디에틸포스포노아세트산에틸에스테르
디에틸포스포노아세트산에틸에스테르 · 트라이에틸 포스포노아세테이트 · ETHYL 2-(DIETHOXYPHOSPHORYL)ACETATE · ETHYL DIETHYLPHOSPHONOACETATE · Triethyl phosphonacetate · Ticagrelor Impurity 150 · Triethyl phosphonoacetat · CarbethoxyMethyldiethyl Phosphonate
식별자 및 물리적 특성
| CAS No. | 867-13-0 |
|---|---|
| 분자식 | C8H17O5P |
| 평균 분자량 | 224.19 g/mol |
| 단동위원소 질량 | 224.08136027 g/mol |
| SMILES | CCOC(=O)CP(=O)(OCC)OCC |
| InChIKey | GGUBFICZYGKNTD-UHFFFAOYSA-N |
| PubChem CID | 13345 |
| ChEMBL | CHEMBL3185304 |
| EC No. | 212-757-6 |
| DTXSID | DTXSID4041573 |
| 현지명 | 디에틸포스포노아세트산에틸에스테르 |
화학 및 물리적 성질
| XLogP | 0.5 |
|---|---|
| 극성 표면적 | 61.8 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 5 |
| 회전 가능 결합 수 | 8 |
| 무거운 원자 수 | 14 |
| 형식 전하 | 0 |
| 복잡도 | 206 |
| 물질 분류 | Other 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 Description | Clear light yellow liquid[Acros Organics MSDS] |
| Collision Cross Section | 143.7 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID4041573] |
| 녹는점 | -24°C |
| 끓는 점 | 142-145 °C9 mm Hg(lit.) |
| 밀도 | 1.13 g/mL at 25 °C(lit.) |
| 증기압 | 0.61Pa at 25℃ |
| 굴절률 | n20/D 1.431(lit.) |
| 인화점 | 165°C |
| 저장 조건 | Keep in dark place,Sealed in dry,Room Temperature |
| 용해도 | 클로로포름(약간 용해됨), 에틸아세테이트(약간 용해됨), 메탄올(약간 용해됨) |
| 물리적 상태 | 액체 |
| 비중 | 1.130 |
| 색상 | 투명한 |
| 용해도 | 물과 약간 섞임. |
| BRN | 1343714 |
| InChI | 1S/C8H17O5P/c1-4-11-8(9)7-14(10,12-5-2)13-6-3/h4-7H2,1-3H3 |
| InChIKey | GGUBFICZYGKNTD-UHFFFAOYSA-N |
| SMILES | CCOC(=O)CP(=O)(OCC)OCC |
| LogP(분배 계수) | 1.13 at 30℃ |
| EPA | Acetic acid, (diethoxyphosphinyl)-, ethyl ester (867-13-0) |
화학적 성질
Triethyl phosphonoacetate is Colorless to light yellow liqui
안전 및 규제
| GHS 분류 | WarningH315 (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. |
|---|---|
| 규제 정보 | Chemical: Acetic acid, (diethoxyphosphinyl)-, ethyl esterRegulation (EC) No 1935/2004 (amended)Status: Active Update: 19-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11013Acetic 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. |
| 유해성 요약 | Oral lethal-dose (rat) > 500 mg/kg[RTECS] An irritant that may cause serious eye injury[Acros Organics MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (22.9%) |
| Toxicity Data | LCLo (mouse) = 1,180 mg/m3/10min |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | AG9800000 |
| 운송 번호(UN) | UN 3082 9/PG 3 |
| 관세 코드 | 29310095 |
| 위험 문구(R) | 51/53-36/37/38 |
| 위험 표시 | N,Xi,Xn |
| 안전 문구(S) | 61-37/39-26-36 |
| 포장분류 | III |
| 위험 등급 | 9Eye Irrit. 2 |
| 기존화학 물질 | 2000-3-1636 |
용도
개요
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].
용도
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.