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| | 1,2-Dimethoxybenzene Chemical Properties |
| Melting point | 15 °C(lit.) | | Boiling point | 206-207 °C(lit.) | | density | 1.084 g/mL at 25 °C(lit.) | | vapor pressure | 0.63 hPa (25 °C) | | FEMA | 3799 | 1,2-DIMETHOXYBENZENE | | refractive index | n20/D 1.533(lit.) | | Fp | 189 °F | | storage temp. | Store below +30°C. | | solubility | 6.69g/l insoluble | | form | Powder | | color | White to cream | | Odor | at 1.00 % in dipropylene glycol. sweet creamy vanilla phenolic musty | | Odor Type | vanilla | | Water Solubility | Soluble in alcohol, diethyl ether, acetone, and methanol. Slightly soluble in water. | | FreezingPoint | 21.0 to 23.0 ℃ | | Merck | 14,9956 | | JECFA Number | 1248 | | BRN | 1364621 | | InChIKey | ABDKAPXRBAPSQN-UHFFFAOYSA-N | | LogP | 1.75-2.22 at 25℃ | | CAS DataBase Reference | 91-16-7(CAS DataBase Reference) | | NIST Chemistry Reference | Benzene, 1,2-dimethoxy-(91-16-7) | | EPA Substance Registry System | Veratrole (91-16-7) |
| Hazard Codes | Xn | | Risk Statements | 22-20/21/22 | | Safety Statements | 36-23-24/25 | | WGK Germany | 1 | | RTECS | CZ6475000 | | TSCA | Yes | | HS Code | 29093090 | | Toxicity | LD50 in rats, mice (mg/kg): 1360, 2020 orally (Jenner) |
| | 1,2-Dimethoxybenzene Usage And Synthesis |
| 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 | 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. | | 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.
| | Uses | 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. | | Uses | 1,2-Dimethoxybenzene was used to investigate the electroantennogram response of vine weevil, Otiorhynchus sulcatus to plant volatiles. | | 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.] |
| | 1,2-Dimethoxybenzene Preparation Products And Raw materials |
| Raw materials | PETROLEUM ETHER-->Catechol-->Chloromethane-->Guaiacol-->1-(3,4-Dimethoxyphenyl)-2-(2-methoxyphenoxy)ethanone Methyl ether-->1,2-DIMETHOXY-4-ETHYLBENZENE-->1-(3,4-DIMETHOXY-PHENYL)-PROPAN-1-ONE | | Preparation Products | 6,7-DIMETHOXY-3-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE-->5-chloro-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile-->3-Methyl-2-(3,4-dimethoxyphenyl)butyronitrile-->2,3-Dimethoxyphenylboronic acid-->(3,4-Dimethoxyphenyl)acetonitrile-->4-Chloro-3',4'-dimethoxybenzophenone-->2,3,6,7,10,11-Triphenylenehexol-->4,5-Dimethoxy-1-cyanobenzocyclobutane-->3,4-Dimethoxyphenol-->ETHYL 3,4-DIMETHOXYPHENYLACETATE-->4-Aminoveratrole-->(R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline-->METHOXYBENZOQUINONE-->6,7-DIMETHOXYISOQUINOLINE-->3-ISOPROPYLCATECHOL |
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