857419-46-6

Basic information

• Product Name: Thieno[3,4-b]-1,4-dioxin, 2-(chloromethyl)-2,3-dihydro-
• Synonyms: Thieno[3,4-b]-1,4-dioxin, 2-(chloromethyl)-2,3-dihydro-;2-Chloromethyl-2,3-dihydrothieno[3,4-b]-1,4-dioxine;2-Chloromethyl-2,3-dihydrothieno[3,4-b]-1,4-dioxine 95%
• CAS NO: 857419-46-6
• Molecular Formula: C7H7ClO2S
• Molecular Weight: 190.65
• Mol File: 857419-46-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 39-44°C
• Appearance: /
• CAS DataBase Reference: Thieno[3,4-b]-1,4-dioxin, 2-(chloromethyl)-2,3-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: Thieno[3,4-b]-1,4-dioxin, 2-(chloromethyl)-2,3-dihydro-(857419-46-6)
• EPA Substance Registry System: Thieno[3,4-b]-1,4-dioxin, 2-(chloromethyl)-2,3-dihydro-(857419-46-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 857419-46-6(Hazardous Substances Data)

Usage

Description

Thieno[3,4-b]-1,4-dioxin, 2-(chloromethyl)-2,3-dihydro-, also known as 2-Chloromethyl EDOT, is a key building block for the incorporation of EDOT (3,4-ethylenedioxythiophene) into copolymers. It can be prepared by reacting 3,4-dimethoxythiophene with 3-chloro-1,2-propanediol via transesterification. The six-membered ring of the molecule exhibits a twisted conformation and acts as an intermediate during the multi-step synthesis of poly(sulfobetaine-3,4-ethylenedioxythiophene) (PSBEDOT), a conjugated polymer.

Uses

Used in Polymer Synthesis:
Thieno[3,4-b]-1,4-dioxin, 2-(chloromethyl)-2,3-dihydrois used as a key building block for the incorporation of EDOT into copolymers. It serves as an intermediate in the multi-step synthesis of poly(sulfobetaine-3,4-ethylenedioxythiophene) (PSBEDOT), a conjugated polymer. This polymer has potential applications in various fields, such as in the development of new materials with unique properties and functionalities.

Upstream product

• 51792-34-8 2,3-dimethoxythiophene 
• 96-24-2 3-monochloro-1,2-propanediol 
• 57090-45-6 (2R)-3-chloro-1,2-propanediol 
• 60827-45-4 (S)-3-chloropropan-1,2-diol 

Downstream Products

• 1003863-35-1 2-(azidomethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine 
• 1003863-36-2 (2,3-dihydrothieno[3,4-b][1,4]di-oxin-2-yl)methanamine 

Relevant articles and documents

Synthesis and electropolymerization of a perylenebisimide-functionalized 3,4-ethylenedioxythiophene (EDOT) derivative

(Chemical Equation Presented) We have developed a convenient and straightforward procedure for the preparation of functionalized 3,4-ethylenedioxythiophene (EDOT) systems by using a new chloromethyl-EDOT derivative as a versatile synthon. Based on this procedure, novel suitably functionalized perylenetetracarboxylic diimide (PDI) dye derivatives covalently linked to 3,4-ethylenedioxythiophene moieties have been synthesized and electrochemically polymerized to yield a donor-acceptor PEDOT derivative with an enhanced absorption cross-section.

Controlling morphology, adhesion, and electrochromic behavior of PEDOT films through molecular design and processing

Poly(3,4-ethylenedioxythiophene) (PEDOT) is a well-known semiconducting polymer with favorable properties which find it often applied as the active material in biological sensors and electrochromic devices. However, PEDOT has several drawbacks which can prohibit its effective or long-term use, including weak adhesion to substrates such as ITO-coated glass, poorly controlled surface morphology, and reduced electrochemical stability over time. While a diverse range of approaches have been explored to overcome these issues, most involve additives or substrate modification, while solutions based on direct covalent adaptation are relatively lacking. We present a novel polymer based on covalently modified EDOT (PEDOT-Crown), featuring polar motifs and a 15-crown-5 moiety. Compared to PEDOT, PEDOT-Crown demonstrates a wealth of advantageous properties including: superior adhesion to ITO under physical and electrochemical duress; a more uniform surface morphology; and electrochemical properties including a higher contrast ratio, red-shifted polaron and bipolaron absorption features, bleaching of the neutral absorption band across a narrower voltage range, and more Faradaic rather than capacitive behavior. Additionally, we note that in the presence of Na+, PEDOT-Crown appears to show modified behavior in long-term electrochemical experiments. These features make PEDOT-Crown a material with improved suitability for application in biological sensing and electrochromic devices, compared to PEDOT.

Preparation method of conductive polymer material capable of specifically identifying tumor cells

The invention discloses a preparation method of a conductive polymer material capable of specifically identifying tumor cells. The preparation method is characterized by comprising the following steps: (1) in a nitrogen atmosphere, adding 28 ml of toluene, 1.36 g and 10.4 mmol of 3,4-dimethoxy thiophene, 2.60 g and 23.1 mmol of 3-chloro-1,2-propylene glycol and 0.16 g and 0.92 mmol of p-toluene sulfonic acid monohydrate into a double-neck flask, carrying out mixing, and carrying out a reaction for 24 hours at a temperature of 90 DEG C; and (2) evaporating the mixture in the step, and then carrying out column chromatography purification to obtain EDOT-Cl. The preparation method disclosed by the invention has the following advantages: the flexible conductive polymer material capable of specifically identifying tumor cells is synthesized, non-labeling of the tumor cells is realized, non-invasive specific recognition is achieved, and an effective means is provided for screening of malignant tumors, early diagnosis of cancers and instant diagnosis.