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Acetoguanamine

Summary

Acetoguanamine is an organic compound with the chemical formula (CNH2)2CCH3N3. It is related to melamine but with one amino group replaced by methyl. Acetoguanamine is used in the manufacturing of melamine resins. Unlike melamine ((CNH2)3N3), acetoguanamine is not a crosslinker. The "aceto" prefix is historical, the compound does not contain an acetyl group. A related compound is benzoguanamine.[2]

Acetoguanamine
Kekulé, skeletal formula of acetoguanamine
Ball-and-stick model of the acetoguanamine molecule
Names
Preferred IUPAC name
6-Methyl-1,3,5-triazine-2,4-diamine[1]
Other names
Diamino-6-methyl-1,3,5-triazine[citation needed]
Identifiers
  • 542-02-9 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
118348
ChEBI
  • CHEBI:72475 ☒N
ChemSpider
  • 10485 checkY
ECHA InfoCard 100.007.998 Edit this at Wikidata
EC Number
  • 208-796-3
  • 10949
UNII
  • AX41T8ULB3 checkY
  • DTXSID5029186 Edit this at Wikidata
  • InChI=1S/C4H7N5/c1-2-7-3(5)9-4(6)8-2/h1H3,(H4,5,6,7,8,9) checkY
    Key: NJYZCEFQAIUHSD-UHFFFAOYSA-N checkY
  • InChI=1/C4H7N5/c1-2-7-3(5)9-4(6)8-2/h1H3,(H4,5,6,7,8,9)
    Key: NJYZCEFQAIUHSD-UHFFFAOYAD
  • Cc1nc(N)nc(N)n1
  • CC1=NC(N)=NC(N)=N1
Properties
C4H7N5
Molar mass 125.135 g·mol−1
Appearance White, opaque crystals
Density 1.391 g cm−3
Melting point 274 to 276 °C (525 to 529 °F; 547 to 549 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 252 °C (486 °F; 525 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

The compound is prepared by condensation of cyanoguanidine with acetonitrile:

(H2N)2C=NCN + MeCN → (CNH2)2(CMe)N3

Safety edit

LD50 (oral, rats) is 2740 mg/kg.

References edit

  1. ^ "Acetoguanamine - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology information.
  2. ^ H. Deim; G. Matthias; R. A. Wagner (2012). "Amino Resins". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_115.pub2. ISBN 978-3527306732.