3-Hydroxyphthalic anhydride Chemical Properties

Melting point:

199-202 °C (lit.)

Boiling point:

365.4±25.0 °C(Predicted)

Density 

1.624±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Acetonitrile (Slightly), DMSO (Slightly)

pka

6.25±0.20(Predicted)

form 

Powder

color 

White to beige

BRN 

135783

Stability:

Hygroscopic

InChI

InChI=1S/C8H4O4/c9-5-3-1-2-4-6(5)8(11)12-7(4)10/h1-3,9H

InChIKey

CCTOEAMRIIXGDJ-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C(O)=CC=C2)C(=O)O1

CAS DataBase Reference

37418-88-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

TI3300000

F 

21

HS Code 

29182900

Toxicity

mouse,LD50,intravenous,75mg/kg (75mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#08845,

MSDS

• Language:English Provider:SigmaAldrich

3-Hydroxyphthalic anhydride Usage And Synthesis

Description

3-Hydroxyphthalic anhydride: a valuable raw material for chemical industry and pharmaceutical research.
Phthalic anhydride derivatives have been applied as plasticizers and heat-resistant polymers in the chemical industry. One of its derivatives is the 3-hydroxyphthalic anhydride (3-HPA), which exhibits a hydroxyl group substituent in position 3. 3-Hydroxyphthalic anhydride can be used as raw material for heat-resistant resins such as epoxy resins, polyesters, polyimides, etc., or as raw material for physiologically active substances such as medicines and pesticides. It has been shown that 3-HPA can serve as a raw material to obtain drugs with potential applications, such as anticancer, antimicrobial and in treating diabetes, herpes, and HIV[1].

Chemical Properties

Beige powder

Uses

3-Hydroxyphthalic Anhydride is used to synthesize 3-Hydroxyphthalic Anhydride-modified human serum albumin whichhas high potency as a microbicide for prevention of the sexual transmission of HIV. It is also used as a reagent in organicsynthesis of other compounds including that of inhibitors of NF-κB derived from thalidomide.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 5092, 1955 DOI: 10.1021/ja01624a042
Synthesis, p. 788, 1985 DOI: 10.1055/s-1985-31350

Synthesis

In the presence of triethylamine, the 2-oxo-2, 5-dihydrofuran, and pivaloyl chloride reactions generate 2-valeryl oxo furans. The affixture with 2-valeryl oxo furans and maleic anhydride uses vitriolization, which thereby generates the method of 3-hydroxyl phthalic anhydride.

References

[1] M. López-Ortega. “Standard enthalpies of formation of 3-hydroxyphthalic anhydride.” Revista Mexicana De Fisica (2022).

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