PRODUCTS

FORMAMIDE

Formamide is an amide derived from formic acid.
Formamide is a colorless liquid which is miscible with water and has an ammonia-like odor.
Formamide is chemical feedstock for the manufacture of sulfa drugs and other pharmaceuticals, herbicides and pesticides, and in the manufacture of hydrocyanic acid.
Formamide has been used as a softener for paper and fiber.
Formamide is a solvent for many ionic compounds.
Formamide has also been used as a solvent for resins and plasticizers.
Some astrobiologists suggest that Formamide may be an alternative to water as the main solvent in other forms of life.

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

CAS: 75-12-7
European Community (EC) Number: 200-842-0

IUPAC Name: formamide

Molecular Formula: CH3NO
HCONH2
Molecular Weight: 45.041 g/mol

Formamide is the simplest monocarboxylic acid amide, obtained by formal condensation of formic acid with ammonia.
The parent of the class of formaldehydes.
Formamide has a role as a solvent.
Formamide is a monocarboxylic acid amide, a one-carbon compound and a member of formamides.
Formamide is functionally related to a formic acid.
Formamide is a tautomer of a formimidic acid.

Formamide, the simplest carboxylic acid amide, is a viscous, odorless, colorless liquid with a melting point of 2 ºC and a boiling point of 210 ºC.
When it is heated to 180 ºC at atmospheric pressure, however, Formamide begins to decompose into carbon dioxide and ammonia.

In 1920, K H. Meyer and L. Orthmer discovered that formamide can be produced by heating CO2 and NH3 under pressure—the reverse of the decomposition reaction.
Today, some formamide is still made this way, but the more common process uses the reaction of methyl formate with NH3.
Byproduct methanol is treated with carbon monoxide to produce additional methyl formate.

Formamide is used as a feedstock in the manufacture of formate esters, as an ionizing solvent, as an RNA stabilizer in gel electrophoresis, and in tissue preservation. More intriguingly, Formamide may be a key compound in the origin of life on Earth.

In 2014, chemist S. Civiš and co-workers at the Central European Institute of Technology (Brno, Czech Republic) simulated asteroid and meteor collisions by bombarding formamide and clay with a powerful laser.
They produced (among many other compounds) guanine, adenine, cytosine, and uracil—the four nitrogen bases that make up DNA.
Formamide is found in great quantities throughout the observable universe, giving credibility to the idea that life on Earth could have originated outside the planet.

Formamide is an amide and it is manufactured from methyl formate and ammonia.
Formamide is a clear liquid, miscible with water, ethanol and acetone and has a slight ammoniacal odor.
In the environment Formamide decomposes into ammonia, carbon dioxide and water.

Formamide is a chemical reactant or solvent in various chemical processes.
Formamide is mostly used as a reactant in the manufacture of agrochemicals (e.g. imidazoles), pharmaceuticals (e.g. allopurinol), and industrial chemicals (e.g. n-vinylformamide) and as a solvent in polymers and resins.

Formamide (HCONH2), a formic acid amide, is appreciated for its versatile properties as an intermediate for the production of 1,2,4-triazoles in the agrochemical and pharmaceutical industries and for the production of vitamins and pyrimidines.
Formamide also serves as an intermediate in paper finishing and as a solvent.

Formamide is a colorless, slightly viscous, hygroscopic liquid that is characterized by its high dielectric constant.

Formamide is the simplest monocarboxylic acid amide and is a clear liquid derived from formic acid.
Formamide has applications in drug, hydrocyanic acid, pesticide, and herbicide manufacturing and is used as a solvent for resins, plasticizers, and ionic compounds.

Formamide, also referred to as methanamide, is an organic compound denoted by the chemical formula CH3NO.
Formamide is a clear, hygroscopic liquid that easily mixes with water and most polar organic solvents.
Formamide serves as an essential solvent for catalytic hydrogenation reactions and acts as a reagent in the creation of diverse organometallic compounds.
Moreover, formamide finds utility in synthesizing peptides, nucleotides, and various other organic compounds.

Experimental Properties

Physical Description: Formamide appears as a colorless liquid with a faint odor of ammonia.
Denser than water.
Freezing point 36 °F.
Color / Form: Slightly viscous, colorless liquid
Odor: Faint ammonia odor
Boiling Point: 410 °F at 760 mmHg (decomposes)
Melting Point: 36.5 °F
Flash Point: 310 °F
Solubility: greater than or equal to 100 mg/mL at 66 °F
Density: 1.1334 at 68 °F
Vapor Density: 1.56
Vapor Pressure: 3 mmHg at 86 °F
Autoignition Temperature: 310 °F
Viscosity: at 20 °C= 4320; at 30 °C= 2926
Heat of Combustion: -568.2 kJ/mole
Heat of Vaporization: 64.98 kJ/mole
pH: 7.1 (0.5 molar aqueous soln)
Surface Tension: 58.35 dyne/cm at 20 °C
Ionization Potential: 10.20 eV

