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Home> Encyclopedia >   /  Cyanide & Cyanate  /  Heterocyclic compounds  /  Amine  /  Organic Intermediate  /  Pharmaceutical Intermediates
Melamine structure
Melamine structure

Melamine

Iupac Name:1,3,5-triazine-2,4,6-triamine
CAS No.:108-78-1
Molecular Weight:126.11994
Introduction: Melamine-formaldehyde resin (MFR) is an activeingredient of strong (reinforced) plasters. Sensitizationwas reported in a plaster-room technician, who appliedresin-reinforced pIaster casts, and in dental technicians.MFR was contained in a strong dental pIasterused for mouldings. Used as a textile finish res in, it wasalso found to be an allergen in a women who replacedclothes in a store. MFR also releases formaldehyde,which may be the sensitizer.
1. Names and Identifiers
1.1 Name
Melamine
1.2 Synonyms

2,4,6-Triamino-1,3,5-triazine 2,4,6-Triamino-1,3,5-triazine Monomer

1.3 CAS No.
108-78-1
1.4 CID
7955
1.5 EINECS(EC#)
203-615-4
1.6 Molecular Formula
C3H6N6 (isomer)
1.7 Inchi
InChI=1S/C3H6N6/c4-1-7-2(5)9-3(6)8-1/h(H6,4,5,6,7,8,9)
1.8 InChkey
JDSHMPZPIAZGSV-UHFFFAOYSA-N
1.9 Canonical Smiles
C1(=NC(=NC(=N1)N)N)N
1.10 Isomers Smiles
C1(=NC(=NC(=N1)N)N)N
2. Properties
3.1 Density
1.573
3.2 Melting Point
354℃
3.3 Boiling Point
299.696°C at 760 mmHg
3.4 Vapour
0.001mmHg at 25°C
3.5 Refractive Index
1.922
3.6 Flash Point
135.052°C
3.7 Appearance
white solid
3.8 Carcinogenicity
A bioassay of melamine wasconducted in rats and mice by NTP. Male F344 rats andB6C3F1 mice were administered melamine in their diets atconcentrations of 2250 or 4500 ppm daily for 103 weeks.Female rats were fed 4500 or 9000 ppm melamine. At the endof 111 weeks, surviving animals were killed and examined.
3.9 Chemical Properties
White Solid
3.10 Color/Form
Powder
3.11 Contact Allergens
Melamine-formaldehyde resin (MFR) results from condensation of melamine and formaldehyde. It is anactive ingredient of strong (reinforced) plasters, such as industrial or some dental plasters used for molding.It is also used as a textile finish resin. MFR acts as an allergen generally because of formaldehyde releasing (see Chap. 40)
3.12 Decomposition
DANGEROUS; WHEN HEATED TO DECOMP, EMITS HIGHLY TOXIC FUMES OF /NITROGEN OXIDES AND HYDROGEN CYANIDE/.
3.13 Heat of Combustion
-1967 kJ/mol at 25 deg C
3.14 PH
7-8 (32g/l, H2O, 20℃)
3.15 pKa
5(at 25℃)
3.16 Solubility
water: soluble25mg/mL, clear to slightly hazy, colorless
3.17 Spectral Properties
MAX ABSORPTION (0.1 N HCL): 235 NM (LOG E= 4.01); (WATER PH= 7): 236 NM (LOG E= 3.4); SADTLER REF NUMBER: 5460 (IR, PRISM); 477 (IR, GRATING)
Index of refraction: 1.872 at 20 degC/D
IR: 2344 (Coblentz Society Spectral Collection)
UV: 1499 (Sadtler Research Laboratories Spectral Collection)
MASS: 2584 (NIST/EPA/MSDC Mass Spectral database, 1990 version)
3.18 Stability
Stable. Incompatible with strong acids, strong oxidizing agents. Nonflammable.
3.19 StorageTemp
−20°C
3.20 VaporDensity
4.34 (NTP, 1992) (Relative to Air)
3.21 Water Solubility
Very slightly sol in hot alc; insol in ether
Sparingly sol in glycol, glycerol, pyridine; very slightly sol in ethanol; insol in benzene, carbon tetrachloride
In water, 3.23X10+3 mg/L at 20 deg C
3. Use and Manufacturing
4.1 Definition
ChEBI: A trimer of cyanamide, with a 1,3,5-triazine skeleton.
4.2 Fire Hazard
Literature sources indicate that Melamine is nonflammable.
4.3 General Description
Colorless to white monoclinic crystals or prisms or white powder. Sublimes when gently heated.
4.4 Potential Exposure
Manufactured from urea, melamineis used in the manufacture of plastics, melamineformaldehyde resins; rubber, synthetic textiles; laminates,adhesives, and molding compound
