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2,2:5,2-terthiophene
alpha-terthienyl

Supplier Sponsors

Name:2,5-dithiophen-2-ylthiophene
CAS Number: 1081-34-1Picture of molecule3D/inchi
FDA UNII: 0P77RAU2RR
Nikkaji Web:J102.960F
Beilstein Number:178604
MDL:MFCD00012167
XlogP3-AA:4.40 (est)
Molecular Weight:248.39076000
Formula:C12 H8 S3
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 0.4228 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
alpha-terthiophene 98%
BOC Sciences
For experimental / research use only.
2,5-Di(2-thienyl)thiophene
Santa Cruz Biotechnology
For experimental / research use only.
2,2':5',2''-Terthiophene ≥99%
Sigma-Aldrich: Aldrich
For experimental / research use only.
2,2':5',2''-Terthiophene 99%
TCI AMERICA
For experimental / research use only.
2,2':5',2''-Terthiophene (purified by sublimation) >98.0%(GC)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
information only not used for fragrances or flavors
Recommendation for 2,2:5,2-terthiophene usage levels up to:
 not for fragrance use.
 
Recommendation for 2,2:5,2-terthiophene flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :65067
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2,5-dithiophen-2-ylthiophene
Chemidplus:0001081341
RTECS:WZ9717750 for cas# 1081-34-1
 
References:
 2,5-dithiophen-2-ylthiophene
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):65067
Pubchem (cas):1081-34-1
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C08460
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2934.99.4400
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
2,5-dithiophen-2-ylthiophene
2,2',5',2''-terthienyl
alpha-terthienyl
alpha-terthiophene
 

Articles:

PubMed:Detection of Ca(2+)-induced acetylcholine released from leukemic T-cells using an amperometric microfluidic sensor.
PubMed:Detection of Nitric Oxide from Living Cells Using Polymeric Zinc Organic Framework-Derived Zinc Oxide Composite with Conducting Polymer.
PubMed:The natural terthiophene α-terthienylmethanol induces S phase cell cycle arrest of human ovarian cancer cells via the generation of ROS stress.
PubMed:Antioxidative cellular response of lepidopteran ovarian cells to photoactivated alpha-terthienyl.
PubMed:Study of the electronic structure of short chain oligothiophenes.
PubMed:Neurotoxicity of a Biopesticide Analog on Zebrafish Larvae at Nanomolar Concentrations.
PubMed:Electron-Transfer Secondary Reaction Matrices for MALDI MS Analysis of Bacteriochlorophyll a in Rhodobacter sphaeroides and Its Zinc and Copper Analogue Pigments.
PubMed:Comparison of a carboxylated terthiophene surface with carboxymethylated dextran layer for surface plasmon resonance detection of progesterone.
PubMed:Amperometric sensing of HIF1α expressed in cancer cells and the effect of hypoxic mimicking agents.
PubMed:A New Bithiophene from the Root of Echinops grijsii.
PubMed:Opinion of the Scientific Committee on Consumer Safety (SCCS) - Opinion on the fragrance ingredients Tagetes minuta and Tagetes patula extracts and essential oils (phototoxicity only) in cosmetic products.
PubMed:Paper-Based Analytical Devices Relying on Visible-Light-Enhanced Glucose/Air Biofuel Cells.
PubMed:A disposable chronocoulometric sensor for heavy metal ions using a diaminoterthiophene-modified electrode doped with graphene oxide.
PubMed:Synthesis and Properties of Ethene-Bridged Terthiophenes.
PubMed:Sulfur-Bridged Terthiophene Dimers: How Sulfur Oxidation State Controls Interchromophore Electronic Coupling.
PubMed:Synthesis, optical properties, and electronic structures of nucleobase-containing π-conjugated oligomers.
PubMed:Branched terthiophenes in organic electronics: from small molecules to polymers.
PubMed:Dithienobenzothiadiazole-based conjugated polymer: processing solvent-relied interchain aggregation and device performances in field-effect transistors and polymer solar cells.
PubMed:Photodynamic inactivation of oropharyngeal Candida strains.
PubMed:A simple and efficient synthesis of substituted 2,2'-bithiophene and 2,2':5',2″-terthiophene.
