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THIAZOLE

Thiazole is a versatile aromatic heterocycle widely used as a building block in pharmaceutical, agrochemical, and specialty chemical synthesis.
Thiazole offers useful reactivity for the preparation of diverse functional and biologically active compounds.
Thiazole derivatives are valued for their broad application potential in advanced organic synthesis and industrial formulations.

CAS Number: 288-47-1
EC Number: 206-021-3
Molecular Formula: C3H3NS
Molecular Weight: 85.13 g/mol

Synonyms: THIAZOLE, 288-47-1, 1,3-Thiazole, Thiazoles, FEMA No. 3615, 320RCW8PEF, DTXSID2059776, CHEBI:43732, RefChem:897653, DTXCID4037875, CHEBI:48901, 206-021-3, MFCD00005315, THIAN-4-ONEOXIME, thiazol, tz, CCRIS 3205, EINECS 206-021-3, UNII-320RCW8PEF, BRN 0103852, a thiazole, racemic thiazole, Thiazole-, Thiazole, 99%, 5H-1,3-thiazole, 1,3-Thiazole #, Thiazole, >=99%, THIAZOLE [FHFI], THIAZOLE [MI], SCHEMBL2665, SCHEMBL3179, SCHEMBL3985, SCHEMBL6291, 4-27-00-00960 (Beilstein Handbook Reference), CHEMBL15605, SCHEMBL105036, SCHEMBL215613, SCHEMBL450348, SCHEMBL451165, SCHEMBL452620, SCHEMBL453026, SCHEMBL454064, orb3029463, SCHEMBL15987514, FEMA 3615, PDK0162, MSK158181, AKOS005146301, CS-W001237, EBC-444083, 28589-79-9, LOM, SY004510, CB7853436, DB-000360, NS00014391, EN300-22312, F002766, InChI=1/C3H3NS/c1-2-5-3-4-1/h1-3, Q413426, 1,3-Thiazol, [German], [IUPAC name – generated by ACD/Name], 1,3-Thiazole, [IUPAC name – generated by ACD/Name], 1,3-Thiazole, [French], [IUPAC name – generated by ACD/Name], 103852, [Beilstein], 206-021-3, [EINECS], 288-47-1, [RN], thiazol, Thiazole, [Wiki] , [Index name – generated by ACD/Name], Unverified, 4-27-00-00960, [Beilstein], 5H-1,3-Thiazole, 5H-Thiazol-1-ium, 98%, EINECS 206-021-3, HYDROCHLORTHIAZIDE, LOM, thiazole(rs20001499), Thiazolidine, TZ, 噻唑, [Chinese]

Thiazole is a 5-membered heterocyclic compound that contains both sulfur and nitrogen.
The term 'thiazole' also refers to a large family of derivatives.

Thiazole itself is a pale yellow liquid with a pyridine-like odor and the molecular formula C3H3NS.
The thiazole ring is notable as a component of the vitamin thiamine (B1).

Thiazole appears as colorless or pale yellow liquid with a foul odor.
Thiazole is a mancude organic heteromonocyclic parent, a monocyclic heteroarene and a member of 1,3-thiazoles.

Thiazole is a naturally occurring compound in sesame seed oil and chicken.
Thiazole is used as a flavoring agent and in the preparation of dyes and rubber accelerators.

Thiazole serves as a component of the vitamin thiamine (B1).
Thiazole acts as a protected formyl group used in natural product synthesis.

Thiazole reacts with alkyl lithium and Grignard’s reagent to prepare organometallic complexes.
Thiazole is involved in the electrophilic aromatic substitution and nucleophilic aromatic substitution at C-5 and C-2 positions respectively.

Further, Thiazole undergoes alkylation reaction to get thiazolium cation, which is used as a catalyst in the Stetter reaction and the Benzoin condensation.
In addition to this, Thiazole is involved in the preparation of alagebrium.

Thiazole derivatives are valued for their versatile reactivity and their role as intermediates in the preparation of biologically active and functional compounds.
Thiazole is a five-membered heterocyclic compound featuring both sulfur and nitrogen in its ring structure, making it a valuable building block in organic synthesis.

Thiazole is recognized for its unique ability to enhance the biological activity of various pharmaceuticals and agrochemicals.
Thiazole derivatives are widely utilized in the development of antifungal, antibacterial, and anti-inflammatory agents, showcasing its significance in medicinal chemistry.

