3-Hydroxyphthalic anhydride CAS#: 37418-88-5; ChemWhat Code: 366103
Identification
| Product Name | 3-Hydroxyphthalic anhydride |
| IUPAC Name | 4-hydroxy-2-benzofuran-1,3-dione |
| Molecular Structure |  |
| CAS Registry Number | 37418-88-5 |
| MDL Number | MFCD00011557 |
| Beilstein Registry Number | 135783 |
| Synonyms | 3-hydroxyphthalic anhydride, 3-Hydroxyphthalic anhydride, 4-hydroxy-2,3-dihydro-1H-isobenzofuran-1,3-dione, 4-hydroxy-1,3-dihydro-2-benzofuran-1,3-dione, 3-hydroxyphthalic acid anhydride, 4-hydroxyisobenzofuran-1,3-dione, 4-hydroxisobenzofuran-1,3-dione |
| Molecular Formula | C8H4O4 |
| Molecular Weight | 164.117 |
| InChI | InChI=1S/C8H4O4/c9-5-3-1-2-4-6(5)8(11)12-7(4)10/h1-3,9H |
| InChI Key | CCTOEAMRIIXGDJ-UHFFFAOYSA-N |
| Canonical SMILES | C1=CC2=C(C(=C1)O)C(=O)OC2=O |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| US4837404 | Process for the preparation of oxy-diphthalic anhydrides | 1989 |
| US4948904 | Process for the preparation of oxydiphthalic anhydrides | 1990 |
| US5985275 | β-Lactoglobulin modified with aromatic anhydride compound for preventing HIV infection | 1999 |
| US5952009 | Methods for preventing the transmission of or treating patients infected with herpesvirus | 1999 |
Physical Data
| Appearance | White to off-white powder |
| Sublimation | 160 – 180 °C |
| Density | 1.625g/cm3 |
| Flash Point | 160.238 °C |
| Melting Point, °C | Solvent (Melting Point) |
| 199 – 202 | |
| 195 | diethyl ether |
| 198 – 199 | xylene |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz | Original Text (NMR Spectroscopy) |
| Chemical shifts | 1H | dimethylsulfoxide-d6 | 400 | |
| Chemical shifts | 1H | tetradeuteriomethanol | 500 | |
| Chemical shifts | 1H | d(4)-methanol | 500 | 1H NMR (CD3OD): δ 7.40 (d, 1H, J=8.1) 7.62 (d, 1H, J=6.9), 7.85 (t, 1H, J=7.8). |
Route of Synthesis (ROS)
| Conditions | Yield |
| at 300℃; Green chemistry; Experimental Procedure 27.0 g (148 mmOl) of 3-hydroxyphthalic acid was placed in a sublimation tube and sublimed at 300 ° C to give a pale yellow solid 3-hydroxyphthalic anhydride 21.9 g, yield: 90percent. | 90% |
| With dicyclohexyl-carbodiimide In dimethyl sulfoxide at 150℃; for 1h; Solvent; Temperature; Reagent/catalyst; Experimental Procedure 300 mL of DMSO was added to a 500 mL three-necked flask, the temperature was raised to 150 ° C, and 3-hydroxyphthalic acid25.00g (0.14mol), DCC195.00g, followed by incubation at 150 ° C for 1h, concentrated under reduced pressure, cooled to room temperature, was added dichloromethane100.00g beaten lh, filtered to give a pale yellow solid, dried at 55 ~ 60 , 17.96g, theory 22.53g, yield79.72percent, purity 98.83percent. | 79.72% |
| at 150℃; | |
| With acetyl chloride | |
| With xylene | |
| Erhitzen unter vermindertem Druck; | |
| at 135 – 140℃; under 0.0375038 Torr; | 4g |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Warning |
| GHS Hazard Statements | H315: Causes skin irritation [Warning Skin corrosion/irritation] H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | Not dangerous goods |
| Under the room temperature and away from light | |
| HS Code | 294200 |
| Storage | Under the room temperature and away from light |
| Shelf Life | |
| Market Price |
| Use Pattern |
| 3-Hydroxyphthalic anhydride CAS#: 37418-88-5 can be used to synthesize physiologically active pharmaceutical and pesticide compounds, and is also one of the important raw materials for heat resistant resins. |
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