PubMed:Substrate steered crystallization of naphthyl end-capped oligothiophenes into nanofibers: the influence of methoxy-functionalization.
PubMed:Synthesis and transistor properties of asymmetric oligothiophenes: relationship between molecular structure and device performance.
PubMed:Temperature-independent hole mobility of a smectic liquid-crystalline semiconductor based on band-like conduction.
PubMed:Photophysical behaviour of cyclometalated iridium(III) complexes with phosphino(terthiophene) ligands.
PubMed:Synthesis and characterization of thieno[3,4-b]pyrazine-based terthienyls: tunable precursors for low band gap conjugated materials.
PubMed:A terthiophene-containing alkynylplatinum terpyridine Pacman complex: controllable folding/unfolding modulated by weak intermolecular interactions.
PubMed:Analysis of rich inelastic electron tunneling spectra: case study of terthiophene on Au(111).
PubMed:Determination of major components and fingerprint analysis of Flaveria bidentis (L.) Kuntze.
PubMed:Antileishmanial activity of 5-methyl-2,2' : 5',2″-terthiophene isolated from Porophyllum ruderale is related to mitochondrial dysfunction in Leishmania amazonensis.
PubMed:Synthesis, optical properties and explosive sensing performances of a series of novel π-conjugated aromatic end-capped oligothiophenes.
PubMed:Current-confinement structure and extremely high current density in organic light-emitting transistors.
PubMed:Solid-state synthesis of poly(3',4'-dimethoxy-2,2':5',2"- terthiophene): comparison with poly(terthiophene) and poly(3',4'-ethylenedioxy-2,2':5',2"- terthiophene).
PubMed:Synthesis of nitrogen-bridged terthiophenes by tandem Buchwald-Hartwig coupling and their properties.
PubMed:Isolation of bioactive components from Flaveria bidentis (L.) Kuntze using high-speed counter-current chromatography and time-controlled collection method.
PubMed:Selective detection of alkaloids in MALDI-TOF: the introduction of a novel matrix molecule.
PubMed:Controlled conjugated backbone twisting for an increased open-circuit voltage while having a high short-circuit current in poly(hexylthiophene) derivatives.
PubMed:Excess-electron injection and transfer in terthiophene-modified DNA: terthiophene as a photosensitizing electron donor for thymine, cytosine, and adenine.
PubMed:Weak epitaxy growth of phthalocyanine on inducing layers of fluorinated 5,5"-bis(biphenyl-4-yl)-2,2':5',2"-terthiophene.
PubMed:In vivo detection of glutathione disulfide and oxidative stress monitoring using a biosensor.
PubMed:Echinopsacetylenes A and B, new thiophenes from Echinops transiliensis.
PubMed:Synthesis and characterization of trans-M2(T(i)PB)2(O2C-CH=CH-2-C4H3S)2 (M = Mo or W) and comments on the metal-to-ligand charge transfer bands in MM quadruply bonded complexes of the type trans-M2(T(i)PB)2L2, where T(i)PB = 2,4,6-triisopropylbenzoate and L = π-accepting carboxylate ligand.
PubMed:Spectroscopy and single-molecule emission of a fluorene-terthiophene oligomer.
PubMed:Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
PubMed:Side chain variations on a series of dicyanovinyl-terthiophenes: a photoinduced absorption study.
PubMed:Electropolymerized self-assembled layer on gold nanoparticles: detection of inducible nitric oxide synthase in neuronal cell culture.
PubMed:Photophysical and electrochemical properties of Ru(II) complexes containing tridentate bisphosphino-oligothiophene ligands.
PubMed:p-i-n Homojunction in organic light-emitting transistors.
PubMed:Coordination mode dependent excited state behavior in group 8 phosphino(terthiophene) complexes.
PubMed:Thiophene derivatives with antileishmanial activity isolated from aerial parts of Porophyllum ruderale (Jacq.) Cass.
PubMed:Photochemical stabilization of terthiophene and its utilization as a new sensing element in the fabrication of monolayer-chemistry-based fluorescent sensing films.
PubMed:Syntheses, and optical, fluorescence, and nonlinear optical characterization of phosphine-substituted terthiophenes.
