70482-71-2

Basic information

• Product Name: 1-(Methoxymethoxy)-4-(2-propen-1-yl)benzene
• Synonyms: 1-(Methoxymethoxy)-4-(2-propen-1-yl)benzene;4-Methoxymethoxy allylbenzene
• CAS NO: 70482-71-2
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.23
• Mol File: 70482-71-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 0.986
• CAS DataBase Reference: 1-(Methoxymethoxy)-4-(2-propen-1-yl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(Methoxymethoxy)-4-(2-propen-1-yl)benzene(70482-71-2)
• EPA Substance Registry System: 1-(Methoxymethoxy)-4-(2-propen-1-yl)benzene(70482-71-2)

Safety Data

• Hazardous Substances Data: 70482-71-2(Hazardous Substances Data)

Usage

General Description

1-(Methoxymethoxy)-4-(2-propen-1-yl)benzene, also known as Eugenol methoxy ether, is a chemical compound with the molecular formula C12H16O2. It is a colorless to pale yellow liquid with a strong, sweet, and spicy odor. 1-(Methoxymethoxy)-4-(2-propen-1-yl)benzene is commonly found in essential oils such as clove oil, nutmeg oil, and cinnamon leaf oil. It is used in the production of perfumes, flavorings, and as an ingredient in dental materials. Eugenol methoxy ether exhibits antifungal and antimicrobial properties, making it a valuable ingredient in various pharmaceutical and personal care products. Additionally, it is also used as a pesticide and insecticide in agricultural applications. However, it is important to handle this chemical with care as it can be toxic and irritating to the skin, eyes, and respiratory system.

Upstream product

• 106-41-2 4-bromo-phenol 
• 25458-45-1 p-methoxymethoxybromobenzene 
• 106-95-6 allyl bromide 
• 501-92-8 4-(prop-2-enyl)phenol 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 163125-71-1 4-Allyl-2-iodophenyl methoxymethyl ether 
• 35354-74-6 Honokiol 
• 10292-61-2 4-cyclopropylphenol 
• 95234-03-0 (Z)-7-{(1S,2S,3S,5R)-3-[2-Hydroxy-3-(4-methoxymethoxy-phenyl)-propylamino]-6,6-dimethyl-bicyclo[3.1.1]hept-2-yl}-hept-5-enoic acid methyl ester 
• 95234-08-5 (Z)-7-{(1S,2S,3S,5R)-3-[2-Hydroxy-3-(4-hydroxy-3-iodo-phenyl)-propylamino]-6,6-dimethyl-bicyclo[3.1.1]hept-2-yl}-hept-5-enoic acid 
• 95234-05-2 (Z)-7-{(1S,2S,3S,5R)-3-[2-Hydroxy-3-(4-hydroxy-phenyl)-propylamino]-6,6-dimethyl-bicyclo[3.1.1]hept-2-yl}-hept-5-enoic acid 
• 93673-81-5 magnolignan A 
• 528-43-8 Magnolol 
• 501-92-8 4-(prop-2-enyl)phenol 
• 95234-02-9 2-(4-Methoxymethoxy-benzyl)-oxirane 

Relevant articles and documents

Concise and practical approach for the synthesis of honokiol, a neurotrophic agent

An improved method has been developed for the synthesis of honokiol using a readily available p-bromophenol as a precursor. The key step involved in this method is ortho-lithiation facilitated by methoxymethyl ether (MOM). Other important steps are ortho-allyl phenyl ether Claisen rearrangement and a Suzuki coupling for the construction of biaryls. This method does not require pre-functionalization of aromatic ring with bromide for the generation of arylboronic acid.

Synthesis of (-)-Monoterpenylmagnolol and Magnolol

(-)-Monoterpenylmagnolol (3) was synthesized in eight steps from (+)-3,9-dibromocamphor (4) and the bis(methoxymethyl) ether (22) of 3-(4-hydroxyphenyl)-1-propanol.Fragmentation of an endo-3-aryl-9-bromocamphor (27) provided the correct absolute stereochemistry.In this total synthesis, dissolving metal conditions were developed to reduce enol phosphate and isopropenyl functions without concomitant reduction of an attached phenol.Palladium(0)-catalyzed cross-coupling of an arylzinc chloride with 4-allyl-2-iodophenyl methoxymethyl ether (34) provided the desired tricyclic 1,2,3,5-tetrasubstituted biaryl 41 in fair yield without optimization and with little isomerization of the allyl group.Magnolol (1) was also synthesized by aryl coupling of 34 and the methoxymethyl ether of 4-allyl-2-lithiophenol via the zinc chloride method as above, as well as from 5,5'-dibromo-2,2'-dimethoxybiphenyl (37) by allylation with allyltributylstannane followed by ether cleavage.