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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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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