5292-21-7

Basic information

• Product Name: Cyclohexylacetic acid
• Synonyms: NCI 204816;Cyclohexylacetic acid ,98%;2-Cyclohexylethanoic acid, (Carboxymethyl)cyclohexane;Cyclohexaneacetic acid >=99%;Cyclohexylacetic Acid , 98.0%(GC&T;Cyclohexylethanoic acid;FEMA 3531;FEMA 2347
• CAS NO: 5292-21-7
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.2
• EINECS: 202-711-3
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;Acids and Derivatives
• Mol File: 5292-21-7.mol

Chemical Properties

• Melting Point: 29-31 °C(lit.)
• Boiling Point: 242-244 °C(lit.)
• Flash Point: >230 °F
• Appearance: White to pale yellow/Low Melting Solid
• Density: 1.007 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00961mmHg at 25°C
• Refractive Index: n20/D 1.463(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: pK1:4.51 (25°C)
• BRN: 2041326
• CAS DataBase Reference: Cyclohexylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexylacetic acid(5292-21-7)
• EPA Substance Registry System: Cyclohexylacetic acid(5292-21-7)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: GU8370000
• TSCA: Yes
• Hazardous Substances Data: 5292-21-7(Hazardous Substances Data)

Usage

Uses

Used in the Food Industry:
Cyclohexylacetic acid is used as a flavoring agent for enhancing the taste and aroma of various food products. Its unique combination of honey, caramellic, maple, and cocoa taste characteristics at 100 ppm makes it a valuable addition to the flavor profile of different culinary creations.
Used in the Fragrance Industry:
Given its distinct aroma and sharp acetic odor, cyclohexylacetic acid can also be employed in the fragrance industry to create unique and appealing scents for perfumes, colognes, and other scented products.
Used in the Chemical Industry:
Due to its chemical properties, cyclohexylacetic acid may find applications in the chemical industry for the synthesis of various compounds and materials, taking advantage of its reactivity and functional groups.

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 3595, 1993 DOI: 10.1021/jo00065a028

InChI:InChI=1/C8H14O2/c9-8(10)6-7-4-2-1-3-5-7/h7H,1-6H2,(H,9,10)

Upstream product

• 33768-74-0 4,5,6,7-tetrahydro-3H-benzofuran-2-one 
• 4709-59-5 ethyl 2-(1-cyclohexenyl)acetate 
• 4132-61-0 6-cyclohex-1-enyl-hexanoic acid 
• 4442-79-9 cyclohexylethan-1-ol 
• 201230-82-2 carbon monoxide 
• 82166-21-0 methyl cyclohexane 
• 144499-18-3 Acetic acid 1-cyano-2-cyclohexyl-1-(pyridin-2-ylsulfanyl)-ethyl ester 
• 5664-21-1 cyclohexylacetaldehyde 
• 15719-64-9 methylammonium carbonate 
• 1072-95-3 cyclohexylmethyl chloride 
• 53723-49-2 1-cyclohex-1-enyl-2-cyclohexyl-ethane 
• 67-64-1 acetone 
• 24476-17-3 1-cyclohexyl-butan-2-one 
• 56-23-5 tetrachloromethane 

Downstream Products

• 96464-43-6 2-cyclohexylmethyl-4,8-dimethyl-chromeno[6,7-d]oxazol-6-one 
• 93150-30-2 N-(5-cyclohexylmethyl-[1,3,4]thiadiazol-2-yl)-toluene-4-sulfonamide 
• 94462-07-4 N-(5-cyclohexylmethyl-[1,3,4]thiadiazol-2-yl)-4-methoxy-benzenesulfonamide 
• 378185-92-3 (4R)-4-Benzyl-3-(2-cyclohexylacetyl)-1,3-oxazolan-2-one 
• 1025908-96-6 Cyclohexyl-acetic acid (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-acetoxy-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl ester 
• 172922-31-5 (S)-2-(2-Cyclohexyl-acetylamino)-4-methyl-pentanoic acid benzyl ester 

Relevant articles and documents

One-step solvent-free aerobic oxidation of aliphatic alcohols to esters using a tandem Sc-Ru?MOF catalyst

