acetoguanamine
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477239060
| ImageFile = Acetoguanamine.png
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 150
| ImageAlt = Kekulé, skeletal formula of acetoguanamine
| ImageFile1 = Acetoguanamine-3D-balls.png
| ImageSize1 = 160
| ImageAlt1 = Ball-and-stick model of the acetoguanamine molecule
| PIN = 6-Methyl-1,3,5-triazine-2,4-diamine{{Cite web|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10949|title = Acetoguanamine - PubChem Public Chemical Database|work = The PubChem Project|location = USA|publisher = National Center for Biotechnology information}}
| OtherNames = Diamino-6-methyl-1,3,5-triazine{{Citation needed|date = June 2011}}
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 542-02-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = AX41T8ULB3
| PubChem = 10949
| ChemSpiderID = 10485
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 208-796-3
| Beilstein = 118348
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 72475
| SMILES = Cc1nc(N)nc(N)n1
| SMILES1 = CC1=NC(N)=NC(N)=N1
| StdInChI = 1S/C4H7N5/c1-2-7-3(5)9-4(6)8-2/h1H3,(H4,5,6,7,8,9)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/C4H7N5/c1-2-7-3(5)9-4(6)8-2/h1H3,(H4,5,6,7,8,9)
| StdInChIKey = NJYZCEFQAIUHSD-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = NJYZCEFQAIUHSD-UHFFFAOYAD
}}
|Section2={{Chembox Properties
| C=4|N=5|H=7
| Appearance = White, opaque crystals
| Density = 1.391 g cm−3
| MeltingPtC = 274 to 276
}}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS exclamation mark}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|305+351+338}}
| NFPA-F = 1
| NFPA-H = 1
| NFPA-R = 0
| FlashPtC = 252
}}
}}
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.{{cite encyclopedia|author1=H. Deim |author2=G. Matthias |author3=R. A. Wagner|title=Amino Resins|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2012|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a02_115.pub2|isbn=978-3527306732 }}
The compound is prepared by condensation of cyanoguanidine with acetonitrile:
:(H2N)2C=NCN + MeCN → (CNH2)2(CMe)N3
Safety
LD50 (oral, rats) is 2740 mg/kg.