ChemicalBook > CAS DataBase List > cis-1,2,3,6-Tetrahydrophthalic anhydride

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

Product Name
cis-1,2,3,6-Tetrahydrophthalic anhydride
CAS No.
935-79-5
Chemical Name
cis-1,2,3,6-Tetrahydrophthalic anhydride
Synonyms
THPA;CIS-4-CYCLOHEXENE-1,2-DICARBOXYLIC ANHYDRIDE;4-CYCLOHEXENE-1,2-DICARBOXYLIC ANHYDRIDE;CIS-4-CYCLOHEXEN-1,2-DIMETHANOIC ANHYDRIDE;(3aR,7aS)-3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione;CIS-THPA;cis-1,2,3,6-Tetrahyd;cis-1,2,3,6-TetrahydrophthaL;Cis-1,2,3,6-Tetrahydrophthalic;6-Tetrahydrophthalic anhydride
CBNumber
CB5728570
Molecular Formula
C8H8O3
Formula Weight
152.15
MOL File
935-79-5.mol
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cis-1,2,3,6-Tetrahydrophthalic anhydride Property

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)
Flash point:
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 limits
ACGIH: 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 Reference
935-79-5(CAS DataBase Reference)
NIST Chemistry Reference
cis-1,2,3,6-Tetrahydrophthalic anhydride(935-79-5)
EPA Substance Registry System
1,3-Isobenzofurandione, 3a,4,7,7a-tetrahydro-, (3aR,7aS)-rel- (935-79-5)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H317May cause an allergic skin reaction

H318Causes serious eye damage

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
136891
Product name
cis-1,2,3,6-Tetrahydrophthalic anhydride
Purity
95%
Packaging
1kg
Price
$53.82
Updated
2024/03/01
Sigma-Aldrich
Product number
136891
Product name
cis-1,2,3,6-Tetrahydrophthalic anhydride
Purity
95%
Packaging
100g
Price
$57.5
Updated
2023/06/20
TCI Chemical
Product number
C0493
Product name
cis-4-Cyclohexene-1,2-dicarboxylic Anhydride
Purity
>98.0%(GC)(T)
Packaging
25g
Price
$21
Updated
2024/03/01
TCI Chemical
Product number
C0493
Product name
cis-4-Cyclohexene-1,2-dicarboxylic Anhydride
Purity
>98.0%(GC)(T)
Packaging
500g
Price
$36
Updated
2024/03/01
Alfa Aesar
Product number
B21431
Product name
cis-4-Cyclohexene-1,2-dicarboxylic anhydride, 95%
Packaging
250g
Price
$29.5
Updated
2024/03/01
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cis-1,2,3,6-Tetrahydrophthalic anhydride Chemical Properties,Usage,Production

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.

Chemical Properties

Tetrahydrophthalic Anhydride (THPA) is a white crystalline powder or FLAKES. It is slightly soluble in benzene and acetone and it is also sensitive to moisture.

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.

Uses

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.

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

cis-1,2,3,6-Tetrahydrophthalic anhydride Preparation Products And Raw materials

Raw materials

1,3-Butadiene Maleic anhydride

Preparation Products

4-Methylphthalic acid Captan 1,2,3,4-Butanetetracarboxylic acid Di-(2-Ethylhexyl)4,5-Epoxytetrahydrophthalate N-Hydroxymethyl-3,4,5,6-tetrahydrophthalimide
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View Lastest Price from cis-1,2,3,6-Tetrahydrophthalic anhydride manufacturers

Hebei Chuanghai Biotechnology Co,.LTD
Product
cis-1,2,3,6-Tetrahydrophthalic anhydride 935-79-5
Price
US $30.00-10.00/kg
Min. Order
10kg
Purity
99%
Supply Ability
100000kg
Release date
2024-08-23
Hebei Fengjia New Material Co., Ltd
Product
cis-1,2,3,6-Tetrahydrophthalic anhydride 935-79-5
Price
US $120.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
1000000
Release date
2024-08-08
Hebei Guanlang Biotechnology Co., Ltd.
Product
cis-1,2,3,6-Tetrahydrophthalic anhydride 935-79-5
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2021-08-09

