22651-87-2

Basic information

• Product Name: cyclohexanecarboxylic anhydride
• Synonyms: cyclohexanecarboxylic anhydride;Bis(cyclohexanecarboxylic)anhydride;Einecs 245-146-8
• CAS NO: 22651-87-2
• Molecular Formula: C₁₄H₂₂O₃
• Molecular Weight: 238.32268
• EINECS: 245-146-8
• Mol File: 22651-87-2.mol

Chemical Properties

• Boiling Point: 156°C/0.7mmHg(lit.)
• Flash Point: 161.2°C
• Appearance: /
• Density: 1.082g/cm³
• Vapor Pressure: 2.82E-05mmHg at 25°C
• Refractive Index: 1.4740-1.4780
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: cyclohexanecarboxylic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: cyclohexanecarboxylic anhydride(22651-87-2)
• EPA Substance Registry System: cyclohexanecarboxylic anhydride(22651-87-2)

Safety Data

• Hazardous Substances Data: 22651-87-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Production:
Cyclohexanecarboxylic anhydride is used as a key intermediate for the production of various chemicals, including agricultural chemicals and pharmaceuticals, due to its reactive nature and ability to form stable derivatives.
Used in Epoxy Resin Industry:
Cyclohexanecarboxylic anhydride is used as a curing agent for epoxy resins, enhancing their hardness and thermal stability, which is crucial for applications in coatings, adhesives, and composite materials.
Used in Plasticizer Industry:
It serves as a raw material in the production of plasticizers, which are additives that increase the flexibility and workability of plastics, making them suitable for a wide range of applications in the manufacturing of consumer goods and industrial products.
Used in Alkyd Resin Industry:
Cyclohexanecarboxylic anhydride is used as a component in alkyd resins, contributing to their properties such as adhesion, gloss, and chemical resistance, which are essential for use in paints and surface coatings.
Used in Manufacturing of Curing Agents:
As a hardener in the production of curing agents for epoxy resins, cyclohexanecarboxylic anhydride plays a critical role in the final properties of the cured epoxy systems, ensuring their performance in demanding environments.
It is important to handle cyclohexanecarboxylic anhydride with care due to its potential irritant and harmful effects on human health and the environment, highlighting the need for proper safety measures during its use and production.

InChI:InChI=1/C14H22O3/c15-13(11-7-3-1-4-8-11)17-14(16)12-9-5-2-6-10-12/h11-12H,1-10H2

Upstream product

• 108-24-7 acetic anhydride 
• 98-89-5 Cyclohexanecarboxylic acid 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 54829-35-5 Cyclohexanecarbothioic acid S-isopropyl ester 
• 54829-34-4 Cyclohexanecarbothioic acid S-propyl ester 
• 136-01-6 cyclohexanecarboxylic acid Na-salt 
• 100-49-2 cyclohexylmethyl alcohol 
• 100-51-6 benzyl alcohol 
• 60-12-8 2-phenylethanol 
• 122-97-4 3-Phenyl-1-propanol 
• 535-80-8 3-chlorobenzoate 
• 65-85-0 benzoic acid 
• 2043-61-0 cyclohexanecarbaldehyde 

Downstream Products

• 117884-78-3 3β-cyclohexanecarbonyloxy-5α,17βH-pregn-20-yn-17-ol 
• 120614-46-2 3β-cyclohexanecarbonyloxy-17βH-pregn-5-en-20-yn-17-ol 
• 4904-55-6 cyclohexanecarbonyl peroxide 
• 25256-34-2 C₂₀H₂₈N₂O₂ 
• 25256-08-0 Cyclohexanecarboxylic acid (3-isobutyrylamino-phenyl)-amide 
• 14272-72-1 (+)-N-<2-Phenyl-2-(cyclohexancarboxylat)aethyl>-4-methyl-thiazolium 
• 111479-71-1 5-cyano-2-cyclohexyl-6-methylthio-1,3-thiazin-4-one 
• 137345-43-8 1-cyclohexyloxomethyl-1-(phenylsulfonyl)cyclohexane 
• 111479-81-3 5-cyano-2-cyclohexyl-6-methylthio-1-phenylpyrimidin-4(1H)-one 
• 89205-29-8 2-(Cyclohexanecarbonyl-amino)-3-oxo-3-(3,4,5-trimethoxy-phenyl)-propionic acid methyl ester 
• 6947-57-5 cyclohexyl phenyl sulfone 
• 111479-84-6 3-cyclohexanecarboxamido-N-cyclohexylcarbonyl-3-(methylthio)acrylamide 
• 20592-38-5 17β-cyclohexanecarbonyloxy-5α-androstan-3-one 
• 103133-50-2 3-oxo-5α-androstan-17α-yl cyclohexanecarboxylate 

