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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
Molecular Weight:
152.15
MDL Number:
MFCD00005916
MOL File:
935-79-5.mol
MSDS File:
SDS
Last updated:2024-12-18 14:15:30

cis-1,2,3,6-Tetrahydrophthalic anhydride 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)
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)
FDA 21 CFR 177.2280
EWG's Food Scores 1-2
FDA UNII W9Q4666NOS
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)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS08
Signal word  Danger
Hazard statements  H317-H318-H334-H412
Precautionary statements  P261-P273-P280-P302+P352-P304+P340+P312-P305+P351+P338
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
NFPA 704
1
2 1

cis-1,2,3,6-Tetrahydrophthalic anhydride price More Price(18)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 136891 cis-1,2,3,6-Tetrahydrophthalic anhydride 95% 935-79-5 1kg $53.82 2024-03-01 Buy
Sigma-Aldrich 136891 cis-1,2,3,6-Tetrahydrophthalic anhydride 95% 935-79-5 100g $57.5 2023-06-20 Buy
TCI Chemical C0493 cis-4-Cyclohexene-1,2-dicarboxylic Anhydride >98.0%(GC)(T) 935-79-5 25g $21 2024-03-01 Buy
TCI Chemical C0493 cis-4-Cyclohexene-1,2-dicarboxylic Anhydride >98.0%(GC)(T) 935-79-5 500g $36 2024-03-01 Buy
Alfa Aesar B21431 cis-4-Cyclohexene-1,2-dicarboxylic anhydride, 95% 935-79-5 250g $29.5 2024-03-01 Buy
Product number Packaging Price Buy
136891 1kg $53.82 Buy
136891 100g $57.5 Buy
C0493 25g $21 Buy
C0493 500g $36 Buy
B21431 250g $29.5 Buy

cis-1,2,3,6-Tetrahydrophthalic anhydride Chemical Properties,Uses,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

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.

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.

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.
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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View Lastest Price from cis-1,2,3,6-Tetrahydrophthalic anhydride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
cis-1,2,3,6-Tetrahydrophthalic anhydride pictures 2024-11-21 cis-1,2,3,6-Tetrahydrophthalic anhydride
935-79-5
US $10.00 / KG 1KG 99% 10 mt Hebei Weibang Biotechnology Co., Ltd
cis-1,2,3,6-Tetrahydrophthalic anhydride pictures 2024-10-22 cis-1,2,3,6-Tetrahydrophthalic anhydride
935-79-5
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
cis-1,2,3,6-Tetrahydrophthalic anhydride pictures 2024-10-11 cis-1,2,3,6-Tetrahydrophthalic anhydride
935-79-5
US $30.00-10.00 / kg 10kg 99% 100000kg Hebei Chuanghai Biotechnology Co,.LTD
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 3A,4,7,7A-TETRAHYDRO-2-BENZOFURAN-1,3-DIONE #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)- 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 cis-1,2,3,6-Tetrahydrophthalic anhydride (3aR,7aS)-1,3,3a,4,7,7a-hexahydro-2-benzofuran-1,3-dione cis-4-Cyclohexene-1,2-dicarboxylic Anhydride > 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%, CIS-4-CYCLOHEXEN-1,2-DIMETHANOIC ANHYDRIDE CIS-4-CYCLOHEXENE-1,2-DICARBOXYLIC ANHYDRIDE 4-CYCLOHEXENE-1,2-DICARBOXYLIC ANHYDRIDE THPA (3aR,7aS)-3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione 935-79-5 C8D6H2O3 Diels-Alder Adducts