Image 1 |
SMILES
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InChI
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Properties | |
Molecular formula | CH3NO |
Molar mass | 45.04 g/mol |
Density | 1.133 g/cm3 |
Melting point |
2-3 °C, 275-276 K, 36-37 °F |
Boiling point |
210 °C, 483 K, 410 °F |
Solubility in water | Miscible |
Vapor pressure | 0.08 mmHg at 20 °C |
Acidity (pKa) | 23.5 (in DMSO)[1] |
Hazards | |
NFPA 704 |
1
2
0
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Flash point | 154 °C (closed cup) |
Related compounds | |
Related compounds | Carbamic acid Dimethylformamide |
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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Infobox references |
Formamide, also known as methanamide, is an amide derived from formic acid. It is a clear liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs, other pharmaceuticals, herbicides, pesticides and the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers.[2]
Formamide will begin to partially decompose into carbon monoxide and ammonia at 180 °C. When heated strongly, formamide decomposes to hydrogen cyanide (HCN) and water vapor.
Contents
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In the past, formic acid was reacted with ammonia to produce ammonium formate, which yielded formamide by heating:
The current industrial process for the manufacture of formamide[2] involves either the reaction of carbon monoxide and ammonia:
or the more important two stage process involving the aminolysis of methyl formate (formed from carbon monoxide and methanol):
with the possibility of the resulting methanol being recycled into more methyl formate, by reaction with carbon monoxide.
Formamide is also a constituent of cryoprotectant vitrification mixtures used for cryopreservation of tissues and organs.
Formamide is also used as an RNA stabiliser in gel electrophoresis by deionizing RNA. In capillary electrophoresis, it is used for stabilizing (single) strands of denatured DNA.
Another use is to add it in sol-gel solutions in order to avoid cracking during sintering.
Formamide, in its pure state, has been used as an alternative solvent for the electrostatic self-assembly of polymer nanofilms.[3]
Formamide is used to prepare primary amines directly from ketones via their N-formyl derivatives, using the Leuckart reaction.
Formamide has also been proposed as an alternative solvent to water, perhaps with the ability to support life with alternative biochemistries to that currently found on Earth. It can be formed by the reaction of hydrogen cyanide and water, has a large dipole moment, and dissolves almost everything that will dissolve in water.[4]
Formamide has been shown to create guanine at 130 °C in the presence of ultra violet light.[5]
Formamide is highly corrosive on contact with skin or eyes and may be deadly if ingested. Inhalation of large amounts of formamide vapor may require medical attention.[6] It is also a teratogen.[7] Formamide should never be handled without proper safety attire including gloves and goggles. There is a small risk of decomposition into hydrogen cyanide and water.
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拡張検索 | 「N-4-(5-nitro-2-furyl)-2-thiazolylformamide」 |
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