Acetoguanamine

Last updated
Acetoguanamine
Acetoguanamine.png
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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
3D model (JSmol)
118348
ChEBI
ChemSpider
ECHA InfoCard 100.007.998 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-796-3
PubChem CID
UNII
  • InChI=1S/C4H7N5/c1-2-7-3(5)9-4(6)8-2/h1H3,(H4,5,6,7,8,9) Yes check.svgY
    Key: NJYZCEFQAIUHSD-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceWhite, 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:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P305+P351+P338
NFPA 704 (fire diamond)
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).
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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]

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.

Related Research Articles

Combinatorial chemistry comprises chemical synthetic methods that make it possible to prepare a large number of compounds in a single process. These compound libraries can be made as mixtures, sets of individual compounds or chemical structures generated by computer software. Combinatorial chemistry can be used for the synthesis of small molecules and for peptides.

Melamine Chemical compound

Melamine is an organic compound with the formula C3H6N6. This white solid is a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 67% nitrogen by mass, and its derivatives have fire retardant properties due to its release of nitrogen gas when burned or charred. Melamine can be combined with formaldehyde and other agents to produce melamine resins. Such resins are characteristically durable thermosetting plastic used in high pressure decorative laminates such as Formica, melamine dinnerware, laminate flooring, and dry erase boards. Melamine foam is used as insulation, soundproofing material and in polymeric cleaning products, such as Magic Eraser.

Peptide synthesis Production of peptides

In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl group of one amino acid to the amino group of another. Protecting group strategies are usually necessary to prevent undesirable side reactions with the various amino acid side chains. Chemical peptide synthesis most commonly starts at the carboxyl end of the peptide (C-terminus), and proceeds toward the amino-terminus (N-terminus). Protein biosynthesis in living organisms occurs in the opposite direction.

In chemistry, solid-phase synthesis is a method in which molecules are covalently bound on a solid support material and synthesised step-by-step in a single reaction vessel utilising selective protecting group chemistry. Benefits compared with normal synthesis in a liquid state include:

Cyanuric acid 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 million kilograms.

Triazine Aromatic, heterocyclic compound

Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is C3H3N3. They exist in three isomeric forms, 1,3,5-triazines being common.

Melon (chemistry)

In chemistry, melon is a compound of carbon, nitrogen, and hydrogen of still somewhat uncertain composition, consisting mostly of heptazine units linked and closed by amine groups and bridges. It is a pale yellow solid, insoluble in most solvents.

Acetaldehyde ammonia trimer Chemical compound

Acetaldehyde ammonia trimer is a chemical compound described by the formula (CH3CHNH)3. The pure material is colourless but samples often appear light yellow or slightly beige due to the degradation by oxidation. It is hygroscopic, and can be found in a trihydrate form.

1,3,5-Triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazines. S-triazine—the "symmetric" isomer—and its derivatives are useful in a variety of applications.

Tyrocidine Chemical compound

Tyrocidine is a mixture of cyclic decapeptides produced by the bacteria Bacillus brevis found in soil. It can be composed of 4 different amino acid sequences, giving tyrocidine A–D. Tyrocidine is the major constituent of tyrothricin, which also contains gramicidin. Tyrocidine was the first commercially available antibiotic, but has been found to be toxic toward human blood and reproductive cells. The function of tyrocidine within its host B. brevis is thought to be regulation of sporulation.

2-Methyl-2-nitrosopropane (MNP or t-nitrosobutane) is the organic compound with the formula (CH3)3CNO. It is a blue liquid that is used in chemical research as a spin trap, i.e. it binds to radicals.

Melamine resin Hard, thermosetting plastic material often used in dinnerware

Melamine resin or melamine formaldehyde is a resin with melamine rings terminated with multiple hydroxyl groups derived from formaldehyde. This thermosetting plastic material is made from melamine and formaldehyde. In its butylated form, it is dissolved in n-butanol and xylene. It is then used to cross-link with alkyd, epoxy, acrylic, and polyester resins, used in surface coatings. There are many types, varying from very slow to very fast curing.

In China, the adulteration and contamination of several food and feed ingredients with inexpensive melamine and other compounds, such as cyanuric acid, ammeline and ammelide, are common practice. These adulterants can be used to inflate the apparent protein content of products, so that inexpensive ingredients can pass for more expensive, concentrated proteins. Melamine by itself has not been thought to be very toxic to animals or humans except possibly in very high concentrations, but the combination of melamine and cyanuric acid has been implicated in kidney failure. Reports that cyanuric acid may be an independently and potentially widely used adulterant in China have heightened concerns for both animal and human health.

2-Cyanoguanidine is a 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 nonpolar organic solvents.

Melem Chemical compound

In chemistry, melem is a compound with formula C
6
N
10
H
6
; specifically, 2,5,8-triamino-heptazine or 2,5,8-triamino-tri-s-triazine, whose molecule can be described as that of heptazine with the three hydrogen atoms replaced by amino groups. It is a white crystalline solid.

ACPD Chemical compound

1-Amino-1,3-dicarboxycyclopentane (ACPD) is a chemical compound that binds to the metabotropic glutamate receptor (mGluR), acting as a mGluR agonist. ACPD is a rigid analogue of the neurotransmitter glutamate and does not activate ionotropic glutamate receptors. However, it has been reported to be an agonist of the glycine site of the NMDA receptor. ACPD can induce convulsions in neonatal rats.

Benzoxazine

Benzoxazines are a group of isomeric bicyclic heterocyclic chemical compounds that consist of a benzene ring fused to an oxazine ring. The different isomers depend on the relative positions of the oxygen and nitrogen atoms in the oxazine ring, on the location of ring fusion, and on the position of the double bond in the oxazine ring. They have the molecular formula C8H7NO.

Benzoguanamine Chemical compound

Benzoguanamine is an organic compound with the chemical formula (CNH2)2(CC6H5)N3. It is related to melamine but with one amino group replaced by phenyl. Benzoguanamine is used in the manufacturing of melamine resins. Unlike melamine ((CNH2)3N3), benzoguanamine is not a crosslinker. The "benzo" prefix is historical, as the compound contains phenyl, not a benzo group. A related compound is acetoguanamine.

Guanamine Organic compound with the formula (H₂NC)₂N₃CR; heterocycles of the triazine class

In organic chemistry, a guanamine is an organic compound with the formula (H2NC)2N3CR. They are heterocycles of the triazine class. Guanamines are closely related to melamine ((H2NC)3N3), except with one amino substituent replaced by an organic group. With two amines, guanamines are bifunctional, whereas melamine is trifunctional. This difference is exploited in the use of guanamines to modify the crosslink density in melamine resins. They are white or colorless solids of low toxicity.

Dimethylol propionic acid Organic compound with one carboxyl and two hydroxyl groups

Dimethylol propionic acid -DMPA is a chemical compound that has the full IUPAC name of 2,2-bis(hydroxymethyl)propionic acid and is an organic compound with one carboxyl and two hydroxy groups. It has the CAS Registry Number of 4767-03-7.

References

  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.