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
• Article Data: 27

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

General Description

Cyclohexanecarboxylic anhydride, also known as hexahydrophthalic anhydride, is a chemical compound and cyclic anhydride of cyclohexanecarboxylic acid. It is a colorless to light yellow liquid with a pungent odor, and is primarily used in the production of epoxy resins, plasticizers, and alkyd resins. It is also used as a hardener in the manufacturing of curing agents for epoxy resins, and as a raw material for the production of agricultural chemicals and pharmaceuticals. With its versatile applications in various industries, the demand for cyclohexanecarboxylic anhydride continues to be significant. However, it is important to handle this chemical with care due to its potential irritant and harmful effects on human health and the environment.

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

• 25256-08-0 Cyclohexanecarboxylic acid (3-isobutyrylamino-phenyl)-amide 
• 14272-72-1 (+)-N-<2-Phenyl-2-(cyclohexancarboxylat)aethyl>-4-methyl-thiazolium 
• 59293-37-7 tetrahydro-1-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)-3-allyl-6-cyclohexylcarbonyloxy-2(1H)-pyrimidinone 
• 1565-74-8 (R)-1-phenyl-1-propanol 
• 613-87-6 (S)-1-phenyl-1-propanol 
• 57794-08-8 (1S,2S)-trans-1,2-Cyclohexanediol 
• 1072-86-2 (1R,2R)-trans-1,2-cyclohexanediol 
• 1448438-60-5 C₁₃H₂₂O₃ 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 

Relevant articles and documents

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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.

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.