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2-Amino-6-methoxybenzothiazole | CAS 1747-60-0

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2-Amino-6-methoxybenzothiazole Basic informationUses

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
pkapK1: 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.
InChIInChI=1S/C8H8N2OS/c1-11-5-2-3-6-7(4-5)12-8(9)10-6/h2-4H,1H3,(H2,9,10)
InChIKeyKZHGPDSVHSDCMX-UHFFFAOYSA-N
SMILESS1C2=CC(OC)=CC=C2N=C1N
CAS DataBase Reference1747-60-0(CAS DataBase Reference)
EPA Substance Registry System2-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 Yes
HazardClass IRRITANT
PackingGroup III
HS Code 29342080
Toxicitymouse,LD50,intravenous,140mg/kg (140mg/kg),Journal of Pharmacology and Experimental Therapeutics. Vol. 105, Pg. 486, 1952.

MSDS Information

ProviderLanguage
6-Methoxy-2-aminobenzothiazole English
SigmaAldrich English
ACROS English
ALFA English

2-Amino-6-methoxybenzothiazole Usage And Synthesis

Chemical PropertiesGeneral DescriptionReactivity ProfileSynthesis
Uses2-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.
off-white to tan-coloured powder
Uses2-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.
Fine off-white to light tan powder.
Air & Water ReactionsInsoluble in water.
2-Amino-6-methoxybenzothiazole may be sensitive to exposure to light. 2-Amino-6-methoxybenzothiazole is incompatible with strong oxidizers.
Fire HazardFlash point data for 2-Amino-6-methoxybenzothiazole are not available; however, 2-Amino-6-methoxybenzothiazole is probably combustible.

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 materialsAniline-->Water-->p-Anisidine-->Sodium thiocyanate-->Congo red paper-->Disulfur dichloride-->4-METHOXYPHENYLTHIOUREA-->Phenolphthalein
Preparation ProductsBASIC 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

Declaration: The products displayed on this website are intended exclusively for industrial applications or scientific research. They are not intended for medical, pharmaceutical, or food use. In accordance with applicable laws and regulations, purchasing organizations must hold valid qualifications and approvals.

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