140-67-0

Basic information

• Product Name: 1 -Methoxy-4-(2-propenyl) benzene
• Synonyms: 1-Allyl-4-methoxybenzene;1-Allyl-4-methoxybenzol;p-Allylphenyl methyl ether;1-Methoxy-4-(prop-2-en-1-yl)benzene;Isoanethole;p-Allylmethoxybenzene;Esdragon;Allylphenyl methyl ether, p-;4-Allylanisole
• CAS NO: 140-67-0
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.20168
• EINECS: 205-427-8
• Mol File: 140-67-0.mol

Chemical Properties

• Melting Point: 28-35 °C
• Boiling Point: 216 °C at 760 mmHg
• Flash Point: 81.1 °C
• Appearance: colourless liquid with an aniseed smell
• Density: 0.938 g/cm³
• Vapor Pressure: 0.21mmHg at 25°C
• Refractive Index: 1.505
• CAS DataBase Reference: 1 -Methoxy-4-(2-propenyl) benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1 -Methoxy-4-(2-propenyl) benzene(140-67-0)
• EPA Substance Registry System: 1 -Methoxy-4-(2-propenyl) benzene(140-67-0)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R22:
• Hazardous Substances Data: 140-67-0(Hazardous Substances Data)

Usage

Uses

Used in the Fragrance and Flavor Industry:
1-Methoxy-4-(2-propenyl) benzene is used as a key ingredient in the fragrance and flavor industry for its distinctive, sweet, and spicy aroma that resembles clove. It is incorporated into perfumes, colognes, and various food products to enhance their sensory appeal.
Used in Cosmetics and Personal Care Products:
In the cosmetics and personal care industry, 1-Methoxy-4-(2-propenyl) benzene is used as a natural preservative and fragrance component. Its antimicrobial properties help to prevent the growth of bacteria and fungi, ensuring the safety and longevity of cosmetic products.
Used in Medicinal Applications:
1-Methoxy-4-(2-propenyl) benzene is utilized in medicinal applications due to its anti-inflammatory and antioxidant properties. It can be found in various pharmaceutical formulations, including creams, ointments, and oral medications, to alleviate inflammation and promote healing.
Used in Antimicrobial Agents:
Due to its antimicrobial properties, 1-Methoxy-4-(2-propenyl) benzene is used as a natural alternative to synthetic preservatives in various industries, including food and beverage, to inhibit the growth of harmful microorganisms and extend the shelf life of products.
Used in the Production of Resins and Plastics:
1-Methoxy-4-(2-propenyl) benzene is also used in the production of certain types of resins and plastics, where it serves as a starting material for the synthesis of various polymers with specific properties, such as heat resistance and chemical stability.

Upstream product

• 556-56-9 allyl iodid 
• 112219-63-3 (4-methoxyphenyl)magnesium iodide 
• 104678-34-4 4-(3-chloro-allyl)-anisole 
• 5406-18-8 3-(p-methoxyphenyl)-1-propanol 
• 108-24-7 acetic anhydride 
• 100-66-3 methoxybenzene 
• 107-05-1 3-chloroprop-1-ene 
• 106-95-6 allyl bromide 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 501-92-8 4-(prop-2-enyl)phenol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 24850-33-7 allyltributylstanane 

Downstream Products

• 53484-54-1 3-(4-methoxyphenyl)prop-2-enyl acetate 
• 132739-69-6 C-(4-Methoxy-1-vinyl)-N-phenyl nitron 
• 87264-35-5 trans-2,3,3a,4,5,6-hexahydro-2-(4-methoxybenzyl)pyrrolo-<1,2-b>isoxazole 
• 73892-88-3 2-(4-methoxyphenyl)-1-thiocyanato-3-chloropropane 
• 73892-89-4 1-acetoxy-2-(4-methoxyphenyl)-3-thiocyanatopropane 
• 40469-24-7 2-(4-methoxyphenyl)-1,3-dithiocyanatopropane 
• 73892-91-8 1-isothiocyanato-2-(4-methoxyphenyl)-3-thiocyanatopropane 
• 73892-90-7 3-(4-methoxyphenyl)-1,2-dithiocyanatopropane 
• 81701-30-6 (E)-4-methoxycinnamyl acetate 
• 90875-08-4 (rac)-4-(2-bromopropyl)-1-methoxybenzene 
• 5406-18-8 3-(p-methoxyphenyl)-1-propanol 
• 134296-80-3 1-iodo-3-(4-methoxyphenyl)2-propanol 
• 134296-74-5 2-fluoro-1-iodo-3-(4-methoxyphenyl)propane 
• 24680-50-0 4-methoxy-trans-cinnamaldehyde 

Relevant articles and documents

Regioselective Allylmetalation of Allenes with Tetraallylmanganate or Allylmagnesium Chloride under MnCl2 Catalysis

(Equation presented) Treatment of allenes with tetraallylmanganate provides allylated products with high regioselectivity. A catalytic amount of MnCl2 combined with allylmagnesium chloride also achieves efficient allylmetalatlon of allenes. The resulting alkenylmagnesium spedes react with various electrophiles. In the presence of molecular oxygen, the alkenylmagnesium undergoes diallylation reaction. A cyclization reaction of 1,2,6-heptatriene with tetraallylmanganate is also described.