Relevant articles and documents

Chiral separation materials based on derivatives of 6-amino-6-deoxyamylose

In order to develop new type of chiral separation materials, in this study, 6-amino-6-deoxyamylose was used as chiral starting material with which 10 derivatives were synthesized. The amino group in 6-amino-6-deoxyamylose was selectively acylated and then the hydroxyl groups were carbamoylated yielding amylose 6-amido-6-deoxy-2,3-bis(phenylcarbamate)s, which were employed as chiral selectors (CSs) for chiral stationary phases of high-performance liquid chromatography. The resulted 6-amido-6-deoxyamyloses and amylose 6-amido-6-deoxy-2,3-bis(phenylcarbamate)s were characterized by IR, 1H NMR, and elemental analysis. Enantioseparation evaluations indicated that most of the CSs demonstrated a moderate chiral recognition capability. The 6-nonphenyl (6-nonPh) CS of amylose 6-cyclohexylformamido-6-deoxy-2,3-bis(3,5-dimethylphenylcarbamate) showed the highest enantioselectivity towards the tested chiral analytes; the phenyl-heterogeneous (Ph-hetero) CS of amylose 6-(4-methylbenzamido)-6-deoxy-2,3-bis(3,5-dimethylphenylcarbamate) baseline separated the most chiral analytes; the phenyl-homogeneous (Ph-homo) CS of amylose 6-(3,5-dimethylbenzamido)-6-deoxy-2,3-bis(3,5-dimethylphenylcarbamate) also exhibited a good enantioseparation capability among the developed CSs. Regarding Ph-hetero CSs, the enantioselectivity depended on the combination of the substituent at 6-position and that at 2- and 3-positions; as for Ph-homo CSs, the enantioselectivity was related to the substituent at 2-, 3-, and 6-positions; with respect to 6-nonPh CSs, the retention factor of most analytes on the corresponding CSPs was lower than that on Ph-hetero and Ph-homo CSPs in the same mobile phases, indicating π–π interactions did occur during enantioseparation. Although the substituent at 6-position could not provide π–π interactions, the 6-nonPh CSs demonstrated an equivalent or even higher enantioselectivity compared with the Ph-homo and Ph-hetero CSs.

PPh3/Selectfluor-Mediated Transformation of Carboxylic Acids into Acid Anhydrides and Acyl Fluorides and Its Application in Amide and Ester Synthesis

By taking the advantage of PPh3/Selectfluor system, carboxylic acids are efficiently converted into the pivotal intermediates acyloxyphosphonium ions that can selectively react with a second carboxylic acid or fluoride to in situ yield the corresponding acid anhydrides or acyl fluorides. The developed protocol features commercially availabile reagents, no involvement of base, room temperature conditions, and simple experimental procedure. Additionally, various amides or esters are readily achieved, respectively, with the addition of amines or alcohols.

Isothiourea-Catalysed Regioselective Acylative Kinetic Resolution of Axially Chiral Biaryl Diols

An operationally simple isothiourea-catalysed acylative kinetic resolution of unprotected 1,1′-biaryl-2,2′-diol derivatives has been developed to allow access to axially chiral compounds in highly enantioenriched form (s values up to 190). Investigation of the reaction scope and limitations provided three key observations: i) the diol motif of the substrate was essential for good conversion and high s values; ii) the use of an α,α-disubstituted mixed anhydride (2,2-diphenylacetic pivalic anhydride) was critical to minimize diacylation and give high selectivity; iii) the presence of substituents in the 3,3′-positions of the diol hindered effective acylation. This final observation was exploited for the highly regioselective acylative kinetic resolution of unsymmetrical biaryl diol substrates bearing a single 3-substituent. Based on the key observations identified, acylation transition state models have been proposed to explain the atropselectivity of this kinetic resolution.

Nickel-Catalyzed Decarboxylative Alkenylation of Anhydrides with Vinyl Triflates or Halides

Decarboxylative cross-coupling of aliphatic acid anhydrides with vinyl triflates or halides was accomplished via nickel catalysis. This methodology works well with a broad array of substrates and features abundant functional group tolerance. Notably, our approach addresses the issue of safe and environmental installation of methyl or ethyl group into molecular scaffolds. The method possesses high chemoselectivity toward alkyl groups when aliphatic/aromatic mixed anhydrides are involved. Furthermore, diverse ketones could be modified with our strategy.

