2-Amino-6-methoxybenzothiazole CAS 1747-60-0
2-Amino-6-methoxybenzothiazole Basic information
| Product Name: | 2-Amino-6-methoxybenzothiazole |
| Synonyms: | 2-amino-6-methoxy-benzothiazol;6-methoxy-2-benzothiazolamin;TIMTEC-BB SBB003746;2-AMINO-6-METHOXYBENZOTHIAZOLE;2-AMINO-6-METHOXYBENZOTHIOPHENE;2-BENZOTHIAZOLAMINE, 6-METHOXY-;AKOS BBS-00005696;AKOS AUF2099 |
| CAS: | 1747-60-0 |
| MF: | C8H8N2OS |
| MW: | 180.23 |
| EINECS: | 217-130-0 |
| Product Categories: | Building Blocks;Heterocyclic Building Blocks;Thiazoles;Heterocyclic Compounds;Sulphur Derivatives;Intermediates of Dyes and Pigments;BENZOTHIAZOLE;bc0001 |
| Mol File: | 1747-60-0.mol |
2-Amino-6-methoxybenzothiazole Chemical Properties
| Melting point | 165-167 °C (lit.) |
| Boiling point | 240°C |
| density | 1.2425 (rough estimate) |
| refractive index | 1.5690 (estimate) |
| storage temp. | Keep in dark place,Inert atmosphere,Room temperature |
| solubility | very slightly in Methanol |
| pka | pK1: 4.50(+1) (25°C) |
| form | Crystalline Powder |
| color | White to beige |
| Water Solubility | <0.1 g/100 mL at 21 ºC |
| Stability: | Stable, but may be light sensitive. Incompatible with strong oxidizing agents. |
| InChI | InChI=1S/C8H8N2OS/c1-11-5-2-3-6-7(4-5)12-8(9)10-6/h2-4H,1H3,(H2,9,10) |
| InChIKey | KZHGPDSVHSDCMX-UHFFFAOYSA-N |
| SMILES | S1C2=CC(OC)=CC=C2N=C1N |
| CAS DataBase Reference | 1747-60-0(CAS DataBase Reference) |
| EPA Substance Registry System | 2-Amino-6-methoxybenzothiazole (1747-60-0) |
Safety Information
| Hazard Codes | Xn,Xi |
| Risk Statements | 22-36/37/38-20/21/22 |
| Safety Statements | 26-36 |
| RIDADR | 2811 |
| WGK Germany | 3 |
| RTECS | DL2100000 |
| TSCA | TSCA listed |
| HazardClass | IRRITANT |
| PackingGroup | III |
| HS Code | 29342080 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Toxicity | mouse,LD50,intravenous,140mg/kg (140mg/kg),Journal of Pharmacology and Experimental Therapeutics. Vol. 105, Pg. 486, 1952. |
| Uses | 2-Amino-6-methoxybenzothiazole is an intermediate used to prepare novel series of Schiff bases and 4-thiazolidinones. It is also used in the synthesis of 2-cyano-6-methoxybenzothiazole. |
| Chemical Properties | off-white to tan-coloured powder |
| Uses | 2-Amino-6-methoxybenzothiazole was used as building block in the syntheses of novel series of Schiff bases and 4-thiazolidinones. It was used in the synthesis of 2-cyano-6-methoxybenzothiazole, key intermediate for the synthesis of firefly luciferin. |
| General Description | Fine off-white to light tan powder. |
| Air & Water Reactions | Insoluble in water. |
| Reactivity Profile | 2-Amino-6-methoxybenzothiazole may be sensitive to exposure to light. 2-Amino-6-methoxybenzothiazole is incompatible with strong oxidizers. |
| Fire Hazard | Flash point data for 2-Amino-6-methoxybenzothiazole are not available; however, 2-Amino-6-methoxybenzothiazole is probably combustible. |
| Synthesis | 333-20-0 104-94-9 1747-60-0 0.1 mole of p-aminoanisole and 0.1 mole of potassium thiocyanate (KCNS) were dissolved in 100 mL of glacial acetic acid (AcOH) and the mixture was cooled and stirred in an ice bath for 10-20 minutes. Subsequently, 0.1 mol of bromine in glacial acetic acid solution was slowly added dropwise, with the rate of dropwise acceleration controlled to maintain the reaction temperature below 10 °C. After the dropwise addition was completed, the reaction mixture was stirred at room temperature for 2-4 hours. After completion of the reaction, the resulting hydrobromide (HBr) salt was separated by filtration, washed with glacial acetic acid and dried. The dried salt was dissolved in hot water and alkalized by adjusting the pH to 11.0 with ammonia solution (NH4OH). The precipitate precipitated was filtered, washed with water and dried to give the target product 2-amino-6-methoxybenzothiazole. The reaction process was monitored by thin layer chromatography (TLC) using toluene: acetone (8:2) as unfolding agent. |
| References | [1] Synlett, 2012, vol. 23, # 15, p. 2219 - 2222 [2] Synlett, 2009, # 16, p. 2682 - 2684 [3] Heterocyclic Communications, 2018, vol. 24, # 5, p. 255 - 258 [4] Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 5, p. 1124 - 1133 [5] European Journal of Medicinal Chemistry, 2008, vol. 43, # 5, p. 1114 - 1122 |
2-Amino-6-methoxybenzothiazole Preparation Products And Raw materials
| Raw materials | Aniline-->Water-->p-Anisidine-->Sodium thiocyanate-->Congo red paper-->Disulfur dichloride-->4-METHOXYPHENYLTHIOUREA-->Phenolphthalein |
| Preparation Products | BASIC BLUE 41 (C.I. 11105)-->Catonic Dark Yellow 2RL-->6-Methoxy-3-methyl-2(3H)-benzothiazolone hydrazone-->Basic Blue 162-->2-Amino-6-ethoxybenzothiazole-->2-Cyano-6-methoxybenzothiazole-->BASIC BLUE 41-->SUPRACET BRILLIANT RED BD-->Basic Blue 162-->3-(3-amino-3-oxopropyl)-2-[[4-[bis(2-chloroethyl)amino]phenyl]azo]-6-methoxybenzothiazolium chloride-->1,2,3,4-Tetrahydro-6-[(6-methoxybenzothiazol-2-yl)azo]benzo[h]quinoline-3,7-diol-->BASIC YELLOW 19 |
