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

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CAS:935-79-5
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Products Intro: Product Name:cis-1,2,3,6-Tetrahydrophthalic anhydride
CAS:935-79-5
Purity:98% Package:10kg,25kg,100kg

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cis-1,2,3,6-Tetrahydrophthalic anhydride Basic information
Product Name:cis-1,2,3,6-Tetrahydrophthalic anhydride
Synonyms:1,3-isobenzofurandion,3a,4,7,7a-tetrahydro-,cis-;3-Isobenzofurandione,3a,4,7,7a-tetrahydro-,cis-1;4,7,7a-tetrahydro-3-isobenzofurandioncis-3a;cis-3a,4,7,7a-Tetrahydro-1,3-isobenzofurandione;CIS-THPA;CIS-DELTA4-TETRAHYDROPHTHALIC ANHYDRIDE;CIS-4-TETRAHYDROPHTHALIC ANHYDRIDE;CIS-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE
CAS:935-79-5
MF:C8H8O3
MW:152.15
EINECS:213-308-7
Product Categories:Diels-Alder Adducts
Mol File:935-79-5.mol
cis-1,2,3,6-Tetrahydrophthalic anhydride Structure
cis-1,2,3,6-Tetrahydrophthalic anhydride Chemical Properties
Melting point 98 °C
Boiling point 234.6°C (rough estimate)
density 1.2143 (rough estimate)
vapor density 5.2 (vs air)
vapor pressure <0.01 mm Hg ( 20 °C)
refractive index 1.4447 (estimate)
Fp 156 °C
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
solubility soluble in Toluene,Benzene
form powder to crystal
color White to Almost white
Water Solubility REACTS
Sensitive Moisture Sensitive
BRN 82341
Exposure limitsACGIH: TWA 0.01 mg/m3
OSHA: TWA 0.25 ppm(1 mg/m3)
NIOSH: IDLH 10 mg/m3; TWA 0.25 ppm(1 mg/m3)
CAS DataBase Reference935-79-5(CAS DataBase Reference)
NIST Chemistry Referencecis-1,2,3,6-Tetrahydrophthalic anhydride(935-79-5)
EPA Substance Registry System1,3-Isobenzofurandione, 3a,4,7,7a-tetrahydro-, (3aR,7aS)-rel- (935-79-5)
Safety Information
Hazard Codes Xn
Risk Statements 41-42/43-52/53
Safety Statements 22-24-26-37/39-61-52/53-42/43-41
RIDADR UN 2698 8/PG 3
WGK Germany 3
RTECS GW5775000
TSCA Yes
HazardClass 8
PackingGroup III
HS Code 29173990
MSDS Information
ProviderLanguage
cis-4-Cyclohexene-1,2-dicarboxylic anhydride English
SigmaAldrich English
ACROS English
ALFA English
cis-1,2,3,6-Tetrahydrophthalic anhydride Usage And Synthesis
DescriptionTetrahydrophthalic 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.
Chemical PropertiesTetrahydrophthalic Anhydride (THPA) is a white crystalline powder or FLAKES. It is slightly soluble in benzene and acetone and it is also sensitive to moisture.
Usescis-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.

UsesTetrahydrophthalic 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.
PreparationA 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.
Preparation of Tetrahydrophthalic Anhydride
Synthesis Reference(s)Journal of the American Chemical Society, 64, p. 802, 1942 DOI: 10.1021/ja01256a018
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