2,2':5',2''-TERTHIOPHENE

ChemicalBook > CAS DataBase List > 2,2':5',2''-TERTHIOPHENE

2,2':5',2''-TERTHIOPHENE

Product Name: 2,2':5',2''-TERTHIOPHENE
CAS No.: 1081-34-1
Chemical Name: 2,2':5',2''-TERTHIOPHENE
Synonyms: 3TH;TTh;S1130;2,2':5';2,2':5',2;terthienyl;TERTHIOPHENE;a-Terthienyl;5-BroMo-[2,2';5-BroMo-[2,2'
CBNumber: CB7713541
Molecular Formula: C12H8S3
Formula Weight: 248.39
MOL File: 1081-34-1.mol

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2,2':5',2''-TERTHIOPHENE Property

Melting point:: 93-95 °C(lit.)
Boiling point:: 160 °C (0.1 mmHg)
Density: 1.4602 (rough estimate)
refractive index: 1.6200 (estimate)
Flash point:: 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.
Merck: 14,9174
BRN: 178604
CAS DataBase Reference: 1081-34-1(CAS DataBase Reference)
EPA Substance Registry System: .alpha.-Terthiophene (1081-34-1)

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Safety

Risk Statements: 36/37/38
Safety Statements: 22-24/25
WGK Germany: 3
RTECS: WZ9717750
F: 8-10
HS Code: 29349990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 311073
Product name: 2,2′:5′,2′′-Terthiophene
Purity: 99%
Packaging: 1g
Price: $242
Updated: 2024/03/01

TCI Chemical

Product number: T1196
Product name: 2,2':5',2''-Terthiophene (purified by sublimation)
Purity: >98.0%(GC)
Packaging: 1g
Price: $71
Updated: 2024/03/01

TCI Chemical

Product number: T1196
Product name: 2,2':5',2''-Terthiophene (purified by sublimation)
Purity: >98.0%(GC)
Packaging: 5g
Price: $212
Updated: 2024/03/01

Alfa Aesar

Product number: A16748
Product name: 2,2':5',2''-Terthiophene, 99%
Packaging: 1g
Price: $186
Updated: 2024/03/01

Alfa Aesar

Product number: A16748
Product name: 2,2':5',2''-Terthiophene, 99%
Packaging: 5g
Price: $592.65
Updated: 2024/03/01

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2,2':5',2''-TERTHIOPHENE Chemical Properties,Usage,Production

Chemical Properties

YELLOW TO YELLOW-BROWN POWDER

Uses

α-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).

Uses

2,2'':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.

Definition

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

Synthesis Reference(s)

Synthetic Communications, 19, p. 307, 1989 DOI: 10.1080/00397918908050983
Synthesis, p. 462, 1991 DOI: 10.1055/s-1991-26494

General Description

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.

Metabolic pathway

When 14C-a-terthienyl is administered orally to rats in a single dose, two metabolites [1,4-di(2'-thienyl)]-1,4- butadione and 2-2' -bithiophene-5-carboxylic acid are identified in the urine.

Purification Methods

Possible impurities are bithienyl and polythienyls. Suspend it in H2O and steam distil it to remove bithienyl. The residue is cooled and extracted with CHCl3, dried (MgSO4), filtered, evaporated and the residue chromatographed on Al2O3 using pet ether/3% Me2CO as eluent. The terphenyl zone is then eluted from the Al2O3 with Et2O, the extract is evaporated and the residue is recrystallised from MeOH (40mL per g). The platelets are washed with cold MeOH and dried in air. [UV: Sease & Zechmeister J Am Chem Soc 69 270 1947; Uhlenbroek & Bijloo Recl Trav Chim Pays-Bas 79 1181 1960.] It has also been recrystallised from MeOH, *C6H6, pet ether or AcOH. [UV: Zechmeister & Sease J Am Chem Soc 69 273 1947, Steinkopf et al. Justus Liebigs Ann Chem 546 180 1941.] It is a phototoxic nematocide [Cooper & Nitsche Bioorg Chem 13 36 1985, Chan et al. Phytochem 14 2295 1975]. [Beilstein 19 III/IV 4763, 19/9 V 226.]

2,2':5',2''-TERTHIOPHENE Preparation Products And Raw materials

Raw materials

2,5-Dibromothiophene 2-Bromothiophene Diethyl ether Magnesium

Preparation Products

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View Lastest Price from 2,2':5',2''-TERTHIOPHENE manufacturers

Shanghai UCHEM Inc.