Additionally, Thiazole is employed in the production of dyes, rubber accelerators, and corrosion inhibitors, highlighting its versatility across multiple industries.
Thiazole's distinct properties, such as thermal stability and reactivity, make it an ideal candidate for various applications, particularly in the synthesis of complex organic molecules.

Researchers and industry professionals can leverage Thiazole's potential to create innovative solutions in drug development and materials science.
Thiazole's role in enhancing the efficacy of active pharmaceutical ingredients (APIs) and its application in agrochemical formulations underscore its importance in advancing both health and agricultural sectors.
By incorporating Thiazole into their projects, professionals can benefit from its unique properties and contribute to the development of effective and sustainable products.

thiazole, any of a class of organic compounds of the heterocyclic series characterized by a ring structure composed of three carbon atoms, one nitrogen atom, and one sulfur atom.
This ring structure occurs in such important biologically active natural products as thiamine (vitamin B1), bacitracin, and the penicillins, and in numerous synthetic drugs, dyes, and industrial chemicals.

The simplest member of the thiazole family is thiazole itself, a rarely prepared liquid with the molecular formula C3H3NS.
Other thiazole compounds include rhodanine and the dye rhodanine red derived from it, and the yellow dye primuline.

Synthetic drugs belonging to the thiazole family include sulfathiazole, sulfasuxidine, and thiazolsulfone (Promizole).
2-Mercaptobenzothiazole (Mertax) is a thiazole derivative used for accelerating the vulcanization of rubber.

Thiazole is a five-membered aromatic heterocyclic compound containing one sulfur atom and one nitrogen atom in the ring.
Thiazole is an important structural unit used in the synthesis of pharmaceuticals, agrochemicals, dyes, and specialty chemicals.
Thiazole derivatives are valued for their versatile reactivity and their role as intermediates in the preparation of biologically active and functional compounds.

Thiazole is a clear to pale yellow flammable liquid with a pyridine-like odor and the molecular formula C3H3NS.
Thiazole is a 5-membered ring, in which two of the vertices of the ring are nitrogen and sulfur, and the other three are carbons.

Thiazole is used for manufacturing biocides, fungicides, pharmaceuticals, and dyes.

Thiazoles and thiazolium salts:
Thiazoles are a class of organic compounds related to azoles with a common thiazole functional group.
Thiazoles are aromatic.

The thiazole moiety is a crucial part of vitamin B1 (thiamine) and epothilone.
Other important thiazoles are benzothiazoles, for example, the firefly chemical luciferin.

Thiazoles are structurally similar to imidazoles.
Like imidazoles, thiazoles have been used to give N-S free carbenes and transition metal carbene complexes.

When the amino atom is alkylated, the resulting thiazolium salt is a salt.
Thiazolium salts are catalysts in the Stetter reaction and the Benzoin condensation.
Thiazole dyes are used for dying cotton.

Oxazoles are related compounds, with sulfur replaced by oxygen.
Thiazoles are well represented in biomolecules; oxazoles are not.

Uses of Thiazole:
Thiazole is used as a flavoring agent and in the preparation of dyes and rubber accelerators.
Thiazole serves as a component of the vitamin thiamine (B1).

Thiazole acts as a protected formyl group used in natural product synthesis.
Thiazole reacts with alkyl lithium and Grignards reagent to prepare organometallic complexes.

Thiazole is involved in the electrophilic aromatic substitution and nucleophilic aromatic substitution at C-5 and C-2 positions respectively.
Further, Thiazole undergoes alkylation reaction to get thiazolium cation, which is used as a catalyst in the Stetter reaction and the Benzoin condensation.
In addition to this, Thiazole is involved in the preparation of alagebrium.

Thiazole is used as a flavoring agent.
Thiazole is used to make fungicides, dyes, and rubber accelerators.

Thiazoles were used to create novel recognition motifs for interaction with divalent and trivalent metal ions in siderophores or antibiotics.

The generation of thiazole derivatives by means of condensation of α-haloketones and thioamidesis referred to as the Hantzsch thiazole synthesis.
This reaction takes place due to the strong nucleophilicity of the sulfur atom in thioamides or thioureas, and gives fantabulous yields for simple thiazoles but low yields for some substituted thiazoles, as of dehalogenation.

Thiazole is a multistep reaction, and the intermediates have been isolated at low temperatures.
This reaction has been changed to reduce the epimerization upon the formation of thiazole.

Additionally, α-tosyloxy ketones have been used to replace α-haloketones for such reactions.
Thiazole has wide application in the preparation of thiazole derivatives.

Thiazole is used as a flavoring agent and in the preparation of dyes and rubber accelerators.
Thiazole serves as a component of the vitamin thiamine (B1).