4.5 Produe Method
The compound now is synthesized from urea.
4.6 Purification Methods
Crystallise Melamine from water or dilute aqueous NaOH. It sublimes at ~240o on prolonged heating. [Beilstein 26 I 74, 26 II 132, 26 III/IV 1253.]
4.7 Safety Profile
Moderately toxic by ingestion and intraperitoneal routes. An eye, skin, and mucous membrane irritant. Causes dermatitis in humans. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx and CN-.
4.8 Storage
Ambient temperatures.
4.9 Usage
A compound that forms synthetic resins with formaldehyde
4. Safety and Handling
5.1 Hazard Codes
Xn
5.2 Risk Statements
R20/21;R44
5.3 Safety Statements
S36/37
5.4 PackingGroup
III
5.5 Transport
3263
5.6 Cleanup Methods
Evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Use HEPA vacuum or wet method to reduce dist during clean-up. Do not dry sweep. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean-up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.
Sweep spilled substance into sealable containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place (extra personal protection: P2 filter respirator for harmful particles).
DISSOLVED CYANURIC ACID, CYANURATES, & OTHER DERIVATIVES (0.2-3.0%) CONTAINED IN WASTE WATER FROM THE MFR OF CHLORINATED CYANURIC ACIDS ARE REMOVED BY SLURRYING WITH POWDERED OR GRANULATED ACTIVE CARBON FOR 0.5-3 HR & FILTRATION.
ACID WASTEWATERS FROM MFR OF CYANURIC ACID & ITS CHLORINATED DERIVATIVES WHICH CONTAIN CYANURIC ACID, MELAMINE, AMMELINE, & AMMELIDE & HAVE PH 0-6, ARE HEATED TO 245-270 DEG C UNDER EVOLVED PRESSURE, WHICH MAY BE 1-30 ATM & ARE HYDROLYZED COMPLETELY.
5.7 DisposalMethods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
5.8 Exposure Standards and Regulations
Melamine is an indirect food additive for use only as a component of adhesives.
5.9 Fire Fighting Procedures
Powder, water spray, foam, carbon dioxide.
Melanine itself does not burn. Use any extinguishing agent suitable for surrounding fire. Poisonous gases including carbon monoxide, hydrogen cyanide, nitrogen oxides, and ammonia are produced in fire. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are expected to fight fires, they must be trained and equipped in OSHA 1910.156.
5.10 Formulations/Preparations
Grade: min-99%
5.11 Incompatibilities
Incompatible with oxidizers (chlorates,nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases,strong acids, oxoacids, epoxides. Melamine neutralizesacids in exothermic reactions to form salts plus water. Maybe incompatible with isocyanates, halogenated organics,peroxides, phenols (acidic), epoxides, anhydrides, and acidhalides. Flammable gaseous hydrogen may be generated incombination with strong reducing agents such as hydrides,nitrides, alkali metals, and sulfides. Melamine Preparation Products And Raw materials Preparation Products
5.12 Octanol/Water Partition Coefficient
log Kow = -1.37
5.13 Reactivities and Incompatibilities
Strong oxidizers, strong acids.
5.14 Toxicity
LD50 orally in Rabbit: 3161 mg/kg LD50 dermal Rabbit > 1000 mg/kg
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

9. Computational chemical data
  • Molecular Weight:126.11994g/mol
  • Molecular Formula:C3H6N6
  • Compound Is Canonicalized:True
  • XLogP3-AA:
  • Exact Mass:126.06539422
  • Monoisotopic Mass:126.06539422
  • Complexity:63.3
  • Rotatable Bond Count:0
  • Hydrogen Bond Donor Count:3
  • Hydrogen Bond Acceptor Count:6
  • Topological Polar Surface Area:117
  • Heavy Atom Count:9
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
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