4160-80-9

Basic information

• Product Name: Glutaric anhydride
• Synonyms: 4-phenyldihydro-2H-pyran-2,6(3H)-dione;4-phenyloxane-2,6-dione;4-phenyltetrahydropyran-2,6-dione
• CAS NO: 4160-80-9
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 114.09934
• Mol File: 4160-80-9.mol

Chemical Properties

• Melting Point: 105.6°C
• Boiling Point: 285.69°C (rough estimate)
• Flash Point: 178.6°C
• Appearance: /
• Density: 1.1752 (rough estimate)
• Vapor Pressure: 1.55E-05mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• CAS DataBase Reference: Glutaric anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: Glutaric anhydride(4160-80-9)
• EPA Substance Registry System: Glutaric anhydride(4160-80-9)

Safety Data

• Hazardous Substances Data: 4160-80-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Glutaric anhydride is used as a chemical intermediate for the synthesis of various industrial products, including pharmaceuticals, dyes, and agricultural chemicals. Its high reactivity allows it to participate in numerous chemical reactions, making it a valuable component in the production of a wide range of compounds.
Used in Polymer and Resin Production:
In the polymer and resin industry, glutaric anhydride is utilized in the manufacturing process to create specific types of polymers and resins. Its ability to react with other compounds contributes to the formation of desired polymeric materials with unique properties.
Used in Plasticizer Manufacturing:
Glutaric anhydride is employed in the production of plasticizers, which are additives used to increase the flexibility and workability of plastics. Its reactivity and ability to form esters make it suitable for creating plasticizers that can be incorporated into various plastic materials.
Used in Adhesive Synthesis:
In the adhesive industry, glutaric anhydride is used in the synthesis of certain types of adhesives. Its reactive nature allows it to form strong bonds with other substances, contributing to the development of adhesives with enhanced bonding capabilities.
Used as a Curing Agent for Epoxy Resins:
Glutaric anhydride is utilized as a curing agent in the production of epoxy resins. Its ability to react with epoxy groups results in the formation of a cross-linked network, which hardens the resin and provides increased strength and stability to the final product.

InChI:InChI=1/C11H10O3/c12-10-6-9(7-11(13)14-10)8-4-2-1-3-5-8/h1-5,9H,6-7H2

Upstream product

• 463-51-4 Ketene 
• 60-29-7 diethyl ether 
• 4165-96-2 3-phenylglutaric acid 
• 100-52-7 benzaldehyde 
• 25631-82-7 4-phenyl-2H-pyran-2,6(3H)-dione 
• 704-80-3 (E)-3-phenyl-2-butenoic acid 
• 68204-17-1 3-phenylbut-2-enoyl chloride 
• 13277-74-2 diethyl 2,4?diacetyl?3?phenylpentanedioate 
• 6768-26-9 2-phenyl-1,1,3,3-tetraethoxycarbonylpropane 
• 4192-77-2 ethyl cinnamate 
• 5394-85-4 2-phenyl-propane-1,1,3-tricarboxylic acid triethyl ester 

Downstream Products

• 102076-28-8 5-oxo-3-phenyl-5-piperidino-valeric acid 
• 132015-40-8 3-phenyl-pentanedioic acid monomethyl ester 
• 106842-97-1 3-phenylpentanedioic acid monoethyl ester 
• 101890-69-1 1-(3-hydroxy-4-methoxy-benzyl)-4-phenyl-piperidine-2,6-dione 
• 103390-98-3 3-phenyl-glutaric acid di[(1R)-menthyl ester] 
• 113510-43-3 (Ξ)-3-phenyl-glutaric acid mono[(1R)-menthyl ester] 
• 4759-69-7 N-(3,4-dimethoxy-phenethyl)-3-phenyl-glutaramic acid 
• 92410-38-3 5-(phenylamino)-5-oxo-3-phenylpentanoic acid 
• 54946-32-6 1,4-diphenyl-piperidine-2,6-dione 
• 54946-26-8 6-Methyl-3-phenyl-glutarimid 
• 62143-51-5 1-(phenylmethyl)-4-phenylpiperidin-2,6-dione 
• 102172-32-7 5-(2,4-dimethoxy-phenyl)-5-oxo-3-phenyl-valeric acid 
• 109595-20-2 3-phenyl-glutaric acid monocyclohexyl ester 
• 61198-49-0 4-phenyltetrahydropyran-2-one 

Relevant articles and documents

Prochiral Recognition in the Reaction of 3-Substituted Glutaric Anhydrides with Chiral Secondary Alcohols

The scope of a previously-reported process for the desymmetrization 3-substituted glutaric anhydrides has been investigated.Thus, prochiral anhydrides 5-9 react with 1-(1'-naphthyl)ethanol (2) to give glutaric acid half-esters, which are esterified by treatment with diazomethane to obtaine the corresponding diesters 16-20.The degree of prochiral recognition is inversely related to the steric bulk of the stereodifferentiating group, which the series TBDMSO, Me, Et, Ph, i-Pr, and t-Bu giving ratios of 40:1, 16:1, 14:1, 8:1, 7:1, and 1:3, respectively.The absolute sense of the prochiral recognition was established by conversion of two of the diesters, 16a and 18a, into 3-substituted valerolactones (22a, 22c) of known absolute configuration.

