1860-99-7

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 13, p. 1099, 1976 DOI: 10.1002/jhet.5570130534

Upstream product

• 3199-44-8 3-formylthiophene diethyl acetal 
• 40032-76-6 2-bromo-3-(bromomethyl)thiophene 
• 13250-82-3 2-(thiophen-3-yl)-1,3-dioxolane 
• 24287-92-1 2-Bromo-3-iodothiophene 
• 68-12-2 N,N-dimethyl-formamide 
• 14282-76-9 2-bromo-3-methylthiophene 
• 70260-16-1 2-bromo-3-hydroxymethylthiophene 
• 616-44-4 3-Methylthiophene 

Downstream Products

• 111796-49-7 (2-bromo-[3]thienyl)-bis-(4-dimethylamino-phenyl)-methane 
• 24287-95-4 2-bromothiophene-3-carboxylic acid 
• 632325-55-4 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-carbaldehyde 
• 1605347-20-3 B-mesityl-dithieno[2,3-b:3',2'-f]borepin 
• 1605347-22-5 C₁₉H₁₆BBrS₂ 
• 1605347-24-7 C₁₉H₁₅⁽²⁾H₂BS₂ 
• 1605347-25-8 C₁₉H₁₅BBr₂S₂ 
• 1605347-27-0 C₄₃H₆₉BS₂Sn₂ 
• 1605347-29-2 C₂₁H₁₇BO₂S₂ 
• 1605347-31-6 C₃₉H₃₅BN₂S₂ 
• 1605347-33-8 C₃₃H₂₃BN₂S₂ 
• 1605347-35-0 C₄₁H₄₃BN₂S₂ 

Relevant academic research and scientific papers

A study on regulating the conjugate position of NLO chromophores for reducing the dipole moment and enhancing the electro-optic activities of organic materials

In order to improve the first-order hyperpolarizability (β) of the chromophore and transform it into a high macroscopic electro-optic activity, a series of novel second-order nonlinear optical chromophores with different push-pull electron groups introduced on the thiophene π-conjugate bridge for tuning the shape and dipole moment (μ) of chromophores were designed and synthesized. These chromophores are based on the same thiophene π-conjugated bridge, where the donor (N,N-diethylaniline) and acceptor (2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile or malononitrile) are linked to positions 2 and 3 of thiophene, respectively, affording a boomerang-like shape instead of a rod-like shape. Besides, an electron-poor group, Br (bromine atom), or an electron-rich group, DEA (N,N-diethylaniline), as an auxiliary acceptor or donor are linked to position 5 of thiophene. In addition, all chromophores showed good thermal stability as per the results from the DSC and TGA analysis. Through UV-vis analysis and DFT calculation, it has been concluded that chromophores with additional electron-rich groups as auxiliary donors display better intermolecular charge-transfer (ICT) absorption and lower HOMO-LUMO energy gaps (ΔE). Furthermore, the boomerang-like chromophore with the same push-pull structure shows a smaller dipole moment (μ) and β value than the traditional FTC. The poling results of guest-host EO polymers FTC/APC, FTC-H/APC, FTC-Br/APC and FTC-DEA/APC with the same number density afford r33 values of 17 pm V-1, 11 pm V-1, 10 pm V-1 and 25 pm V-1, respectively. Although the β value of FTC-DEA is smaller than that of FTC, the r33 value of FTC-DEA (25 pm V-1) is 47% greater than that of FTC (17 pm V-1) under the same number density. Hence, the above-mentioned results indicated that regulating the conjugate position of chromophores can efficiently decrease the dipole moment of the chromophores, weakening the dipole-dipole interactions and thereby enhancing the macroscopic electro-optical activity of poled polymers. These results indicate the potential application of these novel chromophores in electro-optical devices.

A 2 - bromo - 3 - thiophene carboxylic acid intermediates of the synthesis method (by machine translation)

The invention relates to 2 - bromo - 3 - thiophenecarboxylic acid synthesis method, comprises the following synthetic steps: 1): by 3 - methyl thiophene as raw materials, adding N - bromosuccinimide synthesis of 2 - bromo - 3 methyl thiophene; 2): by the 2 - bromo - 3 methyl thiophene to carbon tetrachloride as solvent, azobisisobutyronitrile as initiator with the N - bromosuccinimide synthesis of 2 - bromo - 3 - (bromomethyl) thiophene; 3): by the 2 - bromo - 3 - (bromomethyl) thiophene is 2 - iodo acyl benzoic acid oxidation to obtain 2 - bromo - 3 - thiophene formaldehyde; 4): by the 2 - bromo - 3 - thiophene formaldehyde sodium hydroxide aqueous solution as the solvent, is potassium permanganate oxidation to obtain 2 - bromo - 3 - thiophenecarboxylic acid. The invention has the advantages of: this invention uses the first to 2 of bit bromine substituted, then 3 of the oxidation of the synthetic route, mild reaction conditions, reactants are cheap and easily obtained, the yield is high. 2nd, greatly inhibit the double-bromo product, increasing the yield. (by machine translation)

Domino Direct Arylation and Cross-Aldol for Rapid Construction of Extended Polycyclic π-Scaffolds

Five-membered aromatic heterocycles are a ubiquitous skeleton of π-conjugated organic compounds, and their incorporation requires synthetic protocols that are not easily industrially sustainable or scalable. Improved methodologies for their insertion into π-scaffolds are therefore necessary. We report an efficient and scalable protocol involving a one-pot cross-Aldol direct arylation reaction protocol for the rapid construction of thiophene- and furan-based π-extended organic materials.