Thiazole acts as a protected formyl group used in natural product synthesis.
Thiazole reacts with alkyl lithium and Grignard’s reagent to prepare organometallic complexes.

Molecular and Electronic Structure of Thiazole:
Thiazoles are members of the azoles, heterocycles that include imidazoles and oxazoles.
Thiazole can also be considered a functional group when part of a larger molecule.

Being planar, thiazoles are characterized by significant π electron delocalization and exhibit a degree of aromaticity greater than that of corresponding oxazoles.
This aromaticity is evidenced by the 1H NMR chemical shift of the ring protons, which display resonances between 7.27 and 8.77 ppm, indicating a strong diamagnetic ring current.
The calculated electron density marks C5 as the primary site for electrophilic substitution, and C2-H as susceptible to deprotonation.

Occurrence of Thiazoles and Thiazolium Salts:
Thiazoles are found in a variety of specialized products, often fused with benzene derivatives, the so-called benzothiazoles.
In addition to vitamin B1, the thiazole ring is found in epothilone.

Other important thiazole derivatives are benzothiazoles, for example, the firefly chemical luciferin.
Whereas thiazoles are well represented in biomolecules, oxazoles are not.
Thiazole is found in naturally occurring peptides, and utilised in the development of peptidomimetics (i.e. molecules that mimic the function and structure of peptides).

Commercial significant thiazoles include mainly dyes and fungicides.
Thifluzamide, Tricyclazole, and Thiabendazole are marketed for control of various agricultural pests.

Another widely used thiazole derivative is the non-steroidal anti-inflammatory drug Meloxicam.

The following anthroquinone dyes contain benzothiazole subunits:
Algol Yellow 8 (CAS# [6451-12-3]), Algol Yellow GC (CAS# [129-09-9]), Indanthren Rubine B (CAS# [6371-49-9]), Indanthren Blue CLG (CAS# [6371-50-2], and Indanthren Blue CLB (CAS#[6492-78-0]).

These thiazole dye are used for dyeing cotton.

Synthesis of Thiazole:
Various laboratory methods exist for the organic synthesis of thiazoles.
Prominent is the Hantzsch thiazole synthesis, which is a reaction between haloketones and thioamides.

For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.
In the Cook-Heilbron synthesis, thiazoles arise by the condensation of α-aminonitrile with carbon disulfide.
Thiazoles can be accessed by acylation of 2-aminothiolates, often available by the Herz reaction.

Biosynthesis:
Thiazoles are generally formed via reactions of cysteine, which provides the N-C-C-S backbone of the ring.
Thiamine does not fit this pattern however.

Several biosynthesis routes lead to the thiazole ring as required for the formation of thiamine.
Sulfur of the thiazole is derived from cysteine.
In anaerobic bacteria, the CN group is derived from dehydroglycine.

Organic Synthesis:
Various laboratory methods exist for the organic synthesis of thiazoles.

The Hantzsch thiazole synthesis (1889) is a reaction between haloketones and thioamides.
For example, 2,4-dimethylthiazole is synthesized from acetamide, phosphorus pentasulfide, and chloroacetone.

Another example is given below:
In an adaptation of the Robinson-Gabriel synthesis, a 2-acylamino-ketones reacts with phosphorus pentasulfide.
In the Cook-Heilbron synthesis, an α-aminonitrile reacts with carbon disulfide.
Certain thiazoles can be accessed though application of the Herz reaction.

Reactions of Thiazole:
With a pKa of 2.5 for the conjugate acid, thiazoles are far less basic than imidazole (pKa =7).

Deprotonation with strong bases (e.g. Hauser bases and organolithium compounds) occurs at C2-H.
The negative charge on this position is stabilized as an ylide.
2-Lithiothiazoles are also generated by metal-halogen exchange from 2-bromothiazole.

Electrophilic aromatic substitution occurs at C5 but requires activating groups such as a methyl.
Nucleophilic substitution requires no additional activation.

Nitrogen oxidation gives the aromatic thiazole N-oxide.
Many oxidizing agents, such as mCPBA or hypofluorous acid, suffice; but some of the oxidation takes place at sulfur, leading to a non-aromatic sulfoxide/sulfone.

In palladium-catalysed C-H arylations, the N-oxide shifts the reactivity to reliably favor the 2-position, and allows for much more mild reaction conditions.

Thiazoles can react in cycloadditions, but in general at high temperatures due to favorable aromatic stabilization of the reactant.
Diels-Alder reactions with alkynes precede sulfur extrusion, and the end product is a pyridine.

