4218-87-5

Basic information

• Product Name: 1,2-bis(allyloxy)benzene
• Synonyms: 1,2-bis(allyloxy)benzene;1,2-Bis(2-propenyloxy)benzene;Catechol Diallyl Ether
• CAS NO: 4218-87-5
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.23836
• EINECS: 224-156-6
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 4218-87-5.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 269.8°Cat760mmHg
• Flash Point: 99.7°C
• Appearance: /
• Density: 0.982g/cm³
• Vapor Pressure: 0.0118mmHg at 25°C
• Refractive Index: 1.506
• Solubility: Ethyl Acetate (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1,2-bis(allyloxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-bis(allyloxy)benzene(4218-87-5)
• EPA Substance Registry System: 1,2-bis(allyloxy)benzene(4218-87-5)

Safety Data

• Hazardous Substances Data: 4218-87-5(Hazardous Substances Data)

Usage

Description

1,2-bis(allyloxy)benzene is an organic compound characterized by its chemical structure, which features a benzene ring with two allyl groups attached to the 1 and 2 positions via ether linkages. It is a yellow oil at room temperature, indicating its lipophilic nature and potential for use in various applications.

Uses

1. Used in Chemical Synthesis:
1,2-bis(allyloxy)benzene is used as a chemical intermediate for the synthesis of various organic compounds, particularly those with potential applications in the pharmaceutical, agrochemical, and materials science industries. Its unique structure allows for further functionalization and modification to create a wide range of derivatives.
2. Used in Antenna Response Inhibition:
1,2-bis(allyloxy)benzene is used as a Catechol (C215175) derivative with an inhibitory effect on the antenna response of the Gypsy Moth. This application is particularly relevant in the field of pest control, where it can be employed to disrupt the communication and mating behavior of this invasive species.
3. Used in the Production of Glycerol:
1,2-bis(allyloxy)benzene can be utilized in the production of glycerol, an important industrial chemical with a wide range of applications. Glycerol is used in the manufacture of various products, including cosmetics, pharmaceuticals, and as a component in the production of biodiesel and other biofuels.
4. Used in the Synthesis of Gallotannins:
1,2-bis(allyloxy)benzene can be employed in the synthesis of gallotannins, which are hydrolyzable tannins with potential pharmaceutical applications. Gallotannins have been shown to possess anticancer properties and can be used in drug delivery systems to enhance their therapeutic effects.

InChI:InChI=1/C12H14O2/c1-3-9-13-11-7-5-6-8-12(11)14-10-4-2/h3-8H,1-2,9-10H2

Upstream product

• 5651-91-2 1,2-bis(prop-2-ynyloxy)benzene 
• 120-80-9 benzene-1,2-diol 
• 107-05-1 3-chloroprop-1-ene 
• 106-95-6 allyl bromide 
• 7575-57-7 allyl benzenesulfonate 
• 35466-83-2 allyl methyl carbonate 

Downstream Products

• 76475-54-2 3.6-Diallyl-benzochinon-(1.2) 
• 50916-57-9 3,6-diallylbenzene-1,2-diol 
• 7168-95-8 2,3-dimethoxyterephthalic acid 
• 50916-58-0 3,4-diallylbenzene-1,2-diol 
• 2851-82-3 1,2-bis(oxiran-2-ylmethoxy)-benzene 
• 121910-87-0 2-bromobenzo[b][1,4]dioxine 
• 65041-54-5 2,5-dihydrobenzo-1,6-dioxocin 
• 7156-89-0 6,9,16,19-tetrahydrodibenzo[b,j][1,4,9,12]tetraoxacyclohexadecine 
• 185146-74-1 1,4-bis(2-(allyloxy)phenoxy)but-2-ene 
• 1126-20-1 2-allyloxyphenol 
• 6280-98-4 1,2-dipropoxybenzene 
• 760980-80-1 1,2-bis(1-propenyloxy)benzene 
• 98733-94-9 7,9,18,20-Tetrakis-chloromethyl-6,7,9,10,17,18,20,21-octahydro-5,11,16,22-tetraoxa-8,19-dithia-dibenzo[a,j]cyclooctadecene 
• 124009-60-5 C₂₄H₂₈Cl₂O₄S 

Relevant articles and documents

Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates

The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.

A versatile catalyst system for enantioselective synthesis of 2-substituted 1,4-benzodioxanes

We report the synthesis of enantiomerically enriched 1,4-benzodioxanes containing alkyl, aryl, heteroaryl, and/or carbonyl substituents at the 2-position. The starting 1,4-benzodioxines were readily synthesized via ring closing metathesis using an efficient nitro-Grela catalyst at ppm levels. Excellent enantioselectivities of up to 99:1 er were obtained by using the versatile catalyst system [Ir(cod)Cl]2/BIDIME-dimer in the asymmetric hydrogenation of 2-substituted 1,4-benzodioxines. Furthermore, DFT calculations reveal that the selectivity of the process is controlled by the protonation step; and coordinating groups on the substrate may alter the interaction with the catalyst, resulting in a change in the facial selectivity.

METHODS AND COMPOSITIONS FOR CONTROL OF CABBAGE LOOPER, Trichoplusia ni

The invention provides in part dialkoxybenzene compounds for controlling infestation by a Trichoplusia ni, and methods thereof. The compounds include a compound of Formula I: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl(3-methylbutyl) or allyl; R2 may be at positions 2, 3 or 4 and may be H, methyl, ethyl, propyl, n-butyl, isopentyl(3-methylbutyl) or allyl; and R3 may be optionally present at positions 2, 3 and 4, and is allyl; except that when R2 is at position 2, R3 if present is at position 3, and when R2 is at position 3, R3 if present is at positions 2 or 4, and when R2 is at position 4, R3 if present is at position 2, and when R2 is at position 4 and R3, if present, has reacted with an OH group at position 1 in a Markovnikov sense, then R3 becomes R4, a dihydrofuran.