Nickel catalyzed decarboxylative alkylation of aryl triflates with anhydrides

Aliphatic acid anhydrides are the versatile building blocks and the new method for the conversion of anhydrides is thus of great significance. Herein, we report the decarboxylative alkylation of aryl triflates with aliphatic acid anhydrides via nickel catalysis. This novel method provides a facile access to construct Csp2-Csp3 bond. In addition, this method is compatible with a broad array of functional groups and exhibits good substrates scope.

Visible light-induced transformation of aldehydes to esters, carboxylic anhydrides and amides

A transition metal- and organophotocatalyst free synthesis of esters, carboxylic anhydrides and amides from aldehydes induced by visible-light has been reported. The proposed methodology can be carried out by the use of sunlight or artificial visible light as a blue LED source. The methodology has a very broad applicability and the desired products are obtained in very satisfactory yields.

Direct β-C(sp3)-H Acetoxylation of Aliphatic Carboxylic Acids

The controlled construction of defined oxidation patterns is one of the key aspects in the synthesis of natural products and bioactive molecules. Towards this goal, we herein report a novel protocol for the Pd-catalyzed direct β-C(sp3)-H acetoxylation of aliphatic carboxylic acids. The protocol enables the use of free carboxylic acids in one step and without the need of introducing specialized strong directing groups. In our studies, we found that the use of a "traceless base" was crucial for the development of a synthetically useful transformation. Furthermore, the synthetic utility of the products obtained was demonstrated by their use in subsequent transformations.

METHOD FOR PRODUCING CARBOXYLIC ACID ANHYDRIDE AND METHOD FOR PRODUCING CARBOXYLIC ACID ESTER

Provided is a production method whereby corresponding carboxylic acid anhydrides and carboxylic acid esters can be obtained at high yield from various carboxylic acids even without a solvent and near room temperature. A method for producing a carboxylic acid anhydride represented by formula (II), the method comprising reacting a compound represented by formula (I) and a carboxylic acid in the presence of a Group II metal compound having an ionic ligand containing an oxygen atom. A method for producing a carboxylic acid ester, the method comprising reacting a carboxylic acid anhydride produced by the aforementioned method and an alcohol. In formula (I), R1 represents a C1-20 hydrocarbon group. In formula (II), R2 represents a C1-20 hydrocarbon group.

An investigation on practical synthesis of carboxylic acid derivatives using p-toluenesulfonyl chloride

Carboxylic acid derivatives are well recognized as important class of reagents frequently used in the preparation of a variety of fine or special chemicals such as amides, esters, peptides, drugs, and dyes. Although several methods were developed for the preparation of these compounds, many of them present difficulties, including low yield, high reaction temperature, harsh reaction conditions, tedious work-up, and incompatibility with scale-up. Methods: The synthesis of carboxylic anhydrides is developed through the reaction of carboxylic acids with TsCl in the presence of K2CO3 and acetonitrile as a solvent under ultrasound irradiation and conventional conditions. In addition, one-pot synthesis of acyl azides was carried out in the presence of produced carboxylic anhydrides and the addition of sodium azide under identical condition. Results: A series of carboxylic anhydrides and acyl azides were synthesized using TsCl under ultrasound irradiation and conventional stirring with simple procedure, mild reaction conditions, high yields, and scale-up ability without any restriction. In most cases, the reaction under ultrasound irradiation was better in both yields and the reaction times compared to the conventional method. Conclusion: A convenient method has been developed for the preparation of carboxylic anhydrides and acyl azides under ultrasound irradiation and conventional stirring. The present method is practical and a highly effective alternative for previous reports. The major advantages of this method are: (i) simplicity of the procedure (ii) high yields and high purity of product (iii) scale-up capacity without considerable limitation in conventional system. Under ultrasound irradiation short reaction times as compared to conventional method are observed; yields are comparable to or better than conventional method.

Anhydrides from aldehydes or alcohols via oxidative cross-coupling

A novel type of metal-free oxidative cross-coupling for the synthesis of symmetrical and mixed anhydrides from aldehydes or benzylic alcohols has been developed. The aldehydes or alcohols were converted in situ into their corresponding acyl chlorides, which were then reacted with an array of carboxylic acids. The methodology has a general applicability, and was successfully employed to prepare either aromatic or aliphatic symmetrical anhydrides and mixed anhydrides, which are very unstable compounds.