PubMed:Radical-scavenging activity of melatonin, either alone or in combination with vitamin E, ascorbate or 2-mercaptoethanol as co-antioxidants, using the induction period method.
PubMed:Electropolymerization molecularly imprinted polymer (E-MIP) SPR sensing of drug molecules: pre-polymerization complexed terthiophene and carbazole electroactive monomers.
PubMed:Electropolymerized molecularly imprinted polymer films of a bis-terthiophene dendron: folic acid quartz crystal microbalance sensing.
PubMed:Chirality induced by microaggregation of regioregular polythiophenes with side-chain optically active substituent.
PubMed:Photophysical properties and electropolymerization of gold complexes of 3,3''-diethynyl-2,2':5',2''-terthiophene.
PubMed:Synthesis and evaluation of new spacers for use as dsDNA end-caps.
PubMed:Nanostructured liquid crystals combining ionic and electronic functions.
PubMed:[Effect of alpha-terthienyl on protein, esterase and lipid peroxidation of Aedes albopictus larvae].
PubMed:Electropolymerization of 3',4'-disubstituted 2,2':5',2″-terthiophene derivatives. A theoretical and photovoltaic characterization.
PubMed:Chemical fingerprint of commercial Radix Echinopsis and quantitative analysis of alpha-terthienyl.
PubMed:Comparable susceptibilities of human 293 cells and insect Tn-5B1-4 cells to photoactivated alpha-terthienyl.
PubMed:In situ silicone tube microextraction: a new method for undisturbed sampling of root-exuded thiophenes from marigold (Tagetes erecta L.) in soil.
PubMed:Controlled stability of molecular junctions.
PubMed:The synthesis and photoactivated cytotoxicity of 2-methyl-4-oxo-3-prop-2-yn-1-ylcyclopent-2-en-1-yl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate conjugated with alpha-terthienyl derivatives.
PubMed:Analysis of chlorophylls and their derivatives by matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry.
PubMed:Triplet excited state characters and photosensitization mechanisms of alpha-terthienyl: a theoretical study.
PubMed:Effect of molecular mass on supramolecular organisation of poly(4,4''-dioctyl-2,2':5',2''-terthiophene).
PubMed:Theoretical study of structure, electronic properties, and photophysics of cyano-substituted thiophenes and terthiophenes.
PubMed:The effect of the oxidation state of a terthiophene-conducting polymer and of the presence of a redox probe on its gene-sensing properties.
PubMed:Self-organized ZnO nanorod with photooxidative cell membrane perforation enables large-scale cell manipulation.
PubMed:Ambipolar transport in the smectic E phase of 2-propyl-5''-hexynylterthiophene derivative over a wide temperature range.
PubMed:An amperometric bilirubin biosensor based on a conductive poly-terthiophene-Mn(II) complex.
PubMed:The synthesis and photolarvicidal activity of 2,5-diarylethynylthiophenes.
PubMed:Synthesis and characterization of pi-extended bowl-shaped pi-conjugated molecules.
PubMed:Flip-type disorder in 3-substituted 2,2':5',2''-terthiophenes.
PubMed:Dinuclear palladium-azido complexes containing thiophene derivatives: reactivity toward organic isocyanides and isothiocyanates.
PubMed:Antifeedant and toxicity effects of thiophenes from four Echinops species against the Formosan subterranean termite, Coptotermes formosanus.
PubMed:[Synthesis of thiophene and alpha-terthiophene derivatives with antiproliferative activity].
PubMed:Raman spectroscopy of short-lived terthiophene radical cations generated by photochemical and chemical oxidation.
PubMed:Photo-induced transformations in 2,2':5',2''-terthiophene thin films on silver.
PubMed:Antifungal activity of thiophenes from Echinops ritro.
PubMed:Lipid-bonded conducting polymer layers for a model biomembrane: application to superoxide biosensors.
PubMed:Field-effect transistors based on self-organized molecular nanostripes.
PubMed:Porous metal-organic truncated octahedron constructed from paddle-wheel squares and terthiophene links.
PubMed:Synthesis and properties of terthiophene-modified oligodeoxynucleotides.
PubMed:A theoretical study on the low-lying excited states of 2,2':5',2''-terthiophene and 2,2':5',2'':5'',2'''-quaterthiophene.
