15781-96-1

Basic information

• Product Name: HYDROCINNAMIC ANHYDRIDE
• Synonyms: HYDROCINNAMIC ANHYDRIDE;3-PHENYLPROPIONIC ACID ANHYDRIDE
• CAS NO: 15781-96-1
• Molecular Formula: C₁₈H₁₈O₃
• Molecular Weight: 282.33
• Mol File: 15781-96-1.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: HYDROCINNAMIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: HYDROCINNAMIC ANHYDRIDE(15781-96-1)
• EPA Substance Registry System: HYDROCINNAMIC ANHYDRIDE(15781-96-1)

Safety Data

• Hazardous Substances Data: 15781-96-1(Hazardous Substances Data)

Usage

Description

Hydrocinnamic anhydride, with the chemical formula C9H8O3, is a cyclic anhydride of hydrocinnamic acid. It is a white solid that is insoluble in water but soluble in organic solvents. HYDROCINNAMIC ANHYDRIDE serves as a synthetic building block and a reagent in organic synthesis, playing a significant role in the production of pharmaceuticals, fragrances, and polymers.

Uses

Used in Pharmaceutical Industry:
Hydrocinnamic anhydride is used as a synthetic building block for the development of various pharmaceuticals. Its unique chemical structure allows it to be a key component in the synthesis of medicinal compounds, contributing to the creation of new and effective drugs.
Used in Fragrance Industry:
In the fragrance industry, hydrocinnamic anhydride is utilized as a reagent in the synthesis of dyes and perfumes. Its ability to create a variety of aromatic compounds makes it an essential component in the formulation of scents and dyes.
Used in Polymer Industry:
Hydrocinnamic anhydride also finds application in the polymer industry, where it is used in the production of different types of polymers. Its versatility in organic synthesis allows it to be a valuable asset in the development of new polymer materials with specific properties.
It is important to handle hydrocinnamic anhydride with care, as it may cause skin and eye irritation and can be harmful if ingested or inhaled. Proper safety measures should be taken to minimize any potential risks associated with its use.

Upstream product

• 645-45-4 hydrocinnamic acid chloride 
• 501-52-0 3-Phenylpropionic acid 
• 104-53-0 3-phenyl-propionaldehyde 
• 535-80-8 3-chlorobenzoate 
• 122-97-4 3-Phenyl-1-propanol 
• 56-86-0 L-glutamic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 56-85-9 L-glutamine 
• 2935-35-5 (S)-2-phenylglycine 
• 151418-18-7 Aethoxykohlensaeure-dihydrozimtsaeure-anhydrid 
• 63-91-2 L-phenylalanine 
• 20859-02-3 L-tert-Leucine 
• 72-18-4 L-valine 
• 64-17-5 ethanol 

Downstream Products

• 57794-08-8 (1S,2S)-trans-1,2-Cyclohexanediol 
• 1448438-49-0 (1S,2S)-2-hydroxycyclohexyl 3-phenylpropanoate 
• 1448438-59-2 (1R,2R)-2-hydroxycyclohexyl 3-phenylpropanoate 
• 458-69-5 3-phenylpropanoic acid fluoride 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 

Relevant articles and documents

Rh(I)-Catalyzed C6-Selective Decarbonylative Alkylation of 2-Pyridones with Alkyl Carboxylic Acids and Anhydrides

A Rh-catalyzed chelation-assisted C6-selective C-H activation/alkylation of 2-pyridones with readily available alkyl carboxylic acids or anhydrides is introduced. The reaction proceeds via substrate decarbonylation. This approach merges C-H functionalization with readily available anhydrides, allowing for the efficient synthesis of various C6-alkylated 2-pyridones with good functional group tolerance.

Isothiourea-Catalyzed Atroposelective N-Acylation of Sulfonamides

We report herein an atroposelective N-acylation of sulfonamides using a commercially available isothiourea catalyst, (S)-HBTM, with a simple procedure. The N-sulfonyl anilide products can be obtained in good to high enantiopurity, which represents a new axially chiral scaffold. The application of the product as a chiral iodine catalyst is also demonstrated for the asymmetric α-oxytosylation of propiophenone.

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.