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, too.
1, 2-Dimethoxybenzene is naturally occurring. Its biosynthesis entails the methylation of guaiacol by guaiacol O-methyltransferase.1, 2-Dimethoxybenzene is an insect attractant.
Guaiacol O-methyltransferase gene is first scent gene discovered so far in any plant species.
Uses
Different sources of media describe the Uses of 91-16-7 differently. You can refer to the following data:
1. 1, 2-Dimethoxybenzene is a building block for the organic synthesis of other aromatic compounds. Veratrole is relatively electron-rich and thus readily undergoes electrophilic substitution. An example of the use of veratrole is in the synthesis of Domipizone.
Veratrole can easily be brominated with NBS to give 4-bromoveratrole.
2. Veratrole is common reagent in organic synthesis such as the synthesis of arizonins B1 and C1. Also used in the synthesis of pharmacophores of salmeterol and roflumilast as dual β2-adrenoreceptor agonists-PDE4 inhibitors.
3. 1,2-Dimethoxybenzene was used to investigate the electroantennogram response of vine weevil, Otiorhynchus sulcatus to plant volatiles.
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
Chemical Properties
Colorless crystals or liquid. Soluble in alcohol
and ether; slightly soluble in water.
Occurrence
Reported present in asparagus (raw and cooked), bonito (dried), broccoli (cooked), cauliflower (cooked),
cognac, endive, grape, Gruyere de Comte cheese, guava, leek (raw and heated), olive, peas, rhubarb, rice bran and vanilla extract.
Definition
ChEBI: A dimethoxybenzene with the methoxy groups at ortho-positions.
Preparation
Prepared by methylation of pyrocatechol.
Taste threshold values
Intolerable at 40 ppm.
General Description
1,2-Dimethoxybenzene reacts with Li{N(SO2CF3)2} to yield molecular crystal [Li{N(SO2CF3)2}{C6H4(OCH3)2}2] having solid-state lithium ion conductivity. It is a potential pollinator attractant of the nocturnal moth Hadena bicruris.
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
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Pschorr,Silberbach
, p. 2151 (1904)
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Dimethoxybenzene and preparation method thereof
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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.
Catalytic SNAr Hydroxylation and Alkoxylation of Aryl Fluorides
Kang, Qi-Kai,Li, Ke,Li, Yuntong,Lin, Yunzhi,Shi, Hang,Xu, Lun
supporting information, p. 20391 - 20399 (2021/08/13)
Nucleophilic aromatic substitution (SNAr) is a powerful strategy for incorporating a heteroatom into an aromatic ring by displacement of a leaving group with a nucleophile, but this method is limited to electron-deficient arenes. We have now established a reliable method for accessing phenols and phenyl alkyl ethers via catalytic SNAr reactions. The method is applicable to a broad array of electron-rich and neutral aryl fluorides, which are inert under classical SNAr conditions. Although the mechanism of SNAr reactions involving metal arene complexes is hypothesized to involve a stepwise pathway (addition followed by elimination), experimental data that support this hypothesis is still under exploration. Mechanistic studies and DFT calculations suggest either a stepwise or stepwise-like energy profile. Notably, we isolated a rhodium η5-cyclohexadienyl complex intermediate with an sp3-hybridized carbon bearing both a nucleophile and a leaving group.