63521-92-6

Basic information

• Product Name: 4-PENTENOIC ANHYDRIDE
• Synonyms: 4-PENTENOIC ANHYDRIDE;PENT-4-ENOIC ANHYDRIDE;4-PENTENOIC ANHYDRIDE 99%;Pent-4-enoic anhydride,97%
• CAS NO: 63521-92-6
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.22
• Product Categories: Carbonyl Compounds;Carboxylic Acid Anhydrides;Organic Building Blocks
• Mol File: 63521-92-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 78-81 °C0.4 mm Hg(lit.)
• Flash Point: 230 °F
• Appearance: /
• Density: 0.997 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0737mmHg at 25°C
• Refractive Index: n20/D 1.447(lit.)
• Storage Temp.: Refrigerator (+4°C)
• CAS DataBase Reference: 4-PENTENOIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PENTENOIC ANHYDRIDE(63521-92-6)
• EPA Substance Registry System: 4-PENTENOIC ANHYDRIDE(63521-92-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 63521-92-6(Hazardous Substances Data)

Usage

Description

4-Pentenoic anhydride, a carboxylic anhydride, is a clear colorless to light yellow liquid. It is a chemical compound known for its moisture-sensitive properties and is commonly utilized as an N-protecting reagent for amino acids and amino sugars under deprotecting conditions.

Uses

Used in Pharmaceutical Industry:
4-Pentenoic anhydride is used as an N-protecting reagent for the synthesis and protection of amino acids and amino sugars. This application is crucial in the development of various pharmaceutical compounds, as it aids in the selective protection and deprotection of functional groups during the synthesis process.
Used in Polymer Science:
4-Pentenoic anhydride serves as a versatile monomer in the preparation of glucose functionalized (co)polymers. Its incorporation into polymer structures allows for the creation of materials with specific properties, such as enhanced biocompatibility or targeted drug delivery capabilities.
Used in Biomedical Applications:
As a monomer in the preparation of cross-linked polyanhydrides, 4-Pentenoic anhydride contributes to the development of biocompatible and biodegradable materials. These materials have potential applications in the field of drug delivery systems, medical implants, and tissue engineering.
Used in Material Science:
4-Pentenoic anhydride is used for the preparation of polymers with pendant vinyl or acetylene groups. These polymers can be further modified or functionalized to create materials with tailored properties for various applications, such as adhesives, coatings, or composites.

InChI:InChI=1/C10H14O3/c1-3-5-7-9(11)13-10(12)8-6-4-2/h3-4H,1-2,5-8H2

Upstream product

• 591-80-0 pent-4-enoic acid 
• 39716-58-0 pent-4-enoyl chloride 

Downstream Products

• 845619-08-1 N^α-4-pentenoyl-O-tert-butyl-L-treonine 
• 929619-01-2 2,3,4,6-tetra-O-benzyl-N-pent-4'-enoyl-1-deoxynojirimycin 
• 872522-06-0 4-oxo-2-(S)-(pent-4-enoyl)amino-hexanedioic acid 1-benzyl ester 6-ethyl ester 
• 1032470-80-6 N,N'-bis[4-(5-3,4-butene-1,2,4-oxadiazol-3yl)phenyl]pentanediamide 
• 84642-43-3 (E)-1-phenylhepta-1,6-dien-3-one 
• 172946-54-2 N-Pent-4-enoyl-L-proline benzyl ester 

Relevant articles and documents

Synthesis, Radiolabeling, and in Vivo Imaging of PEGylated High-Generation Polyester Dendrimers

A fifth generation aliphatic polyester dendrimer was functionalized with vinyl groups at the periphery and a dipicolylamine Tc(I) chelate at the core. This structure was PEGylated with three different molecular weight mPEGs (mPEG160, mPEG350, and mPEG750) using thiol-ene click chemistry. The size of the resulting macromolecules was evaluated using dynamic light scattering, and it was found that the dendrimer functionalized with mPEG750 was molecularly dispersed in water, exhibiting a hydrodynamic diameter of 9.2 ± 2.1 nm. This PEGylated dendrimer was subsequently radiolabeled using [99mTc(CO)3(H2O)3]+ and purified to high (>99%) radiochemical purity. Imaging studies were initially performed on healthy rats to allow comparison to previous Tc-labeled dendrimers and then on xenograft murine tumor models, which collectively showed that the dendrimers circulated in the blood for an extended period of time (up to 24 h). Furthermore, the radiolabeled dendrimer accumulated in H520 xenograft tumors, which could be visualized by single-photon emission computed tomography (SPECT). The reported PEGylated aliphatic polyester dendrimers represent a new platform for developing tumor-targeted molecular imaging probes and therapeutics.

N-Hydroxy and N-acyloxy peptides: Synthesis and chemical modifications

The preparation of a series of N-hydroxy peptides is described, along with their acylation on the oxygen of the pseudopeptide bond. Nineteen N-acyloxy peptides, first examples of this new class of pseudopeptides, were thus synthesized; they present a range of acyl groups, including N-protected amino acyl groups. Possibilities of elongation for these pseudopeptides were also investigated. The Royal Society of Chemistry 2006.

2-(Trimethylsilyl)ethyl glycosides. Transformation into the corresponding 1-O-acyl sugars.

(Trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside and (trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,6-tri-O-acetyl-4-O-[2-acetamido-4,6-di-O-ace tyl-2- deoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-beta-D- galactopyranos