Thiazole
Identifiers
CAS number	[288-47-1]
SMILES	N1=CSC=C1
Properties
Boiling point	116-118 °C Image File history File links No higher resolution available. ... Image File history File links Size of this preview: 740 × 599 pixel Image in higher resolution (1000 × 810 pixel, file size: 115 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Thiazole Wikipedia:WikiProject... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ...
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Thiazole, or 1,3-thiazole, is a clear to pale yellow flammable liquid and pyridine-like odor with the molecular formula C₃H₃NS. It is a 5-membered ring, in which two of the vertices of the ring are nitrogen and sulfur, and the other three are carbons ^[1]. In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Pyridine is a chemical compound with the formula C5H5N. It is a liquid with a distinctively putrid odour. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Standard atomic weight 32. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ...

Thiazole is used for manufacturing biocides, fungicides, pharmaceuticals, and dyes. A biocide is a chemical substance capable of killing different forms of living organisms used in fields such as medicine, agriculture, forestry, and mosquito control. ... A Fungicide is one of three main methods of pest control- chemical control of fungi in this case. ... Pharmacology (in Greek: pharmacon is drug, and logos is science) is the study of how chemical substances interfere with living systems. ... A dye can generally be described as a coloured substance that has an affinity to the substrate to which it is being applied. ...

Thiazoles and thiazolium salts

Thiazoles are a class of organic compounds related to azoles with a common thiazole functional group. Benzene is the simplest of the arenes, a family of organic compounds An organic compound is any member of a large class of chemical compounds whose molecules contain carbon and hydrogen; therefore, carbides, carbonates, carbon oxides and elementary carbon are not organic (see below for more on the definition controversy... An azole is a class of five-membered nitrogen heterocyclic ring compounds containing at least one other noncarbon atom, nitrogen, sulfur or oxygen. ... In organic chemistry, functional groups are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ...

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. Look up moiety in Wiktionary, the free dictionary. ... For the similarly-spelled nucleic acid, see Thymine Thiamine or thiamin, also known as vitamin B1, is one of the B vitamins. ... The epothilones are a new class of cytotoxic molecules, including epothilone A, epothilone B, and epothilone D, identified as potential chemotherapy drugs. ... Benzothiazole is a colorless, slightly viscous liquid with a melting point of 2°C, and a boiling point of 227-228°C. The density of benzothiazole is 1. ... Luciferin is a generic name for light-emitting pigments found in organisms capable of bioluminescence, like fireflies, deep-sea fish and microbes. ...

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. Alkylation is the transfer of an alkyl group from one molecule to another. ... A magnified crystal of a salt (halite/sodium chloride) Salt covering the floor of Bad Water in Death Valley, CA, the lowest point in the US. A salt, in chemistry, is any ionic compound composed of cations (positively charged ions) and anions (negative ions) so that the product is neutral... The Stetter reaction is an organic reaction involving the nucleophile catalyzed conjugate addition of an aldehyde to a Michael acceptor such as an enone . ... The Benzoin condensation is a condensation reaction between two aromatic aldehydes, especially benzaldehyde that is catalyzed by a cyanide. ... Cotton ready for harvest. ...

Oxazoles are related compound with sulfur replaced by oxygen. Thiazoles are well represented in biomolecules, oxazoles are not. Oxazole is the parent compound for vast class of heteroaromatic compounds. ... ...

Image File history File links No higher resolution available. ...

Organic synthesis

Various laboratory methods exist for the organic synthesis of thiazoles. Organic synthesis is the construction of organic molecules via chemical processes. ...

• 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 ^[2]. Another example ^[3] 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.

A haloketone in organic chemistry is a functional group consisting of a ketone group with a α-halogen substituent. ... General structure of a thioamide. ... acetamide Acetamide (or Acetic acid amide or Ацетамид) CH3CONH2, the amide of acetic acid, is a white crystalline solid in pure form. ... Phosphorus pentasulfide, also called phosphorus sulfide, sulfur phosphide, diphosphorus pentasulfide and phosphorus persulfide, is an inorganic compound of phosphorus and sulfur. ... Image File history File links Size of this preview: 800 × 208 pixel Image in higher resolution (1021 × 265 pixel, file size: 6 KB, MIME type: image/png) Hantsch Thiazole Synthesis I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the... The Robinson-Gabriel synthesis is a chemical reaction that forms oxazoles by dehydration of 2-acylamino-ketones. ... Phosphorus pentasulfide, also called phosphorus sulfide, sulfur phosphide, diphosphorus pentasulfide and phosphorus persulfide, is an inorganic compound of phosphorus and sulfur. ... Carbon disulfide is a colorless liquid with the formula CS2. ... The Herz-reaction, named after the chemist Richard Herz, is the chemical conversion of an aniline-derivative (1) to a so-called Herz-salt (2) with disulfur dichloride, followed by hydrolysis of this Herz-salt (2) to the corresponding sodium thiolate (3) [1]: // The sodium thiolate 3 can be converted...

