935-79-5 Usage
Description
cis-1,2,3,6-Tetrahydrophthalic anhydride (THPA) is an organic compound with the formula C6H8C2O3, existing as two isomers, with the cis isomer being more common. It is a white crystalline powder or flakes, slightly soluble in benzene and acetone, and sensitive to moisture. THPA is a precursor to other compounds, including tetrahydrophthalic acid and tetrahydrophthalimide, which is a precursor to the fungicide Captan. It is prepared by the Diels-Alder reaction of butadiene and maleic anhydride.
Uses
Used in Coatings Industry:
cis-1,2,3,6-Tetrahydrophthalic anhydride is used as an anhydride hardener for enhancing the properties of coatings, providing improved thermal stability and chemical resistance.
Used in Epoxy Resin Curing Agents Industry:
THPA serves as a curing agent for epoxides, which is crucial for the cross-linking process in the production of epoxy resins, leading to enhanced mechanical properties and durability.
Used in Polyester Resins Industry:
cis-1,2,3,6-Tetrahydrophthalic anhydride is used as a chemical modifier in the modification of polyester resins, improving their thermal stability and performance characteristics.
Used in Adhesives Industry:
THPA is employed as a hardener in adhesive formulations, contributing to the bonding strength and resistance to environmental factors.
Used in Plasticizers Industry:
cis-1,2,3,6-Tetrahydrophthalic anhydride is used as a chemical intermediate for light-colored alkyds, which are essential for the production of plasticizers.
Used in Pesticides Industry:
THPA is utilized as a chemical intermediate in the synthesis of various pesticides, contributing to the development of effective and environmentally friendly products.
Used in Chemical Modifiers for Polystyrene Industry:
cis-1,2,3,6-Tetrahydrophthalic anhydride is used as a chemical modifier in the modification of polystyrene via Friedel-Crafts acylation, enhancing the thermal stability of the polymer.
Used in Synthesis of cis-Tetrahydroisoindole-1,3-Dione Derivatives and Cyclic Diimides:
THPA is employed as a reactant in the synthesis of cis-tetrahydroisoindole-1,3-dione derivatives and cyclic diimides, which have potential applications in various chemical and pharmaceutical processes.
Preparation
A flask containing 500 ml of dry benzene and 196 gm (2 moles) of maleic anhydride is heated with a pan of hot water while butadiene is introduced rapidly (0.6-0.8 liter/min) from a commercial cylinder. The solution is stirred rapidly and the heating is stopped after 3-5 min when the temperature reaches 50°C. In 15-25 min the reaction causes the temperature of the solution to reach 70-75°C. The absorption of the rapid stream of butadiene is nearly complete in 30-40 min. The addition of butadiene is continued at a slower rate for a total of 2\ hr. The solution is poured into a 1-liter beaker which is covered and kept at 0-5°C overnight. The product is collected on a large Buchner funnel and washed with 250 ml of b.p. 35-60°C petroleum ether. A second crop is obtained by diluting the filtrate with an additional 250 ml of petroleum ether. Both crops are dried to constant weight in an oven at 70-80°C to yield 281.5-294.5 gm (96- 97%, m.p. 99-102°C). Recrystallization from ligroin or ether raises the melting point to 103-104°C.
Synthesis Reference(s)
Journal of the American Chemical Society, 64, p. 802, 1942 DOI: 10.1021/ja01256a018
Check Digit Verification of cas no
The CAS Registry Mumber 935-79-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,3 and 5 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 935-79:
(5*9)+(4*3)+(3*5)+(2*7)+(1*9)=95
95 % 10 = 5
So 935-79-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H8O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1,3,5-6H,2,4H2
935-79-5Relevant articles and documents
cis-1,2,3,6-Tetrahydrophthalic anhydride at 173 K
Bolte, Michael,Bauch, Christian
, p. 226 - 228 (1999)
The title compound, C8H8O1, (I), crystallizes with two nearly identical molecules in the asymmetric unit. Each molecule has a boat conformation and non-crystallographic mirror symmetry. The structure was determined in connection with a study of the possible chemical decomposition of the compound in different solvents and in contact with the atmosphere. A similar boat conformation was found in five of six structures retrieved from the Cambridge Structural Database which contain (I) as a moiety. The present structure exhibits nearly the same packing motif as the recently found monoclinic polymorph.
Novel 1,2,3-triazole compounds: Synthesis, In vitro xanthine oxidase inhibitory activity, and molecular docking studies
Tan, Ayse
, (2020/03/25)
In this study, novel 1,2,3-triazole compounds containing carbasugar frameworks (5 and 6) were synthesized by the copper-catalyzed azide-alkyne cycloaddition reactions and their in vitro inhibition effects on the enzyme xanthine oxidase were investigated. All of the synthesized compounds were characterized by spectroscopic methods. According to the enzyme inhibition results, compounds 5 (IC50 = 0.586 ± 0.017 μM) and 6 (IC50 = 0.751 ± 0.021 μM) showed stronger inhibition effects than allopurinol (IC50 = 1.143 ± 0.019 μM), which is a standard drug used for inhibition of xanthine oxidase. The binding modes of the 1,2,3-triazole compounds (5 and 6) with the active site of xanthine oxidase were explained based on molecular docking studies. The molecular docking studies showed that the aromatic structure, π-π interactions and hydrophobic interactions play a major role in xanthine oxidase inhibition for compounds 5 and 6.
Access to amphiphilic cis-configurated polyamide-3 using alcohols as initiators
Maiatska, Olga,Belkin, Alexander,Ritter, Helmut
, p. 2367 - 2369 (2015/05/13)
The synthesis of polyamide-3 from 4a,5,8,8a-tetrahydro-1H-benzo[d][1,3]oxazine-2,4-dione (β-NCA, 1) using methanol, dye (Disperse Red 13), and poly(ethylene glycol) as initiator is described. The ring-opening polymerization under release of CO2 produces polyamides-3 with definite terminal groups, high purity, and relatively narrow dispersity. This route was used for preparation of block copolymers from as an example.
Synthesis of diazacrown compounds with polyfunctional cyclohexane fragments
Shabanov,Mamedov,Mamedov
, p. 589 - 592 (2007/10/03)
A convenient synthetic method was developed for new diazacrown compounds that contained at polyether cavity polyfunctional cyclohexene or cyclohexane fragments of definite configuration. The synthetic procedure consists in fusion in toluene of equimolar quantities of anhydrides of 4-cyclohexene and 4,5-trans-dibromocyclohexane-cis-1,2-dicarboxylic acids with hydroxy-substituted diazacrown ether. The crown compounds synthesized under complexing conditions with AgBF4 undergo disproportionation yielding bis-crown compounds.
