Thiophene-3-acetic acid

Last updated
Thiophene-3-acetic acid
3-Thiophene acetic acid.svg
Names
Preferred IUPAC name
(Thiophen-3-yl)acetic acid
Other names
3-TAA, Thiophen-3-yl-acetic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.027.424 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 230-166-1
PubChem CID
UNII
  • InChI=1S/C6H6O2S/c7-6(8)3-5-1-2-9-4-5/h1-2,4H,3H2,(H,7,8) Yes check.svgY
    Key: RCNOGGGBSSVMAS-UHFFFAOYSA-N Yes check.svgY
  • C1=CSC=C1CC(=O)O
Properties
C6H6O2S
Molar mass 142.18 g/mol
Appearancecolorless or white solid
Density 1.336 g/cm3
Melting point 79–80 °C (174–176 °F; 352–353 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Thiophene-3-acetic acid is an organosulfur compound with the formula HO2CCH2C4H3S. It is a white solid. It is one of two isomers of thiophene acetic acid, the other being thiophene-2-acetic acid.

Thiophene-3-acetic acid has attracted attention as a precursor to functionalized derivatives of polythiophene. [1]

Related Research Articles

Carboxylic acid Organic compound

A carboxylic acid is an organic acid that contains a carboxyl group (C(=O)OH) attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

Acetic acid bacteria (AAB) are a group of Gram-negative bacteria which oxidize sugars or ethanol and produce acetic acid during fermentation. The acetic acid bacteria consist of 10 genera in the family Acetobacteraceae. Several species of acetic acid bacteria are used in industry for production of certain foods and chemicals.

A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid donates a proton (H+) to a base—in other words, it is a base with a hydrogen ion added to it, as in the reverse reaction it loses a hydrogen ion. On the other hand, a conjugate base is what is left over after an acid has donated a proton during a chemical reaction. Hence, a conjugate base is a species formed by the removal of a proton from an acid, as in the reverse reaction it is able to gain a hydrogen ion. Because some acids are capable of releasing multiple protons, the conjugate base of an acid may itself be acidic.

Formic acid Chemical compound

Formic acid, systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula H2CO2. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. The word "formic" comes from the Latin word for ant, formica, referring to its early isolation by the distillation of ant bodies. Esters, salts, and the anion derived from formic acid are called formates. Industrially, formic acid is produced from methanol.

Acetate Chemical compound

An acetate is a salt formed by the combination of acetic acid with a base. "Acetate" also describes the conjugate base or ion typically found in aqueous solution and written with the chemical formula C
2
H
3
O
2
. The neutral molecules formed by the combination of the acetate ion and a positive ion are also commonly called "acetates". The simplest of these is hydrogen acetate with corresponding salts, esters, and the polyatomic anion CH
3
CO
2
, or CH
3
COO
.

Propionic acid Carboxylic acid with chemical formula CH3CH2CO2H

Propionic acid (, from the Greek words protos, meaning "first", and pion, meaning "fat"; also known as propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH3CH2CO2H. It is a liquid with a pungent and unpleasant smell somewhat resembling body odor. The anion CH3CH2CO2 as well as the salts and esters of propionic acid are known as propionates or propanoates.

Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reactions, it resembles benzene. Compounds analogous to thiophene include furan (C4H4O) selenophene (C4H4Se) and pyrrole (C4H4NH), which each vary by the heteroatom in the ring.

Polythiophene

Polythiophenes (PTs) are polymerized thiophenes, a sulfur heterocycle. The parent PT is an insoluble colored solid with the formula (C4H2S)n. The rings are linked through the 2- and 5-positions. Poly(alkylthiophene)s have alkyl substituents at the 3- or 4-position(s). They are also colored solids, but tend to be soluble in organic solvents.

Acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl functional group into a chemical compound. Such compounds are termed acetate esters or acetates. Deacetylation is the opposite reaction, the removal of an acetyl group from a chemical compound.

Acetic anhydride Chemical compound

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

Sodium acetate Chemical compound

Sodium acetate, NaCH3COO, also abbreviated NaOAc, is the sodium salt of acetic acid. This colorless deliquescent salt has a wide range of uses.

Acetyl chloride Chemical compound

Acetyl chloride (CH3COCl) is an acyl chloride derived from acetic acid. It belongs to the class of organic compounds called acyl halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl.

Organic acid anhydride Any chemical compound having two acyl groups bonded to the same oxygen atom

An organic acid anhydride is an acid anhydride that is an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O))2O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. Thus, (CH3CO)2O is called acetic anhydride. Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride (see below), are known, whereby reaction occurs between two different carboxylic acids. Nomenclature of unsymmetrical acid anhydrides list the names of both of the reacted carboxylic acids before the word "anhydride" (for example, the dehydration reaction between benzoic acid and propanoic acid would yield "benzoic propanoic anhydride").

Fluorosulfuric acid (IUPAC name: sulfurofluoridic acid) is the inorganic compound with the chemical formula HSO3F. It is one of the strongest acids commercially available. The formula HSO3F emphasizes its relationship to sulfuric acid, H2SO4; HSO3F is a tetrahedral molecule. It is a colourless liquid, although commercial samples are often yellow.

Ammonium acetate, also known as spirit of Mindererus in aqueous solution, is a chemical compound with the formula NH4CH3CO2. It is a white, hygroscopic solid and can be derived from the reaction of ammonia and acetic acid. It is available commercially.

Cefalotin

Cefalotin (INN) or cephalothin (USAN) is a first-generation cephalosporin antibiotic. It was the first cephalosporin marketed (1964) and continues to be widely used. It is an intravenously administered agent with a similar antimicrobial spectrum to cefazolin and the oral agent cefalexin. Cefalotin sodium is marketed as Keflin (Lilly) and under other trade names.

Acetic acid Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH (also written as CH3CO2H, C2H4O2, or HC2H3O2). Vinegar is no less than 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements.

The molecular formula C6H6O2S (molar mass: 142.18 g/mol, exact mass: 142.0089 u) may refer to:

2-Acetylthiophene Chemical compound

2-Acetylthiophene is an organosulfur compound with the formula CH3C(O)C4H3S. A yellow liquid, it is the more useful of the two isomers of acetylthiophene. It is of commercial interest as a precursor to both thiophene-2-carboxylic acid and thiophene-2-acetic acid. It is prepared by the reaction of thiophene with acetyl chloride in the presence of stannic chloride.

Thiophene-2-acetic acid Chemical compound

Thiophene-2-acetic acid is the organosulfur compound with the formula HO2CCH2C4H3S. Together with thiophene-3-acetic acid, it is one of two isomeric thiophene acetic acids.

References

  1. Huo, Haohua; Shen, Xiaodong; Wang, Chuanyong; et al. (2014). "Asymmetric photoredox transition-metal catalysis activated by visible light". Nature. 515 (7525): 100–103. Bibcode:2014Natur.515..100H. doi:10.1038/nature13892. PMID   25373679. S2CID   4456239.