One study examined the reaction mechanism between 2-(dimethylamino)thiazole and dimethyl acetylenedicarboxylate (DMAD) to a pyridine.
The first intermediate, a zwitterion, appeared in a formal [2+2]cycloaddition to a cyclobutene.

Thiazole then underwent a 4-electron electrocyclic ring opening to a 1,3-thiazepine and then a 6-electron electrocyclic ring closing to a 7-thia-2-azanorcaradiene.

Finally, Thiazole extruded the sulfur atom:

Thiazoles are formyl synthons, but conversion of a thiazole to an aldehyde (R-Ar to R-COH) requires multiple steps:
N-methylation with methyl iodide, organic reduction with sodium borohydride, and finally hydrolysis with mercury(II) chloride in water.

Thiazolium salts:
Alkylation of thiazoles at nitrogen forms a thiazolium cation.
Thiazolium salts are catalysts in the Stetter reaction and the Benzoin condensation.
Deprotonation of N-alkyl thiazolium salts give the free carbenes and transition metal carbene complexes.

Alagebrium is a thiazolium-based drug.

Stability and Reactivity of Thiazole:

Chemical stability:
Thiazole is generally stable under normal ambient temperatures and recommended storage conditions.

Reactivity:
Thiazole may react with strong oxidizing agents and other highly reactive substances.

Conditions to avoid:
Avoid excessive heat, flames, sparks, and prolonged exposure to incompatible materials.

Incompatible materials:
Avoid strong oxidizing agents, strong acids, and strong bases.

Handling and Storage of Thiazole:

Safe handling:
Use in a well-ventilated area and avoid inhalation of vapors and unnecessary contact with skin and eyes.

Storage conditions:
Keep the container tightly closed in a cool, dry, and well-ventilated place away from heat and ignition sources.

First Aid Measures of Thiazole:

Inhalation:
Move the affected person to fresh air and seek medical attention if symptoms persist.

Skin contact:
Wash the affected area thoroughly with soap and plenty of water.

Eye contact:
Rinse cautiously with water for several minutes and obtain medical attention if irritation continues.

Ingestion:
Rinse the mouth and seek medical advice if discomfort occurs.

Firefighting Measures of Thiazole:

Suitable extinguishing media:
Use dry chemical, carbon dioxide, water spray, or suitable foam.

Protective equipment:
Firefighters should wear appropriate protective clothing and self-contained breathing apparatus when necessary.

Accidental Release Measures of Thiazole:

Personal precautions:
Provide adequate ventilation and avoid direct contact with the spilled material.

Cleanup methods:
Absorb with an inert material and transfer into a suitable closed container for disposal.

Exposure Controls/Personal Protective of Thiazole:

Engineering controls:
Provide adequate local or general ventilation to minimize exposure.

Eye protection:
Wear suitable safety glasses or chemical goggles.

Hand protection:
Use appropriate chemical-resistant protective gloves.

Skin protection:
Wear suitable protective clothing.

Respiratory protection:
Use suitable respiratory protection when ventilation is inadequate.

Identifiers of Thiazole:
Empirical Formula (Hill Notation): C3H3NS
CAS Number: 288-47-1
Molecular Weight: 85.13
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 24849155
EC Number: 206-021-3
Beilstein/REAXYS Number: 103852
MDL Number: MFCD00005315
Assay: 99%
Form: liquid

Product Number: T0185
Purity / Analysis Method: >98.0%(GC)
Molecular Formula / Molecular Weight: C__3H__3NS = 85.12
Physical State (20 deg.C): Liquid
Storage Temperature: Room Temperature (Recommended in a cool and dark place, <15°C)
Store Under Inert Gas: Store under inert gas
Condition to Avoid: Light Sensitive,Air Sensitive
CAS RN: 288-47-1
Reaxys Registry Number: 103852
PubChem Substance ID: 87576178
SDBS (AIST Spectral DB): 55
Merck Index (14): 9307
MDL Number: MFCD00005315

CAS Number: 288-47-1
ChEBI: CHEBI:43732
ChEMBL: ChEMBL15605
ChemSpider: 8899
ECHA InfoCard: 100.005.475
EC Number: 206-021-3
PubChem CID: 9256
UNII: 320RCW8PEF
CompTox Dashboard (EPA): DTXSID2059776
InChI: InChI=1S/C3H3NS/c1-2-5-3-4-1/h1-3H
Key: FZWLAAWBMGSTSO-UHFFFAOYSA-N
InChI: InChI=1/C3H3NS/c1-2-5-3-4-1/h1-3H
Key: FZWLAAWBMGSTSO-UHFFFAOYAI
SMILES: n1ccsc1

