65449-59-4

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4-CHLORO-3-HYDROXYTHIOPHENE-2-CARBOXYLATE is used as a building block for the synthesis of various biologically active compounds, contributing to the development of new pharmaceutical agents.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, METHYL 4-CHLORO-3-HYDROXYTHIOPHENE-2-CARBOXYLATE is utilized as a key intermediate in the creation of agrochemicals, potentially enhancing crop protection and yield.
Used in Organic Synthesis:
METHYL 4-CHLORO-3-HYDROXYTHIOPHENE-2-CARBOXYLATE is employed as a valuable intermediate in organic synthesis, participating in a range of chemical reactions that facilitate the production of diverse organic compounds.

InChI:InChI=1/C6H5ClO3S/c1-10-6(9)5-4(8)3(7)2-11-5/h2,8H,1H3

Upstream product

• 5118-06-9 methyl 3-hydroxy-2-thiophenecarboxylate 
• 65449-58-3 2,4-dichloro-2-methoxycarbonyl-3-oxo-2,3-dihydrothiophene 

Relevant academic research and scientific papers

Regioselective and efficient halogenation of 4,5-unsubstituted alkyl 3-hydroxypyrrole/3-hydroxythiophene-2-yl-carboxylates

Substituted heterocycles, such as pyrrole and thiophene, are commonly found in the field of pharmaceutical and material sciences. Here we studied the reactivity of 4,5-unsubstituted alkyl 3-hydroxypyrrol-2-yl-carboxylates and 4,5-unsubstituted alkyl 3-hydroxythiophen-2-yl-carboxylates in different halogenation conditions, due to their interest as building blocks in the synthesis of bioactive compounds and materials. We describe herein the regioselective monohalogenation of 3-hydroxypyrroles and 3-hydroxythiophenes in mild conditions with common halogenation agents. The selectivity of the halogenation was studied. Optimized one-step reaction conditions were found for monobromination and monochlorination. Finally, we observed that bromination with N-bromosuccinimide (NBS) took place at the C4 position of the heterocycle, while chlorination with SO2Cl2 led to C5-halogenated derivatives.

Organic compounds and their use as pharmaceuticals

Compounds of the following formula have pharmacutical properties: STR1 in which R1 and R2 independently are hydrogen, halo, nitro, amino, C2-5 acylamino, C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, C1-4 alkylsulphonyl, N-substituted heterocyclyl, optionally substituted phenyl, optionally substituted phenylthio, optionally substituted phenylsulphonyl or optionally substituted phenylsulphonamido, or R1 and R2 together form a C3-5 alkylene bridge, R3 is C1-4 alkyl or C2-4 alkenyl, and X is (i) --(CH2)n N(R4)2 where each R4 independently is C1-4 alkyl, C2-4 alkenyl or optionally substituted C6 H5 CH2 --, and n is 1, 2 or 3, or (ii) a 5- to 8-membered alicyclic group containing one or two nitrogen atoms and directly attached to the amido nitrogen or attached by a C1-3 alkylene chain; and salts thereof.

Novel 11-desoxy-prostaglandin F2 derivatives

Novel 11-desoxy-prostaglandin F2 derivatives of the formula STR1 wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, an alkali metal, an equivalent of an alkaline earth metal, magnesium or organic amine base, R1 and R2 are individually seleced from the group consisting of hydrogen and methyl and X is selected from the group consisting of STR2 and a 5 to 6 membered heterocycle optionally substituted with at least one member of the group consisting of halogen, --CN and alkyl of 1 to 5 carbon atoms and X1 is a 6 member heterocycle with the wavy lines indicating that the hydroxy may be in either one of the two possible α and β positions having hypotensive activity and process for their preparation.