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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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 ]
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

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