Carbohydrazide

Last updated
Carbohydrazide
Carbohydrazide.png
OC(N2H3)2.png
Names
IUPAC name
1,3-Diaminourea
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.126 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-837-2
PubChem CID
UNII
  • InChI=1S/CH6N4O/c2-4-1(6)5-3/h2-3H2,(H2,4,5,6) Yes check.svgY
    Key: XEVRDFDBXJMZFG-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/CH6N4O/c2-4-1(6)5-3/h2-3H2,(H2,4,5,6)
    Key: XEVRDFDBXJMZFG-UHFFFAOYAS
  • O=C(NN)NN
Properties
CH6N4O
Molar mass 90.09 g/mol
Density 1.341 g/cm3
Melting point 153 to 154 °C (307 to 309 °F; 426 to 427 K)
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 ?)

Carbohydrazide is the chemical compound with the formula OC(N2H3)2. It is a white, water-soluble solid. [1] [2] It decomposes upon melting. [2] 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.

Contents

Production

Industrially the compound is produced by treatment of urea with hydrazine: [3]

OC(NH2)2 + 2 N2H4 → OC(N2H3)2 + 2 NH3

It can also be prepared by reactions of other C1-precursors with hydrazine, such as carbonate esters. [2] It can be prepared from phosgene, but this route cogenerates the hydrazinium salt [N2H5]Cl and results in some diformylation. Carbazic acid is also a suitable precursor:

N2NH3CO2H + N2H4 → OC(N2H3)2 + H2O

Structure

The molecule is nonplanar. All nitrogen centers are at least somewhat pyramidal, indicative of weaker C-N pi-bonding. The C-N and C-O distances are about 1.36 and 1.25 Å, respectively. [4]

Industrial uses

Hazards

Heating carbohydrazide may result in an explosion. Carbohydrazide is harmful if swallowed, irritating to eyes, respiratory system, and skin. Carbohydrazide is toxic to aquatic organisms. [10]

Related Research Articles

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Ammonium perchlorate ("AP") is an inorganic compound with the formula NH4ClO4. It is a colorless or white solid that is soluble in water. It is a powerful oxidizer. Combined with a fuel, it can be used as a rocket propellant called ammonium perchlorate composite propellant. Its instability has involved it in a number of accidents, such as the PEPCON disaster.

<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.

Unsymmetrical dimethylhydrazine (UDMH; 1,1-dimethylhydrazine, НДМГ or codenamed Geptil) is a chemical compound with the formula H2NN(CH3)2 that is used as a rocket propellant. It is a colorless liquid, with a sharp, fishy, ammonia-like smell typical for organic amines. Samples turn yellowish on exposure to air and absorb oxygen and carbon dioxide. It is miscible with water, ethanol, and kerosene. In concentration between 2.5% and 95% in air, its vapors are flammable. It is not sensitive to shock. Symmetrical dimethylhydrazine, 1,2-dimethylhydrazine is also known but is not as useful.

In chemistry, azide is a linear, polyatomic anion with the formula N−3 and structure N=N+=N. It is the conjugate base of hydrazoic acid HN3. Organic azides are organic compounds with the formula RN3, containing the azide functional group. The dominant application of azides is as a propellant in air bags.

<span class="mw-page-title-main">Hydrazoic acid</span> Unstable and toxic chemical compound

Hydrazoic acid, also known as hydrogen azide or azoimide, is a compound with the chemical formula HN3. It is a colorless, volatile, and explosive liquid at room temperature and pressure. It is a compound of nitrogen and hydrogen, and is therefore a pnictogen hydride. It was first isolated in 1890 by Theodor Curtius. The acid has few applications, but its conjugate base, the azide ion, is useful in specialized processes.

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

Guanidine nitrate is the chemical compound with the formula [C(NH2)3]NO3. It is a colorless, water-soluble salt. It is produced on a large scale and finds use as precursor for nitroguanidine, fuel in pyrotechnics and gas generators. Its correct name is guanidinium nitrate, but the colloquial term guanidine nitrate is widely used.

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

Sodium perchlorate is the inorganic compound with the chemical formula NaClO4. It is a white crystalline, hygroscopic solid that is highly soluble in water and in alcohol. It is usually encountered as the monohydrate. The compound is noteworthy as the most water-soluble of the common perchlorate salts.

<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.

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

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

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

Erythritol tetranitrate (ETN) is an explosive compound chemically similar to PETN, though it is thought to be slightly more sensitive to friction and impact.

