20185-55-1

Basic information

• Product Name: METHYL 4-ISOPROPYLBENZOATE
• Synonyms: METHYL 4-ISOPROPYLBENZOATE;RARECHEM AL BF 0112;NSC20013;4-Isopropylbenzoic acid methyl ester;4-Isopropylmethyl benzenecarboxylate;Benzoic acid, 4-(1-methylethyl)-, methyl ester;Benzoic acid, p-isopropyl-, methyl ester;Methyl p-isopropylbenzoate
• CAS NO: 20185-55-1
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.23
• Mol File: 20185-55-1.mol
• Article Data: 43

Chemical Properties

• Boiling Point: 270.46°C (rough estimate)
• Flash Point: 106.9 °C
• Appearance: /
• Density: 1.0180
• Vapor Pressure: 0.0285mmHg at 25°C
• Refractive Index: 1.5150 (estimate)
• CAS DataBase Reference: METHYL 4-ISOPROPYLBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-ISOPROPYLBENZOATE(20185-55-1)
• EPA Substance Registry System: METHYL 4-ISOPROPYLBENZOATE(20185-55-1)

Safety Data

• Hazardous Substances Data: 20185-55-1(Hazardous Substances Data)

Usage

General Description

Methyl 4-isopropylbenzoate is a chemical compound with the molecular formula C11H14O2. It is a clear, colorless liquid with a fruity odor, commonly used as a fragrance ingredient in products such as perfumes, soaps, and lotions. This chemical is an ester, which is a type of organic compound formed from the reaction between an alcohol and an organic acid. Methyl 4-isopropylbenzoate is known for its pleasant aroma and is widely used in the cosmetic and personal care industries. Additionally, it is also used as a flavoring agent in food and beverages. This chemical may also have other industrial applications, such as being used as a solvent or intermediate in organic synthesis processes.

InChI:InChI=1/C11H14O2/c1-8(2)9-4-6-10(7-5-9)11(12)13-3/h4-8H,1-3H3

Upstream product

• 536-66-3 p-isopropylbenzoic acid 
• 77-78-1 dimethyl sulfate 
• 645-13-6 4-isopropylacetophenone 
• 67-56-1 methanol 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 1068-55-9 isopropylmagnesium chloride 
• 1475-10-1 1-(4-isopropylphenyl)ethanol 
• 17356-09-1 4-iodocumene 
• 74-88-4 methyl iodide 
• 619-44-3 methyl 4-iodobenzoate 
• 108-23-6 isopropyl chloroformate 
• 26460-67-3 (S)-methylperillate 
• 23635-14-5 (s)-(-)-perillic acid 
• 18031-40-8 (S)-(-)-perillaldehyde 

Downstream Products

• 111029-53-9 4,4'-(1,1,2,2-tetramethyl-1,2-ethanediyl)bisbenzoic acid dimethyl ester 
• 82027-50-7 2-(p-carbomethoxyphenyl)-2-chloropropane 
• 5351-24-6 4-isopropylbenzoic acid hydrazide 
• 536-66-3 p-isopropylbenzoic acid 
• 536-60-7 cuminol 
• 127588-57-2 methyl 4-(3-thioxo-3H-1,2-dithiol-4-yl)benzoate 
• 153895-11-5 C₃₀H₃₇Cl 
• 177609-50-6 4-[bis[4-(tert-butyl)phenyl][4-(isopropyl)phenyl]methyl]phenol 
• 26581-23-7 4-(1-methylethenyl)benzoic acid methyl ester 
• 177609-53-9 2-(2-{4-[Bis-(4-tert-butyl-phenyl)-(4-isopropyl-phenyl)-methyl]-phenoxy}-ethoxy)-ethanol 
• 177609-57-3 {4-[2-(2-{4-[Bis-(4-tert-butyl-phenyl)-(4-isopropyl-phenyl)-methyl]-phenoxy}-ethoxy)-ethoxy]-phenyl}-methanol 
• 153895-23-9 C₄₇H₅₅ClO₃ 
• 153895-19-3 Toluene-4-sulfonic acid 2-(2-{4-[bis-(4-tert-butyl-phenyl)-(4-isopropyl-phenyl)-methyl]-phenoxy}-ethoxy)-ethyl ester 
• 100-21-0 terephthalic acid 

Relevant articles and documents

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Dilithium Amides as a Modular Bis-Anionic Ligand Platform for Iron-Catalyzed Cross-Coupling

Dilithium amides have been developed as a bespoke and general ligand for iron-catalyzed Kumada-Tamao-Corriu cross-coupling reactions, their design taking inspiration from previous mechanistic and structural studies. They allow for the cross-coupling of alkyl Grignard reagents with sp2-hybridized electrophiles as well as aryl Grignard reagents with sp3-hybridized electrophiles. This represents a rare example of a single iron-catalyzed system effective across diverse coupling reactions without significant modification of the catalytic protocol, as well as remaining operationally simple.

Oxidative esterification of alcohols by a single-side organically decorated Anderson-type chrome-based catalyst

The direct esterification of alcohols with non-noble metal-based catalytic systems faces great challenges. Here, we report a new chrome-based catalyst stabilized by a single pentaerythritol decorated Anderson-type polyoxometalate, [N(C4H9)4]3[CrMo6O18(OH)3C{(OCH2)3CH2OH}], which can realize the efficient transformation from alcohols to esters by H2O2oxidation in good yields and high selectivity without extra organic ligands. A variety of alcohols with different functionalities including some natural products and pharmaceutical intermediates are tolerated in this system. The chrome-based catalyst can be recycled several times and still keep the original configuration and catalytic activity. We also propose a reasonable catalytic mechanism and prove the potential for industrial applications.

Aerobic Oxidative Cleavage and Esterification of C(OH)–C Bonds

C(OH)–C bonds are widely distributed in naturally renewable biomass, such as carbohydrates, lignin, and their platform molecules. Selective cleavage and functionalization of C(OH)–C bonds is an attractive strategy in terms of producing value-added chemicals from biomass. However, effective transformation of alcohols into esters by activation of C(OH)–C bonds has not been achieved so far. Herein, for the first time, we report selective cleavage and esterification of C(OH)–C bonds, catalyzed by inexpensive copper salts, using environmentally benign oxygen as the oxidant, to afford methyl esters in excellent yields. A diverse range of phenylethanol derivatives that contain C(OH)–C bonds were effectively converted into methyl benzoates. Detailed analysis revealed that the high efficiency and selectivity resulted mainly from the fact that, in addition to the major esterification reaction, the side products (e.g., olefins and acids) were also transformed in situ into esters in the reaction system. C(OH)–C bonds are widely distributed in naturally renewable biomass. In the context of developing future biorefineries, selective cleavage and functionalization of C(OH)–C bonds are crucial and represent an attractive strategy in terms of producing value-added chemical compounds from biomass resources. In the current manuscript, we report, for the first time, an effective and selective method for the cleavage and esterification of C(OH)–C bonds of alcohols to produce esters, by using environmentally benign O2 as the terminal oxidant and inexpensive commercially available copper salts as catalysts. Furthermore, a detailed mechanistic study revealed that, in addition to the major esterification route, side products (e.g., olefins and acids), which are inevitably generated under oxidative and basic conditions, were also simultaneously converted into esters, thus significantly improving the final yields of target ester products. Native lignin represents the only naturally sustainable aromatic resource. Transformation of native lignin into valuable aromatics would make a great contribution to our planet. We report, for the first time, the effective transformation of alcohols into esters by esterification of C(OH)–C bonds, which offers a new way for the simultaneous degradation and functionalization of lignin. This reaction promotes new explorations for biomass valorization.