Name: 1,3-thiazole
CAS Number: 288-47-1
ECHA EINECS - REACH Pre-Reg: 206-021-3
FDA UNII: 320RCW8PEF
Nikkaji Web: J26D
Beilstein Number: 0103852
MDL: MFCD00005315
CoE Number: 11642
XlogP3: 0.40 (est)
Molecular Weight: 85.12891000
Formula: C3 H3 N S

CAS No.: 288-47-1
Chemical Name: Thiazole
CBNumber: CB7853436
Molecular Formula: C3H3NS
Molecular Weight: 85.13

CAS: 288-47-1
IUPAC Name: 1,3-thiazole
Molecular Formula: C3H3NS
InChI Key: FZWLAAWBMGSTSO-UHFFFAOYSA-N
SMILES: S1C=CN=C1
Molecular Weight (g/mol): 85.12
Synonym: thiazole

Properties of Thiazole:
Quality Segment: 100
Assay: 99%
Form: liquid
Refractive Index: n20/D 1.538 (lit.)
Boiling Point: 117-118 °C (lit.)
Density: 1.2 g/mL at 25 °C (lit.)
SMILES String: c1cscn1
InChI: 1S/C3H3NS/c1-2-5-3-4-1/h1-3H
InChI Key: FZWLAAWBMGSTSO-UHFFFAOYSA-N

Molecular Weight: 85.13 g/mol
XLogP3: 0.4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 84.99862027 Da
Monoisotopic Mass: 84.99862027 Da
Topological Polar Surface Area: 41.1 Å²
Heavy Atom Count: 5
Complexity: 30.1
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Chemical Formula: C3H3NS
Molar Mass: 85.12 g·mol−1
Boiling Point: 116 to 118 °C (241 to 244 °F; 389 to 391 K)
Acidity (pKa): 2.5 (of conjugate acid)
Magnetic Susceptibility (χ): −50.55·10−6 cm3/mol

Appearance: colorless to yellow clear liquid (est)
Assay: 98.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity: 1.19800 to 1.20200 @ 25.00 °C.
Pounds per Gallon - (est).: 9.969 to 10.002
Refractive Index: 1.53100 to 1.54100 @ 20.00 °C.
Boiling Point: 115.00 to 118.00 °C. @ 760.00 mm Hg
Vapor Pressure: 21.613001 mmHg @ 25.00 °C. (est)
Flash Point: 72.00 °F. TCC (22.22 °C.)
logP (o/w): 0.440

Melting Point: -33°C
Boiling Point: 117-118 °C (lit.)
Density: 1.2 g/mL at 25 °C (lit.)
Refractive Index: n20/D 1.538(lit.)
FEMA: 3615 | THIAZOLE
Flash Point: 72 °F
Storage Temperature: Keep in dark place,Inert atmosphere,2-8°C
pKa: 2.44(at 20℃)
Form: Liquid
Color: Clear colorless to yellow
Specific Gravity: 1.200
Odor: at 0.10 % in propylene glycol. pyridine nutty meaty
Odor Type: fishy
Biological Source: synthetic
Water Solubility: slightly soluble
Sensitive: Air & Light Sensitive
Merck: 14,9307
JECFA Number: 1032
BRN: 103852
Stability: Stable. Incompatible with strong oxidizing agents.
InChI: 1S/C3H3NS/c1-2-5-3-4-1/h1-3H
InChIKey: FZWLAAWBMGSTSO-UHFFFAOYSA-N
SMILES: c1cscn1
LogP: 0.44
CAS DataBase Reference: 288-47-1(CAS DataBase Reference)
NIST Chemistry Reference: Thiazole(288-47-1)
EPA Substance Registry System: Thiazole (288-47-1)

Melting Point: -33 °C
Boiling Point: 118 °C
Flash Point: 26 °C
Specific Gravity (20/20): 1.20
Refractive Index: 1.54
Solubility in Water: Slightly soluble

Specifications of Thiazole:
Form: Liquid
Refractive Index: 1.5330-1.5395 @ 20°C
Appearance (Color): Clear colorless to yellow
Assay (GC): ≥97.5%
Appearance: Colorless to Light yellow clear liquid
Purity (GC): min. 98.0 %

Names of Thiazole:

Preferred IUPAC name:
1,3-Thiazole

Other name:
Thiazole