4-フェニルウラゾール
4-フェニルウラゾール · 4-フェニル-4H-1,2,4-トリアゾール-3,5-ジオール · 4-フェニルテトラヒドロ-1H-1,2,4-トリアゾール-3,5-ジオン · 1,2-ジヒドロ-4-フェニル-4H-1,2,4-トリアゾール-3,5-ジオン · 4-フェニル-4H-1,2,4-トリアゾール-3,5(1H,2H)-ジオン · 4-フェニル-1,2,4-トリアゾリジン-3,5-ジオン · 4-フェニル-1H-1,2,4-トリアゾール-3,5(2H,4H)-ジオン · 4-フェニルウラゾール, 98+%
識別子と物理属性
| CAS No. | 15988-11-1 |
|---|---|
| 分子式 | C8H7N3O2 |
| 平均分子量 | 177.16 g/mol |
| 単同位体質量 | 177.05382646 g/mol |
| SMILES | O=c1[nH][nH]c(=O)n1-c1ccccc1 |
| InChIKey | GOSUFRDROXZXLN-UHFFFAOYSA-N |
| PubChem CID | 85229 |
| ChEMBL | CHEMBL224287 |
| EC No. | 240-127-0 |
| DTXSID | DTXSID5065988 |
| 現地名 | 4-フェニルウラゾール |
化学・物理的性質
| XLogP | 0.7 |
|---|---|
| 極性表面積 | 61.4 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 13 |
| 形式電荷 | 0 |
| 複雑度 | 220 |
| 溶解度 | 17.2 [ug/mL] (The mean of the results at pH 7.4) |
| 融点 | 207-209 °C (lit.) |
| 沸点 | 309.07°C (rough estimate) |
| 密度 | 1.3393 (rough estimate) |
| 屈折率 | 1.6500 (estimate) |
| 貯蔵条件 | Inert atmosphere,2-8°C |
| pKa（酸解離定数） | 5.43±0.30(Predicted) |
| 外観・状態 | powder to crystal |
| 色 | White to Almost white |
| BRN | 163361 |
| InChI | InChI=1S/C8H7N3O2/c12-7-9-10-8(13)11(7)6-4-2-1-3-5-6/h1-5H,(H,9,12)(H,10,13) |
| InChIKey | GOSUFRDROXZXLN-UHFFFAOYSA-N |
| SMILES | N1C(=O)N(C2=CC=CC=C2)C(=O)N1 |
| CAS データベース | 15988-11-1(CAS DataBase Reference) |
| NISTの化学物質情報 | 4-Phenylurazole(15988-11-1) |
| EPAの化学物質情報 | 1,2,4-Triazolidine-3,5-dione, 4-phenyl- (15988-11-1) |
化学的特性
white to light beige cryst. powder or granules
安全性と法規制
| GHS 分類 | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | 1,2,4-Triazolidine-3,5-dione, 4-phenyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| 税関コード | 29339990 |
| 安全措置（S） | 22-24/25 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
用途
有機合成原料。
説明
4-phenylurazole is a kind of laboratory chemicals used for the manufacturing of some substances. It can be used as the precursor to the Diels-Alder trapping agent, 4-phenyl-1, 2, 4-triazoline-3, 5-Dione. Its derivative, azo dyes, has wide applications in dyes industry. In the presence of phosgene, terephthaloyl chloride and epichlorohydrin, it can be polymerized to yield insoluble polymer.
使用
Precursor to the Diels-Alder trapping agent, 4-phenyl-1,2,4-triazoline-3,5-dione.1,2,3
一般的な説明
4-Phenylurazole undergoes oxidation in the presence of NO2-N2O4 to yield 4-phenyl-1,2,4-trizoline-3,5-dione. It undergoes acetylation reaction with excess acetyl chloride in N,N-dimethylacetamide solution. It polymerizes in the presence of phosgene, terephthaloyl chloride and epichlorohydrin to yield insoluble polymer. It is precursor to the Diels-Alder trapping agent, 4-phenyl-1,2,4-triazoline-3,5-dione. This urazole was recently demonstrated in the traceless, chemoselective labeling of peptides and proteins through electrochemical tyrosine-click (e-Y-CLICK) chemistry.
製法・合成法
純化方法
Crystallise 4-phenylurazole from water or 95% EtOH. Dissolve 35g in 80mL of boiling 95% EtOH and on cooling 90-95% is recovered with m 209-210o. It has IR with 1685 and 3120cm-1. [Cookson et al. Org max Synth 51 121 1971, Beilstein 26 I 64, 26 III/IV 540.]