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136891

Sigma-Aldrich

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
Beilstein:
82341
EC Number:
213-308-7
MDL number:
MFCD00005916
UNSPSC Code:
12162002
PubChem Substance ID:
24848300
NACRES:
NA.23
Pricing and availability is not currently available.

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.[1][2]
  • A chemical modifier in the modification of polystyrene via Friedel-Crafts acylation for enhancing the thermal stability of the polymer.[3]
  • A reactant for the synthesis of cis-tetrahydroisoindole-1,3-dione derivatives and cyclic diimides.[3]

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

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

312.8 °F - closed cup

Flash Point(C)

156 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBD4960V
STBD0460V
STBB3135V
STBB3135
S85964

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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)
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)
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)
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

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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