58966-09-9

Basic information

• Product Name: (E)-beta-methoxy-alpha-methylstyrene
• Synonyms: (E)-beta-methoxy-alpha-methylstyrene;(E)-1-Methoxy-2-phenyl-1-propene;[(E)-1-Methyl-2-methoxyvinyl]benzene;[(E)-2-Methoxy-1-methylethenyl]benzene;[(E)-β-Methylstyryl] methyl ether;Methyl [(E)-β-methylstyryl] ether;Einecs 261-528-7
• CAS NO: 58966-09-9
• Molecular Formula: C10H12O
• Molecular Weight: 148.20168
• EINECS: 261-528-7
• Mol File: 58966-09-9.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-beta-methoxy-alpha-methylstyrene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-beta-methoxy-alpha-methylstyrene(58966-09-9)
• EPA Substance Registry System: (E)-beta-methoxy-alpha-methylstyrene(58966-09-9)

Safety Data

• Hazardous Substances Data: 58966-09-9(Hazardous Substances Data)

Usage

General Description

(E)-beta-methoxy-alpha-methylstyrene, also known as octyl methoxycinnamate, is a widely used organic compound in the cosmetic and sunscreen industry. It is a clear liquid with a fruity odor and is insoluble in water but soluble in most organic solvents. It is primarily used as a UV-filter and absorbs UV-B rays to protect the skin from sun damage. Additionally, it is used in the production of various personal care products such as lipsticks, hair sprays, and nail polishes due to its ability to stabilize formulations and protect against UV radiation. However, there is ongoing research into its potential impact on human health and the environment, especially concerning its potential endocrine-disrupting effects. Despite this, (E)-beta-methoxy-alpha-methylstyrene remains a key ingredient in many sunscreen and cosmetic products.

Upstream product

• 90-87-9 2-phenylpropionaldehyde dimethyl acetal 
• 34713-70-7 2-Phenylpropanal 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 
• 210298-83-2 6-trifluoroomethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 473895-19-1 methyl 6-(trifluoromethylsulfonyloxy)-1,2,3,4-tetrahydropyridine-1-carboxylate 
• 591-50-4 iodobenzene 
• 13169-00-1 Methoxyallene 
• 19149-98-5 (3-methoxyprop-1-en-2-yl)benzene 
• 98-83-9 isopropenylbenzene 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 98-86-2 acetophenone 

Relevant articles and documents

Saegusa Oxidation of Enol Ethers at Extremely Low Pd-Catalyst Loadings under Ligand-free and Aqueous Conditions: Insight into the Pd(II)/Cu(II)-Catalyst System

A highly efficient and practical Pd(II)/Cu(OAc)2-catalyst system of Saegusa oxidation, which converts enol ethers to the corresponding enals with a number of diverse substrates at extremely low catalyst loadings (500 mol ppm) under ligand-free and aqueous conditions, is described. Its synthetic utility was demonstrated by large-scale applications of the catalyst system to important nature molecules. This work allows Saegusa oxidation to become a highly practical approach to preparing enals and also suggests new insight into the Pd(II)/Cu(II)-catalyst system for dehydrogenation of carbonyl compounds and decreasing Pd-catalyst loadings.

Radical Isomerization and Cycloisomerization Initiated by H? Transfer

Under H2 pressure, CoII(dmgBF2)2L2 (L = H2O, THF) generates a low concentration of an H? donor. Transfer of the H? onto an olefin gives a radical that can either (1) transfer an H? back to the metal, generating an isomerized olefin, or (2) add intramolecularly to a double bond, generating a cyclized radical. Transfer of an H? back to the metal from the cyclized radical results in a cycloisomerization. Both outcomes are favored by the low concentration of the cobalt H? donor, whereas hydrogenation and cyclohydrogenation are more likely with other catalysts (when the concentration of the H? donor is high).

Synthesis of α-acyl-functionalized azacycles by Pd-catalyzed cross-coupling reactions of α-alkoxyboronates with lactam-derived vinyl triflates

Alkoxydienyl- and alkoxystyrylboronates were used for Pd-catalyzed cross-coupling reactions with lactam-derived vinyl triflates. The hydrolysis of the coupling products with alkoxystyrylboronates provided the corresponding α-acyl-substituted 3,4-dihydro-(2H)-pyridines and 2,3,4,5-tetrahydroazepines in good to high yields. The hydrolysis of the coupling products with alkoxydienylboronates, performed in the presence of Amberlyst 15, resulted in a Nazarov-type cyclization that afforded hexahydro[1]pyrindin-7-ones and 3,4,5,6,7,8-hexahydro-(2H)-cyclopenta[b]azepin-8-ones. This methodology represents a novel and efficient procedure for the preparation of these classes of azacyclic compounds.