Formamide

Base Information

• Chemical Name: Formamide
• CAS No.: 75-12-7
• Deprecated CAS: 23296-41-5,1156543-55-3,1158234-15-1,1158234-15-1
• Molecular Formula: CH3NO
• Molecular Weight: 45.0409
• Hs Code.: 2924199090
• European Community (EC) Number: 200-842-0
• ICSC Number: 0891
• NSC Number: 748
• UNII: 4781T907ZS
• DSSTox Substance ID: DTXSID8025337
• Nikkaji Number: J1.941K
• Wikipedia: Formamide
• Wikidata: Q283917,Q27110288
• Metabolomics Workbench ID: 37854
• ChEMBL ID: CHEMBL266160
• Mol file: 75-12-7.mol

Synonyms:Carbamaldehyde;Formimidic acid;Methanamide;NSC 748;

Chemical Property of Formamide

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 0.08 mm Hg ( 20 °C)
• Melting Point: 2-3 °C
• Refractive Index: n20/D 1.447(lit.)
• Boiling Point: 210.5 °C at 760 mmHg
• PKA: 16.50±0.50(Predicted)
• Flash Point: 81.1 °C
• PSA: 43.09000
• Density: 0.978 g/cm³
• LogP: 0.43770
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: H2O: 10 M at 20 °C, clear, colorless
• Water Solubility.: miscible
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 45.021463719
• Heavy Atom Count: 3
• Complexity: 12.3

Purity/Quality:

98% ^*data from raw suppliers

Formamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 61-41-37/38-48/22-40
• Safety Statements: 53-45-36/37/39-26-23-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Amides (
• Canonical SMILES: C(=O)N
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is moderately irritating to the eyes and skin. The substance may cause effects on the central nervous system.
• Effects of Long Term Exposure: May cause toxicity to human reproduction or development.
• Uses: It can be used as the raw material for synthesizing imidazole, pyrimidine, 1, 3, 5-triazine, caffeine as well as the solvents for making spinning of acrylonitrile copolymer and plastic anti-static coating, etc. Formamide has active reactive and special dissolving capability. It can be used as the raw material for organic synthesis, paper processing agents, softening agent of fiber industry and animal glue as well as being used as the analytical reagent for measuring the amino acid content of rice. In the field of organic synthesis, it has most application in medicine as well as a lot of applications in other fields such as pesticides, dyes, pigments, fragrances and additives. It is also a kind of excellent organic solvent and is mainly applied to the spinning of acrylonitrile copolymers and ion exchange resins and plastics antistatic coating or conductive coating. In addition, it can also be used for separating chlorosilane and purifying grease. Formamide can have various kinds of reactions, in addition to have its three hydrogen atoms participate in the reaction, can also be subject to dehydration, CO removal, the introduction of an amino group, an acyl group and cyclization reaction. Take cyclization as an example, diethyl malonate can have cyclization reaction with formamide to generate the intermediate of vitamin B4, the 4, 6-dihydroxypyrimidine. O-aminobenzoic acid can have cyclization reaction with formamide to generate the quinazolinone-4 which is the intermediate for the synthesis of antiarrhythmic drug phenantrolihne. 3--amino-4-ethoxycarbonyl-pyrazole can have cyclization reaction with formamide to generate the inhibitor of the xanthine oxidase, allopurinol. EDTA can have cyclization reaction with formamide to give anti-cancer drugs ethylenediamine. Methyl ethyl methoxymalonate can have cyclization reaction with formamide to generate the intermediate of sulfonamide drug, 5-methoxy-4, 6-dihydroxy pyrimidine disodium. It can be used as analytical reagents, solvents and softening agents as well as being used in organic synthesis. It can be applied to medicine and pesticide industry. Formamide destabilizes nucleic acid duplexes and may be used, typically, at a concentration of 50%, in hybridization protocols requiring lower hybridization temperatures. As ionizing solvent, manufacture of formic esters, hydrocyanic acid by catalytic dehydration, as softener for paper, animal glues, water-sol gums. Formamide is a good solvent for proteins and salts owing to its high dielectric constant. Its main applications are as a solvent in the chemical industry, as a softener for paper, as an intermediate for the manufacturing of formic acid and esters and hydrocyanic acid, and as a reaction medium.
• Production method: 1. One-Step method: the first step is through the reaction of carbon monoxide and methanol for generating methyl formate in the presence of sodium methoxide. The second step: the methyl formate is further subject to aminolysis for generation of formamide with the reaction conditions being 80-100 ℃ and 0.2-0.6 MPa. This method has relative problems. 2. The method of formic acid; the formic acid first has esterification reaction with methanol to generate methyl formate which undergoes aminolysis to generate formamide with the separation of methanol and impurities through distillation to obtain the final product. Owing to its high cost, this method has been gradually eliminated. 3. One Step method: this is via the reaction of carbon monoxide and ammonia for the direct synthesis of formamide in high pressure (10-30 MPa) and a temperature of 80-100 ℃ with the sodium methylate as the catalyst. 4. The formic acid and urea method. 5. The new method has sodium and ammonium salts for reaction to generate formamide at a certain temperature and pressure. This method has already applied domestic invention patent.

Technology Process of Formamide

There total 2 articles about Formamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0) → formic acid (64-18-6) + 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) + 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone (2455-14-3,74978-25-9) + formamidic acid (75-12-7) + 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenylimino)-2,5-cyclohexadien-1-one (4610-03-1) + 4--2,6-di-tert-butyl-2,5-cyclohexadien-1-one

Guidance literature:

With ammonium hydroxide; oxygen; In ethanol; at 45 ℃; for 3h; Product distribution; Mechanism; Rate constant; other bases; var. temp.;

Reference yield:

formamide (77287-34-4,77287-35-5,60100-09-6) → formamidic acid (75-12-7)

Guidance literature:

In various solvent(s); at -263.16 ℃; Irradiation;

DOI:10.1002/(SICI)1099-0690(200003)2000:6<1061::AID-EJOC1061>3.0.CO;2-5

upstream raw materials:

3,5-di-t-butyl-4-hydroxybenzaldehyde

formamide

Refernces

• 1、 Leineko, I. P.,Fedulina, T. G.,Pranovich, A. V.. "INFLUENCE OF THE NATURE OF THE BASE ON THE OXIDATION OF 3,5-DI-tert-BUTYL-4-HYDROXYBENZALDEHYDE". . p. 113 - 117. Retrieved 2007/10/02.