1-メチル-4-ピペリドン
1-メチル-4-ピペリドン · 1-メチル-4-ピペリジノン · 1-メチル-4-オキソピペリジン · N-メチル-4-ピペリドン · 1-メチルピペリジン-4-オン · 1メチル4ピペリドン · 1‐メチル‐4‐ピペリドン · N-METHYL-4-PIPERIDONE
識別子と物理属性
| CAS No. | 1445-73-4 |
|---|---|
| 分子式 | C6H11NO |
| 平均分子量 | 113.16 g/mol |
| 単同位体質量 | 113.08406397 g/mol |
| SMILES | CN1CCC(=O)CC1 |
| InChIKey | HUUPVABNAQUEJW-UHFFFAOYSA-N |
| PubChem CID | 74049 |
| EC No. | 215-895-5 |
| DTXSID | DTXSID20162735 |
| 現地名 | 1-メチル-4-ピペリドン |
化学・物理的性質
| XLogP | -0.3 |
|---|---|
| 極性表面積 | 20.3 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 0 |
| 重原子数 | 8 |
| 形式電荷 | 0 |
| 複雑度 | 90 |
| Physical Description | Clear dark yellow liquid[Sigma-Aldrich MSDS] |
| 融点 | 192-193 °C(Solv: ethyl acetate (141-78-6)) |
| 沸点 | 55-60 °C11 mm Hg(lit.) |
| 密度 | 0.92 g/mL at 25 °C (lit.) |
| 屈折率 | n20/D 1.460 |
| 引火点 | 140 °F |
| 貯蔵条件 | Store below +30°C. |
| 溶解度 | Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)混和性 |
| pKa（酸解離定数） | 8.02±0.20(Predicted) |
| 外観・状態 | 液体 |
| 比重 | 0.92 |
| 色 | クリアイエロー～オレンジ |
| pH | 12 (100g/l, H2O, 20℃) |
| BRN | 106924 |
| 主な用途 | PFAS検査 |
| InChI | 1S/C6H11NO/c1-7-4-2-6(8)3-5-7/h2-5H2,1H3 |
| InChIKey | HUUPVABNAQUEJW-UHFFFAOYSA-N |
| SMILES | CN1CCC(=O)CC1 |
| CAS データベース | 1445-73-4(CAS DataBase Reference) |
| NISTの化学物質情報 | 4-Piperidinone, 1-methyl-(1445-73-4) |
化学的特性
clear yellow to orange liquid
安全性と法規制
| GHS 分類 | DangerH226 (100%): Flammable liquid and vapor [Warning Flammable liquids]H314 (10.7%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 84 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 規制情報 | Chemical: 4-Piperidinone, 1-methyl-Status: Active Update: 04-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/225751-Methyl-4-piperidinone: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | May cause irritation[Sigma-Aldrich MSDS] See 1-Benzyl-4-piperidone. |
| Hazard Classes and Categories | Flam. Liq. 3 (100%)Skin Corr. 1B (10.7%) |
| 水環境危害等級（WGK） | 3 |
| 輸送番号（UN） | UN 1224 3/PG 3 |
| 税関コード | 29333999 |
| 危険文句（R） | 34-10-36/37/38 |
| 化審法 | (9)-2198 |
| 消防法 | 危-4-2-III |
| 危険表示 | C,Xi |
| hazard_note | Irritant |
| 安全措置（S） | 23-24/25-37/39-26 |
| 危険等級 | 3Flam. Liq. 3 |
用途
用途
有機合成原料。
使用
1-Methyl-4-piperidone, are widely used in artificial fibre industry. They are polymerizable and used as nylon precursors. They have excellent applications as solvents and as intermediates for organic synthesis. They are used in the aqueous carrier medium and amide penetrants in inks and water soluble paints.
製法・合成法
製造方法
[JACS (1948) vol 70 p 1820] for the synthesis of 1-methyl-4-piperidone: To a one-liter flask containing 350 ml of 20 % hydrochloric acid was added 86 g. of 1-methyl-3-carbethoxy-4-piperidone hyrdrochloride. After refluxing for one hour, the ferric chloride reagent gave no coloration. The solution was evaporated to dryness on a steam-bath at 10 mm. pressure. The solid product, heated at 100 °C for 4 hours at 0.1 mm and further dried over solid KOH for 24 hours, weighed 57.7 g, m.p. 80 - 120 °C.Although this melting range goes above that of the pure comound 0.45 of crude material dissolved in 90 ml. of hot acetone gave 0.40 g of pure compoundd melting at 93 - 95 °C. Other samples of crude piperidone hydrochloride showed even higher melting points than the one mentioned above, yet this apperently impure material always gave good yields of sharp melting product when recrystallized.
純化方法
It is best purified by fractional distillation The hydrochloride of the hydrate (4-diol) has m 94.7-95.5o, but the anhydrous hydrochloride which crystallises from CHCl3/Et2O has m 165-168o (164-167o) and can also be obtained by sublimation at 120o/2mm. The oxime has m 130-132o (from Me2CO). The methiodide crystallises from MeOH, the crystals with 1MeOH have m 189-190o, and the solvent-free iodide has m 202-204o(dec). [Lyle et al. J Org Chem 24 342 1959, Bowden & Greeen J Chem Soc 1164 1952, Tomita Yakugaku Zasshi (J Pharm Soc Japan) 71 1053 1951, Beilstein 21 IIII/IV 3183, 21/6 V 419.]