91-16-7 Usage
Description
1,2-Dimethoxybenzene, commonly known as veratrole, is an organic compound with the formula C6H4(OCH3)2. It is a colorless liquid with a pleasant odor and slight solubility in water. It is the dimethyl ether derived from pyrocatechol and is naturally occurring. Its biosynthesis entails the methylation of guaiacol by guaiacol O-methyltransferase. 1,2-Dimethoxybenzene is also an insect attractant.
Uses
Used in Organic Synthesis:
1,2-Dimethoxybenzene is used as a building block for the organic synthesis of other aromatic compounds. Due to its relatively electron-rich nature, it readily undergoes electrophilic substitution. Examples of its use include the synthesis of Domipizone and the formation of 4-bromoveratrole through bromination with NBS.
Used in Pharmaceutical Synthesis:
Veratrole serves as a common reagent in organic synthesis for the synthesis of pharmacophores of salmeterol and roflumilast, which are dual β2-adrenoreceptor agonists-PDE4 inhibitors. It is also used in the synthesis of arizonins B1 and C1.
Used in Insect Attraction Research:
1,2-Dimethoxybenzene has been utilized to investigate the electroantennogram response of vine weevil, Otiorhynchus sulcatus, to plant volatiles, providing insights into insect attraction and behavior.
References
1.https://en.wikipedia.org/wiki/1,2-Dimethoxybenzene
2.https://pubchem.ncbi.nlm.nih.gov/compound/1_2-Dimethoxybenzene#section=Chemical-and-Physical-Properties
Preparation
Prepared by methylation of pyrocatechol.
Purification Methods
Steam distil veratrole, then fractionally distil it from BaO, CaH2 or Na. Crystallise it from *benzene or low-boiling pet ether at 0o. Fractionally crystallise it from its melt. Store it over anhydrous Na2SO4. [Beilstein 6 IV 5564.]
Check Digit Verification of cas no
The CAS Registry Mumber 91-16-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 1 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 91-16:
(4*9)+(3*1)+(2*1)+(1*6)=47
47 % 10 = 7
So 91-16-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3
91-16-7Relevant articles and documents
-
Pschorr,Silberbach
, p. 2151 (1904)
-
Dimethoxybenzene and preparation method thereof
-
Paragraph 0043-0065, (2021/05/29)
The invention relates to the field of etherification of organic compounds, and discloses dimethoxybenzene and a preparation method thereof. The method comprises the following steps that 1, in the presence of a catalyst, catechol serves as a raw material, dimethyl carbonate serves as a methylation reagent, a methylation reaction is conducted, and imethoxybenzene is obtained, wherein the catalyst is 1, 8-diazabicyclo [5.4. 0] undec-7-ene; and 2) the reaction product obtained in the step 1) is distilled to recover the dimethyl carbonate, and then reduced pressure distillation is performed to obtain the dimethoxybenzene. According to the method, the green and environment-friendly methylation reagent dimethyl carbonate is adopted, no waste water or solid is generated, the yield is high, and the method is very suitable for industrial production and meets the green and environment-friendly process requirements.
Metal-Free Photoredox-Catalyzed Hydrodefluorination of Fluoroarenes Utilizing Amide Solvent as Reductant
Toriumi, Naoyuki,Yamashita, Kazuya,Iwasawa, Nobuharu
supporting information, p. 12635 - 12641 (2021/08/03)
A metal-free photoredox-catalyzed hydrodefluorination of fluoroarenes was achieved by using N,N,N’,N’-tetramethyl-para-phenylenediamine (1) as a strong photoreduction catalyst. This reaction was applicable not only to electron-rich monofluoroarenes but also to polyfluoroarenes to afford non-fluorinated arenes. The experimental mechanistic studies indicated that the amide solvent NMP plays an important role for regeneration of the photocatalyst, enabling additive-free photoreduction catalysis.