Organic reactions

Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. This is evidenced by the position of the ring protons in proton NMR (between 7.27 and 8.77 ppm) clearly indicating a strong diamagnetic ring current. In chemistry, delocalized electrons are electrons in a molecule that do not belong to a single atom or a covalent bond. ... Oxazole is the parent compound for vast class of heteroaromatic compounds. ... Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. ... Pacific Northwest National Laboratorys high magnetic field (800 MHz, 18. ... A diagram of an aromatic ring current. ...

The calculated pi-electron density marks C5 as the primary electrophilic site and C2 as the nucleophilic site.

The reactivity of a thiazole can be summarized as follows: Image File history File links No higher resolution available. ...

• Deprotonation at C2, the negative charge on this position is stabilized as an ylide. Grignard reagents and organolithium compounds react at this site replacing the proton.

2-(trimethylsiliyl)thiazole ^[4] (with a trimethylsilyl group in the 2-position) is a stable substitute and reacts with a range of electrophiles such as aldehydes, acyl halides and ketenes.

• Alkylation at nitrogen forms a thiazolium salt.
• Electrophilic aromatic substitution at C5 requires activating groups such as a methyl group in this bromination:

• Nucleophilic aromatic substitution often requires an electrofuge at C2 such as chlorine with

• Organic oxidation at nitrogen gives the thiazole N-oxide. Many oxidizing agents exist such as mCPBA, a novel one is hypofluorous acid prepared from fluoride and water in acetonitrile. Some of the oxidation takes place at sulfur leading to a sulfoxide ^[5]:

• Thiazoles are formyl synthons. Conversion of R-thia to the R-CHO aldehyde takes place with ^[4] respectively methyl iodide (N-methylation), organic reduction with sodium borohydride and hydrolysis with mercury chloride in water.

• Thiazoles can react in cycloadditions but in general at high temperatures due to favorable aromatic stabilization of the reactant. Diels-Alder reactions with alkynes are followed by extrusion of sulfur and the endproduct is a pyridine. In one study ^[3] a very mild reaction of a 2-(dimethylamino)thiazole with dimethyl acetylenedicarboxylate (DMAD) to a pyridine was found to proceed through a zwitterionic intermediate in a formal [2+2]cycloaddition to a cyclobutene, then to a 1,3-thiazepine in an 4-electron electrocyclic ring openening and then to a 7-thia-2-azanorcaradiene in an 6-electron electrocyclic ring closing before extruding the sulfur atom.

