カルバジン酸tert-ブチル
カルバジン酸tert-ブチル · N-アミノカルバミド酸tert-ブチル · ヒドラジンカルボン酸tert-ブチル · カルバジン酸1,1-ジメチルエチル · 1-(tert-ブトキシカルボニル)ヒドラジン · ヒドラジンカルボン酸1,1-ジメチルエチル · アミノカルバミド酸tert-ブチル · Boc-ヒドラジン
識別子と物理属性
| CAS No. | 870-46-2 |
|---|---|
| 分子式 | C5H12N2O2 |
| 平均分子量 | 132.16 g/mol |
| 単同位体質量 | 132.08987762 g/mol |
| SMILES | CC(C)(C)OC(=O)NN |
| InChIKey | DKACXUFSLUYRFU-UHFFFAOYSA-N |
| PubChem CID | 70091 |
| EC No. | 212-795-3 |
| DTXSID | DTXSID7061227 |
| 現地名 | カルバジン酸tert-ブチル |
化学・物理的性質
| XLogP | 0.2 |
|---|---|
| 極性表面積 | 64.4 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 2 |
| 重原子数 | 9 |
| 形式電荷 | 0 |
| 複雑度 | 106 |
| 融点 | 39-42 °C (lit.) |
| 沸点 | 63-65 °C/0.1 mmHg (lit.) |
| 密度 | 1.02 |
| 屈折率 | 1.4496 (estimate) |
| 引火点 | 197 °F |
| 貯蔵条件 | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| 溶解度 | エタノール、メタノールに可溶。 |
| pKa（酸解離定数） | 10.74±0.20(Predicted) |
| 外観・状態 | 結晶塊 |
| 色 | 白色～やや黄色 |
| BRN | 1756967 |
| 主な用途 | ペプチド合成 |
| InChI | 1S/C5H12N2O2/c1-5(2,3)9-4(8)7-6/h6H2,1-3H3,(H,7,8) |
| InChIKey | DKACXUFSLUYRFU-UHFFFAOYSA-N |
| SMILES | O=C(NN)OC(C)(C)C |
| CAS データベース | 870-46-2(CAS DataBase Reference) |
| EPAの化学物質情報 | Hydrazinecarboxylic acid, 1,1-dimethylethyl ester (870-46-2) |
化学的特性
White to pale yellow lumps
安全性と法規制
| GHS 分類 | DangerH228 (100%): Flammable solid [Danger Flammable solids]P210, P240, P241, P264, P270, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, P370+P378, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 59 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Status: Active Update: 21-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/21858Hydrazinecarboxylic acid, 1,1-dimethylethyl ester: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Flam. Sol. 2 (100%) |
| CSL Reaction Information | CSL00008NITRIC ACID + TERT-BUTYL CARBAZATEExplosion during workup when half of the solvent was evaporatedExplosiveBOCN3 formationUser-Reported |
| F | 21 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| 輸送番号（UN） | 1325 |
| 税関コード | 29280090 |
| 危険文句（R） | 48-36/37/38-24/25-11 |
| 消防法 | 危-5-II |
| 危険表示 | T-F,T,F |
| 安全措置（S） | 45-36/37/39-16-24/25 |
| 危険等級 | 4.1Flam. Sol. 1 |
| 包装等級 | III |
| 貯蔵分類 | 4.1B - Flammable solid hazardous materials |
用途
使用
tert-Butyl carbazate is used in a palladium-catalyzed cross-coupling with vinyl halides to prepare N-Boc-N-alkenylhydrazines. It is utilized in solid phase peptide synthesis and in the optical purity determination of alfa-amino aldehyde. It reacts with aldehydes to get hydrazones, which finds application as an intermediate in the synthesis of HIV-1 protease inhibitors. In addition to this, it is used as a starting material for the preparation of BOC-azide, sulfonic and carboxylic hydrazides.
製法・合成法
純化方法
Distil it in a Claisen flask with a water or oil bath at ca 80o. After a couple of drops have distilled, the carbazate is collected as an oil which solidifies to a snow white solid. It can be crystallised with 90% recovery from a 1:1 mixture of pet ether (b 30-60o) and pet ether (b 60-70o). [Carpino et al. Org Synth Coll Vol V 166 1973, Caprino et al. Org Synth 44 20 1964, Beilstein 3 IV 175.]