72424-08-9

Basic information

• Product Name: 3-propylisobenzofuran-1(3H)-one
• Synonyms: 3-propylisobenzofuran-1(3H)-one;3-propyl-3H-2-benzofuran-1-one
• CAS NO: 72424-08-9
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21178
• EINECS: -0
• Mol File: 72424-08-9.mol

Chemical Properties

• Boiling Point: 116 °C(Press: 1 Torr)
• Appearance: /
• Density: 1.100±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 3-propylisobenzofuran-1(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-propylisobenzofuran-1(3H)-one(72424-08-9)
• EPA Substance Registry System: 3-propylisobenzofuran-1(3H)-one(72424-08-9)

Safety Data

• Hazardous Substances Data: 72424-08-9(Hazardous Substances Data)

Usage

Uses

Used in Fragrance and Flavor Industry:
3-propylisobenzofuran-1(3H)-one is used as a flavoring agent for its sweet, floral, and herbal aroma, contributing to the unique scents and tastes in various consumer products such as perfumes, cosmetics, and food flavorings.
Used in Medicinal and Therapeutic Applications:
3-propylisobenzofuran-1(3H)-one is being researched for its potential medicinal and therapeutic properties, including anti-inflammatory and antioxidant effects, which could lead to its use in pharmaceutical formulations and treatments for various health conditions.

Upstream product

• 85-44-9 phthalic anhydride 
• 107-08-4 1-iodo-propane 
• 17369-59-4 3-(n-propylidene)phthalide 
• 16859-59-9 3-hydroxy-1(3H)-isobenzofuranone 
• 106-94-5 propyl bromide 
• 1696-17-9 N,N-diethylbenzamide 
• 123-72-8 butyraldehyde 
• 54887-23-9 2-butylbenzoic acid 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 72424-20-5 3-Hydroxy-3-propyl-3H-isobenzofuran-1-one 
• 1248010-13-0 1-(2-bromophenyl)butan-1-ol 
• 27326-43-8 2-vinylbenzoic acid 
• 855472-09-2 2-butyryl-benzoic acid ethyl ester 

Downstream Products

• 65-85-0 benzoic acid 
• 107-92-6 butyric acid 
• 117436-86-9 α-propyl benzenedimethanol-1,2 
• 952412-99-6 C₁₁H₁₄O₃ 
• 117436-87-0 (bromo-1 butyl)-1 bromomethyl-2 benzene 

Relevant articles and documents

Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp3)-H Lactonization of 2-Alkylbenzoic Acids

A mild and practical C(sp3)-H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2-alkylbenzoic acid substrate, magnesium ion, and bromate anion.

Palladium-Catalyzed Direct Oxidative Coupling of Iodoarenes with Primary Alcohols Leading to Ketones: Application to the Synthesis of Benzofuranones and Indenones

In the present study, a palladium-catalyzed direct oxidative acylation through cross-dehydrogenative coupling has been investigated, utilizing readily available primary alcohols as acylating sources. Overall, this oxidative coupling proceeds via three distinct transformations such as oxidation, radical formation, and cross-coupling in one catalytic process. This protocol does not involve the assistance of a directing group or activation of the carbonyl group by any other means. Furthermore, this reaction made use of no toxic CO gas as carbonylating agent; instead, feedstock primary alcohols have been utilized as acylation source. Notably, the synthesis of benzofuranones and indenones is enabled. This strategy was also applied to the synthesis of n-butylphthalide, fenofibrate, pitofenone, and neo-lignan.

Synthesis of 1,2-phenylenedimethanols by base-promoted reduction of isobenzofuran-1(3H)-ones with silane

An efficient method for preparation of substituted 1,2-phenylenedimethanols and aliphatic 1,4-diols that are valuable intermediates in organic synthesis, has been developed by the base-promoted reduction of isobenzofuran-1(3H)-ones and γ-lactones with silane under mild conditions. Compared with traditional procedures using stoichiometric amounts of metal hydrides and alkyl reductants, the present method avoids the use of sensitive reagents and is operationally simple and a broad variety of functional groups are tolerated.

Saturated oxygen and nitrogen heterocycles: Via oxidative coupling of alkyltrifluoroborates with alkenols, alkenoic acids and protected alkenylamines

Saturated heterocycles are important components of many bioactive compounds. The method disclosed herein enables a general route to a range of 5-, 6- and 7-membered oxygen and nitrogen heterocycles by coupling potassium alkyltrifluoroborates with heteroat

Electron-Transfer-Induced Intramolecular Heck Carbonylation Reactions Leading to Benzolactones and Benzolactams

A metal-catalyst-free intramolecular Heck carbonylation reaction of benzyl alcohols and benzyl amines with carbon monoxide under heating at 250 °C affords the corresponding benzolactones and benzolactams in good to excellent yields. A hybrid radical/ionic chain mechanism, involving electron transfer from radical anions generated by nucleophilic attack of alcohols or amines on intermediate acyl radicals, is proposed.

Ruthenium-Catalyzed Enantioselective Hydrogenation/Lactonization of 2-Acylarylcarboxylates: Direct Access to Chiral 3-Substituted Phthalides

Highly enantioselective tandem hydrogenation/lactonization of various 2-acylarylcarboxylates including 2-aroylarylcarboxylates were realized by using [RuCl(benzene)(S)-SunPhos]Cl as the catalyst under mild reaction conditions. Excellent enantioselectivities (up to 99.6 % ee) and activities (S/C=1000) were obtained. This convenient and practical method enables a direct access to a series of highly optically pure 3-substituted phthalides that are very important molecules as valuable pharmacological compounds and diversified synthons for medicinal chemistry. Moreover, a gram-scale reaction was performed to further demonstrate the practicality of this approach.

Domino [Pd]-Catalysis: One-Pot Synthesis of Isobenzofuran-1(3H)-ones

An efficient domino [Pd]-catalysis for the synthesis of isobenzofuran-1(3H)-ones is presented. The strategy shows broad substrate scope and is amenable to o-bromobenzyl tertiary/secondary/primary alcohols. Significantly, the method was applied to the synthesis of antiplatelet drug n-butyl phthalide and cytotoxic agonist 3a-[4′-methoxylbenzyl]-5,7-dimethoxyphthalide.

Cu-MEDIATED ANNULATION FOR THE EFFECTIVE SYNTHESIS OF 3-SUBSTITUTED PHTHALIDES

The present invention disclosed herein is a novel commercially feasible, one pot synthesis of library of 3-substituted phthalides of formula I via CuCN mediated oxidative cyclization in high yield. Formula I

Cu-MEDIATED ANNULATION FOR THE EFFECTIVE SYNTHESIS OF 3-SUBSTITUTED PHTHALIDES

The present invention disclosed herein is a novel commercially feasible, one pot synthesis of library of 3-substituted phthalides of formula I via CuCN mediated oxidative cyclization in high yield. Formula I

Synthesis, resolution, and antiplatelet activity of 3-substituted 1(3H)-isobenzofuranone

A series of 3-substituted-1(3H)-isobenzofuranone 6a-g and 7a-g were synthesized from phthalic anhydride. The compound 6a-g was resolved. The antiplatelet activities of these compounds were evaluated using in vitro experiment of platelet aggregation. The levels of antiplatelet activity were displayed as following sequence: l-isomer > dl-isomer > d-isomer, respectively. The alkylphthalide is more active than the corresponding alkenephthalide. All these compounds were less active than n-butylphthalide (NBP, 6c) and Aspirin (Asp).