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Sigma-Aldrich

1,4-Difluoro-2,5-dimethoxybenzene

99%

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About This Item

Linear Formula:
F2C6H2(OCH3)2
CAS Number:
199866-90-5
Molecular Weight:
174.14
MDL number:
MFCD00142553
UNSPSC Code:
12352100
PubChem Substance ID:
24864020
NACRES:
NA.22

Assay

99%

mp

123-125 °C (lit.)

SMILES string

COc1cc(F)c(OC)cc1F

InChI

1S/C8H8F2O2/c1-11-7-3-6(10)8(12-2)4-5(7)9/h3-4H,1-2H3

InChI key

QNQUBUBFPGHXAL-UHFFFAOYSA-N

General description

1,4-Difluoro-2,5-dimethoxybenzene is an alkoxy arene. It undergoes 1:3 reaction with TaF5 in chloroform at 40-50°C to afford long-lived radical cation salts [1,4-F2-2,5-(MeO)2C6H2][Ta2F11].

Application

1,4-Difluoro-2,5-dimethoxybenzene is suitable reagent used in a study to investigate the direct anodic electrodeposition of polypyrrole, poly(3,4-ethylenedioxythiophene) and polythiophene on Cu electrodes by employing a corrosion inhibitor. It may be used in the following studies:
  • Synthesis of 7-fluoro-5,8-dimethoxy-1-naphthol.
  • As novel precursor for the iterative double benzyne-furan Diels-Alder reactions.
  • Synthesis of 1,4-bis(phosphino)-2,5-difluoro-3,6-dimethoxybenzenes.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Gillian E Morton et al.
The Journal of organic chemistry, 70(9), 3525-3529 (2005-04-23)
[reaction: see text] The use of 1,4-difluoro-2,5-dimethoxybenzene as a novel precursor for iterative two-directional benzyne-furan Diels-Alder reactions, using a range of 2- and 3-substituted furans, is reported. Substituted oxabenzonorbornadienes were synthesized following the initial Diels-Alder reaction, which upon ring opening
Electrodeposition of Conducting Polymers on Copper in Nonaque-ous Media by Corrosion Inhibition.
Lee S and Lee H.
Journal of Electrochemical Science and Technology, 3(2), 85-89 (2012)
1, 4-Bis (phosphine)-2, 5-difluoro-3, 6-dihydroxybenzenes and their P-oxides: Syntheses, structures, ligating and electronic properties.
Pignotti LR, et al.
Journal of Organometallic Chemistry, 693(20), 3263-3272 (2008)
Gillian E Morton et al.
Organic letters, 8(13), 2859-2861 (2006-06-16)
[reaction: see text] 7-Fluoro-5,8-dimethoxy-1-naphthol, prepared from the lithiation and benzyne formation from 1,4-difluoro-2,5-dimethoxybenzene and Diels-Alder cycloaddition with furan, was sequentially C-glycosidated under Suzuki conditions and O-glycosidated using di-O-acetyl-L-rhamnal to provide the corresponding beta-naphthyl C,O-disaccharide. Further lithiation, benzyne formation, and cycloaddition
Fabio Marchetti et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 19(41), 13962-13969 (2013-08-21)
The 1:3 reactions of the alkoxy arenes 1,4-(MeO)2 C6 H4 and 1,4-F2 -2,5-(MeO)2 C6 H2 with TaF5 in chloroform at 40-50 °C resulted in formation in about 35 % yield of the long-lived radical cation salts [1,4-(MeO)2 C6 H4 ][Ta2 F11 ]

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