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162590

Sigma-Aldrich

2-Amino-6-methoxybenzothiazole

98%

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About This Item

Empirical Formula (Hill Notation):
C8H8N2OS
CAS Number:
1747-60-0
Molecular Weight:
180.23
EC Number:
217-130-0
MDL number:
MFCD00005787
UNSPSC Code:
12352100
PubChem Substance ID:
24849994
NACRES:
NA.22

assay

98%

form

solid

mp

165-167 °C (lit.)

SMILES string

COc1ccc2nc(N)sc2c1

InChI

1S/C8H8N2OS/c1-11-5-2-3-6-7(4-5)12-8(9)10-6/h2-4H,1H3,(H2,9,10)

InChI key

KZHGPDSVHSDCMX-UHFFFAOYSA-N

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General description

2-Amino-6-methoxybenzothiazole undergoes Sandmeyer reaction on heating with isoamyl nitrite and CuBr2 to yield 2-bromo-6-methoxybenzothiazole.

Application

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Navin B Patel et al.
Saudi pharmaceutical journal : SPJ : the official publication of the Saudi Pharmaceutical Society, 18(3), 129-136 (2010-07-01)
A novel series of Schiff bases 5a-j and 4-thiazolidinones 6a-j have been prepared from the building blocks 2-chloro pyridine-3-carboxylic acid [1] and 2-amino-6-methoxy-benzothiazole [2]. All of the synthesized compounds have been confirmed by elemental analyses, IR, (1)H NMR and (13)C
An efficient palladium catalyzed synthesis of 2-arylbenzothiazoles.
Majo VJ, et al.
Tetrahedron Letters, 44(47), 8535-8537 (2003)
A Convenient Synthetic Method of 2-Cyano-6-methoxybenzothiazole,-A Key Intermediate for the Synthesis of Firefly Luciferin.
Toya Y, et al.
Bulletin of the Chemical Society of Japan, 65(2), 392-395 (1992)
Effect of Aroclor 1254 dose upon S9 activation of aromatic amine bacterial mutagens.
C Z Thompson et al.
Mutation research, 77(4), 361-366 (1980-04-01)
V Arjunan et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 102, 327-340 (2012-12-12)
Extensive vibrational investigations of 2-amino-4-methoxybenzothiazole have been carried out with FTIR and FT-Raman spectral techniques. The electronic structure of the molecule has been analysed by UV-Visible and NMR spectroscopies. The DFT studies were carried out with B3LYP and HF methods

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