1128-05-8

Usage

Chemical Properties

yellow crystalline powder

Safety Profile

A poison by parenteral route. A flammable liquid. When heated to decomposition it emits toxic vapors of SOx.

InChI:InChI=1/C10H8OS/c1-7(11)9-6-12-10-5-3-2-4-8(9)10/h2-6H,1H3

Upstream product

• 24434-84-2 benzo[b]thiophene-3-carbonitrile 
• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 39827-12-8 benzothiophene-3-carbonyl chloride 
• 506-82-1 dimethylcadmium 
• 108-24-7 acetic anhydride 
• 95-15-8 Benzo[b]thiophene 
• 75-36-5 acetyl chloride 
• 7342-82-7 3-Bromothianaphthene 
• 127-19-5 N,N-dimethyl acetamide 
• 36748-88-6 3-iodobenzo[b]thiophene 
• 86119-84-8 phosphoric acid 
• 7553-56-2 iodine 
• 7705-08-0 iron(III) chloride 

Downstream Products

• 61-40-5 1-benzo[b]thiophen-3-yl-3-dimethylamino-propan-1-one; hydrochloride 
• 362-57-2 1-benzo[b]thiophen-3-yl-2H,2H-heptafluoro-hexane-1,3-dione 
• 109562-19-8 1-benzo[b]thiophen-3-yl-ethanon-[(N-acetyl-sulfanilyl)-hydrazone] 
• 26167-44-2 3-Chloroacetylbenzo-[b]thiophene 
• 26167-45-3 3-bromoacetylbenzo[b]thiophene 
• 392-29-0 1-(3-benzo{b}thienyl)-4,4,4-trifluoro-1,3-butanedione 
• 7146-33-0 3,4-bis(benzo[b]thien-3-oyl)-1,2,5-oxadiazole-N-oxide 
• 94541-39-6 3-(1-phenyl-1-propen-2-yl)benzothiophene 
• 769-59-5 3-phenyl-butan-2-one 
• 219907-62-7 1-(benzo[b]thiophen-3-yl)-3-[4-(2-methoxyphenyl)piperazin-1-yl]propan-1-one 

Relevant academic research and scientific papers

Site-Specific Oxidation of (sp3)C-C(sp3)/H Bonds by NaNO2/HCl

A site-specific oxidation of (sp3)C-C(sp3) and (sp3)C-H bonds in aryl alkanes by the use of NaNO2/HCl was explored. The method is chemical-oxidant-free, transition-metal-free, uses water as the solvent, and proceeds under mild conditions, making it valuable and attractive to synthetic organic chemistry.

Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream

We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.

Metal Sulfonate Polymers as Catalysts for the Heterogeneous Acylation of Aromatic Derivatives

A series of metal sulfonate salts attached to a poly(ether ether ketone) (PEEK) polymer were prepared by ultrasonic activation and then examined as heterogeneous catalysts in the Friedel–Crafts acylation of aromatic derivatives.

BENZOTHIOPHENE ALKANOL PIPERAZINE DERIVATIVES AND THEIR USE AS ANTIDEPRESSANT

The invention discloses benzothiophene alkanol piperazine derivatives and their use as antidepressants. The invention discloses the said benzothiophene alkanol piperazine derivative having triple inhibition effect on the reuptake of 5-HT, NA and DA. Compared with clinical used antidepressants so far having single target, e.g. desipramine and fluoxetine, and clinical used antidepressants so far having double targets, e.g venlafaxine and duloxetine, the said benzothiophene alkanol piperazine derivatives of the present invention may have a broader indication range and less toxic and side effects to nervous system. The benzothiophene alkanol piperazine derivatives are the compounds with the following formula or their pharmaceutically acceptable salts, wherein Ar1, R1-R4, X, Y, m and n have the same definition as defined in claim 1.

Chemoenzymatic synthesis of (R)- and (S)-1-heteroarylethanols

A chemoenzymatic methodology for the synthesis of highly enantiomerically enriched (S)- and (R)-1-heteroarylethanols by enantioselective bioreduction with baker's yeast of the corresponding 1-heteroarylethanones followed by three racemization free chemical steps including a Mitsunobu reaction was developed.

Chiral helicenoid diarylethene with large change in specific optical rotation by photochromism

A diarylethene possessing one [4]thiaheterohelicene and one benzothiophene, the latter with a chiral methoxymethoxyethyl group on its C-3 position, was proved to work as a switch of specific optical rotation at a wavelength at which both colored and colorless forms have no absorption in solution. The difference of the specific optical rotation was 1300° between the open form and the photostationary state. The specific optical rotation of one of the isolated optically active major colored forms was -4680°. The conversion to the colored form was 64%, and the diastereomeric excess of photocyclization was 47%.

