1,3-ジメチルバルビツル酸
1,3-ジメチルバルビツル酸 · 1,3-ジメチルピリミジン-2,4,6(1H,3H,5H)-トリオン · 1,3-ジメチル-2,4,6(1H,3H,5H)-ピリミジントリオン · 1,3-ジメチルヘキサヒドロピリミジン-2,4,6-トリオン · 1,3-ジメチルピリミジン-2,4,6(1H,2H,5H)-トリオン · 1,3-ジメチルハルビツール酸 · ヘキサヒドロ-1,3-ジメチルピリミジン-2,4,6-トリオン · 1,3-ジメチルバルビツール酸
識別子と物理属性
| CAS No. | 769-42-6 |
|---|---|
| 分子式 | C6H8N2O3 |
| 平均分子量 | 156.14 g/mol |
| 単同位体質量 | 156.05349212 g/mol |
| SMILES | CN1C(=O)CC(=O)N(C)C1=O |
| InChIKey | VVSASNKOFCZVES-UHFFFAOYSA-N |
| PubChem CID | 69860 |
| EC No. | 212-211-7 |
| DTXSID | DTXSID0061115 |
| 現地名 | 1,3-ジメチルバルビツル酸 |
化学・物理的性質
| XLogP | -0.8 |
|---|---|
| 極性表面積 | 57.7 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 0 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 214 |
| 医薬品 | DEA NFLIS-Drug Category -> Depressants and Tranquilizers |
| 融点 | 121-123 °C (lit.) 121-123 °C |
| 沸点 | 228.1±23.0 °C(Predicted) |
| 密度 | 1.322±0.06 g/cm3(Predicted) |
| 貯蔵条件 | -20°C Freezer |
| 溶解度 | 熱湯：可溶0.5g/10mL 無色透明～微黄色水に溶ける。 |
| 外観・状態 | 結晶性粉末 |
| pKa（酸解離定数） | pK1:4.68(+1) (25°C) |
| 色 | ホワイト/クリーム/ペールイエロー |
| pH | 2.5 (20°C, 100g/L in H2O, slurry) |
| BRN | 139810 |
| InChI | 1S/C6H8N2O3/c1-7-4(9)3-5(10)8(2)6(7)11/h3H2,1-2H3 |
| InChIKey | VVSASNKOFCZVES-UHFFFAOYSA-N |
| SMILES | CN1C(=O)CC(=O)N(C)C1=O |
| CAS データベース | 769-42-6(CAS DataBase Reference) |
| NISTの化学物質情報 | 1,3-Dimethylbarbituric acid(769-42-6) |
| EPAの化学物質情報 | 2,4,6(1H,3H,5H)-Pyrimidinetrione, 1,3-dimethyl- (769-42-6) |
化学的特性
Yellow or brownish powder
安全性と法規制
| GHS 分類 | DangerH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 51 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | 2,4,6(1H,3H,5H)-Pyrimidinetrione, 1,3-dimethyl-: 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 | 29339900 |
| 危険文句（R） | 22-41 |
| 危険表示 | Xn |
| 安全措置（S） | 26-36/39 |
| 危険等級 | Acute Tox. 4 OralEye Dam. 1 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
使用
1,3-Dimethylbarbituric acid is used as a catalyst in the Knoevenagel condensation of a series of aromatic aldehydes. It is also used in the synthesis of 5-aryl-6-(alkyl- or aryl-amino)-1,3-dimethylfuro [2,3-d]pyrimidine derivatives and enantioselective synthesis of isochromene pyrimidinedione derivatives.
一般的な説明
1,3-Dimethylbarbituric acid (1,3-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione) is an active methylene compound. It undergoes hollow Pd6 water-soluble cage, [{(tmen)Pd}6(timb)4](NO3)12 (tmen= N,N,N′,N′-tetramethylethylenediamine, timb=1,3,5-tris(1-imidazolyl)benzene)-catalyzed Knoevenagel condensation reaction with pyrene-1-carboxaldehyde. It undergoes self-sorted Pd7 molecular boat having an internal nanocavity (catalyst)-assisted Knoevenagel condensation reaction with various aromatic aldehydes. It has been synthesized by reacting 1,3-dimethylurea, malonic acid and acetic anhydride in acetic acid. It is widely used for the synthesis of various synthetic intermediates and heterocyclic compounds.
製法・合成法
純化方法
Crystallise the acid from water and sublime it in a vacuum. Also purify it by dissolving 10g in 100mL of boiling CCl4/CHCl3 (8:2) (1g charcoal), filtering and cooling to 25o. Dry it in vacuo [Kohn et al. Anal Chem 58 3184 1986]. [Beilstein 24 III/IV 1875.]