カルバミン酸ベンジル
カルバミン酸ベンジル · ベンジルウレタン · ベンジル=カルバマート · カルバミド酸ベンジル · ベンジルオキシカルボニルアミン · ベンジルカーバメート · (ベンジルオキシカルボニル)アミン · ベンジル カルバマート
識別子と物理属性
| CAS No. | 621-84-1 |
|---|---|
| 分子式 | C8H9NO2 |
| 平均分子量 | 151.16 g/mol |
| 単同位体質量 | 151.06332853 g/mol |
| SMILES | NC(=O)OCc1ccccc1 |
| InChIKey | PUJDIJCNWFYVJX-UHFFFAOYSA-N |
| PubChem CID | 12136 |
| ChEMBL | CHEMBL2259788 |
| EC No. | 210-710-4 |
| DTXSID | DTXSID00211159 |
| 現地名 | カルバミン酸ベンジル |
化学・物理的性質
| XLogP | 1.2 |
|---|---|
| 極性表面積 | 52.3 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 3 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 130 |
| 融点 | 86-89 °C (lit.) |
| 沸点 | 273.17°C (rough estimate) |
| 密度 | 1.2023 (rough estimate) |
| 屈折率 | 1.5810 (estimate) |
| 貯蔵条件 | Keep in dark place,Sealed in dry,Room Temperature |
| 溶解度 | クロロホルム（微量）、メタノール（微量）68.02g/L(37℃) |
| 外観・状態 | パウダーまたはフレーク |
| pKa（酸解離定数） | 13.42±0.50(Predicted) |
| 色 | オフホワイトからライトベージュ |
| BRN | 1865635 |
| InChI | InChI=1S/C8H9NO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10) |
| InChIKey | PUJDIJCNWFYVJX-UHFFFAOYSA-N |
| SMILES | C(OCC1=CC=CC=C1)(=O)N |
| CAS データベース | 621-84-1(CAS DataBase Reference) |
| NISTの化学物質情報 | Carbamic acid, benzyl ester(621-84-1) |
化学的特性
Off-white to light beige powder or flakes, melting point 87-89 ℃. Insoluble in water, soluble in organic solvents such as benzene.
安全性と法規制
| GHS 分類 | WarningH302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (50%) |
| 水環境危害等級（WGK） | 3 |
| 税関コード | 29242995 |
| 危険文句（R） | 20/21/22-36/37/38 |
| 危険表示 | Xn |
| 安全措置（S） | 22-24/25-36-26 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
用途
有機合成原料。
使用
Benzyl carbamate is a reagent used for the nucleophilic introduction of an amino-protected group, Benzyl carbamates can be considered as a benzyloxycarbonyl (otherwise known as carbobenzyloxy, Cbz or Z) protecting group for amino groups. It was introduced as a versatile alternative to the ethoxy carbamate group in peptide synthesis.
製法・合成法
製造方法
Benzyl carbamate is prepared by reacting benzyl chloroformate with ammonia. Benzyl chloroformate was slowly added to 5 times the volume of cold ammonia water (relative density 0.90) under vigorous stirring, the reaction mixture was placed at room temperature for 30 minutes, the precipitate was filtered out, washed with water and dried to obtain the finished product of benzyl carbamate.
純化方法
If it smells of NH3, then dry it in a vacuum desiccator and recrystallise it from 2 volumes of toluene and dry it in a vacuum desiccator again. It forms glistening plates from toluene, and can be recrystallised from H2O [Martell & Herbst J Org Chem 6 878 1941, Carter et al. Org Synth Coll Vol III 168 1955]. [Beilstein 6 IV 2278.]