イサト酸無水物
イサト酸無水物 · 1H-3,1-ベンゾオキサジン-2,4-ジオン · 4H-3,1-ベンゾオキサジン-2(1H),4-ジオン · 無水イサト酸 · 1,4-ジヒドロ-2H-3,1-ベンゾオキサジン-2,4-ジオン · 4H-3,1-ベンゾオキサジン-2,4(1H)-ジオン · 2H-3,1-ベンゾオキサジン-2,4(1H)-ジオン · 1,2-ジヒドロ-4H-3,1-ベンゾオキサジン-2,4-ジオン
識別子と物理属性
| CAS No. | 118-48-9 |
|---|---|
| 分子式 | C8H5NO3 |
| 平均分子量 | 163.13 g/mol |
| 単同位体質量 | 163.02694302 g/mol |
| SMILES | O=c1[nH]c2ccccc2c(=O)o1 |
| InChIKey | TXJUTRJFNRYTHH-UHFFFAOYSA-N |
| PubChem CID | 8359 |
| ChEMBL | CHEMBL1235999 |
| EC No. | 204-255-0 |
| DTXSID | DTXSID6026955 |
| 現地名 | イサト酸無水物 |
化学・物理的性質
| XLogP | 1 |
|---|---|
| 極性表面積 | 55.4 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 0 |
| 重原子数 | 12 |
| 形式電荷 | 0 |
| 複雑度 | 226 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| Polymers | Plastics & Rubber -> Acid Anhydrides, Cyclic |
| SpringerMaterials Properties | Chemical shift |
| Color/Form | PRISM FROM ALC OR GLACIAL ACETIC ACIDCRYSTALS FROM ALCOHOL OR DIOXANETAN POWDER |
| 溶解度 | MISCIBLE IN WATER, HOT ALC, AND ACETONEINSOL IN ETHER, BENZENE, AND CHLOROFORM0.3g/l分解する |
| 融点 | 243 °C WITH DECOMPOSITION233 °C (dec.) (lit.) |
| Physical Description | Dry PowderTan solid[Hawley] Grey powder[MSDSonline] |
| 沸点 | 290.19°C (rough estimate) |
| 密度 | 1,52 g/cm3 |
| 蒸気密度 | 5.6 (vs air) |
| 屈折率 | 1.5510 (estimate) |
| 引火点 | 308 °C |
| 貯蔵条件 | Store below +30°C. |
| pKa（酸解離定数） | 11.06±0.20(Predicted) |
| 外観・状態 | 粉 |
| 色 | ベージュからブラウン |
| BRN | 136786 |
| InChI | 1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)9-8(11)12-7/h1-4H,(H,9,11) |
| InChIKey | TXJUTRJFNRYTHH-UHFFFAOYSA-N |
| SMILES | O=C1Nc2ccccc2C(=O)O1 |
| LogP（分配係数） | 0.978 (est) |
| CAS データベース | 118-48-9(CAS DataBase Reference) |
| NISTの化学物質情報 | Isatoic anhydride(118-48-9) |
| EPAの化学物質情報 | 2H-3,1-Benzoxazine-2,4(1H)-dione (118-48-9) |
化学的特性
BEIGE TO BROWN POWDER
安全性と法規制
| GHS 分類 | WarningH317: May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 5.2% (11 of 210) of reports.H317 (94.8%): May cause an allergic skin reaction [Warning Sensitization, Skin] |
|---|---|
| 規制情報 | Chemical: 2H-3,1-Benzoxazine-2,4(1H)-dione2H-3,1-Benzoxazine-2,4(1H)-dione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2H-3,1-Benzoxazine-2,4(1H)-dione are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.Status: Active Update: 25-01-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/18515Isatoic anhydride: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | An eye irritantMay cause skin sensitization[eChemPortal: ESIS] Danger of skin sensitization[MAK] An irritant[MSDSonline] See ACID ANHYDRIDES. |
| Hazard Classes and Categories | Skin Sens. 1 (94.8%)Eye irritation - category 2Eye Irrit. 2 |
| 有害作用 | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| Non-Human Toxicity Excerpts | TESTED FOR ANTIFERTILITY EFFECTS IN MICE AFTER ORAL ADMIN FOR 21 DAYS, WITH MALES INTRODUCED @ END OF 1ST WK, & AFTER INJECTIONS TWICE DAILY FOR 5 DAYS. EFFECTIVE IN DECR NUMBER OF MICE WITH LITTERS @ LEAST 50%. |
| F | 3 |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | DM3100000 |
用途
用途
キナゾリン誘導体の合成に用いられる。
使用
Isatoic anhydride is a potent inactivator of α-chymotrypsin and inactivates stoichiometrically. Isatoic Anhydride is an important compound in the preparation of serine protease inhibitors.
製法・合成法
製造方法
Phosphorus tribromide (0.035 mol) was added to a solution of N-carbethoxy- or N-carbobenzoxy-anthranilic acid (0.1 mol;prepared by coupling anthranilic acid with the corresponding carbalkoxy chloride in the usual way) in anhydrous diethyl ether (100 mL). After 24 h at room temperature, isatoic anhydride had separated as a microcrystalline product. It was collected by filtration, washed with dry diethyl ether, and recrystallized from ethanol. Yield ca. 90%.
純化方法
Recrystallise it from EtOH or 95% EtOH (30mL/g) or dioxane (10mL/g) and dry it in a vacuum. [Wagner & Fegley Org Synth Coll Vol III 488 1955, Ben-Ishai & Katchalski J Am Chem Soc 74 3688 1952, UV: Zentmyer & Wagner J Org Chem 14 967 1949, Beilstein 27 II 299, 27III/IV 3330.]