Thioxanthone

Last updated
Thioxanthone
9H-thioxanthen-9-one 200.svg
Names
Preferred IUPAC name
9H-Thioxanthen-9-one
Other names
Thioxanthenone; 9-Oxothioxanthene; Thioxanthen-9-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.046 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-749-4
PubChem CID
UNII
  • InChI=1S/C13H8OS/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H COPY
    Key: YRHRIQCWCFGUEQ-UHFFFAOYSA-N
  • c1ccc2c(c1)c(=O)c3ccccc3s2
Properties
C13H8OS
Molar mass 212.27 g·mol−1
AppearancePale yellow solid [1]
Melting point 211 °C (412 °F; 484 K) [2]
Boiling point 273 °C (523 °F; 546 K) [2] (940 hPa)
Nearly insoluble
Solubility in sulfuric acidSoluble [2]
-130·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Thioxanthone is a heterocyclic compound that is a sulfur analog of xanthone.

Thioxanthone can be prepared by the reaction of diphenyl sulfide with phosgene in the presence of catalytic aluminium chloride. [2] This synthesis can be seen as a special case of the Friedel-Crafts acylation. The reduction product is thioxanthene.

Thioxanthone dissolves in concentrated sulfuric acid to give a yellow colored liquid with intense green fluorescence. A mixture of the thioxanthone derivatives of 2- and 4-isopropylthioxanthone (ITX) is used in the printing industry. Pharmaceutical drugs that are derivatives of thioxanthone include hycanthone and lucanthone.

Related Research Articles

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A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles.

Sulfur Chemical element, symbol S and atomic number 16

Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula S8. Elemental sulfur is a bright yellow, crystalline solid at room temperature.

Sulfate Oxyanion with a central atom of sulfur surrounded by 4 oxygen atoms

The sulfate or sulphate ion is a polyatomic anion with the empirical formula SO2−
4
. Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salts of sulfuric acid and many are prepared from that acid.

Sulfide (organic)

An organic sulfide or thioether is a functional group in organosulfur chemistry with the connectivity C–S–C as shown on right. Like many other sulfur-containing compounds, volatile sulfides have foul odors. A sulfide is similar to an ether except that it contains a sulfur atom in place of the oxygen. The grouping of oxygen and sulfur in the periodic table suggests that the chemical properties of ethers and sulfides are somewhat similar, though the extent to which this is true in practice varies depending on the application.

Sulfur dyes are the most commonly used dyes manufactured for cotton in terms of volume. They are inexpensive, generally have good wash-fastness, and are easy to apply. Sulfur dyes are predominantly black, brown, and dark blue. Red sulfur dyes are unknown, although a pink or lighter scarlet color is available.

Thiazole, or 1,3-thiazole, is a 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).

Sulfonic acid

A sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound (with the organic substituent replaced by hydrogen) is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

Thionyl chloride Chemical compound

Thionyl chloride is an inorganic compound with the chemical formula SOCl
2
. It is a moderately volatile colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons.

Benzothiazole Chemical compound

Benzothiazole is an aromatic heterocyclic compound with the chemical formula C
7
H
5
NS
. It is colorless, slightly viscous liquid. Although the parent compound, benzothiazole is not widely used, many of its derivatives are found in commercial products or in nature. Firefly luciferin can be considered a derivative of benzothiazole.

Sulfoxide

A sulfoxide is a chemical compound containing a sulfinyl (SO) functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are the oxidized derivatives of sulfides. Examples of important sulfoxides are alliin, a precursor to the compound that gives freshly crushed garlic its aroma, and dimethyl sulfoxide (DMSO), a common solvent.

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Thionyl fluoride Chemical compound

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2
. This colourless gas is mainly of theoretical interest, but it is a product of the degradation of sulfur hexafluoride, an insulator in electrical equipment. The molecule adopts a distorted pyramidal structure, with Cs symmetry. The S-O and S-F distances are 1.42 and 1.58 Å, respectively. The O-S-F and F-S-F angles are 106.2 and 92.2°, respectively. Thionyl chloride and thionyl bromide have similar structures, although these compounds are liquid at room temperature. Mixed halides are also known, such as SOClF, thionyl chloride fluoride.

Chlorosulfuric acid Chemical compound

Chlorosulfuric acid (IUPAC name: sulfurochloridic acid) is the inorganic compound with the formula HSO3Cl. It is also known as chlorosulfonic acid, being the sulfonic acid of chlorine. It is a distillable, colorless liquid which is hygroscopic and a powerful lachrymator. Commercial samples usually are pale brown or straw colored.

Sulfur tetrafluoride Chemical compound

Sulfur tetrafluoride is the chemical compound with the formula SF4. It is a colorless corrosive gas that releases dangerous HF upon exposure to water or moisture. Despite these unwelcome characteristics, this compound is a useful reagent for the preparation of organofluorine compounds, some of which are important in the pharmaceutical and specialty chemical industries.

Sulfinic acid

Sulfinic acids are oxoacids of sulfur with the structure RSO(OH). In these organosulfur compounds, sulfur is pyramidal.

1-Naphthylamine Chemical compound

1-Naphthylamine is an aromatic amine derived from naphthalene. It can cause bladder cancer. It crystallizes in colorless needles which melt at 50 °C. It possesses a disagreeable odor, sublimes readily, and turns brown on exposure to air. It is the precursor to a variety of dyes.

Oxon (chemical)

An oxon is an organic compound derived from another chemical in which a phosphorus-sulfur bond in the parent chemical has been replaced by a phosphorus-oxygen bond in the derivative.

Antimony pentasulfide is an inorganic compound of antimony and sulfur, also known as antimony red. It is a nonstoichiometric compound with a variable composition. Its structure is unknown. Commercial samples are usually contaminated with sulfur, which may be removed by washing with carbon disulfide in a Soxhlet extractor.

Ammonium bisulfate Chemical compound

Ammonium bisulfate, also known as ammonium hydrogen sulfate, is a white, crystalline solid with the formula (NH4)HSO4. This salt is the product of the half-neutralization of sulfuric acid by ammonia.

Nereistoxin Chemical compound

Nereistoxin is a natural product identified in 1962 as the toxic organic compound N,N-dimethyl-1,2-dithiolan-4-amine. It had first been isolated in 1934 from the marine annelid Lumbriconereis heteropoda and acts by blocking the nicotinic acetylcholine receptor. Researchers at Takeda in Japan investigated it as a possible insecticide. They subsequently developed a number of derivatives that were commercialised, including those with the ISO common names bensultap, cartap, thiocyclam and thiosultap.

References