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EXO-3,6-EPOXY-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE is an organic compound that serves as an intermediate in various chemical syntheses. It is characterized by its epoxy and anhydride functional groups, which make it a versatile building block for creating a range of different molecules.

6118-51-0

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  • Exo-3, 6-Epoxy-1, 2, 3, 6-Tetrahydrophthalic Anhydride

    Cas No: 6118-51-0

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6118-51-0 Usage

Uses

Used in Chemical Synthesis:
EXO-3,6-EPOXY-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE is used as an intermediate in the synthesis of 4,4-dialkyl-2-butenolides. It is particularly useful for this application due to its reactive epoxy and anhydride groups, which can undergo a series of reactions with Grignard reagents, followed by cycloreversion (elimination of furan) to release the desired double bond.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, EXO-3,6-EPOXY-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE may be used as a key intermediate in the development of new drugs. Its unique chemical structure allows for the creation of novel compounds with potential therapeutic applications.
Used in Polymer Industry:
EXO-3,6-EPOXY-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE can also be utilized in the polymer industry as a monomer or a comonomer for the production of various types of polymers. Its anhydride functionality can be used to create polyesters, polycarbonates, or other polymers with specific properties, depending on the desired application.
Used in Coatings and Adhesives:
EXO-3,6-EPOXY-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE may also find use in the development of coatings and adhesives, where its epoxy functionality can be exploited to create cross-linked networks with enhanced mechanical properties and chemical resistance.

Check Digit Verification of cas no

The CAS Registry Mumber 6118-51-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,1,1 and 8 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 6118-51:
(6*6)+(5*1)+(4*1)+(3*8)+(2*5)+(1*1)=80
80 % 10 = 0
So 6118-51-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H6O4/c9-7-5-3-1-2-4(11-3)6(5)8(10)12-7/h1-6H/t3-,4+,5-,6+

6118-51-0 Well-known Company Product Price

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  • Alfa Aesar

  • (L03620)  exo-7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, 98+%   

  • 6118-51-0

  • 5g

  • 158.0CNY

  • Detail
  • Alfa Aesar

  • (L03620)  exo-7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, 98+%   

  • 6118-51-0

  • 25g

  • 290.0CNY

  • Detail
  • Alfa Aesar

  • (L03620)  exo-7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, 98+%   

  • 6118-51-0

  • 100g

  • 870.0CNY

  • Detail
  • Aldrich

  • (330736)  exo-3,6-Epoxy-1,2,3,6-tetrahydrophthalicanhydride  

  • 6118-51-0

  • 330736-25G

  • 709.02CNY

  • Detail
  • Aldrich

  • (330736)  exo-3,6-Epoxy-1,2,3,6-tetrahydrophthalicanhydride  

  • 6118-51-0

  • 330736-100G

  • 1,946.88CNY

  • Detail

6118-51-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name exo-3,6-Epoxy-1,2,3,6-tetrahydrophthalic anhydride

1.2 Other means of identification

Product number -
Other names anhydride of rel-(1R,2S,3R,4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6118-51-0 SDS

6118-51-0Synthetic route

furan
110-00-9

furan

maleic anhydride
108-31-6

maleic anhydride

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride
6118-51-0

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
In neat (no solvent, solid phase) for 1h; Diels-Alder Cycloaddition; Milling;100%
In toluene at 110℃; for 24h; Diels-Alder Cycloaddition; Reflux; stereospecific reaction;100%
at 25℃; for 16h; Diels-Alder reaction;98%
furan
110-00-9

furan

maleic anhydride
108-31-6

maleic anhydride

A

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride
6118-51-0

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

B

endo, cis-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dicarboxylic acid
51112-81-3

endo, cis-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dicarboxylic acid

Conditions
ConditionsYield
With trans-1,2-bis(4-pyridyl)ethylene In neat (no solvent, solid phase) for 25h; Milling;A 93%
B 7%
With trans-1,2-bis(4-pyridyl)ethylene In neat (no solvent, solid phase) for 25h; Milling; UV-irradiation;A 35%
B 65%
furan
110-00-9

furan

maleic anhydride
108-31-6

maleic anhydride

diethyl ether
60-29-7

diethyl ether

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride
6118-51-0

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
In diethyl ether at 38℃; for 1h;85.75%
furan
110-00-9

furan

maleic anhydride
108-31-6

maleic anhydride

A

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride
6118-51-0

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

B

7-oxabicyclo<2.2.1>heptene-exo-2,3-dicarboxylic anhydride
6766-44-5

7-oxabicyclo<2.2.1>heptene-exo-2,3-dicarboxylic anhydride

Conditions
ConditionsYield
In acetone at 20℃; under 760 Torr; for 282h; Kinetics; Product distribution; effect of high pressure: different pressures and times; rate constants; 40 deg C, deuteroacetonitrile;
In acetone at 20℃; under 735059 Torr; Thermodynamic data; Kinetics; Rate constant; other pressure, ΔV(excit);
With K10 montmorillonite at 0℃; for 3h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
In ethyl acetate at 20℃; Kinetics; Diels-Alder reaction;
In ethyl acetate at 20℃; Diels-Alder reaction;
furan
110-00-9

