2,2':5',2''-Terthiophene
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Basic information
- CAS
1081-34-1- Standard SMILES
c1csc(-c2ccc(-c3cccs3)s2)c1- InChIKey
KXSFECAJUBPPFE-UHFFFAOYSA-N- Molecular formula
- C12H8S3
- Average molar mass
- 248.4 g/mol
- Monoisotopic mass
- 247.97881326
Overview
2,2':5',2''-terthiophene is a terthiophene.
Names & identifiers
- Preferred name
- 2,2':5',2''-Terthiophene
- IUPAC
- 2,5-dithiophen-2-ylthiophene
- English name
- 2,2':5',2''-Terthiophene
- Molecular formula
- C12H8S3
- Molecular weight
- 248.39
Names & synonyms
2,2':5',2''-Terthiophene1081-34-1alpha-Terthienyl2,2',5',2''-Terthienyl2,5-dithiophen-2-ylthiophene0P77RAU2RRCHEBI:103352,2,5,2''-terthiopheneRefChem:555954640-441-1alpha-Terthiophene2,5-Di(2-thienyl)thiophene
Show more names
α-TerthiopheneterthienylTERTHIOPHENE3THTThS11302,2':5'2,2':5',2a-Terthienyl5-BroMo-[2,2'
2,5-bis(2-thienyl)thiopheneMFCD00012167C12H8S35-(thiophen-2-yl)-2,2'-bithiopheneDTXSID20412062,2:5,2-Terthiophene.alpha.-Terthienyl2,2':5'2''-Terthiophene
Database identifiers
- CAS
1081-34-1- PubChem CID
- 65067
- DTXSID
DTXSID2041206- ChEMBL
CHEMBL90017- ChEBI
CHEBI:10335- UNII
- 0P77RAU2RR
- EC Number
- 640-441-1
- Nikkaji
- J102.960F
Properties
Computed structural propertiesFilling in
- XLogP
- 4.4
- Topological polar surface area
- 84.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 197
Experimental & physicochemical properties
SpringerMaterials PropertiesAngular frequency
Collision Cross Section146.4 Ų [M]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID2041206]
Physicochemical properties
- Melting point
- 93 · 93-95 °C(lit.)
- Boiling point
- 160 °C · 160 °C (0.1 mmHg)
- Density
- 1.4602 · 1.4602 (rough estimate)
- refractive index
- 1.62 · 1.6200 (estimate)
- Flash point
- 160 °C/0.1mm · 160°C/0.1mm
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- color
- Light Yellow
- Water Solubility
- Insoluble in water.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 50% (2 of 4) of reports.
Warning
H315 (25%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (25%)
Safety data
- F
- 8-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- WZ9717750
- hs_code
- 29349990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms.
Uses & manufacturing
UsesSynthetic Polymer MALDI Matrix Compounds
Applications
Usesα-Terthienyl was first recognized as a nematicidal constituent of marigolds, but in the presence of light, it is also highly toxic to larvae of several insect species, including mosquitoes. This electron donor thiophenederivative phototoxin is biosynthesized from polyacetylene precursors and appears to function as a photosensitizer catalyzing the formation of reactive oxygen species at the target site (25).
Uses2,2'':5'',2''''-Terthiophene is a thiophene compound isolated from the roots of Echinops transiliensis, and was studied for its larvicidal activity against Aedes aegypti. 2,2'':5'',2''''-Terthiophene also showed inhibitory effects on dispersal ability of Bursaphelenchus xylophilus when used synergistically with certain antibiotics.
2,2′:5′,2′′-Terthiophene (TTh) may be prepared by nickel catalysed coupling reaction of grignard′s reagent derived from 2-bromothiophene and magnesium. It generates singlet oxygen. In nature, it is found in the floral extract of Tagetes minuta and Echinops grijisii. It is known to be toxic to mosquitoes. It also exihibits antifungal activity.
Related reactions
10 records
Compound notes
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