Production
Historical production
In the past, formamide was produced by treating formic acid with ammonia, which produces ammonium formate, which in turn yields formamide upon heating:

HCOOH + NH3 → HCOO−NH+4
HCOO−NH+4 → HCONH2 + H2O
Formamide is also generated by aminolysis of ethyl formate:

HCOOCH2CH3 + NH3 → HCONH2 + CH3CH2OH

Modern production
The current industrial process for the manufacture of formamide involves the carbonylation of ammonia:

CO + NH3 → HCONH2
An alternative two-stage process involves the ammonolysis of methyl formate, which is formed from carbon monoxide and methanol:

CO + CH3OH → HCOOCH3
HCO2CH3 + NH3 → HCONH2 + CH3OH

Applications
Formamide is used in the industrial production of hydrogen cyanide.
Formamide is also used as a solvent for processing various polymers such as polyacrylonitrile.

Reactions
Formamide decomposes into carbon monoxide and ammonia at 180 °C.

HCONH2 → CO + NH3
Traces of hydrogen cyanide (HCN) and water are also observed.

In the presence of solid acid catalysts, formamide dehydrates to HCN:

HC(O)NH2 → HCN + H2O

Niche or laboratory applications
Formamide is 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.

Formamide is used to prepare primary amines directly from ketones via their N-formyl derivatives, using the Leuckart reaction.

Biochemistry

Formamides are intermediates in the methanogenesis cycle.

Prebiotic chemistry

Main article: Hypothetical types of biochemistry
Formamide has been proposed as an alternative solvent to water, perhaps with the ability to support life with alternative biochemistries to that currently found on Earth. Formamide forms by the hydrolysis of hydrogen cyanide.
With a large dipole moment, its solvation properties are similar to those of water.

Formamide has been shown to convert to traces of guanine upon heating in the presence of ultraviolet light.

SYNONYMS:

formamide
75-12-7
Methanamide
carbamaldehyde
Formimidic acid
Formic acid, amide
formamid
Methanoic acid, amide
Methanimidic acid
Amid kyseliny mravenci
NSC 748
HSDB 88
Methanamid
CCRIS 6240
Amid kyseliny mravenci [Czech]
DTXSID8025337
Formic amide
Ameisensaeureamid
AI3-15357
Methanamide;Formimidic acid
EINECS 200-842-0
Amide C1
Formamide (deionizde)
UNII-4781T907ZS
CHEBI:16397
NSC-748
HCONH2
MFCD00007941
4781T907ZS
FORMAMIDE-1-D1
DTXCID805337
Formamide-13C-15N (9CI)
EC 200-842-0
60100-09-6
FORMAMIDE (USP-RS)
FORMAMIDE [USP-RS]
CAS-75-12-7
Formamide, puriss. p.a., ACS reagent, >=99.5% (GC/T)
imidoformic acid
N-formyl amine
amino-formaldehyde
primary carboxamide
Imino-methylalkohol
Formamide,Deionized
primary carboxamides
MB8
Formamide, ACS reagent
NH2CHO
FORMAMIDE [MI]
FORMAMIDE [HSDB]
WLN: ZVH
bmse000267
Formamide, >=99.0%
Formamide, >=99.5%
Formamide, p.a., 99.5%
CHEMBL266160
GTPL4739
NSC748
Formamide, reagent grade, 98%
CHEBI:48431
HY-Y0842B
AMY3583
CHEBI:140324
Formamide, Spectrophotometric Grade
HY-Y0842
Tox21_201942
Tox21_302824
Formamide, ACS reagent, >=99.5%
Formamide, BioXtra, >=99% (GC)
AKOS009031608
Residual Solvent Class 2 - Formamide
Formamide, SAJ first grade, >=98.5%
NCGC00091516-01
NCGC00091516-02
NCGC00256321-01
NCGC00259491-01
Formamide, p.a., ACS reagent, 99.5%
Formamide, JIS special grade, >=98.5%
Formamide, Vetec(TM) reagent grade, 98%
CS-0015817
CS-0898265
F0045
Formamide, spectrophotometric grade, >=99%
FT-0631311
FT-0637321
NS00008593
EN300-19895
Formamide, ReagentPlus(R), >=99.0% (GC)
C00488
InChI=1/CH3NO/c2-1-3/h1H,(H2,2,3
A838330
Q283917
J-521386
Q27110288
F0001-1892
Formamide, BioUltra, for molecular biology, >=99.5% (T)
Formamide, for molecular biology, >=99.5% (GC), liquid
Formamide, >=99.5% (GC), BioReagent, for molecular biology
Formamide; Carbamaldehyde; Formimidic acid; Methanamide; NSC 748