Deprotonation is a chemistry term that refers to the removal of a proton (hydrogen ion H+) from a molecule, forming the conjugate base. ... An ylide is a neutral molecule with positive and negative charges on adjacent atoms. ... A Grignard Reagent is an alkyl- or aryl- magnesium halide. ... An organolithium compound is an organometallic compound containing a carbon-metal bond. ... Image File history File links Size of this preview: 800 × 114 pixel Image in higher resolution (929 × 132 pixel, file size: 3 KB, MIME type: image/png) Thiazole Deprotonation I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms... Chemical structure of Tetramethylsilane Chemical structure of a Trimethylsilyl group The name Tetramethylsilane stands for a chemical compound whose molecular structure is essentially like a silane (SiH4) molecule with four methyl groups substituted for the four hydrogen atoms in it. ... An aldehyde. ... An acyl halide (also known as an acid halide) is an organic compound containing a carbon atom which is double_bonded to an oxygen atom and singly bonded to a chlorine atom. ... Ketene is an organic compound with the formula CH2CO. Ketene is very reactive, tending to attach itself to other molecules in the form of an acetyl group. ... Alkylation is the transfer of an alkyl group from one molecule to another. ... Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, in an aromatic system is replaced by an electrophile. ... In organic chemistry, a functional group is called an activating group if a benzene molecule to which it is attached more readily participates in electrophilic substitution reactions. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Halogenation is a chemical reaction that replaces a hydrogen atom with a halogen atom. ... Image File history File links No higher resolution available. ... A nucleophilic substitution is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide on an aromatic ring. ... A electrofuge is a leaving group which does not retain the lone pair from its previous bond with another species. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... Image File history File links No higher resolution available. ... Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. ... General structure of an amine oxide An amine oxide, also known as amine-N-oxide and N-oxide, is a chemical compound that contains the functional group R3N+-O− (sometimes written as R3N=O or R3N→O). ... A peroxy acid, is an acid in which an acidic -OH group has been replaced by an -OOH group. ... Hypofluorous acid is the chemical compound with the formula HOF. It is an intermediate in the oxidation of water by fluorine, which affords HF and oxygen. ... Fluoride is the ionic form of fluorine. ... Acetonitrile is an organic molecule, often used as a solvent, with the chemical formula of CH3CN. Also known as methyl cyanide, it is the simplest of the organic nitriles. ... A sulfoxide is a chemical compound containing a sulfinyl functional group with a sulfur oxygen double bond attached to two carbon atoms. ... Image File history File links Size of this preview: 800 × 247 pixel Image in higher resolution (1057 × 327 pixel, file size: 7 KB, MIME type: image/png) Thiazole Oxidation I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms... In organic chemistry, formyl is the radical or functional group with the formula -COH and structure - C = O | H The formyl group is the acyl of formic acid and the chief functional group of aldehydes. ... A synthon is a concept in retrosynthetic analysis. ... Iodomethane, commonly called methyl iodide, is a dense volatile liquid. ... Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. ... Sodium borohydride, also known as sodium tetrahydroborate, has the chemical formula NaBH4. ... Hydrolysis is a chemical reaction or process in which a chemical compound reacts with water. ... Mercury chloride can refer to: Mercury_(II)_chloride (HgCl2) Mercury_(I)_chloride (Hg2Cl2) This is a disambiguation page — a navigational aid which lists other pages that might otherwise share the same title. ... A Cycloaddition is a pericyclic reaction in which the net result is loss of two pi bonds and gain of two sigma bonds. ... The Diels-Alder reaction The Diels-Alder reaction is an organic chemical reaction (specifically, a cycloaddition) between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system. ... Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms. ... Pyridine is a chemical compound with the formula C5H5N. It is a liquid with a distinctively putrid odour. ... An amino acid, in its (1) normal (unionized) and (2) zwitterionic forms. ... An electrocyclic reaction is a type of pericyclic rearrangement reaction where the net result is one pi bond being converted into one sigma bond. ... Image File history File links Size of this preview: 800 × 579 pixel Image in higher resolution (1050 × 760 pixel, file size: 17 KB, MIME type: image/png) Thiazole Cycloaddition I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms...

References

1. ^ The Chemistry of Heterocycles : Structure, Reactions, Syntheses, and Applications Theophil Eicher, Siegfried Hauptmann ISBN 3-527-30720-6
2. ^ 2,4-dimethylthiazole George Schwarz Organic Syntheses, Coll. Vol. 3, p.332 (1955); Vol. 25, p.35 (1945) Link
3. ^ ^{a b} On the [2+2] Cycloaddition of 2-Aminothiazoles and Dimethyl Acetylenedicarboxylate. Experimental and Computational Evidence of a Thermal Disrotatory Ring Opening of Fused Cyclobutenes Mateo Alajarín, José Cabrera, Aurelia Pastor, Pilar Sánchez-Andrada, and Delia Bautista J. Org. Chem.; 2006; 71(14) pp 5328 - 5339; (Article) DOI:10.1021/jo060664c
4. ^ ^{a b} Organic Syntheses, Coll. Vol. 9, p.52 (1998); Vol. 72, p.21 (1995). Article
5. ^ Easy access to the family of thiazole N-oxides using HOF·CH3CN Elizabeta Amir and Shlomo Rozen Chemical Communications, 2006, 2262 - 2264 DOI:10.1039/b602594c

Organic Syntheses is a scientific journal that Since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... The Journal of Organic Chemistry (abbreviated as ) is a scientific journal for original contributions of fundamental research in organic and bioorganic chemistry. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Organic Syntheses is a scientific journal that Since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Chemical Communications or ChemComm is a is a peer-reviewed scientific journal in the chemical sciences published since 1996 by the Royal Society of Chemistry. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...

External links

• Links to external chemical sources