31936-92-2

Basic information

• Product Name: dithiophen-3-ylmethanol
• Synonyms: Di(3-thienyl)methanol
• CAS NO: 31936-92-2
• Molecular Formula: C₉H₈OS₂
• Molecular Weight: 196.2892
• Mol File: 31936-92-2.mol

Chemical Properties

• Boiling Point: 358.4°C at 760 mmHg
• Flash Point: 170.6°C
• Density: 1.344g/cm³
• Vapor Pressure: 9.23E-06mmHg at 25°C
• Refractive Index: 1.659
• CAS DataBase Reference: dithiophen-3-ylmethanol(CAS DataBase Reference)
• NIST Chemistry Reference: dithiophen-3-ylmethanol(31936-92-2)
• EPA Substance Registry System: dithiophen-3-ylmethanol(31936-92-2)

Safety Data

• Hazardous Substances Data: 31936-92-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Dithiophen-3-ylmethanol is used as a reagent in organic synthesis for its ability to form metal complexes, making it a versatile compound for a wide range of applications in industry and research.
Used in Pharmaceutical and Agrochemical Production:
Dithiophen-3-ylmethanol is used as a building block for the production of various pharmaceuticals and agrochemicals, contributing to the development of new and effective products in these industries.
Used in Mining Industry:
Dithiophen-3-ylmethanol is used as a flotation agent in the mining industry to separate valuable minerals from gangue materials, improving the efficiency and effectiveness of mineral extraction processes.
It is important to handle dithiophen-3-ylmethanol with care, as it may be irritating to the skin and eyes, and can be harmful if ingested or inhaled.

Upstream product

• 1192-06-9 3-thienyl lithium 
• 498-62-4 3-thiophene carboxaldehyde 
• 872-31-1 3-Bromothiophene 
• 109-94-4 formic acid ethyl ester 
• 107-31-3 Methyl formate 
• 98-03-3 thiophene-2-carbaldehyde 

Downstream Products

• 26453-81-6 di(thiophen-3-yl)methanone 
• 920515-35-1 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,4-di(2-ethylhexyl)-4H-cyclopenta-[2,1-b:3,4-b']dithiophene 
• 1315276-46-0 6-[4-(diphenylamino)phenyl]-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene-2-carbaldehyde 
• 153312-86-8 4,4-dihexyl-4H-cyclopenta[1,2-b:5,4-b’]dithiophene 
• 1221821-39-1 6-bromo-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene-2-carbaldehyde 
• 474416-61-0 bis(2-iodo-3-thienyl)methanone 
• 365547-21-3 2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene 
• 25796-77-4 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one 
• 365547-20-2 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene 
• 389-58-2 4H-cyclopenta[2,1-b;3,4-b']dithiophene 

Relevant articles and documents

Efficient One-Pot Synthesis of Dithieno(dibenzothieno)-Fused Cycloheptanones, Tropones, and Cyclooctanones

The reactions of α,β-unsaturated amide/triflic anhydride complexes (generated in situ from the corresponding amides and triflic anhydride) with dithiophenes and dithienylmethanes proceed as tandem alkylation-Vilsmeier-Haack acylation to form dithieno- and dibenzothieno-fused cycloheptanones and cyclooctanones in moderate to good yields. The reactions of 2-bromo-N,N-dimethylacrylamide/triflic anhydride complex allow preparation of tropones in a simple one-pot procedure. The reaction of 2,2-dibenzothienylmethane with dimethylacrylamide/triflic anhydride complex proceeds unusually to afford dimethylaminonaphthalene in addition to the predictable fused cyclooctanone.

