2-Amino-5-methylthiazole
Meloxicam EP Impurity B · 2,5-amth · NSC 523150 · AKOS BBS-00006638 · BUTTPARK 18\10-87 · Meloxicam usp RC B · 2-Amino-5-methylthia · LABOTEST-BB LT00080645
Identifiers & Physical Properties
| CAS No. | 7305-71-7 |
|---|---|
| Molecular formula | C4H6N2S |
| Average molar mass | 114.17 g/mol |
| Monoisotopic mass | 114.02516919 g/mol |
| SMILES | Cc1cnc(N)s1 |
| InChIKey | GUABFMPMKJGSBQ-UHFFFAOYSA-N |
| PubChem CID | 351770 |
| ChEMBL | CHEMBL502447 |
| EC No. | 423-800-5 |
| DTXSID | DTXSID10223329 |
Chemical & Physical Properties
| XLogP | 1 |
|---|---|
| Topological polar surface area | 67.2 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 0 |
| Heavy atoms | 7 |
| Formal charge | 0 |
| Complexity | 66.7 |
| Melting point | 93-98 °C (lit.) |
| Boiling point | 232.5±9.0 °C(Predicted) |
| Density | 1.258±0.06 g/cm3(Predicted) |
| Vapor pressure | 0.153-1.24Pa at 20-40℃ |
| Storage conditions | 2-8°C |
| Solubility | soluble in Methanol |
| pKa (acidity coefficient) | 5.42±0.10(Predicted) |
| Physical state | Powder |
| Color | Brown |
| BRN | 109603 |
| InChI | 1S/C4H6N2S/c1-3-2-6-4(5)7-3/h2H,1H3,(H2,5,6) |
| InChIKey | GUABFMPMKJGSBQ-UHFFFAOYSA-N |
| SMILES | Cc1cnc(N)s1 |
| LogP (partition coefficient) | 1.61 at 38℃ |
| Surface tension | 72.6mN/m at 1.02g/L and 20℃ |
| CAS DataBase Reference | 7305-71-7(CAS DataBase Reference) |
| FDA UNII | 7RAB78AF2P |
| NIST Chemistry Reference | Thiazole, 2-amino-5-methyl-(7305-71-7) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS07,GHS08,GHS09 |
| Signal word | Warning |
| GHS hazard statements | H302-H373-H410 |
| GHS precautionary statements | P260-P264-P270-P273-P301+P312-P314 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xn,N,Xi |
| Risk statements (R) | 22-48/22-50/53-36/37/38 |
| Safety statements (S) | 60-61-29-26-37/39 |
| UN transport number | 2811 |
| Water hazard class (WGK) | 3 |
| Hazard Note | Irritant/Keep Cold |
| Hazard class | 9Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1STOT RE 2 |
| Packing group | III |
| Customs code | 29341000 |
| Storage class | 11 - Combustible Solids |
| REACH registrations | Active |
| Limited quantities | 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| GHS classification | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P260, P264, P270, P273, P301+P317, P319, P330, P391, and P501 (click each P-code to see the statement)H302 (96.4%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatory information | Status: Active Update: 17-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/25186 |
| Hazard Classes and Categories | Acute Tox. 4 (96.4%)Acute Tox. 4 (100%)Acute toxicity - category 4Acute Tox. 4 * |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| UN transport number | 2811 |
| Customs code | 29341000 |
| Risk statements (R) | 22-48/22-50/53-36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07,GHS08,GHS09 |
| Hazard symbols | Xn,N,Xi |
| hazard_note | Irritant/Keep Cold |
| Safety statements (S) | 60-61-29-26-37/39 |
| Hazard class | 9Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1STOT RE 2 |
| Storage class | 11 - Combustible Solids |
| Packing group | III |
| GHS hazard statements | H302-H373-H410 |
| Limited quantities | 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
| REACH registrations | Active |
| GHS precautionary statements | P260-P264-P270-P273-P301+P312-P314 |
Applications & Uses
Uses
2-Amino-5-methylthiazole may be used in the preparation of acrylamide monomer, 5-methyl-2-thiozyl methacrylamide (MTMAAm).
Uses
An aminothiazole derivative used in characterization and DNA-interaction studies via formation of metal complexes that bind competitively to DNA. 2-Amino-5-methylthiazole can be used in solar cells to influence the interaction with the TiO2 photoelectrode, which in turn alters the dye-sensitized solar cell performance.
General Description
2-Amino-5-methylthiazole is a heterocyclic building block. It is one of the major alkaline metabolite of tenoxicam (TX) and meloxicam (MX).
Preparation & Synthesis
Preparation
Using 1,2,3-trichloropropane as a starting material, it reacts with sodium hydroxide to produce 2,3-dichloro-1-propene, which then reacts with potassium thiocyanate and isomerizes to produce 2-chloro-2-propenyl isothiocyanate. This is then reacted with ammonia to give N-(2-chloro-2-propenyl)thiourea, which is subsequently cyclized in the presence of 80% sulfuric acid to give 2-amino-5-methylthiazole.