Synthesis and biological activity of various derivatives of a novel class of potent, selective, and orally active prostaglandin D2 receptor antagonists. 2. 6,6-dimethylbicyclo[3.1.1]heptane derivatives

In an earlier paper, we reported that novel prostaglandin D2 (PGD2) receptor antagonists having the bicyclo[2.2.1]heptane ring system as a prostaglandin skeleton were a potent new class of antiallergic agents and suppressed various allergic inflammatory responses such as those observed in conjunctivitis and asthma models. In the present study, we synthesized PGD2 receptor antagonists having the 6,6-dimethylbicyclo [3.1.1]heptane ring system. These derivatives have the amide moiety, in contrast to those with the bicyclo[2.2.1]heptane ring system, which have the sulfonamide group. The derivatives having the 6,6-dimethylbicyclo[3.1.1]heptane ring also exhibited strong activity in PGD2 receptor binding and cAMP formation assays. In in vivo assays such as allergic rhinitis, conjunctivitis, and asthma models, these series of derivatives showed excellent pharmacological profiles. In particular, compound 45 also effectively suppressed eosinophil infiltration in allergic rhinitis and asthma models. This compound (45, S-5751) is now being developed as a promising alternative antiallergic drug candidate.

Photocycloaddition of Two Captodative Alkenes to 3-Acetylthianaphthene

Photoexcited 3-acetylbenzothiophene (1c) adds 2-morpholinopropenenitrile (2a) in a mode at the C-2-C-3 bond regioselectively but stereounselectively with formation of cyclobutabenzothiophenes 3a and 4a.In addition, the isomeric adduct 5 is formed from 2a and excited 2-acetylbenzothiophene (1b) accompanying 1c as an impurity.Similarly, 2-(tert-butylthio)propenenitrile (2b) undergoes a smooth and highly regioselective but stereounselective photoaddition to 1c yielding a mixture of two isomeric adducts from which compound 3b may be separated by recrystallization.The configuration of 5 was unambiguously confirmed by an X-ray crystal structure analysis.The structures of the other cycloadducts were derived by a comparison of their 1H-NMR spectral data with those of closely related substances from other work. - Keywords: Cyclobutabenzothiophenes; Direction of cycloaddition; X-ray crystal structure analysis

Indole, benzofuran, benzothiophene containing lipoxygenase inhibiting compounds

Compounds of the formula: STR1 wherein R1 is (1) hydrogen, (2) C1 to C4 alkyl, (3) C2 to C4 alkenyl, or (4) NR2 R3, wherein R2 and R3 are independently selected from (1) hydrogen, (2) C1 to C4 alkyl and (3) hydroxyl, but R2 and R3 are not simultaneously hydroxyl; wherein X is oxygen, sulfur, SO2, or NR4, wherein R4 is (1) hydrogen, (2) C1 to C6 alkyl, (3) C1 to C6 alkoyl, (4) aroyl, or (5) alkylsulfonyl; A is selected from C1 to C6 alkylene and C2 to C6 alkenylene; n is 1-5; Y is selected independently at each occurrence from (1) hydrogen, (2) halogen, (3) hydroxy, (4) cyano, (5) halosubstituted alkyl, (6) C1 to C12 alkyl, (7) C2 to C12 alkenyl, (8) C1 to C12 alkoxy, (9) C3 to C8 cycloalkyl, (10) C1 -C8 thioalkyl, (11) aryl, (12) aryloxy, (13) aroyl, (14) C1 to C12 arylalkyl, (15) C2 to C12 arylalkenyl, (16) C1 to C12 arylalkoxy, (17) C1 to C12 arylthioalkoxy, and substituted derivatives of (18) aryl, (19) aryloxy, (20) aroyl, (21) C1 to C12 arylalkyl, (22) C2 to C12 arylalkenyl, (23) C1 to C12 arylalkoxy, or (24) C1 to C12 arylthioalkoxy, wherein substituents are selected from halo, nitro, cyano, C1 to C12 alkyl, alkoxy, and halosubstituted alkyl; Z is oxygen or sulfur; and M is hydrogen, a pharmaceutically acceptable cation, aroyl, or C1 to C12 alkoyl, are potent inhibitors of 5- and/or 12-lipoxygenase enzymes. Also disclosed are lipoxygenase inhibiting compositions and a method for inhibiting lipoxygenase activity.