491-36-1
4-Hydroxyquinazoline
CAS: 491-36-1;17227-47-3
Molecular Formula: C8H6N2O
491-36-1 - Names and Identifiers
| Name | 4-Hydroxyquinazoline |
| Synonyms | 4-Quinazolinol Quinazolone, 4- 4-Quinazolinone 4-Oxoquinazoline 4-HydroxyquinazoL 4(3H)-Quinazolone Hydroxyquinazoline quinazolidin-4-one 1H-quinazolin-4-one 4(3H)-Quinazolinone 4-Hydroxyquinazoline quinazolin-4(3H)-one 4-hydroxy quinazoline Quinazolin-4-ol, 4-Quinazolinol |
| CAS | 491-36-1 17227-47-3 |
| EINECS | 207-735-8 |
| InChI | InChI=1/C8H6N2O/c11-8-6-3-1-2-4-7(6)9-5-10-8/h1-5H,(H,9,10,11) |
| InChIKey | QMNUDYFKZYBWQX-UHFFFAOYSA-N |
491-36-1 - Physico-chemical Properties
| Molecular Formula | C8H6N2O |
| Molar Mass | 146.15 |
| Density | 1.2312 (rough estimate) |
| Melting Point | 216-219 °C (lit.) |
| Boling Point | 265.75°C (rough estimate) |
| Flash Point | 137.3°C |
| Water Solubility | Soluble in DMSO (100 mM), ethanol, methanol, and water (10 mM). |
| Solubility | Soluble in DMSO (100 mM), ethanol, methanol, and water (10 mM). |
| Vapor Presure | 0.015Pa at 20℃ |
| Appearance | White crystal |
| Color | Off-white to light beige |
| BRN | 118473 |
| pKa | 2.69±0.20(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 1 month. |
| Sensitive | Hygroscopic |
| Refractive Index | 1.4900 (estimate) |
| MDL | MFCD00511302 |
| Physical and Chemical Properties | This product is white crystal, m.p.214 ~ 215 ℃, insoluble in water. |
491-36-1 - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S22 - Do not breathe dust. |
| WGK Germany | 3 |
| RTECS | VA2300000 |
| HS Code | 29335995 |
| Hazard Class | IRRITANT |
491-36-1 - Reference
| Reference Show more | 1. Liwei He, Fangtian Fan, Xianbang Hou, Hongyan Wu, Juan Wang, Huiqin Xu, Yun Sun, 4(3H)-Quinazolone regulates innate immune signaling upon respiratory syncytial virus infection by moderately inhibiting the RIG-1 pathway in RAW264.7 cell, International Immun |
491-36-1 - Nature
Open Data Verified Data
White needle-like crystals. Molecular weight 146.15, melting point 217~221 C (215~216 C).
Last Update：2024-01-02 23:10:35
491-36-1 - Preparation Method
Open Data Verified Data
obtained by cyclization of anthranilic acid with formamide. The process is to add anthranilic acid and formamide to the stainless steel reaction pot, stir and heat for 4H, maintain the oil bath temperature of 140~150 ℃; Then add cold water under stirring, when the temperature drops below 60 ℃, product
Water was added, stirred evenly, left overnight, filtered, washed with water, washed with alcohol, and dried at 100-120 ° C. To obtain quinazolone with a yield of 80%.
Last Update：2022-01-01 10:53:46
491-36-1 - Application
Open Data Verified Data
This product is used for the synthesis of antiarrhythmic drug changanthroline.
Last Update：2025-08-19 16:24:40
491-36-1 - Safety
Open Data Verified Data
irritation, LD50 609mg/kg (mouse oral).
Last Update：2022-01-01 10:53:47
491-36-1 - Reference Information
| LogP | 0.94 at 20℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| Biological activity | 4-Hydroxyquinazoline (Quinazolin-4-ol, 4-Quinazolinol) is an inhibitor of PARP, and the IC50 value for PARP-1 is 9.5 μM. |
| Target | Value |
| PARP1 (Cell-free assay) | 9.5 μM |
| use | 4-(3H) quinazolinone is an intermediate of acaricide quinite ether. This product is an intermediate of the antiarrhythmic drug Chang-roline. |
| Production method | is obtained by the cyclization of anthranilic acid and formamide. Add o-aminobenzoic acid and methylamine into a stainless steel reaction pot, stir and heat for 4 hours, and the oil bath temperature is 140-150 ℃. Add cold water under stirring, and when the temperature drops below 60 ℃, add water to the product and stir evenly, and leave it overnight. Filtration, water washing, alcohol washing, drying at 100-120 ℃ to obtain quinazolone with 80% yield. the preparation method is to add anthranilic acid and formamide into a four-mouth flask, heat to 125~130 ℃ under stirring, react for 4h to obtain a light red solid, and recrystallize to obtain a finished product. |
Last Update：2024-04-09 02:00:08
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