Atomistic band gap engineering in donor-acceptor polymers

We have synthesized a series of cyclopentadithiophene- benzochalcogenodiazole donor-acceptor (D-A) copolymers, wherein a single atom in the benzochalcogenodiazole unit is varied from sulfur to selenium to tellurium, which allows us to explicitly study sulfur to selenium to tellurium substitution in D-A copolymers for the first time. The synthesis of S- and Se-containing polymers is straightforward; however, Te-containing polymers must be prepared by postpolymerization single atom substitution. All of the polymers have the representative dual-band optical absorption profile, consisting of both a low- and high-energy optical transition. Optical spectroscopy reveals that heavy atom substitution leads to a red-shift in the low-energy transition, while the high-energy band remains relatively constant in energy. The red-shift in the low-energy transition leads to optical band gap values of 1.59, 1.46, and 1.06 eV for the S-, Se-, and Te-containing polymers, respectively. Additionally, the strength of the low-energy band decreases, while the high-energy band remains constant. These trends cannot be explained by the present D and A theory where optical properties are governed exclusively by the strength of D and A units. A series of optical spectroscopy experiments, solvatochromism studies, density functional theory (DFT) calculations, and time-dependent DFT calculations are used to understand these trends. The red-shift in low-energy absorption is likely due to both a decrease in ionization potential and an increase in bond length and decrease in acceptor aromaticity. The loss of intensity of the low-energy band is likely the result of a loss of electronegativity and the acceptor unit's ability to separate charge. Overall, in addition to the established theory that difference in electron density of the D and A units controls the band gap, single atom substitution at key positions can be used to control the band gap of D-A copolymers.

Synthesis and anticancer activity of di(3-thienyl)methanol and di(3-thienyl)methane

Di(3-thienyl)methanol (2) and di(3-thienyl)methane (3) have been synthesized and screened against the T98G (brain cancer) cell line. Treatment induced cell death (MTT and macro-colony assay), growth inhibition, cytogenetic damage (micronuclei formation), were studied as cellular response parameters. Treatment with the compounds enhanced growth inhibition and cell death in a concentration dependent manner in both T98G and HEK (normal) cell lines. At higher concentrations (>20 μ g/mL) the cytotoxic effects of the compounds were highly significant. The effect on clonogenic capacity and micronuclei formation observed after treatment of cells. Amongst the compounds, compound 2 exhibited potent activity against T98G brain cancer cells. Despite potent in vitro activity, both compounds exhibited less cytotoxicity against normal human HEK cells at all effective concentrations.

Thiophene containing trisubstituted methanes [TRSMs] as identified lead against Mycobacterium tuberculosis

Triarylmethanes (TRAMs) and thiophene containing trisubstituted methanes (TRSMs) have been reported by us, having potential against Mycobacterium tuberculosis and Mycobacterium fortuitum strains, respectively. Further, extension through synthesis and biol

A versatile synthesis of long-wavelength-excitable BODIPY dyes from readily modifiable cyclopenta[2,1- B:3,4- B′ ]dithiophenes

Knoevenagel condensation of a simple methylated borondipyrromethene (Bodipy) with 4,4′-dihexyl-4H-cyclopenta-[2,1-b:3,4-b′]dithiophenes functionalized at one end by a triphenylamine residue and at the other by a carbaldehyde fragment leads to novel dye species. These bisvinylic derivatives exhibit pronounced absorption in the visible range extending above 850 nm. Addition of other Bodipy units by coupling to a central iodophenyl entity enables filling of the gaps in absorption of the pivotal starting material. Efficient cascade energy transfer between the Bodipys is facilitated by spectral overlap between the energy donor and the energy acceptor. All photons between 350 nm and 750 nm are channeled to the distyryl centers which emit at 864 nm. Georg Thieme Verlag Stuttgart. New York.

Synthesis and basic properties of tetrathieno[2,3-a:3′,2′-c: 2″,3″-f:3a€?,2a€?-h]naphthalene: A new π-conjugated system obtained by photoinduced electrocyclization- dehydrogenation reactions of tetra(3-thienyl)ethene

A method for the synthesis of tetrathieno[2,3-a:3′,2′-c: 2″,3″-f:3a€?,2a€?-h]naphthalene (3), utilizing photoinduced electrocyclization-dehydrogenation reactions of tetra(3-thienyl)ethene (1), was developed. Photoirradiation of a toluene or CHCl3 solution of 1, containing a small amount of I2, leads to modestly efficient production of 3. In contrast to the UV-vis absorption property of the typical p-type organic transistor material pentacene, that of 3 does not experience a time-dependent change under aerated conditions, indicating that 3 has high stability against molecular oxygen. The results of X-ray crystallographic analysis demonstrate that 3 possesses a columnar crystalline structure in which molecules are aligned in a face-to-face manner with a high degree of the π-π overlap between adjacent molecules. This phenomenon should result in efficient charge-carrier transport properties of the crystalline form of this substance.

