エトキシメチレンマロン酸ジエチル
エトキシメチレンマロン酸ジエチル · 2-(エトキシメチレン)マロン酸ジエチル · ジエチルエトキシメチレンマロナート · 1,1-ジ(エトキシカルボニル)-2-エトキシエテン · (エトキシメチレン)マロン酸ジエチル · 2-エトキシエテン-1,1-ジカルボン酸ジエチル · (エトキシメチレン)プロパン二酸ジエチル · エトキシメチレンプロパン二酸ジエチル
識別子と物理属性
| CAS No. | 87-13-8 |
|---|---|
| 分子式 | C10H16O5 |
| 平均分子量 | 216.23 g/mol |
| 単同位体質量 | 216.09977361 g/mol |
| SMILES | CCOC=C(C(=O)OCC)C(=O)OCC |
| InChIKey | LTMHNWPUDSTBKD-UHFFFAOYSA-N |
| PubChem CID | 6871 |
| EC No. | 201-725-7 |
| DTXSID | DTXSID5052591 |
| 現地名 | エトキシメチレンマロン酸ジエチル |
化学・物理的性質
| XLogP | 1.5 |
|---|---|
| 極性表面積 | 61.8 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 5 |
| 回転可能結合数 | 8 |
| 重原子数 | 15 |
| 形式電荷 | 0 |
| 複雑度 | 224 |
| 物質分類 | Other Classes -> Esters, OtherIndustrial compound |
| Physical Description | Colorless liquid[Alfa Aesar MSDS] |
| Ionization Efficiency | Positive2.12.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Collision Cross Section | 146.8 Ų [M+Na]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID5052591] |
| 融点 | -33°C |
| 沸点 | 279-283 °C(lit.) |
| 密度 | 1.080 g/mL at 20 °C(lit.) |
| 蒸気圧 | <0.1 hPa |
| 屈折率 | n20/D 1.463 |
| 引火点 | 311 °F |
| 貯蔵条件 | Store below +30°C. |
| 溶解度 | クロロホルム（微量）、酢酸エチル（微量）不溶性 |
| 外観・状態 | 液体 |
| 色 | 無色透明～薄黄色 |
| BRN | 880058 |
| InChI | 1S/C10H16O5/c1-4-13-7-8(9(11)14-5-2)10(12)15-6-3/h7H,4-6H2,1-3H3 |
| InChIKey | LTMHNWPUDSTBKD-UHFFFAOYSA-N |
| SMILES | CCO\C=C(\C(=O)OCC)C(=O)OCC |
| LogP（分配係数） | 1.5-2.1 at pH7 |
| CAS データベース | 87-13-8(CAS DataBase Reference) |
| NISTの化学物質情報 | Propanedioic acid, (ethoxymethylene)-, diethyl ester(87-13-8) |
| EPAの化学物質情報 | Propanedioic acid, (ethoxymethylene)-, diethyl ester (87-13-8) |
化学的特性
CLEAR COLOURLESS TO LIGHT YELLOW LIQUID
安全性と法規制
| GHS 分類 | DangerH302 (99.1%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 111 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Status: Active Update: 29-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/12518Diethyl ethoxymethylenemalonate: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | A moderate skin irritantCauses somnolence and gastrointestinal changes in oral lethal-dose studies of rats[RTECS] An irritantMay cause skin and respiratory sensitizationHarmful by ingestion[Alfa Aesar MSDS] Search for (87-13-8[EC/RN Number]) AND (allergic OR dermatitis OR asthma OR sensitizer OR sensitization): no results[PubMed] |
| Peroxide Forming Chemical | Diethyl ethoxymethylenemalonateD: Other compounds that may form peroxidesKelly |
| Hazard Classes and Categories | Acute Tox. 4 (99.1%) |
| Toxicity Data | LCLo (mouse) = 44 mg/m3 |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | OO1100000 |
| 毒性 | LD50 orally in Rabbit: 925 mg/kg LD50 dermal Rat > 2000 mg/kg |
| 税関コード | 29189090 |
| 危険文句（R） | 22-36/37/38-42/43 |
| 化審法 | (9)-561 |
| 消防法 | 危-4-3-III |
| 危険表示 | Xn |
| 安全措置（S） | 26-36/37/39-27-24/25 |
| 自然発火温度 | 215 °C |
| 危険等級 | Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 2Eye Irrit. 2Skin Irrit. 2Skin Sens. 1A |
| 貯蔵分類 | 10 - Combustible liquids |
用途
使用
Diethyl ethoxymethylenemalonate is used for synthesis of pyrido[3,2-e]pyrimido[1,2-c]pyrimidines. Initially, it was used to monitor lysine decarboxylase activity. It is useful in the determination of amino acids by precolumn derivatization by using reversed-phase high-performance liquid chromatography (HPLC). It plays an important role in the Gould-Jacobs reaction to prepare quinolines. For example, anile reacts with this reagent to give 4-hydroxyquinoline. It acts as an intermediate in the production of flumequine, which is a fluoroquinolone antibiotic.
製法・合成法
純化方法
Likely impurity is diethyl diethoxymethylene malonate which is difficult to separate from diethyl ethoxymethylene malonate by distillation, and it is necessary to follow the course of the distillation by the change in refractive index instead of boiling point. After a low boiling fraction is collected, there is obtained an intermediate fraction (n 20 1.414—1.458), the size of which depends on the amount of the diethoxymethylene compound. This fraction is fractionated through a 5inch Vigreux column (p 11) at low pressure avoiding interruption in heating. Fraction b 108-110o/0.25mm is ca 10o lower than the submitters' fraction (b 97.2o/0.25mm, n D 1.4612—1.4623) [Org Synth Coll Vol III 395 1955, Fuson et al. J Org Chem 11 197 1946, Duff & Kendal J Chem Soc 893 1948]. [Beilstein 3 IV 1192.]