10135-00-9

Usage

Uses

Used in Chemical Research:
3-Bromobenzothiophene-2-carboxaldehyde is used as a key intermediate in the synthesis of various complex chemical compounds for [application reason]. Its unique structure and functional groups make it a valuable building block in the development of new molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
3-Bromobenzothiophene-2-carboxaldehyde is used as a starting material or intermediate in the synthesis of pharmaceutical compounds for [application reason]. Its bromine atom and carboxaldehyde group can be further modified or functionalized to create novel drug candidates with potential therapeutic properties.
Used in Agrochemical Industry:
3-Bromobenzothiophene-2-carboxaldehyde is used as a precursor in the development of agrochemicals, such as pesticides and herbicides, for [application reason]. Its reactivity and structural features allow for the creation of new molecules with improved efficacy and selectivity in controlling pests and weeds.
Used in Material Science:
3-Bromobenzothiophene-2-carboxaldehyde is used as a component in the synthesis of advanced materials, such as polymers and coatings, for [application reason]. Its unique properties can contribute to the development of materials with enhanced performance characteristics, such as improved stability, durability, or specific functional properties.
Used in Dye and Pigment Industry:
3-Bromobenzothiophene-2-carboxaldehyde is used as a building block in the synthesis of dyes and pigments for [application reason]. Its structural features can lead to the development of new colorants with unique hues, improved lightfastness, or other desirable properties for various applications, such as textiles, plastics, or inks.

InChI:InChI=1/C9H5BrOS/c10-9-6-3-1-2-4-7(6)12-8(9)5-11/h1-5H

Upstream product

• 3541-37-5 benzothiophene-2-carboxaldehyde 
• 93-61-8 N-methyl-N-phenylformamide 
• 6287-82-7 2,3-dibromobenzo[b]thiophene 
• 68-12-2 N,N-dimethyl-formamide 
• 130-03-0 thioindoxyl 
• 95-15-8 Benzo[b]thiophene 
• 7342-82-7 3-Bromothianaphthene 
• 4394-85-8 4-morpholinecarboxaldehyde 

Downstream Products

• 124140-83-6 (3-bromo-benzo[b]thiophen-2-yl)-bis-(4-dimethylamino-phenyl)-methane 
• 100954-36-7 3-bromo-benzo[b]thiophene-2-carbaldehyde-phenylhydrazone 
• 29174-66-1 3-bromo-benzo[b]thiophene-2-carboxylic acid 
• 19722-96-4 3-phenylbenzo(b)thiophene-2-carboxaldehyde 
• 415717-55-4 3-(2-methylthiophenyl)benzo[b]thiophene-2-carbaldehyde 
• 912952-83-1 3-(2-formyl-phenyl)-benzo[b]thiophene-2-carbaldehyde 
• 272459-78-6 1-(3-phenylbenzo[b]thiophen-2-yl)ethan-1-one 
• 1210329-74-0 3-(4-tert-butylphenoxy)benzo[b]thiophene-2-carbaldehyde 
• 30126-05-7 thieno[3,2-b]-[1]benzothiophene-2-carboxylic acid 
• 247-52-9 benzo<4,5>thieno<3,2-b>thiophene 
• 1393176-58-3 3-o-tolylbenzo[b]thiophene-2-carbaldehyde 
• 1403583-75-4 6-(4-methoxyphenyl)benzo[4,5]imidazo[1,2-a]benzo[4,5]thieno[2,3-c]pyridine 
• 1403583-76-5 6-[4-(tert-butyl)phenyl]benzo[4,5]imidazo[2,1-a]benzo[4,5]thieno[2,3-c]pyridine 
• 1401716-02-6 3-((4-methoxyphenyl)ethynyl)benzo[b]thiophene-2-carbaldehyde 

Relevant academic research and scientific papers

Catalytic Deprotonative α-Formylation of Heteroarenes by an Amide Base Generated in Situ from Tetramethylammonium Fluoride and Tris(trimethylsilyl)amine

Heteroarene formylations in DMF solution proceed in the presence of an amide base catalyst generated in situ from tetramethylammonium fluoride (TMAF) and tris(trimethylsilyl)amine (N(TMS)3). The reaction proceeds at room temperature and has an operationally simple procedure. Various heteroarenes, including benzothiophene, thiophene, benzothiazole, oxazole, and indole derivatives, can be formylated with high functional group tolerance.

Aminobenzoannulated hetero- and carbocycles from 2-azahepta-2,4-dien-6- ynyllithium compounds: Scope and limitation of a novel benzoannulation reaction

Deprotonation of the N-benzylhetarylmethanimines 9, 12, 15, and 18 at -78°C with subsequent warming to room temperature over 16 hours and treatment with electrophiles furnished polysubstituted aminobenzoannulated heterocycles 19-25 in good to excellent yields. In a similar fashion, the deprotonation of the N-allyl-2-(alk-1-ynyl)phenylmethanimines 26 and 27 led to 2-vinylnaphthalen-1-amines 28 and 29, respectively, in moderate yields. The reaction of N-[(trimethylsilyl)methyl]imine 31 afforded naphthalen-1-amine 33, unsubstituted at the ortho position after removal of the trimethylsilyl group. The deprotonation of imine 34, bearing a trimethylsilyl group on the C≡C bond, gave none of expected amines, but the substituted imine 35, whose structure was identified using 2D NMR spectroscopy. Georg Thieme Verlag Stuttgart.

Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes

Upon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular with regard to the type of integrated (het)aryl moieties as well as the location of the formyl residue, and the probes' intrinsic reactivity with primary and secondary amines was optimized. Utilizing an ancillary base, the initially formed rearrangement product can engage in a subsequent catalytic cycle, leading to an amplified decoloration process. This additional catalytic pathway allows us to enhance the sensitivity of our method and successfully discriminate between amines and thiols. Moreover, probes that exhibit strong analyte-induced fluorescence modulation have been designed to further decrease the detection limit by using a more sensitive read-out. The optimized DAE probes are promising molecular components for future programmable sensing materials and devices.

ROBUST PHOTOCHROMIC COMPOUNDS WITH SILICON- OR PHOSPHORUS-CONTAINING HETEROCYCLIC RING AND PRODUCTION THEREOF

In one embodiment, provided are a new class of diarylethene-containing photochromic compounds with the incorporation of silicon-or phosphorus-containing heterocycles into the "ethene" part of the diarylethene backbone that has been shown to be capable of displaying tunable, robust and thermally stable photochromic properties. Also provided are methods for synthesizing these compounds, as well as uses of these compounds as these compounds may be used as the photochromic layer in an optical recording material and other optical functioning devices.

Naphtho[2,1-b:3,4-b′]bisthieno[3,2-b][1]benzothiophene-based semiconductors for organic field-effect transistors

A novel series of air-stable and highly extended π-conjugated naphtho[2,1-b:3,4-b′]bisthieno[3,2-b][1]benzothiophene derivatives, NBTBT-n (n = 6, 8, 10, and 12) and NBTBTF-10, was developed. The influence of various alkoxy-side groups including straight chain with different chain lengths and branched chain on the FET device performance was also investigated. There was a progressive enhancement in the NBTBT-based OFET device performance with an increase in the annealing temperature. The OFET devices based on NBTBT-10 fabricated by vacuum deposition exhibited the best performance with a hole mobility of 0.25 cm2 V-1 s-1 and an on/off ratio of 105-106 after annealing at 220 °C. In addition, fluorinated naphtho[2,1-b:3,4-b′]bisthieno[3,2-b][1]benzothiophene, NBTBTF-10, showed good p-type transistor behaviour with a hole mobility of 0.24 cm2 V-1 s-1 and an on/off ratio of 106-107 which was achieved at a lower annealing temperature of 140 °C, suggesting the important contribution of the dipole-dipole interactions induced by the fluorine atoms in the molecular packing. As a result, the naphtho[2,1-b:3,4-b′]bisthieno[3,2-b][1]benzothiophene framework shows promise as a useful building block to construct organic semiconductors for next-generation high performance organic electronics.

Directed metalation and regioselective functionalization of 3-bromofuran and related heterocycles with NaHMDS

A mild and regioselective functionalization protocol for 3-bromofuran and analogs has been developed. Selective metalation and functionalization of C2 can be achieved as a result of the directing effect of the adjacent electron-withdrawing bromo group. In addition, the C5 position can also be selectively functionalized by blocking the C2 position via silylation or by simply controlling the reaction temperature. These functionalized compounds bearing a C3 bromo substituent may be further elaborated by utilizing a Suzuki-Miyaura cross-coupling procedure.

Synthesis of novel 2-aminoimidazo[4,5-b]pyridines, including the thieno analogue of the cooked-food mutagen IFP

Eight new compounds, including three new ring systems obtained via the Friedlunder condensation of ortto-aminothiophenecarbaldehydes 11, 21 and 24 with creatinine (8), are reported. The condensation afforded 1, which is the thieno analogue of the cooked-food mutagen IFP (2-amino-1,6-dimethylfuro[2,3-e] imidazo[4,5-b]pyridine), and the benzothieno[2,3-e]- and benzothieno[3,2-e] imidazo[4,5-b]pyridines 2 and 3. Attempts to condense 11 with isocreatinine (12) were unsuccesful. Desulfurization of 3 gave the known cooked-food carcinogen PhIP, The 2-nitro (4) and 2-hydroxy (5) derivatives of 3 are reported. The related 2-amino-1-methyl-imidazo[4,5-b]benzothiophene (25) was synthesized by a different route. Fully assigned 1H and 13C nmr data of all new compounds are reported.

Palladium-catalyzed coupling reaction of 3-bromo benzo[b]furan, -thiophene and -selenophene 2-carboxaldehyde. Preparation of tetracyclic heteroaromatic derivatives

3-Oxo-2,3-dihydrobenzo[b]furans, -thiophenes and -selenophenes 1a-c afforded the bromo-aldehydes 2 under Vilsmeier-Haack-Arnold conditions. Palladium-catalysed aryl-aryl coupling of 2 with o-formyl-phenylboronic acid allowed the formation of dialdehydes 3 which underwent McMurry cyclisation or pinacol condensation to yield polycyclic aromatic derivatives 4 or the dihydroxylated compounds 5.

Synthesis of novel chiral thiophene-, benzothiophene- and benzofuran-oxazoline ligands and their use in the enantioselective Pd-catalyzed allylation

Novel thiophene, benzothiophene and benzofuran-oxazoline ligands 6-11 containing a diphenylphosphino group at different positions of the heterocyclic skeleton have been prepared and used in the enantioselective allylation. The advantage of these new ligands is their easy accessibility and their high reactivity. The best results were obtained with ligand 9 to give the product 13 in 97.0% ee with 92% yield in 2 hours at 0°C.