Fluorescent cyclopentadithiophene derivatives having phenyl-substituted silyl moieties

4,4-Dimethylcyclopenta[2,1-b:3,4-b′]dithiophene derivatives bearing trimethyl-, dimethylphenyl-, diphenylmethyl-, or triphenyl-silyl moieties were synthesized. The introduction of the silyl moieties onto cyclopenta[2,1-b:3,4- b′]dithiophene induced fluorescent emission as well as the bathochromic shift of wavelength at the maximum absorption and fluorescence. It was found that the larger number of phenyl group on silyl moiety resulted in the higher fluorescence quantum yield.

Synthesis and characterization of bridged bithiophene-based conjugated polymers for photovoltaic applications: Acceptor strength and ternary blends

Six of three-component donor-acceptor random copolymers P1-P6, symbolized as (thiophene donor)m -(thiophene acceptor)n, were rationally designed and successfully synthesized by the palladium-catalyzed Stille coupling. The 4H-cyclopenta[2,l-b:3,4-b']dithiophene (CPDT) unit serves as the donor for Pl-P4, while the benzothiadiazole (BT), quinoxaline (QU), dithienoquinoxaline, and thienopyrazine (TP) units are used as the acceptor for P1, P2, P3, and P4, respectively. P5 and P6 are structurally analogous to P1 and P2 except for using the dithieno[3,2-b:2',3'-d]silole (DTS) unit as the donor. Because the band gap lowering ability of the acceptor units in the polymer is in the order TP > BT > QU presumably due to the quinoid form population in the polymers, the optical band gaps can be well adjusted to be 1.2,1.6, and 1.8 eV for P4, P1, and P2, respectively. It is found that the two bridged bithiophene units, CPDT and DTS, have similar steric and electronic effects on the P1 and P5 as well as P2 and P6, respectively, leading to comparable intrinsic properties and device performances. Bulk heterojunction photovoltaic cells based on ITO/PEDOT:PSS/polymer:PC7BM/Ca/Al configuration were fabricated and characterized. Although P4 exhibits the lowest optical band gap, broadest absorption spectrum, and highest mobility, the too low-lying LUMO level hinders the efficient exciton dissociation, resulting in a low PCE of 0.7%. Compared with poly[2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b'] dithiophene)-alt-4,7-(2,l,3-benzothiadiazole)] (PCPDTBT), random copolymer P1 shows more blue-shifted, broader absorption spectrum, comparable mobility, and a higher PCE of 2.0%. In view of the fact that P1 shows a higher band gap with strong absorption in visible region, while PCPDTBT has a lower band gap to mainly absorb NIR light, a BHJ device with the active layer containing ternary blend of PCPDTBT/P1/PC71BM was investigated and achieved an enhanced PCE of 2.5%, which outperforms the devices based on the binary blending systems of PCPDTBT/ PC71BM(PCE = 1.4%)orP1/PC71BM(PCE = 2.0%) under the identical conditions. Such an improvement is ascribed to the complementary absorption and compatible structure of P1 and PCPDTBT polymers.

3-(diheteroarylmethylene)-8-azabicyclo[3.2.1]octane and 3-((aryl)(heteroaryl)methylene)-8-azabicyclo[3.2.1]octane derivatives

This invention is directed to 3-(diheteroarylmethylene)-8-azabicyclo[3.2.1] octane and 3-((aryl)(heteroaryl)methylene)-8-azabicyclo[3.2.1] octane derivatives useful as δ-opioid, μ-opioid, or δ-opioid and μ-opioid receptor receptor modulators. Depending on

Substituted thioacetamides

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