Esters are an important class of chemicals in industry. Traditionally, ester production is a multi-step process involving the use of corrosive acids or acid derivatives (e.g. acid chloride, anhydride, etc.). Therefore, the development of a green synthetic protocol is highly desirable. This work reports the development of a metal-organic framework (MOF) supported tandem catalyst that can achieve direct alcohol to ester conversion (DAEC) using oxygen as the sole oxidizing agent under strictly solvent-free conditions. By incorporating Ru nanoparticles (NPs) along with a homogeneous Lewis acid catalyst, scandium triflate, into the nanocavities of a Zr MOF, MOF-808, the compound catalyst, Sc-Ru?MOF-808, can achieve aliphatic alcohol conversion up to 92% with ester selectivity up to 91%. A mechanistic study reveals a unique “via acetal” pathway in which the alcohol is first oxidized on Ru NPs and rapidly converted to an acetal on Sc(iii) sites. Then, the acetal slowly decomposes to release an aldehyde in a controlled manner for subsequent oxidation and esterification to the ester product. To the best of our knowledge, this is the first example of DAEC of aliphatic alcohols under solvent-free conditions with high conversion and ester selectivity.

Mild and Selective Rhodium-Catalyzed Transfer Hydrogenation of Functionalized Arenes

Diboron-mediated rhodium-catalyzed transfer hydrogenation of functionalized arenes is reported. In addition to good functional group tolerance, the reaction features operational simplicity and controllable chemoselectivity. The general applicability of this procedure is demonstrated by the selective hydrogenation of a range of arenes, including functionalized benzenes, biphenyls, and polyaromatics.

Method for preparing carboxylic acid by one-pot method

The invention discloses a method for preparing carboxylic acid by a one-pot method, which comprises the steps of carrying out a Corey-Fuchs process on 1,1-dibromo olefin under the action of n-butyllithium, reacting with isopropanol pinacol borate, quenching with hydrogen chloride, oxidizing with an oxidant, separating and purifying to obtain carboxylic acid. The method disclosed by the invention is a one-pot preparation method, is simple and convenient to operate, does not need to use metal catalysis, uses cheap and easily available reagents for reaction, is green and environment-friendly, hasmild reaction conditions and wide substrate applicability, and provides a new way for rapidly preparing a series of carboxylic acids containing different functional groups.

Method for synthesizing cyclohexanecarboxylic acid by catalyzing hydrogenation of benzene rings through rubidium-gallium-loaded catalytic material

The invention relates to the fine chemical engineering field and particularly relates to a method for synthesizing cyclohexanecarboxylic acid by catalyzing hydrogenation of benzene rings through a rubidium-gallium-loaded catalytic material. According to the method, aromatic ring carboxylic acid is catalyzed by virtue of the rubidium-gallium-loaded catalytic material in deionized water and generates selective addition reaction with hydrogen at a low temperature and a relatively low pressure so as to generate cyclohexanecarboxylic acid; the reaction temperature is low, the reaction pressure is lower than that in the prior art, no organic solvent is adopted, the side reactions are few, and the product is conveniently purified, and the method is suitable for industrial production; and the prepared rubidium-gallium-loaded catalytic material can be recycled, is high in catalytic activity and strong in selectivity and is a very promising novel catalytic material.

Pd-Catalyzed Highly Chemo- And Regioselective Hydrocarboxylation of Terminal Alkyl Olefins with Formic Acid

An efficient Pd-catalyzed hydrocarboxylation of alkenes with HCOOH is described. A wide variety of linear carboxylic acids bearing various functional groups can be obtained with excellent chemo- and regioselectivities under mild reaction conditions. The reaction process is operationally simple and requires no handling of toxic CO.