PubMed:[Toxicity of alpha-terthienyl to the larvae of Aedes albopictus].
PubMed:Spectroscopic and theoretical study of the molecular and electronic structures of a terthiophene-based quinodimethane.
PubMed:Toward functionalized conducting polymers: synthesis and characterization of novel beta-(styryl)terthiophenes.
PubMed:Characterization of an EDTA bonded conducting polymer modified electrode: its application for the simultaneous determination of heavy metal ions.
PubMed:Comet assays to assess DNA damage and repair in grass shrimp embryos exposed to phototoxicants.
PubMed:Identification of the major metabolite of 2,5-bis(5-hydroxymethyl-2-thienyl)furan (NSC 652287), an antitumor agent, in the S9 subcellular fraction of dog liver cells.
PubMed:[Preliminary studies on chemical constituents and pharmacological action of Eclipta prostrata L].
PubMed:Phototoxic process after rapid photosensitive membrane damage of 5,5"-bis(aminomethyl)-2,2':5',2"-terthiophene dihydrochloride.
PubMed:Participation of the photosensitizer alpha-terthienyl in the peroxidase-catalyzed oxidation of indole-3-acetic acid.
PubMed:Synergistic insecticidal mode of action between sesquiterpene lactones and a phototoxin, alpha-terthienyl.
PubMed:Novel protein kinase C inhibitors: synthesis and PKC inhibition of beta-substituted polythiophene derivatives.
PubMed:Novel protein kinase C inhibitors: alpha-terthiophene derivatives.
PubMed:Light dose and time dependency of photodynamic cell membrane damage.
PubMed:Quantitative assay of photoinduced antibiotic activities of naturally-occurring 2,2':5',2"-terthiophenes.
PubMed:Study of photoinduced energy and electron transfer in alpha-terthienyl-bovine serum albumin conjugates: a laser flash photolysis study.
PubMed:Metal binding and resultant loss of phototoxicity of alpha-terthienyl: metal detoxification versus alpha-terthienyl inactivation.
PubMed:Pharmacokinetics, metabolism and toxicity of the plant-derived photoxin alpha-terthienyl.
PubMed:Singlet oxygen and peroxyl radicals regulate carotenoid biosynthesis in Phaffia rhodozyma.
PubMed:Butenylbithiophene, alpha-terthienyl and hydroxytremetone as contact allergens in cultivars of marigold (Tagetes sp.).
PubMed:QSAR Evaluation of .alpha.-Terthienyl Phototoxicity.
PubMed:Photoactive terthiophenes: the influence of serum on anti-HIV (human immunodeficiency virus) activities.
PubMed:Some naturally occurring phytophototoxins for mosquito control.
PubMed:Antifungal activity of some 2,2':5',2"-terthiophene derivatives.
PubMed:Antiviral assays on phytochemicals: the influence of reaction parameters.
PubMed:UV-A coexposure enhances the toxicity of aromatic hydrocarbons, munitions, and metals to Photobacterium phosphoreum.
PubMed:Phototoxicology. 2. Near-ultraviolet light enhancement of Microtox assays of trinitrotoluene and aminodinitrotoluenes.
PubMed:Biological activities of terthiophenes and polyynes from the Asteraceae.
PubMed:Effects of α-Terthienyl on the midgut detoxification enzymes of the European corn borer,Ostrinia nubilalis.
PubMed:The anti-HIV activities of photoactive terthiophenes.
PubMed:Phototoxicity of (1H-indenyl)thiophenes.
PubMed:Intracellular target for alpha-terthienyl photosensitization: involvement of lysosomal membrane damage.
PubMed:Light-mediated activities of thiarubrines against human immunodeficiency virus.
PubMed:The anti-HIV activity of the phytochemical alpha-terthienyl.
PubMed:Structure-activity studies of photoactivated antiviral and cytotoxic tricyclic thiophenes.
PubMed:Toxicity and residual action of the photoactivated compound, cyano-alpha-terthienyl, and its efficacy for reducing pre-imaginal populations of mosquitoes.
PubMed:Generation of superoxide anion radical by alpha-terthienyl in the anal gills of mosquito larvae Aedes aegypti: a new aspect in alpha-terthienyl phototoxicity.
