Semicarbazide

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Semicarbazide
Semicarbazide.png
Semicarbazide 3D ball.png
Names
IUPAC name
Aminourea [1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.308 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/CH5N3O/c2-1(5)4-3/h3H2,(H3,2,4,5) Yes check.svgY
    Key: DUIOPKIIICUYRZ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/CH5N3O/c2-1(5)4-3/h3H2,(H3,2,4,5)
    Key: DUIOPKIIICUYRZ-UHFFFAOYAJ
  • C(=O)(N)NN
Properties
H2NNHC(=O)NH2
Molar mass 75.08 g/mol
Melting point 96 °C
Hazards
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg
Danger
H301, H315, H319, H335
P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P330, P332+P313, P337+P313, P362, P403+P233, P405
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Semicarbazide is the chemical compound with the formula OC(NH2)(N2H3). It is a water-soluble white solid. It is a derivative of urea.

Contents

Synthesis

The compound prepared by treating urea with hydrazine: [2]

OC(NH2)2 + N2H4 → OC(NH2)(N2H3) + NH3

A further reaction can occur to give carbohydrazide:

OC(NH2)(N2H3) + N2H4 → OC(N2H3)2 + NH3

Derivatives

Semicarbazide is frequently reacted with aldehydes and ketones to produce semicarbazones via a condensation reaction. This is an example of imine formation resulting from the reaction of a primary amine with a carbonyl group. The reaction is useful because semicarbazones, like oximes and 2,4-DNPs, typically have high melting points and crystallize, facilitating purification or identification of reaction products. [3]

Properties

Semicarbazide products (semicarbazones and thiosemicarbazones) are known to have an activity of antiviral, antiinfective and antineoplastic through binding to copper or iron in cells.

Uses, occurrence, detection

Semicarbazide is used in preparing pharmaceuticals including nitrofuran antibacterials (furazolidone, nitrofurazone, nitrofurantoin) and related compounds. It is also a product of degradations of the blowing agent azodicarbonamide (ADC). Semicarbazide forms in heat-treated flour containing ADC as well as breads made from ADC-treated flour. [4] [5]

Semicarbazide is used as a detection reagent in thin layer chromatography (TLC). Semicarbazide stains α-keto acids on the TLC plate, which can then be viewed under ultraviolet light.

See also

Related Research Articles

Urea, also called carbamide, is an organic compound with chemical formula CO(NH2)2. This amide has two amino groups joined by a carbonyl functional group. It is thus the simplest amide of carbamic acid.

<span class="mw-page-title-main">Hydrazine</span> Colorless flammable liquid with an ammonia-like odor

Hydrazine is an inorganic compound with the chemical formula N2H4. It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly toxic unless handled in solution as, for example, hydrazine hydrate.

The peroxide process is a method for the industrial production of hydrazine.

Hydantoin, or glycolylurea, is a heterocyclic organic compound with the formula CH2C(O)NHC(O)NH. It is a colorless solid that arises from the reaction of glycolic acid and urea. It is an oxidized derivative of imidazolidine. In a more general sense, hydantoins can refer to groups or a class of compounds with the same ring structure as the parent compound. For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule.

<span class="mw-page-title-main">Thiourea</span> Organosulfur compound (S=C(NH2)2)

Thiourea is an organosulfur compound with the formula SC(NH2)2 and the structure H2N−C(=S)−NH2. It is structurally similar to urea, except that the oxygen atom is replaced by a sulfur atom ; however, the properties of urea and thiourea differ significantly.

<span class="mw-page-title-main">Cyanuric acid</span> Chemical compound belonging to the class of triazine

Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a component of bleaches, disinfectants, and herbicides. In 1997, worldwide production was 160 000 tonnes.

<span class="mw-page-title-main">Sulfamic acid</span> Chemical compound

Sulfamic acid, also known as amidosulfonic acid, amidosulfuric acid, aminosulfonic acid, sulphamic acid and sulfamidic acid, is a molecular compound with the formula H3NSO3. This colourless, water-soluble compound finds many applications. Sulfamic acid melts at 205 °C before decomposing at higher temperatures to water, sulfur trioxide, sulfur dioxide and nitrogen.

Potassium cyanate is an inorganic compound with the formula KOCN. It is a colourless solid. It is used to prepare many other compounds including useful herbicide. Worldwide production of the potassium and sodium salts was 20,000 tons in 2006.

<span class="mw-page-title-main">Azodicarbonamide</span> Chemical compound

Azodicarbonamide, ADCA, ADA, or azo(bis)formamide, is a chemical compound with the molecular formula C2H4O2N4. It is a yellow to orange-red, odorless, crystalline powder. It is sometimes called a 'yoga mat' chemical because of its widespread use in foamed plastics. It was first described by John Bryden in 1959.

