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Merck
CN

136891

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

95%

Synonym(s):

cis-4-Cyclohexene-1,2-dicarboxylic anhydride

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About This Item

Empirical Formula (Hill Notation):
C8H8O3
CAS Number:
935-79-5
Molecular Weight:
152.15
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
24848300
EC Number:
213-308-7
Beilstein/REAXYS Number:
82341
MDL number:
MFCD00005916

Key Documents

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Product Name

cis-1,2,3,6-Tetrahydrophthalic anhydride, 95%

InChI key

KMOUUZVZFBCRAM-OLQVQODUSA-N

InChI

1S/C8H8O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-2,5-6H,3-4H2/t5-,6+

SMILES string

[H][C@@]12CC=CC[C@]1([H])C(=O)OC2=O

vapor density

5.2 (vs air)

vapor pressure

<0.01 mmHg ( 20 °C)

assay

95%

form

flakes

mp

97-103 °C (lit.)

Quality Level

100

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Application

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.

pictograms

Health hazardCorrosion
GHS08,GHS05

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Eye Dam. 1 - Resp. Sens. 1 - Skin Sens. 1

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

312.8 °F - closed cup

flash_point_c

156 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBD4960V
STBD0460V
STBB3135V
STBB3135
S85964

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Influence of cure schedule and stoichiometry on the dynamic mechanical behaviour of tetrafunctional epoxy resins cured with anhydrides
Guerrero P, et al.
Polymer, 37(11), 2195-2200 (1996)
Polymer networks derived from curing of epoxidised linseed oil: influence of different catalysts and anhydride hardeners
Boquillon N and Fringant C
Polymer, 41(24), 8603-8613 (2000)
Chemical modification of polystyrene?IV. Electrophilic substitution of polystyrene with cis-1, 2, 3, 6 tetrahydrophthalic anhydride
Biswas M and Chatterjee S
European Polymer Journal, 19(4), 317-320 (1983)
Cong Zhang et al.
Journal of controlled release : official journal of the Controlled Release Society, 226, 193-204 (2016-02-21)
Stepwise pH-responsive nanoparticle system containing charge reversible pullulan-based (CAPL) shell and poly(β-amino ester) (PBAE)/poly(lactic-co-glycolic acid) (PLAG) core is designed to be used as carriers of paclitaxel (PTX) and combretastatin A4 (CA4) for combining antiangiogenesis and chemotherapy to treat hepatocellular carcinoma
Montmorillonite K-10 supported one-pot synthesis of some symmetric diimides and 3a, 4, 7, 7a-tetrahydroisoindole-1, 3-dione derivatives under solvent-free conditions using microwaves
Habibi D and Marvi O
J. Serb. Chem. Soc., 70(4), 579-583 (2005)

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