2-Cyanoguanidine

2-Cyanoguanidine
2-Cyanoguanidine
Identifiers
CAS number 461-58-5 YesY
PubChem 10005
ChemSpider 9611 YesY
EC number 207-312-8
RTECS number ME9950000
Jmol-3D images Image 1
Properties
Molecular formula C2H4N4
Molar mass 84.08 g/mol
Appearance White crystals
Density 1.400 g/cm3
Melting point

209.5 °C

Boiling point

252 °C

Solubility in water 41.3 g/l
log P -0.52
kH 2.25·10-10 atm.m³/mol
Hazards
R-phrases R20/21/22
S-phrases S24/25
Main hazards harmful (Xn)
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2-Cyanoguanidine or commonly dicyandiamide is an nitrile derived from guanidine. It is a dimer of cyanamide, from which it can be prepared. 2-Cyanoguanidine is a colourless solid that is soluble in water, acetone, and alcohol, but not in diethyl ether or chloroform.[1]

Contents

Production and use

2-Cyanoguanidine is produced by treating cyanamide with base. It is produced in soil by decomposition of cyanamide. A variety of useful compounds are produced from 2-cyanoguanidine, guanidines and melamine. It is also used as a slow fertilizer. Formerly, it was as a fuel in some explosives. It is used in the adhesive industry as a curing agent for epoxies.

Tautomers and salts

It is possible to draw a tautomer of 2-cyanoguanidine with the structure NC-NH-C(NH)NH2. Further tautomerization gives NC-NH-C(N-)NH3+. Formal loss of neutral ammonia (NH3) from this latter tautomer followed by deprotonation gives the anion commonly referred to the dicyanamide ion, (NC)2N-. The dicyanamide ion has been used extensively as a counterion in the chemistry of organic and inorganic salts, for example in the synthesis of what was, in 1990, a superconductor with novel properties[2] where we can see the anion depicted as N(CN)2-.

References

  1. ^ Thomas Güuthner; Bernd Mertschenk (2006). "Cyanamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_139.pub2. 
  2. ^ A new ambient-pressure organic superconductor, κ-(ET)2Cu[N(CN)2]Br, with the highest transition temperature yet observed (inductive onset Tc= 11.6 K, …, AM Kini, U Geiser, HH Wang, KD Carlson…, Inorganic Chemistry 1990, 29, 2555-2557.

External links


Wikimedia Foundation. 2010.

Игры ⚽ Нужно решить контрольную?

Look at other dictionaries:

  • cyanoguanidine — diciandiamidas statusas T sritis chemija formulė H₂NC(=NH)NHC≡N atitikmenys: angl. cyanoguanidine; dicyanodiamide rus. дициандиамид; циангуанидин ryšiai: sinonimas – cianguanidinas …   Chemijos terminų aiškinamasis žodynas

  • cyanoguanidine — /suy euh noh gwah ni deen , din, suy an oh /, n. Chem. dicyandiamide. [CYANO 2 + GUANIDINE] * * * …   Universalium

  • cyanoguanidine — cy·a·no·guanidine …   English syllables

  • cyanoguanidine — |sīə(ˌ)nō+ noun Etymology: cyan + guanidine : dicyandiamide * * * /suy euh noh gwah ni deen , din, suy an oh /, n. Chem. dicyandiamide. [CYANO 2 + GUANIDINE] …   Useful english dictionary

  • Metformin — Chemical structure (top) and ball and stick model (bottom) of metformin System …   Wikipedia

  • DCD — is a three letter abbreviation with multiple meanings, including: Contents 1 Health and chemicals 2 Music and entertainment 3 Technology and design 4 Institutions …   Wikipedia

  • Cyanamide — Not to be confused with cyanimide. Cyanamide …   Wikipedia

  • List of organic compounds — This page aims to list well known organic compounds, including organometallic compounds, to stimulate the creation of Wikipedia articles. Note that purely inorganic compounds, minerals, and chemical elements are not included on this list. There… …   Wikipedia

  • Pinacidil — Chembox new ImageFile = Pinacidil.png ImageSize = IUPACName = 3 cyano 1 (4 pyridyl) 2 (1,2,2 trimethylpropyl)guanidine OtherNames = Section1 = Chembox Identifiers CASNo=85371 64 8 PubChem=4826 SMILES=CC(C(C)(C)C)N=C(NC#N)NC1=CC=NC=C1 Section2 =… …   Wikipedia

  • 461-58-5 — Dicyandiamide Dicyandiamide Général No CAS …   Wikipédia en Français

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”