Synthetic method of terminal carboxylic acid

The invention discloses a synthetic method of a terminal carboxylic acid. The synthetic method is characterized by comprising the steps of adding an olefin represented by a formula (3) shown in the description, formic acid, acetic anhydride, Pd(OAc)2 and a monophosphorus ligand TFPP into an organic solvent in a proportion, carrying out hydrogen carbonylation reaction on the olefin represented by the formula (3) shown in the description, formic acid and acetic anhydride at 80-90 DEG C for 48h-72h under the catalysis of the metal palladium salt Pd(OAc)2 and the monophosphorus ligand TFPP so as to obtain the terminal carboxylic acid represented by a formula shown in the description, and separating a target product, namely the terminal carboxylic acid after the reaction is finished, wherein olefin represented by the formula (3) is selected from cycloolefins, or linear olefins of which the R1 is electron donating groups. By virtue of the method disclosed by the invention, corresponding terminal carboxylic acid and a derivative thereof can be prepared through the reaction under mild conditions of low temperature and no high pressure; and the steps of the synthetic method are simple and convenient, the operation is convenient, the yield is high, the energy source can be greatly saved, and the synthetic efficiency can be greatly improved.

Polysilane-Immobilized Rh-Pt Bimetallic Nanoparticles as Powerful Arene Hydrogenation Catalysts: Synthesis, Reactions under Batch and Flow Conditions and Reaction Mechanism

Hydrogenation of arenes is an important reaction not only for hydrogen storage and transport but also for the synthesis of functional molecules such as pharmaceuticals and biologically active compounds. Here, we describe the development of heterogeneous Rh-Pt bimetallic nanoparticle catalysts for the hydrogenation of arenes with inexpensive polysilane as support. The catalysts could be used in both batch and continuous-flow systems with high performance under mild conditions and showed wide substrate generality. In the continuous-flow system, the product could be obtained by simply passing the substrate and 1 atm H2 through a column packed with the catalyst. Remarkably, much higher catalytic performance was observed in the flow system than in the batch system, and extremely strong durability under continuous-flow conditions was demonstrated (>50 days continuous run; turnover number >3.4 × 105). Furthermore, details of the reaction mechanisms and the origin of different kinetics in batch and flow were studied, and the obtained knowledge was applied to develop completely selective arene hydrogenation of compounds containing two aromatic rings toward the synthesis of an active pharmaceutical ingredient.

Selective hydrogenation of benzoic acid to cyclohexane carboxylic acid over microwave-activated Ni/carbon catalysts

High yields of cyclohexane carboxylic acids were obtained by direct hydrogenation of aromatic carboxylic acids over different Ni/carbon catalysts having distinctive surface properties. The catalysts were characterized by SEM, TEM, H2-TPR and N2 adsorption isotherms for the determination of BET surface area and porosity. The hydrogenation reaction was carried out in batch pressure reactor in gas-liquid phase at 200 °C. High selectivity (100%) of cyclohexane carboxylic acids at 86.2 mol% conversion of benzoic acid was achieved over microwave-activated biochar supported non-precious metal Ni catalyst. The 10%Ni/CSC-b catalyst has been investigated for hydrogenation of benzoic acid to cyclohexane carboxylic acids and shown little deactivation in stability test. The effects of Ni loading, high dispersion of Ni species, appropriate power of microwave heating and strong interaction of Ni species with carbon are of benefit to the reaction.

CATALYTIC CARBOXYLATION OF ACTIVATED ALKANES AND/OR OLEFINS

The present invention relates to a method of reacting starting materials with an activating group, namely alkanes carrying a leaving group and/or olefins, with carbon dioxide under transition metal catalysis to give carboxyl group-containing products. It is a special feature of the method of the present invention that the carboxylation predominantly takes place at a preferred position of the molecule irrespective of the position of the activating group. The carboxylation position is either an aliphatic terminus of the molecule or it is a carbon atom adjacent to a carbon carrying an electron withdrawing group. The course of the reaction can be controlled by appropriately choosing the reaction conditions to yield the desired regioisomer.

Silver-Catalyzed Dehydrogenative Synthesis of Carboxylic Acids from Primary Alcohols

A simple silver-catalyzed protocol has been developed for the acceptorless dehydrogenation of primary alcohols into carboxylic acids and hydrogen gas. The procedure uses 2.5 % Ag2CO3 and 2.5–3 equiv of KOH in refluxing mesitylene to afford the potassium carboxylate which is then converted into the acid with HCl. The reaction can be applied to a variety of benzylic and aliphatic primary alcohols with alkyl and ether substituents, and in some cases halide, olefin, and ester functionalities are also compatible with the reaction conditions. The dehydrogenation is believed to be catalyzed by silver nanoparticles that are formed in situ under the reaction conditions.