2,2':5',2''-Terthiophene

HCID 65067CAS 1081-34-1

Basic information

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 properties

XLogP
4.4
Topological polar surface area
84.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
15

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 4 items

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 · 3 items

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.

General Description2,2′: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.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]

Additional notes

DefinitionChEBI: 2,2':5',2''-terthiophene is a terthiophene.

Related reactions

10 records

Linked notes

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