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
-
Pschorr,Silberbach
, p. 2151 (1904)
-
Role of Catalyst Support's Physicochemical Properties on Catalytic Transfer Hydrogenation over Palladium Catalysts
Batalha, Nuno,Fraga, Gabriel,Hasan, M. D.,Konarova, Muxina,Laycock, Bronwyn,Pratt, Steven,Santos, Mirella S.
, p. 5191 - 5202 (2021/10/29)
Catalytic transfer hydrogenation (CTH) is a promising reaction for valorisation of bio-based feedstocks via hydrogenation without needing to use H2. Unlike standard hydrogenation, CTH occurs via dehydrogenation (DHD) of a hydrogen donor (H-donor) and hydrogenation (HYD) of a substrate. Therefore, the “ideal” CTH catalyst must balance the catalysis of both reactions to maximize the hydrogen transfer between H-donor and substrate with minimal H2 loss to gas (high atom efficiency). Additionally, the H-donor must be highly stable to prevent secondary reactions with the substrate. Herein we study the impact of the catalyst's properties on CTH of guaiacol using bicyclohexyl, a liquid organic hydrogen carrier, as a H-donor. The reaction was promoted by palladium dispersed on three typical support materials (γ-Al2O3, MgO, and SiO2). The performance of these catalysts in the conversion of bicyclohexyl and guaiacol was evaluated, allowing to estimate the H-transfer efficiency, as well as the potential for recycling the spent H-donor (bicyclohexyl). The apparent activation energies for DHD of bicyclohexyl and HYD of guaiacol revealed that slow DHD combined with fast HYD, as is the case with Pd/MgO, favours hydrogen transfer efficiency and selectivity towards hydrogenated products. In addition, an investigation of the DHD of bicyclohexyl and HYD of guaiacol independently showed that the affinity between the organic molecules and the support significantly impacts CTH. Indeed, Pd/SiO2 was highly active for both reactions individually and almost inactive for CTH. Consequently, these findings highlight the importance of the interaction between solvent-substrate-support in designing catalysts for transfer hydrogenation.
Nickel-Catalyzed Photodehalogenation of Aryl Bromides
Higginson, Bradley,Sanjosé-Orduna, Jesus,Gu, Yiting,Martin, Ruben
supporting information, p. 1633 - 1636 (2021/04/23)
Herein, we describe a Ni-catalyzed photodehalogenation of aryl bromides under visible-light irradiation that utilizes tetrahydrofuran as hydrogen source. The protocol obviates the need for exogeneous amine reductants or photocatalysts and is characterized by its simplicity and broad scope, including challenging substrate combinations.