Product: 2,2':5',2''-TERTHIOPHENE 1081-34-1
Price: US $47.00-393.00/g
Min. Order: 25g
Purity: 0.98
Supply Ability: 25kg
Release date: 2023-12-25

Hebei Weibang Biotechnology Co., Ltd

Product: 2,2':5',2''-TERTHIOPHENE 1081-34-1
Price: US $10.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 5tons
Release date: 2024-12-04

Henan Fengda Chemical Co., Ltd

Product: alpha-Terthiophene 1081-34-1
Price: US $200.00-1.00/KG
Min. Order: 1KG
Purity: 99%, 99.5% Sublimated
Supply Ability: g-kg-tons, free sample is available
Release date: 2023-12-30

1081-34-1, 2,2':5',2''-TERTHIOPHENERelated Search:

ALPHA-SEXITHIOPHENE O-QUARTERPHENYL 5,5μμ-Dibromo-2,2μ:5μ,2μμ-terthiophene 2,2':5',2''-TERTHIOPHENE-5-CARBOXALDEHYDE,5-FORMYL-2,2':5',2''-TERTHIOPHENE 2,2':5',2''-TERTHIOPHENE 3'-Methyl-2,2':5',2''-terthiophene 3'-Decyl-2,2':5',2''-terthiophene 2-Bromoterthiophene 5''-BROMO-3'-DECYL-2,2',5',2''-TERTHIOPHENE 5-BROMO-5''-FORMYL-2,2':5',2''-TERTHIOPHENE,5''-BROMO-2,2':5',2''-TERTHIOPHENE-5-CARBOXALDEHYDE 5-BROMO-3'-DECYL-2,2',5',2''-TERTHIOPHENE,5-BROMO-3'-DECYL-2,2':5',2''-TERTHIOPHENE 3,3''-DIMETHYL-2,2',5',2''-TERTHIOPHENE 2,2':5',2''-Terthiophene-5-carbonitrile 2 2':5' 2''-TERTHIOPHENE-5 5''-DICARBOX& 2,2':5',2''-Terthiophene-5,5''-dicarbonitrile,5,5''-Dicyano-2,2':5',2''-terthiophene SALOR-INT L162191-1EA SALOR-INT L161616-1EA SALOR-INT L164909-1EA

2,5-BIS(2-THIENYL)THIOPHENE

2,5-DI(2-THIENYL)THIOPHENE

2,2′:5′,2′′-Terthiophene,α-Terthienyl, 2,5-Di(2-thienyl)thiophene

2,2':5',2-TERTHIENYL

2,2',5',2''-TERTHIOPHENE

2,2':5',2''-Terthiophene 99%

2,2':5',2''-Terthiophene (purified by sublimation)

ALPHA-TERTHIENYL

2,5-Di(thien-2-yl)thiophene

2,2 :5 ,2 -Terthiophene&nbsp

2,5-Di(2-thienyl)thiophene alpha-Terthienyl

2,2':5',2''-Terthiophene (=α-Terthienyl)

5-BroMo-[2,2'

2,3-dithiophen-2-ylthiophene

2,2':5',2''-TERTHIOPHENE

TERTHIOPHENE

alpha-terthiophene

terthienyl

alpha-TERTHIENYL (2,2':5',2

5',2''Terthiophene

2,2':5'

2''-TERTHIOPHENE

2,2':5',2''-Terthiophene (=alpha-Terthienyl)

α-Terthienyl, 2,5-Di(2-thienyl)thiophene

Alpha-terthienyl,99+%

2,5-Bis(thiophene-2-yl)thiophene

3TH

a-Terthienyl

2,2':5',2''-Terthiophene ,99%

2,5-Di(2-thienyl)thiophene alpha-Terth

TTh

Alpha-trithiophene

JACS-1081-34-1

2,2':5',2''-Terthiophene, 99%, for synthesis

α-Terthiophene

2,2':5',2''-TERTHIOPHENE ISO 9001：2015 REACH

S1130

Sanlian thiophene

2,2':5',2''-Terthiophene (7CI, 8CI, 9CI, ACI)

Osa（2-octen-1-ylsuccinic anhydride, mixture of cis and trans）

2,2 ': 5', 2 '' - Trithiophene

2,2',2''-Terthiophene

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

2,2',2''-Terthiophene

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

2,2':5',2

2,2':5',2'-TERTHIOPHENE

2,2,5,2-Terthiophene in isooctane

2,2,5,2-Terthiophene in toluene

5',2'']terthiophene

5-BroMo-[2,2'

1081-34-1

1081-34-4

108-34-1

C12H8S3

Heterocyclic Building Blocks

Thiophenes

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