ジエチルホスホノ酢酸エチル
Triethyl phosphonoacetate
データを補完しています。しばらくしてからページを更新すると最新の内容を表示できます
基本情報
- CAS
867-13-0- 標準SMILES
CCOC(=O)CP(=O)(OCC)OCC- InChIKey
GGUBFICZYGKNTD-UHFFFAOYSA-N- 分子式
- C8H17O5P
- 平均分子量
- 224.19 g/mol
- 単同位体質量
- 224.08136027
名称と識別子
- 優先名称
- Triethyl phosphonoacetate
- IUPAC
- ethyl 2-diethoxyphosphorylacetate
- 現地名
- ジエチルホスホノ酢酸エチル
- 英語名
- Triethyl phosphonoacetate
- 分子式
- C8H17O5P
- 分子量
- 224.19
名称と別名
Triethyl phosphonoacetate867-13-0Ethyl (diethoxyphosphoryl)acetateEthyl (diethylphosphono)acetateTriethyl phosphonoethanoateAcetic acid, (diethoxyphosphinyl)-, ethyl esterDiethyl carbethoxymethylphosphonateDiethyl ethoxycarbonylmethanephosphonateDiethyl carboethoxymethylphosphonateEthyl diethoxyphosphoryl acetateTL 465ETHYL (DIETHOXYPHOSPHINYL)ACETATE
名称をさらに表示
ジエチルホスホノ酢酸エチル2-オキソ-2-エトキシエチルホスホン酸ジエチル(ジエトキシホスフィニル)酢酸エチルジエトキシホスフィニル酢酸エチル2-(ジエトキシホスフィニル)酢酸エチルエトキシカルボニルメチルホスホン酸ジエチルホスホノ酢酸トリエチルトリエチル ホスホノ酢酸トリエチルホスホノアセテートエトキシカルボニルメタンホスホン酸ジエチルジエチルホスホノ酢酸エチルエステルETHYL 2-(DIETHOXYPHOSPHORYL)ACETATEETHYL DIETHYLPHOSPHONOACETATETriethyl phosphonacetateTicagrelor Impurity 150Triethyl phosphonoacetatCarbethoxyMethyldiethyl PhosphonateDIETHYLPHOSPHONOACETIC ACID ETHYL ESTERDIETHYL ETHOXYCARBONYLMETHYLPHOSPHONATEtl465
Phosphonoacetic acid, triethyl esterAcetic acid, phosphono-, triethyl esterDiethyl phosphonoacetic acid, ethyl esterAcetic acid, 2-(diethoxyphosphinyl)-, ethyl ester(Ethoxycarbonylmethyl)diethoxyphospshine oxideDTXSID4041573Acetic acid, diethylphosphono-, ethyl esterNSC-13898
データベース識別子
- CAS
867-13-0- PubChem CID
- 13345
- DTXSID
DTXSID4041573- ChEMBL
CHEMBL3185304- UNII
- 022826171T
- EC Number
- 212-757-6
- Nikkaji
- J54.207E
物性
構造計算による物性補完中
- XLogP
- 0.5
- 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
- 14
- 形式電荷
- 0
- 複雑度
- 206
実験および物理化学的性質
Chemical ClassesOther Classes -> Organophosphates, Other
Food Contact Substances
FCS -> FDA Cumulative Estimated Daily Intake (CEDI)
FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical DescriptionClear light yellow liquid; [Acros Organics MSDS]
Collision Cross Section143.7 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID4041573]
物理化学的性質
- 融点
- -24 °C · -24°C
- 沸点
- 142 · 142-145 °C9 mm Hg(lit.)
- 比重(密度)
- 1.13 g/mL · 1.13 g/mL at 25 °C(lit.)
- 蒸気圧
- 0.61 Pa · 0.61Pa at 25℃
- 屈折率
- 20 · n20/D 1.431(lit.)
- 闪点
- 165 °C · 165°C
- 貯蔵温度
- Keep in dark place,Sealed in dry,Room Temperature
- 溶解性
- Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
- 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
Warning
H315 (22.9%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 70 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Chemical: Acetic acid, (diethoxyphosphinyl)-, ethyl ester
Regulation (EC) No 1935/2004 (amended)
Status: Active Update: 19-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11013
Acetic acid, (diethoxyphosphinyl)-, ethyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazards SummaryOral lethal-dose (rat) > 500 mg/kg; [RTECS] An irritant that may cause serious eye injury; [Acros Organics MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (22.9%)
毒性情報
Toxicity DataLCLo (mouse) = 1,180 mg/m3/10min
安全データ
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AG9800000
- ridadr
- UN 3082 9/PG 3
- hs_code
化学と産業
用途と製造
UsesUsed to make large scale and fine chemicals, active pharmaceutical ingredients or fragrances, and to polymerize bottle grade PET; [ExPub: ECHA REACH Registrations]
General Manufacturing InformationAcetic acid, 2-(diethoxyphosphinyl)-, ethyl ester: ACTIVE
応用分野
用途有機合成原料。
説明Triethyl phosphonoacetate is a reagent for organic synthesis used in the Horner-Wadsworth-Emmons reaction (HWE) or the Horner-Emmons modification. This compound can be added dropwise to sodium methoxide solution to prepare a phosphonate anion. It has an acidic proton that can easily be abstracted by a weak base. When used in an HWE reaction with a carbonyl, the resulting alkene formed is usually the E alkene and is generated with excellent regioselectivity. It can synthesize β-Keto Phosphonates via an acylation reaction of triethyl phosphonoacetate with carboxylic acid chlorides in the presence of magnesium chloride-triethylamine followed by decarbethoxylation. Acylation of triethyl phosphonoacetate using magnesium ethoxide affords acyl phosphonoacetates, which, on treatment with catalytic p-TsOH in water, are converted into 2-aryl-2-oxoalkylphosphonates[1-2].
使用Triethyl phosphonoacetate serves as a reactant used in Horner-Wadsworth-Emmons reactions, Tsuji-Trost type reactions, Intramolecular Heck-type cyclization and isomerizations and Intramolecular aryne-ene reactions. In Horner-Wadsworth-Emmons reaction, it is utilized as a reagent to prepare chiral 2-methylcyclopropanecarboxylic acid from (S)-propylene oxide.
調製方法
純化方法Purify it by fractional distillation, preferably in vacuo. NMR has P resonance at 19.5 relative to orthophosphate. [Kosolapoff & Powell J Am Chem Soc 68 1103 1946, Kosolapoff & Powell J Am Chem Soc 72 4198 1950, Speziale & Freeman J Org Chem 23 1586 1958, Beilstein 4 IV 3613.]
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