935-79-5, cis-1,2,3,6-Tetrahydrophthalic anhydrideRelated Search:

Succinic anhydride 3,4,5,6-Tetrahydrophthalic anhydride CIS-BUTENEDIOIC ANHYDRIDE Di-tert-butyl dicarbonate Methyl tetrahydrophthalic anhydride Pralmorelin 5-Chlorovaleric acid Diphenolic acid Erythromycin Estolate Phthalic anhydride DL-α-Tocopherol Glutaric anhydride cis-Hexahydrophthalic acid CIS-1,2-CYCLOHEXANEDICARBOXYLIC ANHYDRIDE Dimethyl cyclohexane-1,2-dicarboxylate EXO-3,6-EPOXY-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE ENDO-BICYCLO[2.2.2]OCT-5-ENE-2,3-DICARBOXYLIC ANHYDRIDE Acetic anhydride

  • 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-4-CYCLOHEXEN-1,2-DIMETHANOIC ANHYDRIDE
  • CIS-4-CYCLOHEXENE-1,2-DICARBOXYLIC ANHYDRIDE
  • CIS-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE
  • 4-CYCLOHEXENE-1,2-DICARBOXYLIC ANHYDRIDE
  • 3A,4,7,7A-TETRAHYDRO-2-BENZOFURAN-1,3-DIONE
  • THPA
  • #ncis-1,2,3,6-Tetrahydrophthalic anhydride
  • Cis-1,2,3,6-Tetrahydrophthalic
  • CIS-4-CYCLOHEXENEDICARBOXYLIC ANHYDRIDE: 1,2,3,6-THPA: THPA
  • CIS-1,2,3,6-TETRAHYDROPHTHALICACIDANHYDRIDE
  • cis-1,2,3,6-Tetrahydrophthalic anhydride (THPA)
  • (3aR,7aS)-3a,4,7,7a-Tetrahydro-2-benzofuran-1,3-dione
  • 1,3-Isobenzofurandione, 3a,4,7,7a-tetrahydro-, (3aR,7aS)-
  • (3aR,7aS)-1,3,3a,4,7,7a-hexahydro-2-benzofuran-1,3-dione
  • cis-4-Cyclohexene-1,2-dicarboxylic acid anhydride
  • (3aR)-3aβ,4,7,7aβ-Tetrahydroisobenzofuran-1,3-dione
  • 1,3,3aα,4,7,7aα-Hexahydroisobenzofuran-1,3-dione
  • 7,7aα-Dihydroisobenzofuran-1,3(3aαH,4H)-dione
  • Cyclohexene-4α,5α-dicarboxylic anhydride
  • cis-1,2,3,6-Tetrahydrophthalic anhydride/thpa ,99%
  • cis-1,2,3,6-Tetrahyd
  • 6-Tetrahydrophthalic anhydride
  • 1,3-Isobenzofurandione,3a,4,7,7a-tetrahydro-, (3aR,7aS)-rel-
  • cis-1,2,3,6-Tetrahydrophthalic anhydride, 98% 500GR
  • rel-(3aR,7aS)-3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione
  • trans-4-Cylohexene-1,2-dicarboxylic anhydride
  • (3aR,7aS)-rel-3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione
  • (3aR,7aS)-3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione
  • <i>cis</i>-1,2,3,6-Tetrahydrophthalic anhydride
  • cis-4-Cyclohexene-1,2-dicarboxylic Anhydride &gt
  • cis-1,2,3,6-TetrahydrophthaL
  • cis-3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione
  • Tetrahydrophthalic anhydride CAS 935-79-5
  • cis-4-Cyclohexene-1,2-dicarboxylic anhydride, 95%,
  • is-1,2,3,6-Tetrahydrophthalic anhydride
  • 935-79-5
  • C8D6H2O3
  • Diels-Alder Adducts