<span class="mw-page-title-main">Azine</span> Chemical compound

Azines are a functional class of organic compounds with the connectivity RR'C=N-N=CRR'. These compounds are the product of the condensation of hydrazine with ketones and aldehydes, although in practice they are often made by alternative routes. Ketazines are azines derived from ketones. For example, acetone azine is the simplest ketazine. Aldazines are azines derived from aldehydes.

Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula H2NCOOH. It can be obtained by the reaction of ammonia NH3 and carbon dioxide CO2 at very low temperatures, which also yields ammonium carbamate [NH4]+[NH2CO2]. The compound is stable only up to about 250 K (−23 °C); at higher temperatures it decomposes into those two gases. The solid apparently consists of dimers, with the two molecules connected by hydrogen bonds between the two carboxyl groups –COOH.

<span class="mw-page-title-main">Carbohydrazide</span> Chemical compound

Carbohydrazide is the chemical compound with the formula OC(N2H3)2. It is a white, water-soluble solid. It decomposes upon melting. A number of carbazides are known where one or more N-H groups are replaced by other substituents. They occur widely in the drugs, herbicides, plant growth regulators, and dyestuffs.

In chemistry, the amino radical, ·NH2, also known as the aminyl radical or azanyl radical, is the neutral form of the amide ion. Aminyl radicals are highly reactive and consequently short-lived, like most radicals; however, they form an important part of nitrogen chemistry. In sufficiently high concentration, amino radicals dimerise to form hydrazine. While NH2 as a functional group is common in nature, forming a part of many compounds, the radical cannot be isolated in its free form.

<span class="mw-page-title-main">Biurea</span> Chemical compound

Biurea is a chemical compound with the molecular formula C2H6N4O2. It is produced in food products containing azodicarbonamide, a common ingredient in bread flour, when they are cooked. Upon exposure, biurea is rapidly eliminated from the body through excretion.

Transamidation is a chemical reaction in which an amide reacts with an amine to generate a new amide:

<span class="mw-page-title-main">Pentaamine(dinitrogen)ruthenium(II) chloride</span> Chemical compound

Pentaamine(nitrogen)ruthenium(II) chloride is an inorganic compound with the formula [Ru(NH3)5(N2)]Cl2. It is a nearly white solid, but its solutions are yellow. The cationic complex is of historic significance as the first compound with N2 bound to a metal center. [Ru(NH3)5(N2)]2+ adopts an octahedral structure with C4v symmetry.

<span class="mw-page-title-main">Ammonium carbamate</span> Chemical compound

Ammonium carbamate is a chemical compound with the formula [NH4][H2NCO2] consisting of ammonium cation NH+4 and carbamate anion NH2COO. It is a white solid that is extremely soluble in water, less so in alcohol. Ammonium carbamate can be formed by the reaction of ammonia NH3 with carbon dioxide CO2, and will slowly decompose to those gases at ordinary temperatures and pressures. It is an intermediate in the industrial synthesis of urea (NH2)2CO, an important fertilizer.

<span class="mw-page-title-main">4-Amino-3-hydrazino-5-mercapto-1,2,4-triazole</span> Chemical compound

4-Amino-3-hydrazino-5-mercapto-1,2,4-triazole is an organic compound with the formula SC2N3H(NH2)(N2H3). The compound consists of a 1,2,4-triazole heterocycle with three functional groups: amine, thioamide and hydrazyl. X-ray crystallography shows that this molecule is polar but with a C=S double bond. It is prepared by the reaction of hydrazine with thiourea:

<span class="mw-page-title-main">Chromium(III) perchlorate</span> Chemical compound

Chromium(III) perchlorate is an inorganic compound with the chemical formula Cr(ClO4)3. It's hexahydrate Cr(ClO4)3·6H2O is a cyan solid that dissolves in water.

Neodymium(III) iodide is an inorganic salt of iodine and neodymium with the formula NdI3. Neodymium uses the +3 oxidation state in the compound. The anhydrous compound is a green powdery solid at room temperature.

References

  1. CID 5196 from PubChem
  2. Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi : 10.1002/14356007.a13_177.
  3. John McMurry (1984). Organic Chemistry. Brooks/Cole. p. 676.
  4. Becalski, Adam; Lau, Benjamin; Lewis, David; Seaman, Stephen (2004). "Semicarbazide Formation in Azodicarbonamide-Treated Flour: A Model Study". J. Agric. Food Chem. 52 (18): 5730–4. doi:10.1021/jf0495385. PMID   15373416.
  5. Maria Beatriz de la Calle; Elke Anklam (2005). "Semicarbazide: occurrence in food products and state-of-the-art in analytical methods used for its determination". Anal. Bioanal. Chem. 382 (4): 968–977. doi:10.1007/s00216-005-3243-z. PMID   15947918. S2CID   10765283.