エトキシメチレンマロン酸ジエチル
Diethyl (ethoxymethylene)malonate
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基本情報
- CAS
87-13-8- 標準SMILES
CCOC=C(C(=O)OCC)C(=O)OCC- InChIKey
LTMHNWPUDSTBKD-UHFFFAOYSA-N- 分子式
- C10H16O5
- 平均分子量
- 216.23 g/mol
- 単同位体質量
- 216.09977361
名称と識別子
- 優先名称
- Diethyl (ethoxymethylene)malonate
- IUPAC
- diethyl 2-(ethoxymethylidene)propanedioate
- 現地名
- エトキシメチレンマロン酸ジエチル
- 英語名
- Diethyl ethoxymethylenemalonate
- 分子式
- C10H16O5
- 分子量
- 216.23
名称と別名
Diethyl ethoxymethylenemalonate87-13-8Diethyl (ethoxymethylene)malonateEthoxymethylenemalonic acid diethyl esterDiethyl EMMEPropanedioic acid, (ethoxymethylene)-, diethyl esterDTXSID5052591NSC-9068MALONIC ACID, (ETHOXYMETHYLENE)-, DIETHYL ESTER6KF8220SZ8NSC-62117DTXCID2031164
名称をさらに表示
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EMMEエトキシメチレンマロン酸ジエチルエステル１，１ジカルボエトキシ２エトキシエチレン1，1-ジカルボエトキシ-2-エトキシエチレン1,3-ジエチル 2-(エトキシメチリデン)プロパンジオアートEMMEDEEMMDiethyl 2-(ethoxymethylene)propanedioatediethyl (ethoxymethylidene)propanedioate2-Ethoxymethylene-malonic acid diethyl esteronatetl1483enemaL
Propanedioic acid, 2-(ethoxymethylene)-, 1,3-diethyl esterRefChem:133377Propanedioic acid, 2-(ethoxymethylene)-, diethyl ester201-725-7Diethyl 2-(ethoxymethylene)malonateDiethyl Ethoxymethylidenemalonate1,3-diethyl 2-(ethoxymethylidene)propanedioateMFCD00009148
データベース識別子
- CAS
87-13-8- PubChem CID
- 6871
- DTXSID
DTXSID5052591- UNII
- 6KF8220SZ8
- EC Number
- 201-725-7
- Nikkaji
- J61.661C
物性
構造計算による物性補完中
- XLogP
- 1.5
- 極性表面積
- 61.8 Ų
- 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
実験および物理化学的性質
Chemical Classes
Other Classes -> Esters, Other
Industrial compound
Physical DescriptionColorless liquid; [Alfa Aesar MSDS]
Ionization Efficiency
Positive
2.1
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Collision Cross Section146.8 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID5052591]
物理化学的性質
- 融点
- -33 °C · -33°C
- 沸点
- 279 · 279-283 °C(lit.)
- 比重(密度)
- 1.08 g/mL · 1.080 g/mL at 20 °C(lit.)
- 蒸気圧
- 0.1 hPa · <0.1 hPa
- 屈折率
- 20 · n20/D 1.463
- 闪点
- 311 °F · 311 °F
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- クロロホルム（微量）、酢酸エチル（微量）
- 外見
- 液体
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Danger
H302 (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.
危険有害性情報
Regulatory Information
Status: Active Update: 29-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/12518
Diethyl ethoxymethylenemalonate: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
A moderate skin irritant; Causes somnolence and gastrointestinal changes in oral lethal-dose studies of rats; [RTECS] An irritant; May cause skin and respiratory sensitization; Harmful 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 ethoxymethylenemalonate
D: Other compounds that may form peroxides
Kelly
Hazard Classes and CategoriesAcute Tox. 4 (99.1%)
毒性情報
Toxicity DataLCLo (mouse) = 44 mg/m3
安全データ
化学と産業
用途と製造
UsesUsed to make fine chemicals; [ExPub: ECHA REACH Registrations]
General Manufacturing InformationPropanedioic acid, 2-(ethoxymethylene)-, 1,3-diethyl ester: ACTIVE
応用分野
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.
調製方法
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.]
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