(4S)-2-(6-Hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid

Basic Information

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CAS Number

2591-17-5

Molecular Formula

C11H8N2O3S2

Molecular Weight

280.33 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Melting Point

186°C(dec.)

Boiling Point

587.6°C at 760 mmHg

Flash Point

240.3ºC

Refractive Index

1.5650 (estimate)

Specific Rotation

D22 -36° (c = 1.2 in DMF)

SMILES

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C1C(N=C(S1)C2=NC3=C(S2)C=C(C=C3)O)C(=O)O

InChI

InChI=1S/C11H8N2O3S2/c14-5-1-2-6-8(3-5)18-10(12-6)9-13-7(4-17-9)11(15)16/h1-3,7,14H,4H2,(H,15,16)/t7-/m1/s1

InChIKey

BJGNCJDXODQBOB-SSDOTTSWSA-N

LogP

1.9485

Topological Polar Surface Area

82.78 Å²

Hydrogen Bond Donor/Acceptor

2 / 5

Complexity

391

Safety Information

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Hazard Statement

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Synonyms & References

English

Photinus luciferin
CHEBI:17165
(4S)-2-(6-Hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
TD8085
FIREFLY LUCIFERIN [MI]
EN300-99574
IWJYWBVPCGUPLO-BFUDMSGGSA-N
CS-4970
D-firefly luciferin
D-Luciferin, Potassium Salt
EX-A617
D(-)-Luciferin, D(-)-2-(6'-Hydroxy-benzothiazolyl)D2-thiazoline-4-carboxylic acid from Photinus pyralis, synthetic
SCHEMBL49401
D-Luciferin Free Acid
BJGNCJDXODQBOB-SSDOTTSWSA-N
D-Luciferin, free acid
DTXSID00894865
(4S)-4,5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid
Firefly luciferin
D-Luciferin, synthetic, BioXtra, >=99% (HPLC)
4-Thiazolecarboxylic acid, 4,5-dihydro-2-(6-hydroxy-2-benzothiazolyl)-, (4S)-
Luciferin
D-Luciferin,freeacid
AKOS037644789
C02740
BDBM50440036
CCG-267246
(S)-4,5-dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid
MFCD00042929
(S)-2-(6-Hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
AS-54711

MDL Number

MFCD00042929

Customs Code

2934999090

FAQ

What are the physical and chemical properties of (4S)-2-(6-Hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid (CAS: 2591-17-5)?

This compound is a solid with a crystalline form. Its molecular weight is approximately 324.33 g/mol. It has a low solubility in water but dissolves well in organic solvents like ethanol and methanol. It is moderately reactive, showing good stability in neutral to acidic conditions but can be susceptible to hydrolysis in basic solutions.

How is (4S)-2-(6-Hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid (CAS: 2591-17-5) typically synthesized?

This compound is typically synthesized via the condensation of 2-aminobenzothiazole with 2-formylthiazole followed by hydroxylation at the benzothiazole position. The reaction is catalyzed by metal complexes and proceeds with good selectivity and yield, often around 85%.

What industries use (4S)-2-(6-Hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid (CAS: 2591-17-5)?

This compound is used in various industries, including pharmaceuticals for its potential as an antibacterial agent, in sensors for its ability to detect certain analytes, and in polymer chemistry for its cross-linking properties. It is also explored in semiconductor applications for its electron-donating capabilities.

What precautions should be taken when handling (4S)-2-(6-Hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid (CAS: 2591-17-5)?

When handling this compound, it is recommended to use personal protective equipment (PPE) such as gloves, goggles, and a lab coat. Work should be done in a fume hood to minimize exposure. Spills should be carefully cleaned up with absorbent materials, and the area should be flushed with water to ensure complete removal. Always refer to the Safety Data Sheet (SDS) for detailed information on handling and disposal.