85-43-8

Basic information

• Product Name: CIS-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE; >98%
• Synonyms: 1,2,3,6-Tetrahydrophthalic acid anhydride;1,2,3,6-tetrahydrophthalicacidanhydride;1,2,3,6-tetrahydro-phthalicanhydrid;1,2,3,6-tetrahydrophthalicanhydride[qr];1,3-Isobenzofurandione, 3a,4,7,7a-tetrahydro-, cis-;1,3-isobenzofurandione,3a,4,7,7a-tetrahydro-[qr];3a,4,7,7a-tetrahydro-1,3-benzofurandione;3a,4,7,7a-tetrahydro-3-isobenzofurandione
• CAS NO: 85-43-8
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.14732
• EINECS: 201-605-4
• Product Categories: Pyridines
• Mol File: 85-43-8.mol

Chemical Properties

• Melting Point: 101-102°C
• Boiling Point: 195°C 5mm
• Flash Point: 157°C
• Appearance: /
• Density: 1,375 g/cm3
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.4810 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 3.84[at 20 ℃]
• Water Solubility: REACTS
• CAS DataBase Reference: CIS-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE; >98%(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE; >98%(85-43-8)
• EPA Substance Registry System: CIS-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE; >98%(85-43-8)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: 41-42/43-52/53
• Safety Statements: 26-36/37/39
• RIDADR: 2698
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 85-43-8(Hazardous Substances Data)

Usage

Uses

Chemical intermediate for light-colored alkyds, polyesters, plasticizers, and adhesives; intermediate for pesticides; hardener for resins.

Definition

ChEBI: 1,2,3,6-tetrahydrophthalic anhydride is a cyclic dicarboxylic anhydride that is 1,3,3a,4,7,7a-hexahydro-2-benzofuran carrying oxo groups at positions 1 and 3. It is a cyclic dicarboxylic anhydride and a tetrahydrofurandione.

General Description

Clear colorless to light yellow slight viscous liquid. Highly toxic and a strong irritant to skin, eyes and mucous membranes. Corrosive to skin and metal. Used in making polyester, alkyd resins, and plasticizers.

Air & Water Reactions

Reacts exothermically with water to form memtetrahydrophthalic acid.

Reactivity Profile

CIS-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE; >98% is combustible. Reacts with oxidizers. Reacts exothermically with water. These reactions are usually slow, but can become violent when local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. A corrosive irritant to skin, eyes, and mucous membranes. Combustible when exposed to heat or flame. Will react with water or steam to produce heat; can react with oxidizing materials. To fight fre, use water, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ANHYDRIDES.

InChI:InChI=1/C8H8O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1,3,5-6H,2,4H2

Upstream product

• 108-31-6 maleic anhydride 
• 590-19-2 2,3-dimethylbutene 
• 106-99-0 buta-1,3-diene 
• 88-98-2 cyclohex-4-ene-1,2-dicarboxylic acid 
• 88-98-2 trans-cyclohex-4-ene-1,2-dicarboxylic acid 
• 4841-84-3 dimethyl cis-1,2,3,6-tetrahydrophthalate 
• 17673-68-6 dimethyl trans-cyclohex-4-ene-1,2-dicarboxylate 
• 95-47-6 o-xylene 
• 7500-55-2 dimethyl cyclohex-4-ene-1,2-dicarboxylate 
• 77-79-2 3-Sulfolene 

Downstream Products

• 100171-79-7 6β-((1Ξ)-ξ-6-carboxy-cyclohex-3-enecarbonylamino)-penicillanic acid 
• 19692-02-5 6-thiazol-2-ylcarbamoyl-cyclohex-3-enecarboxylic acid 
• 39214-27-2 1,2,3,6-Tetrahydrophthalsaeure-bis-dimethylamid 
• 40634-95-5 trimethylsilyl cis-2-isocyanato-4-cyclohex-1-ene carboxylate 
• 1703-58-8 racem.-butane-1,2,3,4-tetracarboxylic acid 
• 129760-94-7 5,10-Dihydro-4-ethyl-2-phenylpyrazolo<1,5-a><1,3>-7-cyclohexendiazepin-5,10-dione 
• 87024-43-9 (Z)-10-Nitro-8-phenyl-1,4,4a,6,13,14a-hexahydro-6,7,13-triaza-dibenzo[a,f]cyclodecene-5,14-dione 
• 136606-69-4 C₃₄H₃₆O₁₂ 
• 87024-42-8 (Z)-10-Bromo-8-phenyl-1,4,4a,6,13,14a-hexahydro-6,7,13-triaza-dibenzo[a,f]cyclodecene-5,14-dione 
• 136606-66-1 Cyclohex-4-ene-1,2-dicarboxylic acid mono-(2,6,13,16,19-pentaoxa-tricyclo[18.4.0.0^7,12]tetracosa-1⁽²⁴⁾,7,9,11,20,22-hexaen-4-yl) ester 
• 89446-98-0 3-(1,3-Dioxo-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-benzoic acid 
• 90619-37-7 2-[3-(4-p-Tolyl-piperazin-1-yl)-propyl]-3a,4,7,7a-tetrahydro-isoindole-1,3-dione; hydrochloride 
• 90619-38-8 2-{3-[4-(2-Chloro-phenyl)-piperazin-1-yl]-propyl}-3a,4,7,7a-tetrahydro-isoindole-1,3-dione; hydrochloride 
• 80575-39-9 6-[5-(5-Oxo-2,5-dihydro-furan-3-yl)-2,3-dihydro-indole-1-carbonyl]-cyclohex-3-enecarboxylic acid 

Relevant articles and documents

Method for preparing butane tetracarboxylic dianhydride

The invention discloses a method for preparing butane tetracarboxylic dianhydride, and belongs to the field of fine chemical preparation methods. The method comprises the following steps: using maleicanhydride and 1,3-butadiene as starting materials to synthesize tetrahydrophthalic anhydride as an intermediate product through a 1,4-addition reaction in a high temperature molten state; subjectingtetrahydrophthalic anhydride to hydrolysis, ozone oxidation, hydrogen peroxide oxidation reaction to obtain butane tetracarboxylic acid as an intermediate product; using acetic anhydride or propionicanhydride as a dehydrating agent, and subjecting the butane tetracarboxylic acid to synthesize butane tetracarboxylic dianhydride through dehydration closed-ring. Compared with the traditional process, the method has the advantages of mild reaction conditions, high product purity, high yield, and no pollution, and is suitable for large-scale industrial production.

Heterogeneous catalysts for the cyclization of dicarboxylic acids to cyclic anhydrides as monomers for bioplastic production

Cyclic anhydrides, key intermediates of carbon-neutral and biodegradable polyesters, are currently produced from biomass-derived dicarboxylic acids by a high-cost multistep process. We present a new high-yielding process for the direct intramolecular dehydration of dicarboxylic acids using a reusable heterogeneous Lewis acid catalyst, Nb2O5·nH2O. Various dicarboxylic acids, which can be produced by a biorefinery process, are transformed into the corresponding cyclic anhydrides as monomers for polyester production. This method is suitable for the production of renewable polyesters in a biorefinery process.

Solvent-free Diels-Alder reaction in a closed batch system

Solvent-free Diels-Alder reactions were carried out by heating a mixture of a volatile diene, such as 1,3-butadiene, isoprene, or 2,3-dimethyl-1,3- butadiene, and a dienophile, such as methyl vinyl ketone, methyl acrylate, or maleic anhydride, in a closed batch reactor. High yields of Diels-Alder products were obtained without using solvents and catalysts within a short reaction time in most of the reactions. In particular, several reactions of dienophiles with 1,3-butadiene, which is known as a diene with low reactivity because of its gaseous form, also proceeded with high yields of Diels-Alder products in the closed batch reactor under conditions pressured by the reactant vapor. Solvent-free reactions provided high yields compared to reactions in solvent since the reaction heat directly resulted in increasing the reaction temperature and pressure. Energy in the exothermic reaction was used effectively in the closed batch system under solvent-free conditions.

CATALYST FOR ALKYLATION AND PROCESS FOR PRODUCING ALKYLAROMATIC HYDROCARBON COMPOUND USING THE CATALYST

A catalyst for alkylation contains an inorganic structural material having an ion-exchange ability and a metal ion having a valency of 2 or more. The metal ion is supported on the inorganic structural material. The inorganic structural material is preferably a zeolite. The metal ion is preferably a lanthanide metal. The catalyst for alkylation imparts industrially satisfiable activity and selectivity and can be readily separated, collected and recycled. Furthermore, the process for producing an alkylaromatic hydrocarbon compound includes reacting an aromatic hydrocarbon compound and a compound having an unsaturated bond in the presence of the catalyst for alkylation.

Synthetic approach to cis and trans-decalins via Diels - Alder reaction and ring-closing metathesis as key steps: Further extension to dioxapropellane derivative by ring-closing metathesis

9,10-Substituted cis and trans-decalins were synthesized by a simple route using the Diels-Alder reaction and ring-closing metathesis (RCM) as key steps. Later, the cis-decalin system has been extended to 3,8-dioxa[8.4.4]propellane derivative by RCM sequence as a key step. Copyright

Synthesis of new cantharimide analogues derived from 3-sulfolene

New types of norcantharimide analogues were prepared by three methods: epoxidation, photooxidation, and bromination. Epoxidation of deoxynorcantharimide with m-chloroperoxybenzoic acid gave an isomeric mixture. The selective formation of the syn-isomers was attributed to dipole-dipole interactions between the peracid and imide moiety. Photooxidation of deoxynorcanthamide gave syn-and anti-hydroperoxide analogues through ene addition of singlet oxygen; the anti-hydroperoxide was the major product in this case, as a result of the steric effect of the imide ring. Bromination of deoxynorcantharimide and subsequent transformations gave a pyrrolidine and the phthalimide core structure. Georg Thieme Verlag Stuttgart.

Dicarboxylic diester, process for producing the same, and refrigerating machine lubricating oil comprising the ester

A diester represented by the formula wherein A represents a cyclohexane ring, cyclohexene ring or benzene ring, X is H or methyl group, RX and RY are the same or different and each is C3-C18 branched-chain alkyl group, C1-C18 straight-chain alkyl group, C2-C18 straight-chain alkenyl or C3-C18 cycloalkyl, provided that when A is a benzene ring, RX and RY are different from each other and —COORX and —COORY are attached to two adjacent carbon atoms of the benzene ring, and having the following properties: 1) a total acid number of 0.05 mgKOH/g or less, 2) a sulfated ash content of 10 ppm or less, 3) a sulfur content of 20 ppm or less, 4) a phosphorus content of 20 ppm or less, 5) a peroxide value of 1.0 meq/kg or less, 6) a carbonyl value of 10 or less; 7) a volume resistivity of 1×1011 Ω·cm or more, 8) a hydroxyl value of 3 mgKOH/g or less, and 9) a water content of 100 ppm or less, a process for preparing the same and a refrigerator lubricating oil comprising the diester.

STEREOCHEMICAL STUDIES 83. SATURATED HETEROCYCLES 76. PREPARATION AND CONFORMATIONAL STUDY OF PARTIALLY SATURATED 3,1-BENZOXAZINES, 3,1-BENZOXAZIN-2-ONES AND 3,1-BENZOXAZINE-2-THIONES

The cis- and trans-2-amino-4-cyclohexene-1-carboxylic acids 1 and 3 react with imidates to give the condensed-skeleton, bicyclic cis- and trans-pyrimidin-4-ones 8 and 9.The amino acids 1 and 3 were reduced to the cis- and trans-1,3-aminoalcohols 6 and 7, which were cyclized by means of imidates to the bicyclic tetrahydro-4H-3,1-benzoxazines 10 and 11, or were converted, via the corresponding carbamates 14 and 15 into the tetrahydro-4H-3,1-benzoxazin-2(1H)-ones 16 and 17.The 2-thioxo analogues 18 and 19 were prepared by cyclization of the dithiocarbamates obtained from the aminoalcohols 6 and 7 by treatment with carbon disulphide.The trans-aminoalcohol 7 and its saturated analogue reacted with p-chlorobenzaldehyde to furnish the hexahydro 13 and octahydro-4H-3,1-benzoxazine 13a, respectively. 1H and 13C NMR studies showed that, similarly to the earlier-investigated analogues containing oxygen or unsubstituted nitrogen at position 1, the synthesized cis isomers 8, 10, 16 and 18 occurred as the preferred conformer in the heterocyclic twist inverse form of N-inside type (quasiaxal C6-N bond) (B).In the trans isomers containing a saturated C-2 atom (13 and 13a), H-2 and H-6 are in cis relative positions.

Stereoselective Total Synthesis of Racemic (3S,4R/3R,4S)- and a Diastereoisomeric Mixture of (6E,10Z)-3,4,7,11-Tetramethyltrideca-6,10-dienal (Faranal); The Trail Pheromone of the Pharaoh's Ant

Racemic (3S,4R/3R,4S)-faranal has been synthesised by a convergent, stereospecific route which employed the addition of alkylcopper complexes to terminal acetylenes, to generate two trisubstituted double bonds, and a Diels-Alder reaction to establish the relative stereochemistry of the C-3, C-4 methyl groups.A diastereoisomeric mixture of faranals, enriched in the (3S,4S/3R,4R)-enantiomeric pair , has been synthesised by a somewhat shorter route via an intermediate diester, obtained from electrochemical dimerisation of ethyl crotonate.