furan

maleic anhydride
108-31-6

maleic anhydride

diethyl ether
60-29-7

diethyl ether

A

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride
6118-51-0

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

B

7-oxa-norborn-5-ene-2endo,3endo-dicarboxylic acid-anhydride

7-oxa-norborn-5-ene-2endo,3endo-dicarboxylic acid-anhydride

furan
110-00-9

furan

maleic anhydride
108-31-6

maleic anhydride

water
7732-18-5

water

A

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride
6118-51-0

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

B

7-oxa-norborn-5-ene-2endo,3endo-dicarboxylic acid-anhydride

7-oxa-norborn-5-ene-2endo,3endo-dicarboxylic acid-anhydride

Conditions
ConditionsYield
Product distribution; Einfluss der Reaktionsdauer auf die Ausbeute;
furan
110-00-9

furan

maleic anhydride
108-31-6

maleic anhydride

A

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride
6118-51-0

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

B

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With water for 1h; Diels-Alder Cycloaddition; Inert atmosphere; Darkness;A 68 %Spectr.
B n/a
furan
110-00-9

furan

succinic acid anhydride
108-30-5

succinic acid anhydride

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride
6118-51-0

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
In ethyl acetate at 20℃;

6118-51-0Relevant articles and documents

EFFECT OF HIGH PRESSURE ON THE RATE CONSTANT OF THE DIELS-ALDER REACTION BETWEEN FURAN AND MALEIC ANHYDRIDE

Zhulin, V. M.,Kel'tseva, M. V.,Bogdanov, V. S.,Koreshkov, Yu. D.,Kabotyanskaya, E. B.

, p. 456 - 459 (1990)

The effect of high pressure (up to 700 MPa) on the rate of the Diels-alder reaction between furan and maleic anhydride has been investigated in deuterated acetone at 20 deg C.The volume effect of the reaction at atmospheric pressure is found to be ΔV

Stereoselective synthesis of 3,4,5,6-tetrahydroxycyclohexyl β-amino acid derivatives

Chola, Joshua,Masesane, Ishmael B.

, p. 5680 - 5682 (2008)

Stereoselective syntheses of racemic (1S,2R,3R,4R,5S,6R)- and (1S,2R,3R,4S,5S,6R)-3,4,5,6-tetrahydroxy derivatives of 2-aminocyclohexanecarboxylic acid have been achieved by a stereospecific Diels-Alder reaction between furan and maleic anhydride, a Curtius rearrangement and hydroxylation reactions.

Antimicrobial activities of phosphonium containing polynorbornenes

Süer, N. Ceren,Demir, Ceren,ünübol, Nihan A.,Yal?in, ?zlem,Kocag?z, Tanil,Eren, Tarik

, p. 86151 - 86157 (2016)

In this study, amphiphilic polyoxanorbornene with different alkyl and aromatic phosphonium side chains was synthesized. The biological activities of these polymers were determined by the minimal inhibitory concentration (MIC) against E. coli, S. aureus, M. tuberculosis and the yeast C. albicans, and cytotoxicity studies on red blood cells were performed. A series of polymers with different alkyl and aromatic substituents (methyl, ethyl, tripropyl, tert-butyl, phenyl, and tris 4-methoxyphenyl) and two types different molecular weight, 3000 g mol-1 and 10 000 g mol-1, were prepared. It was observed that the biological activity of the polymers with aromatic group substituents had an MIC of 16, 8, 64 and 128 μg mL-1 against E. coli, S. aureus, M. tuberculosis and C. albicans, respectively, while those with non-aromatic carbons had a higher MIC compared to those with aromatic carbons. The aromaticity of the repeat unit had impressive effects on hemolytic activities as well. Zeta potential measurements of E. coli incubated with active and inactive polymer concentration revealed a relationship between the MIC and membrane surface charge density. Polymers bearing aromatic groups killed the bacteria with widespread damage after the polymers, holding the threshold concentration, were added to the bacteria.

EFFECT OF HIGH PRESSURE ON THE COMPOSITION OF STEREOISOMERS OF THE DIELS-ALDER REACTION BETWEEN FURAN AND MALEIC ANHYDRIDE

Zhulin, V. M.,Bogdanov, V. S.,Kel'tseva, M. V.,Kabotyanskaya, E. B.,Koreshkov, Yu. D.

