24165-65-9

Basic information

• Product Name: 1-(3-METHOXY-PHENYL)-BUT-3-EN-1-OL
• Synonyms: 1-(3-METHOXY-PHENYL)-BUT-3-EN-1-OL
• CAS NO: 24165-65-9
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.22766
• Mol File: 24165-65-9.mol
• Article Data: 55

Chemical Properties

• Boiling Point: 102 °C(Press: 0.1 Torr)
• Appearance: /
• Density: 1.032±0.06 g/cm3(Predicted)
• PKA: 14.29±0.20(Predicted)
• CAS DataBase Reference: 1-(3-METHOXY-PHENYL)-BUT-3-EN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-METHOXY-PHENYL)-BUT-3-EN-1-OL(24165-65-9)
• EPA Substance Registry System: 1-(3-METHOXY-PHENYL)-BUT-3-EN-1-OL(24165-65-9)

Safety Data

• Hazardous Substances Data: 24165-65-9(Hazardous Substances Data)

Usage

Description

1-(3-METHOXY-PHENYL)-BUT-3-EN-1-OL, also known as isosafrol, is a chemical compound with the molecular formula C10H12O2. It is a colorless to pale yellow liquid that is commonly found in the essential oils of various plants. Isosafrol possesses potential anti-inflammatory and anti-tumor properties, making it a compound of interest for various applications.

Uses

Used in Perfumery and Flavor Industry:
1-(3-METHOXY-PHENYL)-BUT-3-EN-1-OL is used as a key component in the synthesis of perfumes and flavorings due to its unique and appealing scent. Its presence in essential oils from various plants contributes to the distinct fragrances and flavors in these industries.
Used in Pharmaceutical Industry:
1-(3-METHOXY-PHENYL)-BUT-3-EN-1-OL is used as a precursor in the pharmaceutical industry for the synthesis of various drugs. Its potential anti-inflammatory and anti-tumor properties are being studied for the development of new medications to address these health concerns.
Used in Controlled Substances:
1-(3-METHOXY-PHENYL)-BUT-3-EN-1-OL is used as a precursor to the illegal drug MDMA (3,4-methylenedioxymethamphetamine). Due to its potential for abuse, isosafrol is a controlled substance in many countries, highlighting the need for strict regulation and monitoring of its production and distribution.

Upstream product

• 556-56-9 allyl iodid 
• 591-31-1 3-methoxy-benzaldehyde 
• 24850-33-7 allyltributylstanane 
• 106-95-6 allyl bromide 
• 1730-25-2 allylmagnesium bromide 
• 1286204-60-1 4-(3-methoxyphenyl)-4-trimethylsiloxy-1-butene 
• 591-87-7 Allyl acetate 
• 762-72-1 allyl-trimethyl-silane 
• 7393-43-3 tetraallyl tin 
• 2622-05-1 allylmagnesium bromide 

Downstream Products

• 1335143-97-9 6-(3-methoxyphenyl)-5,6-dihydro-2H-pyran-2-one 
• 1335143-78-6 1-(3-methoxyphenyl)but-3-enyl acrylate 
• 20766-31-8 (E)-4-(3-methoxyphenyl)but-3-en-2-one 
• 1620206-52-1 (E)-4-(3-methoxystyryl)-2-(trichloromethyl)-4,5-dihydro-oxazole 

Relevant articles and documents

Organocatalytic Asymmetric Synthesis of Cyclic Acetals with Spirooxindole Skeleton

An organocatalytic asymmetric synthesis of cyclic acetal with spirooxindole skeleton has been developed via a domino reaction between isatin and γ-hydroxy enones. Bifunctional squaramide catalyst with adamantyl motif was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst, the desired products were obtained in 1.8:1 to 9:1 diastereo- and 86% to >99% enantioselectivities from a range of substituted isatins and γ-hydroxy enones. (Figure presented.).

Photoredox Allylation Reactions Mediated by Bismuth in Aqueous Conditions

Organometallic allylic reagents are widely used in the construction of C?C bonds by Barbier-type reactions. In this communication, we have described a photoredox Barbier allylation of aldehydes mediated by bismuth, in absence of other metals as co-reductants. Mild reaction conditions, tolerance of oxygen, and use of aqueous solvent make this photoredox methodology attractive for green and sustainable synthesis of homoallylic alcohols.

Nickel-Catalyzed Hydroarylation of in Situ Generated 1,3-Dienes with Arylboronic Acids Using a Secondary Homoallyl Carbonate as a Surrogate for the 1,3-Diene and Hydride Source

The nickel-catalyzed hydroarylation of 1,3-dienes with arylboronic acids using a secondary homoallyl carbonate as a surrogate for the 1,3-diene and hydride source has been developed. The synthetic strategy allowed an efficient access to a wide array of hydroarylation products in high yields with high functional group compatibility without the use of an external hydride source. Mechanistic experiments indicated that the alkene-directed oxidative addition and subsequent β-hydride elimination would be a critical process in this transformation.