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Sigma-Aldrich

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

95%

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Synonym(s):
cis-4-Cyclohexene-1,2-dicarboxylic anhydride
Empirical Formula (Hill Notation):
C8H8O3
CAS Number:
935-79-5
Molecular Weight:
152.15
Beilstein:
82341
EC Number:
213-308-7
MDL number:
MFCD00005916
UNSPSC Code:
12162002
PubChem Substance ID:
24848300
NACRES:
NA.23

vapor density

5.2 (vs air)

Quality Level

100

vapor pressure

<0.01 mmHg ( 20 °C)

Assay

95%

form

flakes

mp

97-103 °C (lit.)

SMILES string

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

InChI

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

InChI key

KMOUUZVZFBCRAM-OLQVQODUSA-N

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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

Signal Word

Danger

Hazard Statements

H317,H318,H334,H412

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
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)
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)
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

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