Preparation and regioselective magnesiation or lithiation of bis(trimethylsilyl)methyl-substituted heteroaryls for the generation of highly functionalized heterocycles

A wide range of bis(trimethylsilyl)methyl (BTSM)- substituted heteroaryl derivatives has been prepared by using Kumada-Corriu or Negishi cross-coupling reactions. The regioselective lithiation or magnesiation of these building blocks bearing a bulky BTSM

Thiophene-fused borepins as directly functionalizable boron-containing π-electron systems

Synthetic protocols were developed for the gram-scale preparation of two isomeric dithienoborepins (DTBs), boron-containing polycyclic aromatics featuring the fusion of borepin and thiophene rings. DTBs exhibit reversible cathodic electrochemistry and boron-centered Lewis acidity in addition to enhanced electronic delocalization relative to benzo-fused analogues. Borons precise position within the conjugation pathway of DTBs significantly affected electronic structure, most clearly demonstrated by the variation in spectroscopic responses of each isomer to fluoride ion binding. In addition to excellent stability in the presence of air and moisture, DTBs could also be subjected to electrophilic aromatic substitution and metalation chemistry, the latter enabling the direct, regiospecific functionalization of the unsubstituted thiophene rings. Subsequent tuning of molecular properties was achieved through installation of donor and acceptor π-substituents, leading to compounds featuring multistep electrochemical reductions and polarizable electronic structures. As rare examples of directly functionalizable, π-conjugated, boron-containing polycyclic aromatics, DTBs are promising building blocks for the next generation of organoboron π-electron materials whose development will demand broad scope for molecular diversification in addition to chemical robustness.

MULTICYCLIC COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are multicyclic compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.

Selective metallation of 3-halothiophenes: Practical methods for the synthesis of 2-bromo-3-formylthiophene

Selective lithiation of 3-bromothiophene was accomplished under controlled conditions without formation of undesired thienyllithium compounds. A thienyl Grignard reagent derived from 2-bromo-3-iodothiophene was transformed into 2-bromo-3-formylthiophene in high selectivity by formylation with dimethylformamide (DMF) at optimal reaction temperature. Copyright Taylor & Francis Group, LLC.

Interheteroaryl 7-oxabicyclic [2.2.1]heptane oxazoles as prostaglandin F2α antagonists

The present invention provides novel compounds represented by the general formula I. wherein m, n, X, Y, Z, R, R1and R2are as defined in the specification or a pharmaceutically acceptable salt thereof. The novel compounds are PGF2αantagonists, useful in pharmaceutical compositions for treating PGF2α-mediated disease responses such as inflammatory reactions relating to rheumatoid arthritis and psoriasis, reproductive disorders, bronchoconstrictive disorders (asthma), excessive bone breakdown (osteoporosis), peptic ulcers, heart disease, platelet aggregation and thrombosis.

Synthesis of 2,3-Substituted Thienylboronic Acids and Esters

A noncryogenic protocol for the synthesis of 2-substituted 3-thienylboronic acids and esters as well as 3-substituted 2-thienylboronic acids and esters has been developed. Electrophiles were introduced regiospecifically in the 2-position of 2,3-dibromothiophene and in the 3-position of 2-bromo-3-iodothiophene by halogen-magnesium exchange followed by quenching with electrophiles. Palladium-catalyzed borylation of the 2,3-substituted halothiophenes with pinacolborane and P(t-Bu)3 as ligand for Pd produced 9 and 10. The borylation protocol was tolerated by a range of functional groups; however, strongly electron-withdrawing substituents decreased the stability of the thienylboronic acids and esters.

Interheteroaryl 7-oxabicyclic [2.2.1]heptane oxazoles as prostaglandin F2α antagonists

The present invention provides novel compounds represented by the general formula I. wherein m is an integer of from 1 to 3; n is 0 or an integer of from 1 to 4; R is selected from the group consisting of CO2H, CO2R6, CH2OH, CH2O R6P(O)(OH)2, ?and CONR3R4; R1and R2are independently selected from the group consisting of H, R6, C1-C6alkenyl, C1-C6alkynyl, C3-C7cycloalkyl, C4-C12alkylcycloalkyl, C6-C10aryl, C7-C12alkyl aryl radicals and heteroatom-substituted derivatives thereof, wherein one or more of the hydrogen or carbon atoms in said radicals is replaced with a halogen, nitrogen or sulfur-containing radical; R3and R4are selected from the group consisting of H and R6; and X is selected from the group consisting of H, R6, hydroxy, N(R6)2, CON(R6)2, SR6, sulfoxy, sulfone, halogen, COOR6, NO2, CN and OR6, wherein R6is C1-C6alkyl; Y is O or S; Z is N or CH and pharmaceutically acceptable salts thereof. The novel compounds are PGF2αantagonists, useful in pharmaceutical compositions for treating PGF2α-mediated disease responses such as inflammatory reactions relating to rheumatoid arthritis and psoriasis, reproductive disorders, bronchoconstrictive disorders (asthma), excessive bone breakdown (osteoporosis), peptic ulcers, heart disease, platelet aggregation and thrombosis.