An NMR method for determination of configuration of β-substituted carboxylic acids

The absolute configuration of the stereogenic center at the β-position of a carboxylic acid can be determined via derivatization with chiral benzylic amines [PhCH(Me)NH2 or 1-NpCH(Me)NH2]. Acids of known configuration and with a variety of β-substituents were subjected to derivatization. Analysis of the signs of the chemical shift differences of substituent protons permits determination of the absolute configuration. (C) 2000 Elsevier Science Ltd.

Novel amide derivatives of 3-phenylglutaric acid as potent soluble epoxide hydrolase inhibitors

Abstract: Soluble epoxide hydrolase (sEH) enzyme plays an important role in the metabolism of endogenous chemical mediators, epoxyeicosatrienoic acids, which are involved in the regulation of blood pressure and inflammation. According to the pharmacophoric model suggested for sEH inhibitors, some new amide-based derivatives of 3-phenylglutaric acid were designed, synthesized and biologically evaluated. Docking study illustrated that the amide group as a primary pharmacophore had a suitable distance from the three amino acids of Tyr383, Tyr466 and Asp335 for effective hydrogen binding. Most of the compounds showed moderate to high sEH inhibitory activities in in vitro test in comparison with 12-(3-Adamantan-1-yl-ureido)-dodecanoic acid, as a potent urea-based sEH inhibitor. Compound 6o with phenethyl in R position exhibited the highest activity with IC50 value of 0.5?nM. Graphic abstract: In this study, some new amide-based derivatives of 3-phenylglutaric acid were designed, synthesized and biologically evaluated. Most of the synthesized compounds provided nanomolar range inhibition against sEH enzyme. The best observed IC50 value was 0.5?nM. Incorporating a carboxylic moiety into these structures by forming carboxylate salts would increase the solubility and improving physicochemical properties.[Figure not available: see fulltext.]

Glycinamide derivative as well as preparation method and application thereof

The invention discloses a glycinamide derivative as well as a preparation method and application thereof. The derivative with a structural formula as shown in the following formula (I) is provided; and in the formula, R1 is selected from Cl and H, R2 is one selected from H, CH3 and CH2CH3; and X is one selected from NHCH3, NHCH2CH3, N (CH2CH3) 2, a pyrrolyl group and a piperidyl group. During preparation, different phenyl glutaric acid compounds are selected as raw materials and are respectively subjected to amidation reaction twice with an aminoindane hydrochloride derivative and an ethylenediamine derivative to obtain a target derivative. The prepared derivative or the pharmaceutically acceptable salt thereof, or the pharmaceutical composition thereof can be used as an S-adenosyl homocysteine hydrolase inhibitor for the development of antitumor drugs .

Carboxylative Cyclization of 2-Butenoates with Carbon Dioxide: Access to Glutaconic Anhydrides

Cyclic anhydrides are versatile synthons and functional comonomers. Herein, we reported an organic base-promoted carboxylative cyclization of 2-butenoates with carbon dioxide to produce important glutaconic anhydrides in good yields. This metal-free react

TRICYCLIC MODULATORS OF TNF SIGNALING

The invention provides tricyclic heterocyclic compounds, pharmaceutically acceptable salts, prodrugs, biologically active metabolites, stereoisomers and isomers thereof wherein the variables are defined herein. The compounds of the invention may be useful for treating immunological and oncological conditions.

Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from cis-1-Amino-indan-2-ol

Enantioselective reductive desymmetrization of glutarimides has been achieved employing an oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol. The reaction was found to proceed through a stereoablative process that upgraded the enantioselectivity of an intermediate hydroxy-lactam. The reaction was generally tolerant of a number of substituents in the 4-position, giving enantiomeric excesses of greater than 82%.

Synthesis and biological evaluation of pentanedioic acid derivatives as farnesyltransferase inhibitors

Structure-based virtual screening of a commercial library identified pentanedioic acid derivatives (6 and 13b) as a kind of novel scaffold farnesyltransferase inhibitors (FTIs). Chemical modifications of the lead compounds, biological assays and analysis of the structure-activity relationships (SAR) were conducted to discover more potent FTIs. Some of them displayed excellent inhibition against FTase, and among them, the most active compound 13n with an IC50 value of 0.0029 μM and SAR analysis might be helpful to the discovery of more potent FTIs. This journal is

ALLOSTERIC PROTEIN KINASE MODULATORS

The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.

METHOD FOR PRODUCING CARBOXYLIC ANHYDRIDE AND ARYLBORONIC ACID COMPOUND

When phthalic acid is heated in heptane under azeotropic reflux conditions in the presence of a catalytic amount of an arylboronic acid compound (such as 2,6-(diisopropylaminomethyl)phenylboronic acid or 2,6-bis(diisopropylaminomethyl)phenylboronic acid), phthalic anhydride is obtained in high yield.