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
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About This Item
Empirical Formula (Hill Notation):
C7H7ClO2S
CAS Number:
Molecular Weight:
190.65
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Product Name
2-Chloromethyl-2,3-dihydrothieno[3,4-b]-1,4-dioxine, 95%
InChI
1S/C7H7ClO2S/c8-1-5-2-9-6-3-11-4-7(6)10-5/h3-5H,1-2H2
SMILES string
ClCC1COc2cscc2O1
InChI key
UOXHKOVMJCKBOG-UHFFFAOYSA-N
assay
95%
form
solid
mp
39-44 °C
transition temp
flash point >230 °F
functional group
chloro
Quality Level
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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)
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.
signalword
Warning
hcodes
pcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Electroactive poly (sulfobetaine-3,4-ethylenedioxythiophene)(PSBEDOT) with controllable antifouling and antimicrobial properties.
Cao B, et al.
Chemical Science, 7(3), 1976-1981 (2016)
Synthesis and electronic properties of anthraquinone-, tetracyanoanthraquinodimethane-, and perylenetetracarboxylic diimide-functionalized poly (3, 4-ethylenedioxythiophenes).
Segura JL, et al.
Chemistry of Materials, 18(12), 2834-2847 (2006)
2-Chloromethyl-2,3-dihydrothieno [3,4-b][1,4] dioxine.
Xu J, et al.
Acta Crystallographica Section E, Structure Reports Online, 65(4), o668- o668 (2009)
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