936-72-1

Basic information

• Product Name: ALLYL O-TOLYL ETHER
• Synonyms: 1-(Allyloxy)-2-methylbenzene;Benzene, 1-methyl-2-(2-propenyloxy)-;Ortho-allyloxytoluene;2-ALLYLOXYTOLUENE;ALLYL O-TOLYL ETHER;O-ALLYLOXYTOLUENE;TIMTEC-BB SBB008365;1-methyl-2-prop-2-enoxybenzene
• CAS NO: 936-72-1
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.2
• Mol File: 936-72-1.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 208.81°C (rough estimate)
• Flash Point: 76.5 °C
• Appearance: /
• Density: 0.9698
• Vapor Pressure: 0.34mmHg at 25°C
• Refractive Index: 1.5188 (estimate)
• CAS DataBase Reference: ALLYL O-TOLYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: ALLYL O-TOLYL ETHER(936-72-1)
• EPA Substance Registry System: ALLYL O-TOLYL ETHER(936-72-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 936-72-1(Hazardous Substances Data)

Usage

Uses

Allyl O-Tolyl Ether is used in the research studies of the effect of ortho and para substituents on the Claisen rearrangement of allyl substituted Phenyl ethers.

InChI:InChI=1/C10H12O/c1-3-8-11-10-7-5-4-6-9(10)2/h3-7H,1,8H2,2H3

Upstream product

• 95-48-7 ortho-cresol 
• 106-95-6 allyl bromide 
• 4225-37-0 o-<(trimethylsilyl)methyl>toluene 
• 107-18-6 allyl alcohol 
• 67-56-1 methanol 
• 5652-20-0 1-methyl-2-(2-propynyloxy)benzene 
• 107-05-1 3-chloroprop-1-ene 
• 615-37-2 ortho-methylphenyl iodide 
• 95-46-5 2-methylphenyl bromide 
• 51896-43-6 (Z)-1-methyl-2-(prop-1-en-1-yloxy)benzene 

Downstream Products

• 3354-58-3 2-allyl-6-methylphenol 
• 58013-41-5 allyl-(4-chloromethyl-2-methyl-phenyl)-ether 
• 36895-23-5 3-phenyl-5-o-tolyloxymethyl-4,5-dihydro-isoxazole 
• 80448-09-5 1-(dimethylamino)-2-acetoxy-3-(2-methylphenoxy)propane 
• 80448-08-4 1-(diethylamino)-2-acetoxy-3-(2-methylphenoxy)propane 
• 99179-39-2 (2-methylphenoxy)acetaldehyde 
• 51896-43-6 (Z)-1-methyl-2-(prop-1-en-1-yloxy)benzene 
• 51896-44-7 (E)-1-methyl-2-(1-propenyloxy)benzene 
• 1610349-77-3 (E)-2-methoxycinnamyl 2-methylphenyl ether 
• 1610349-76-2 (E)-4-acetylcinnamyl 2-methylphenyl ether 
• 1610349-75-1 (E)-4-methylcinnamyl 2-methylphenyl ether 
• 1610349-74-0 (E)-4-methoxycinnamyl 2-methylphenyl ether 
• 474669-90-4 3-phenyl-1-(o-methylphenoxy)prop-2-ene 
• 95-48-7 ortho-cresol 

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.

Regioselective Alkoxycarbonylation of Allyl Phenyl Ethers Catalyzed by Pd/dppb under Syngas Conditions

A simple and regioselective synthesis of phenoxy esters and phenylthio esters is reported. The products are obtained by selective alkoxycarbonylation catalyzed by Pd2(dba)3, 1,4-bis(diphenylphisphino)butane (dppb), and syngas (CO/H2) in chloroform/alcohol. This methodology affords bifunctional products in good yield with excellent n-selectivity and without the need to use additives.

PdI2-catalyzed regioselective cyclocarbonylation of 2-allyl phenols to dihydrocoumarins

A simple, efficient, and regioselective synthesis of 3-methyl-3,4-dihydrocoumarins is reported. The reaction of 2-allyl phenols with synthesis gas was catalyzed by PdI2, and 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane (L1) and 1,3,5,7-tetramethyl-6-tetradecyl-2,4,8-trioxa-6-phosphaadamantane (L2) were effective as ligands, affording good product selectivity in all cases.