Tetraalkylammonium salt-based catalyst systems for directing Heck-type reactions. Arylation of allyltrimethylsilane

An appropriate selection of the [Pd/base/QX] catalyst systems allows one to direct at will the palladium-catalysed arylation of allyltrimethylsilane towards the formation of either (E)-1-aryl-3-(trimethylsilyl)-1-propene or 3-aryl-1-propene, by preventing

Stannylated polynorbornenes as new reagents for a clean stille reaction

New functionalized polynorbornenes have been obtained in good yields by vinylic copolymerization of norbornene with a (norbornenyl)Sn-Bu2Cl monomer, catalyzed by [Ni(C6F5)2(SbPh 3)2]. Subsequent functionalization produces a wide variety of polymers with different -SnBu2R groups (R = aryl, vinyl, alkynyl). The polymers can be used as R-transfer reagents in Stille couplings, thereby providing easy workup and separation of the polymeric tin byproducts from the coupling products. Tin contents of around 0.05 wt% are found in the Stille products. The stannylated polymers can be recycled and reused with good efficiency.

Batch stille coupling with insoluble and recyclable stannylated polynorbornenes

The Stille coupling can be carried out in a batch process using insoluble tin supports. The new type of support consists of stannylated polymers based on the vinylic polynorbornene skeleton that allow one to use a set-up where the tin reagent is immobilized in a column. The immobilized stannylated polymeric reagent can be easily reused. The coupling products are thus obtained by a very simple work-up procedure and have very low levels of tin contamination.

A novel palladium catalyst for cross-coupling of allyl acetates with arylboronic acids

The palladium-catalyzed coupling reactions of various arylboronic acids and allylic acetates take place readily under mild conditions. The choice of ligand in the palladium catalyst and the solvent are critical to the yields of coupled products. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

A simple synthetic approach to allylated aromatics via the Suzuki-Miyaura cross-coupling reaction

The Pd-catalyzed cross-coupling reaction of aromatic iodides and bromides with allylboronic acid esters (2a,b) in the presence of CsF gave allylated aromatics. Georg Thieme Verlag Stuttgart.

Electron-transfer-induced intermolecular [2 + 2] cycloaddition reactions based on the aromatic "redox tag" strategy

Novel electron-transfer-induced intermolecular [2 + 2] cycloaddition reactions between an aliphatic cyclic enol ether and several unactivated olefins have been demonstrated on the basis of the aromatic "redox tag" strategy. The aromatic "redox tag" was oxidized during the formation of the cyclobutane ring, affording the relatively long-lived aromatic radical cation, which was then reduced to complete the overall reaction that constructed the corresponding [2 + 2] cycloadducts. The aromatic "redox tag" was also found to facilitate electron-transfer-induced cycloreversion reactions of cyclobutane rings.

Polyphosphazenes for the Stille reaction: A new type of recyclable stannyl reagent

A random phosphazene copolymer {[NP((CH2)7-Br)Ph]0.5[NPMePh]0.5}n (2) and a block copolyphosphazene {[NP((CH2)7-Br)Ph]0.5[NPMePh]0.5}45-b-[NP(O2C12H8)]55 (5), having a branch with two randomly distributed units, have been synthesized and used as precursors for the stannyl derivatives {[NP((CH2)7-SnBu2An)Ph]0.5[NPMePh]0.5}n (3) and {[NP((CH2)7-SnBu2An)Ph]0.5[NPMePh]0.5}45-b-[NP(O2C12H8)]55 (6, An = p-MeOC6H4). Polymers 3 and 6 were tested as recyclable tin reagents in the Stille cross-coupling reaction with ArI, using various Pd catalysts and different experimental conditions. Polymer 6 can be recycled without a significant release of tin, but its efficiency decreased after three consecutive cycles. This effect was explained by studying the self-assembly of the polymer under the same conditions used for the catalytic experiments, which evidenced the progressive coalescence of the polymeric vesicles (polymersomes) leading to stable and bigger core-shell aggregates by the attraction of the [NP(O2C12H8)] rich membranes, thus decreasing the accessibility of the tin active centers.

Nickel-Catalyzed Negishi-Type Arylation of Trialkylsulfonium Salts

Negishi-type arylation of trialkylsulfonium salts with arylzinc reagents has been accomplished under nickel catalysis. The use of cyclohexanethiol as an additional ligand was found to be particularly important to promote C-S cleavage. The present reaction accommodates one-pot arylation of dialkyl sulfides by combining with S -methylation with MeOTf. Mechanistic experiments suggest that C-S cleavage would proceed via single-electron transfer (SET) to generate the most stable carbon-centered radical and that the thiolate ligand would promote the C-S cleavage and radical recombination step.

Mild and efficient desulfurization of thiiranes with MoCl5/Zn system

Desulfurization of a variety of thiiranes to alkenes occurs chemoselectively in high yields upon treatment with MoCl5/Zn system under mild conditions. The new methodology demonstrates high functional group tolerance toward chloro, bromo, fluoro, methoxy, ester, ether and keto groups.