PubMed:alpha-Terthienyl photosensitizes damage to pBR322 DNA.
PubMed:Superoxide dismutase in the anal gills of the mosquito larvae of Aedes aegypti: its inhibition by alpha-terthienyl.
PubMed:Production of nematocidal compounds by hairy root cultures of Tagetes patula L.
PubMed:Efficiency of the photoprocesses leading to singlet oxygen (1 delta g) generation by alpha-terthienyl: optical absorption, optoacoustic calorimetry and infrared luminescence studies.
PubMed:Identification of carotenoids in Erwinia herbicola and in a transformed Escherichia coli strain.
PubMed:Ultraviolet-mediated antimycotic activity of alpha-terthienyl on Microsporum cookei.
PubMed:Photosensitization with alpha-terthienyl: the formation of superoxide ion in aqueous media.
PubMed:Toxicity, localization and elimination of the phototoxin, alpha-terthienyl, in mosquito larvae.
PubMed:Role of cloned carotenoid genes expressed in Escherichia coli in protecting against inactivation by near-UV light and specific phototoxic molecules.
PubMed:Comparative effects of two plant secondary metabolites on host-parasitoid association.
PubMed:Potentially useful antimicrobial and antiviral phototoxins from plants.
PubMed:Polycyclic aromatic compounds as phototoxic mosquito larvicides.
PubMed:Light-dependent effects of alpha-terthienyl in eggs, larvae, and pupae of mosquitoAedes aegypti.
PubMed:Comparison of the antiviral effects of naturally occurring thiophenes and polyacetylenes.
PubMed:Antiviral activity of the photoactive thiophene alpha-terthienyl.
PubMed:Characterization of cutaneous phototoxicity induced by topical alpha-terthienyl and ultraviolet A radiation.
PubMed:Inactivation and mutagenesis by phototoxins usingEscherichia coli strains differing in sensitivity to near- and far-ultraviolet light.
PubMed:Efficacy of the plant phototoxinα-terthienyl againstAedes intrudens and effects on nontarget organisms.
PubMed:Light-mediated allelochemical effects of naturally occurring polyacetylenes and thiophenes from asteraceae on herbivorous insects.
PubMed:The mode of action of polyacetylene and thiophene photosensitizers on liposome permeability to glucose.
PubMed:Synthesis and evaluation of the naturally occurring phototoxin, alpha-terthienyl, as a control agent for larvae of Aedes intrudens, Aedes atropalpus (Diptera: Culicidae) and Simulium verecundum (Diptera: Simuliidae).
PubMed:Excited state properties of alpha-terthienyl and related molecules.
PubMed:The inactivation of acetylcholinesterase by alpha-terthienyl and ultraviolet light. Studies in vitro and in larvae of the mosquito Aedes aegypti.
PubMed:Light-dependent toxicity of α-terthienyl and anthracene toward late embryonic stages ofRana pipiens.
PubMed:Comparison of the phototoxicity of alpha-terthienyl with that of a selenium and of an oxygen analogue.
PubMed:Photodynamic hemolysis caused by alpha-terthienyl.
PubMed:Allelopathic properties of α-terthienyl and phenylheptatriyne, naturally occurring compounds from species of asteraceae.
PubMed:Phototoxicity mechanisms: chlorpromazine photosensitized damage to DNA and cell membranes.
PubMed:Examination of naturally occurring polyacetylenes and alpha-terthienyl for their ability to induce cytogenetic damage.
PubMed:Phototoxic effects of naturally occurring polyacetylenes and alpha-terthienyl on human erythrocytes.
PubMed:Candida utilis as a convenient and safe substitute for the pathogenic yeast C. albicans in Daniels' phototoxicity test.
PubMed:Photoinactivation of human erythrocyte enzymes by alpha-terthienyl and phenylheptatriyne, naturally occurring compounds in the Asteraceae.
PubMed:Phototoxic polyacetylenes and their thiophene derivatives. (Effects on human skin).
PubMed:Photoactivation of the nematicidal compound alpha-terthienyl from roots of marigolds (Tagetes species). A possible singlet oxygen role.
PubMed:Phototoxicity evoked by alpha-terthienyl.
 
Notes:
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