, p. 2303 - 2308 (1989)

The kinetic data on the Diels-Alder reaction between furan and maleic anhydride at atmospheric pressure and 20 and 40 deg C correspond to a scheme of the process which includes transformation of an endo-isomer into an exo-isomer without preliminary decomp

Hierarchical preferences of hydroxylated oxanorbornane-based achiral amphiphiles

Janni, D. Sirisha,Manheri, Muraleedharan K.

, p. 15182 - 15190 (2013)

Achiral amphiphiles with hydroxylated oxanorbornane headgroups showed specific morphological characteristics and hierarchical preferences depending upon the nature of lipophilic units. Detailed scanning electron microscopic (SEM) studies showed that twist

A simple route for the synthesis of novel norcantharimide derivatives via acidolysis with hydrochloric acid(gas)

K?se, Aytekin

, p. 1171 - 1178 (2021/03/08)

In this work, seven new norcantharimide derivatives were synthesized by an acidolysis method. The compounds were prepared by acidolyzing trans-1,4-diacetate and trans-1,2-chloroacetate structures, which were obtained by stereospecific cleavage of the internal etheric bond of the tricyclic imides. The HCl(gas) was produced from the reaction of H2SO4 with NaCl. The resulting gas was bubbled into the reaction mixture. Trans-1,4-diacetate and trans-1,2-chloroacetate were thus acidolyzed, and the corresponding diol and halohydrin products were obtained respectively in moderate overall yields from low-cost starting materials, using simple and easily scalable chemistry. The products were characterized by means of spectroscopic techniques. The synthesized compounds have high potential as anticancer agents and can be valuable for studies in this area.

Cyclohexanedicarboxylic acid derivative with bridge ring and pharmaceutical composition and application thereof

-

Paragraph 0081-0085, (2021/11/10)

The invention discloses a cyclohexane dicarboxylic acid derivative with a bridged ring represented by general formula (I). The application of the stereoisomers and the pharmaceutically acceptable salts in the preparation of antitumor drugs has obvious inhibition effects on leukemia, liver cancer, lung cancer, gastric cancer and ovarian cancer. The compound disclosed by the invention has high anti-tumor activity, wide anti-tumor spectrum and low toxicity, and is suitable for preparing anti-cancer drugs.

The Wittig bioconjugation of maleimide derived, water soluble phosphonium ylides to aldehyde-tagged proteins

Asbjarnarson, Arni,Gudjonsson, Thorarinn,Hartmann, Rafael W.,Helgudottir, Hildur Run,Lehmann, Fredrik,Nilvebrant, Johan,Nygren, Per-?ke,Odell, Luke R.,Pijnappel, Matthijs,Traustadottir, Gunnhildur Asta

supporting information, p. 10417 - 10423 (2021/12/17)

Herein we disclose the transformation of maleimides into water-soluble tris(2-carboxyethyl)phosphonium ylides and their subsequent application in the bioconjugation of protein- and peptide-linked aldehydes. The new entry into Wittig bioconjugate chemistry proceeds under mild conditions and relies on highly water soluble reagents, which are likely already part of most biochemists' inventory. This journal is

Synthesis of l-ascorbic acid-amino acid-norcantharidin conjugates and their biological activity evaluation in vitro

Wang, Xianheng,Wu, Caoyuan,Zhang, Jidong,Zhao, Changkuo,Zhou, Yiqi

, (2022/01/06)

Three components of L-ascorbic acid, amino acid and functionalized norcantharidins were constructed together in several steps to form 42 norcantharidin derivatives in a high yield. The structure of these synthesized l-ascorbic acid-amino acid-norcantharidin conjugates are determined by 1HNMR, 13CNMR and MS spectrum. The results showed that compounds 6e, 6g, 6j, 6l, 6m, 6b, 6e, 6i, and 6n showed high cytotoxicity to HepG2 and compounds 6b, 6e-g, 6l, 6n, 7b, 7d, 7h, 7i, 7n, 8g, 8i exhibited high cytotoxicity to SW480; Meanwhile, besides 6b, 6e, 6g, and 6k, the other compounds showed less toxic to LO2 at a concentration of 50 μg/mg after 72 h. Compound 6g can induce Mφ-type macrophages derived from mouse bone marrow to polarize to M1-type macrophages.

Supramolecular chemistry under mechanochemical conditions: A small molecule template generated and integrated into a molecular-to-supramolecular and back-to-molecular cascade reaction

MacGillivray, Leonard R.,Swenson, Dale C.,Yelgaonkar, Shweta P.

, p. 3569 - 3573 (2020/04/15)

We describe the integration of a small-molecule hydrogen-bond-donor template into a cascade reaction that is comprised of a combination of molecular and supramolecular events. The cascade is performed mechanochemically and in the presence of μL amounts of

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