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Formamide information


Formamide
Structural formula of the formamide molecule
Ball and stick model of formamide
Ball and stick model of formamide
Space-filling model of the formamide molecule
Space-filling model of the formamide molecule
Names
Preferred IUPAC name
Formamide[1]
Systematic IUPAC name
Methanamide
Other names
Carbamaldehyde
Identifiers
CAS Number
  • 75-12-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:48431 checkY
ChEMBL
  • ChEMBL266160 checkY
ChemSpider
  • 693 checkY
ECHA InfoCard 100.000.766 Edit this at Wikidata
IUPHAR/BPS
  • 4739
KEGG
  • C00488 checkY
PubChem CID
  • 713
UNII
  • 4781T907ZS checkY
CompTox Dashboard (EPA)
  • DTXSID8025337 Edit this at Wikidata
InChI
  • InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3) checkY
    Key: ZHNUHDYFZUAESO-UHFFFAOYSA-N checkY
  • InChI=1/CH3NO/c2-1-3/h1H,(H2,2,3)
    Key: ZHNUHDYFZUAESO-UHFFFAOYAQ
SMILES
  • O=CN
Properties
Chemical formula
CH3NO
Molar mass 45.04 g/mol
Appearance Colorless, oily liquid[2]
Density 1.133 g/cm3
Melting point 2 to 3 °C (36 to 37 °F; 275 to 276 K)
Boiling point 210 °C (410 °F; 483 K)
Solubility in water
Miscible
Vapor pressure 0.08 mmHg at 20 °C
Acidity (pKa) 23.5 (in DMSO)[3]
Magnetic susceptibility (χ)
−2.19×10−5 cm3/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 154 °C (309 °F; 427 K) (closed cup)
NIOSH (US health exposure limits):
PEL (Permissible)
none[2]
REL (Recommended)
TWA 10 ppm (15 mg/m3) [skin][2]
IDLH (Immediate danger)
N.D.[2]
Related compounds
Related compounds
Carbamic acid
Dimethylformamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Formamide is an amide derived from formic acid. It is a colorless liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs and other pharmaceuticals, herbicides and pesticides, and in 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.[4] Some astrobiologists suggest that it may be an alternative to water as the main solvent in other forms of life.[5]

Formamides are compounds of the type RR′NCHO. One important formamide is dimethylformamide, (CH3)2NCHO.

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 841. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The traditional name 'formamide' is retained for HCO-NH2 and is the preferred IUPAC name.
  2. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0295". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ F. G. Bordwell; J. E. Bartmess; J. A. Hautala (1978). "Alkyl effects on equilibrium acidities of carbon acids in protic and dipolar aprotic media and the gas phase". J. Org. Chem. 43 (16): 3095–3101. doi:10.1021/jo00410a001.
  4. ^ Hohn, A. (1999). "Formamide". In Kroschwitz, Jacqueline I. (ed.). Kirk-Othmer Concise Encyclopedia of Chemical Technology (4th ed.). New York: John Wiley & Sons, Inc. pp. 943–944. ISBN 978-0471419617.
  5. ^ "How to improve the search for aliens". The Economist.

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Formamide

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Formamide is an amide derived from formic acid. It is a colorless liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock...

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Leuckart reaction

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formate or formamide as the nitrogen donor and reducing agent. It requires high temperatures, usually between 120 and 130 °C; for the formamide variant,...

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Purine

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be synthesized artificially. Purine (1) is obtained in good yield when formamide is heated in an open vessel at 170 °C for 28 hours. This remarkable reaction...

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Azodicarbonamide

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Azodicarbonamide, ADCA, ADA, or azo(bis)formamide, is a chemical compound with the molecular formula C2H4O2N4. It is a yellow to orange-red, odorless...

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Adenine

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industrial-scale production of adenine is a modified form of the formamide method. This method heats up formamide under 120 degree Celsius conditions within a sealed...

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Diethylformamide

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formula C5H11NO. As its name indicates, it is structurally related to formamide, having two ethyl groups in place of the two hydrogens. It is used in...

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Dimethylformamide

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reduced pressure. As its name indicates, it is structurally related to formamide, having two methyl groups in the place of the two hydrogens. DMF is a...

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Ammonium formate

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(CH3)2CHNHCHO + H2O → (CH3)2CHNH2 + HCO2H Pure ammonium formate decomposes into formamide and water when heated, and this is its primary use in industry. Formic...

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Formic acid

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indirectly by first treating the methyl formate with ammonia to give formamide, which is then hydrolyzed with sulfuric acid: HCO2CH3 + NH3 → HC(O)NH2...

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Cyanide hydratase

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enzyme cyanide hydratase (EC 4.2.1.66) catalyzes the chemical reaction formamide ⇌ {\displaystyle \rightleftharpoons } cyanide + H2O This enzyme belongs...

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Isocyanide

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developed. Commonly, isocyanides are synthesized by dehydration of formamides. The formamide can be dehydrated with toluenesulfonyl chloride, phosphorus oxychloride...

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Formamidase

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chemical reaction formamide + H2O ⇌ {\displaystyle \rightleftharpoons } formate + NH3 Thus, the two substrates of this enzyme are formamide and H2O, whereas...

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Formetorex

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three steps. For amphetamine synthesis, a mixture of phenylacetone and formamide (sometimes in the presence of formic acid) or ammonium formate, is heated...

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Amide

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(alkanoyl) group (R−C(=O)−) joined to an amine group. Common of amides are formamide (H−C(=O)−NH2), acetamide (H3C−C(=O)−NH2), benzamide (C6H5−C(=O)−NH2),...

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Benzylamine

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accidentally by Rudolf Leuckart in the reaction of benzaldehyde with formamide in a process now known as the Leuckart reaction, a general process in...

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Deuterated DMF

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Deuterated DMF Names IUPAC name 1-Deuterio-N,N-bis(trideuteriomethyl)formamide[citation needed] Other names Dimethylformamide-d7[citation needed] N...

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Imidazole

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(3,4) bonds can also be formed from N-substituted α-aminoketones and formamide with heat. The product will be a 1,4-disubstituted imidazole, but here...

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Ethanol

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Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne...

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Relative permittivity

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HCONMe2 dimethyl formamide (DMF) 36.7 298 K (25 °C) CH3CN acetonitrile 37.5 293 K (20 °C) H2O water 78.4 298 K (25 °C) HCONH2 formamide 109 293 K (20 °C)...

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Potassium fluoride

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chlorides). Such reactions usually employ polar solvents such as dimethyl formamide, ethylene glycol, and dimethyl sulfoxide. More efficient fluorination...

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Abiogenesis

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hydrogen cyanide (HCN) and ammonia. Formamide produces all four ribonucleotides when warmed with terrestrial minerals. Formamide is ubiquitous in the Universe...

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CH3NO

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mass: 45.04 g/mol, exact mass: 45.0215 u) may refer to: Formaldoxime Formamide, or methanamide Nitrosomethane [Wikidata] Oxaziridine This set index page...

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Carbon dioxide

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Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne...

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