802247

2-Chloromethyl-2,3-dihydrothieno[3,4-b]-1,4-dioxine

95%

• Synonym(s): 2-Chloromethyl EDOT, 2-Chloromethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine
• Empirical Formula (Hill Notation): C₇H₇ClO₂S
• CAS Number: 857419-46-6
• Molecular Weight: 190.65
• MDL number: MFCD17014651
• UNSPSC Code: 12352100
• PubChem Substance ID: 329768732
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 95%
• form: solid
• mp: 39-44 °C
• transition temp: flash point >230 °F
• functional group: chloro
• SMILES string: ClCC1COc2cscc2O1
• InChI: 1S/C7H7ClO2S/c8-1-5-2-9-6-3-11-4-7(6)10-5/h3-5H,1-2H2
• InChI key: UOXHKOVMJCKBOG-UHFFFAOYSA-N

Description

General description

2-Chloromethyl-2,3-dihydrothieno[3,4-b]-1,4-dioxine (EDOT-Cl) can be prepared by reacting 3,4-dimethoxythiophene with 3-chloro-1,2-propanediol via transesterification. The six-memebered ring of the molecule exhibits twisted conformation. It acts as an intermediate during the multi-step synthesis of poly(sulfobetaine-3,4-ethylenedioxythiophene) (PSBEDOT), a conjugated polymer.

Application

2-Chloromethyl EDOT is a key building block for the incorporation of EDOT (3,4-ethylenedioxythio-phene) into copolymers.

It may be used in the synthesis of the following EDOT derivatives:

• 2-[((6-hexyloxy-9,10-anthraquinone)-2-yl)oxymethyl]-2,3-dihydrothieno[3,4-b][1,4]dioxine (AQ-EDOT)
• 2-[(N′-(10-nonadecyl)perylene-3,4,9,10-biscarboximide-N-yl)4-phenoxymethyl]-2,3-dihydrothieno[3,4-b][1,4]dioxine (PTCDI-EDOT)
• 2-[((6-hexyloxy-11,11,12,12-tetracyanoanthraquinodimethane)-2-yl)-oxymethyl]-2,3-dihydrothieno[3,4-b][1,4]dioxine (TCAQ-EDOT)

Other Notes

EDOT-Based Copolymers with Pendant Anthraquinone Units: Analysis of Their Optoelectronic Properties within the Double-Cable Context

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P301 + P312 + P330
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable