cis-1,2,3,6-Tetrahydrophthalic anhydride

Base Information

• Chemical Name: cis-1,2,3,6-Tetrahydrophthalic anhydride
• CAS No.: 935-79-5
• Deprecated CAS: 54684-06-9,439919-47-8,478856-60-9,954148-35-7,1446101-65-0,1632398-54-9,1639268-88-4,1690350-49-2,2226787-93-3,2497588-65-3
• Molecular Formula: C8H8 O3
• Molecular Weight: 152.15
• Hs Code.: H8O3 MOL WT. 152.15
• European Community (EC) Number: 213-308-7
• NSC Number: 49672
• UNII: W9Q4666NOS
• DSSTox Substance ID: DTXSID80883570
• Nikkaji Number: J208.190C
• Wikipedia: Tetrahydrophthalic_anhydride
• Wikidata: Q27292510
• ChEMBL ID: CHEMBL2228342
• Mol file: 935-79-5.mol

Synonyms:1,3-Isobenzofurandione,3a,4,7,7a-tetrahydro-, cis-;4-Cyclohexene-1,2-dicarboxylic anhydride, cis- (8CI);NSC 49672;cis-1,2,3,6-Tetrahydrophthalic acid anhydride;cis-4-Cyclohexene-1,2-dicarboxylicacid anhydride;cis-4-Cyclohexene-1,2-dicarboxylic anhydride;cis-D4-Tetrahydrophthalic anhydride;

Chemical Property of cis-1,2,3,6-Tetrahydrophthalic anhydride

Chemical Property:

• Appearance/Colour: white flakes
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Melting Point: 98 °C
• Refractive Index: 1.529
• Boiling Point: 305.6 °C at 760 mmHg
• Flash Point: 148.2 °C
• PSA: 43.37000
• Density: 1.289 g/cm³
• LogP: 0.65220
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: soluble in Toluene,Benzene
• Water Solubility.: REACTS
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 218

Purity/Quality:

99% ^*data from raw suppliers

cis-1,2,3,6-Tetrahydrophthalic anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 41-42/43-52/53
• Safety Statements: 22-24-26-37/39-61-52/53-42/43-41

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Plastics & Rubber -> Acid Anhydrides, Cyclic
• Canonical SMILES: C1C=CCC2C1C(=O)OC2=O
• Isomeric SMILES: C1C=CC[C@H]2[C@@H]1C(=O)OC2=O
• Description: Tetrahydrophthalic anhydride is an organic compound with the formula C6H8C2O3. The compound exists as two isomers, this article being focused on the more common cis isomer. It is a precursor to other compounds including the dicarboxylic acid tetrahydrophthalic acid as well the tetrahydrophthalimide, which is a precursor to the fungicide Captan. It is a white solid that is soluble in organic solvents.Tetrahydrophthalic anhydride, the cis isomer, is prepared by the Diels-Alder reaction of butadiene and maleic anhydride.
• Uses: Tetrahydrophthalic Anhydride is an anhydride hardener mainly used in the fields of coatings, epoxy resin curing agents, polyester resins, adhesives, plasticizers, pesticides, etc. It is also used as a chemical intermediate for light colored alkyds.Tetrahydrophthalic Anhydride is an organic compound obtained from the reaction of Maleic Anhydride and Butadiene. cis-1,2,3,6-Tetrahydrophthalic anhydride (THPA) can be used as: A curing agent for epoxides. A chemical modifier in the modification of polystyrene via Friedel-Crafts acylation for enhancing the thermal stability of the polymer. A reactant for the synthesis of cis-tetrahydroisoindole-1,3-dione derivatives and cyclic diimides.

Technology Process of cis-1,2,3,6-Tetrahydrophthalic anhydride

There total 15 articles about cis-1,2,3,6-Tetrahydrophthalic anhydride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

maleic anhydride (108-31-6) + 3-Sulfolene (77-79-2) → cis-1,2,3,6-tetrahydrophthalic anhydride (935-79-5)

Guidance literature:

In benzene; at 100 ℃; for 5h;

Reference yield: 83.0%

maleic anhydride (108-31-6) + 4-bromo-buta-1,2-diene (18668-68-3) → cis-1,2,3,6-tetrahydrophthalic anhydride (935-79-5)

Guidance literature:

4-bromo-buta-1,2-diene; With indium; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Inert atmosphere;

maleic anhydride; In N,N-dimethyl-formamide; at 80 ℃; for 2h; Inert atmosphere;

With water; sodium hydrogencarbonate; In N,N-dimethyl-formamide; Inert atmosphere;

DOI:10.1021/ol902530k

Reference yield: 79.0%

trans-cyclohex-4-ene-1,2-dicarboxylic acid (88-98-2,2305-26-2,15573-40-7,50987-15-0,51096-07-2,51096-08-3) → trans-4-Cylohexene-1,2-dicarboxylic anhydride (85-43-8,935-79-5,13149-03-6,51268-23-6)

Guidance literature:

With acetic anhydride; at 60 - 70 ℃;

DOI:10.1016/S0040-4020(01)96537-8

upstream raw materials:

trans-4-Cylohexene-1,2-dicarboxylic anhydride

maleic anhydride

3-Sulfolene

buta-1,3-diene

Downstream raw materials:

(1SR,6RS)-6-(pyrrolidine-1-carbonyl)cyclohex-3-enecarboxylic acid

2-(3-morpholino-propyl)-(3ar,7ac)-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

(+/-)-cis-6-thiazol-2-ylcarbamoyl-cyclohex-3-enecarboxylic acid

2-[3-(4-methyl-piperazino)-propyl]-(3ar,7ac)-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

Refernces

• 1、 Weininger et al.. "-". . p. 3732. Retrieved 1964.
• 2、 K?se, Aytekin,ünal, Asli,?ahin, Ertan,Bozkaya, U?ur,Kara, Yunus. "An anomalous addition of chlorosulfonyl isocyanate to a carbonyl group: The synthesis of ((3aS,7aR,E)-2-ethyl-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-ylidene)sulfamoyl chloride". . p. 931 - 936. Retrieved 2019/06/08.
• 3、 Mo, Juntae,Kim, Sung Hong,Lee, Phil Ho. "Tandem Diels-Alder/cross-coupling reactions of generated in situ organoindium reagents in a one-pot process". supporting information; experimental part. p. 424 - 427. Retrieved 2010/04/24.