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

Xylitol pentanitrate (XPN) is a nitrated ester primary explosive first synthesized in 1891 by Gabriel Bertrand. Law enforcement has taken an interest in XPN along with erythritol tetranitrate (ETN) and pentaerythritol tetranitrate (PETN) due to their ease of synthesis, which makes them accessible to amateur chemists and terrorists.

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

Ammonium dinitramide (ADN) is the ammonium salt of dinitraminic acid. ADN decomposes under heat to leave only nitrogen, oxygen, and water. The ions are the ammonium ion NH4+ and the dinitramide N(NO2)2.

<span class="mw-page-title-main">Pentazenium</span> Polytomic cation (N–N–N–N–N)

In chemistry, the pentazenium cation is a positively-charged polyatomic ion with the chemical formula N+5 and structure N−N−N−N−N. Together with solid nitrogen polymers and the azide anion, it is one of only three poly-nitrogen species obtained in bulk quantities.

<span class="mw-page-title-main">Karl O. Christe</span> German inorganic chemist

Karl Otto Christe is an inorganic chemist. He is the best reference in respectful handling of a huge number of extremely reactive components and his extensive experience in fluorine chemistry earned him the title of 'The Fluorine God'. His research covers fluorine chemistry of nitrogen and halogens and the synthesis of new energetic materials.

<span class="mw-page-title-main">Hydrazinium</span> Cation

Hydrazinium is the cation with the formula [N2H5]+. This cation has a methylamine-like structure. It can be derived from hydrazine by protonation. Hydrazinium is a weak acid with pKa = 8.1.

Azidotetrazolate (CN7) is an anion which forms a highly explosive series of salts. The ion is made by removing a proton from 5-azido-1H-tetrazole. The molecular structure contains a five-membered ring with four nitrogen atoms, and an azido side chain connected to the carbon atom. Several salts exist, but they are unstable and spontaneously explode. Rubidium azidotetrazolate was so unstable that it explodes while crystallizing. The potassium and caesium salt also spontaneously explode when dry.

Hydrazinium azide or hydrazine azide is a chemical compound with formula H
5
N
5
or [N
2
H+
5
]
[N
3
]
. It is a salt of the hydrazinium cation N
2
H+
5
and the azide anion N
3
. It can be seen as a derivative of hydrazine N
2
H
4
and hydrazoic acid HN
3
. It is an unstable solid.

<span class="mw-page-title-main">Nickel(II) perchlorate</span> Compound of nickel

Nickel(II) perchlorate is a inorganic compound with the chemical formula of Ni(ClO4)2, and it is a strong oxidizing agent. Its colours are different depending on water. For example, the hydrate forms cyan crystals, the pentahydrate forms green crystals, but the hexahydrate (Ni(ClO4)2·6H2O) forms blue crystals.

References

  1. Inorganic Syntheses Volume IV. McGraw-Hill Book Company, Inc. 1953. p. 35. ISBN   9780470132678.
  2. 1 2 3 4 5 6 Kurzer, Frederick; Michael Wilkinson (February 1970). "Chemistry of carbohydrazide and thiocarbohydrazide". Chemical Reviews. 70 (1): 111–149. doi:10.1021/cr60263a004. PMID   4391877.
  3. Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi : 10.1002/14356007.a13_177.
  4. Ottersen, T.; Hope, H. "The Structure and Electron Deformation Density Distribution of Carbonohydrazide (Carbohydrazide) at 85 K" Acta Crystallographica B 1979, volume 35, p373-p378. doi : 10.1107/S0567740879003575
  5. Buecker, Brad (1997). Power Plant Water Chemistry A Practical Guide. PennWell Publishing Company. pp. 13–16. ISBN   978-0-87814-619-2.
  6. "Patent US4269717" . Retrieved 8 October 2012.
  7. "Patent US2970899" . Retrieved 8 October 2012.
  8. Fischer, Niko; Klapötke, Thomas M.; Stierstorfer, Jörg (June 2011). "Explosives Based on Diaminourea". Propellants, Explosives, Pyrotechnics. 36 (3): 225–232. doi:10.1002/prep.201100001. S2CID   97871632.
  9. Joas, Manuel; Klapötke, Thomas M. (April 2015). "Laser Initiation of Tris(carbohydrazide)metal(II) Perchlorates and Bis(carbohydrazide)diperchloratocopper(II)". Propellants, Explosives, Pyrotechnics. 40 (2): 246–252. doi:10.1002/prep.201400142.
  10. "MSDS" . Retrieved 8 October 2012.