Ethyl 1,3-dithiane-2-carboxylate
Carboethoxy-1,3-dithiane · 2-Carboethoxy-1,3-dithiane · 2-Ethoxycarbonyl-1,3-dithiane · ETHYL 1,3-DITHIANE-2-CARBOXYLATE · 1,3-dithioalkane-2-ethyl formate · Ethyl1,3-Dithiane-2-carboxylate>Ethyl 1,3-dithiane-2-carboxylate, 98+% · ETHYL-1 3-DITHIANE-2-CARBOXYLATE 99% (& · ETHYL 1,3-DITHIANE-2-CARBOXYLATE FOR SYN
식별자 및 물리적 특성
| CAS No. | 20462-00-4 |
|---|---|
| 분자식 | C7H12O2S2 |
| 평균 분자량 | 192.3 g/mol |
| 단동위원소 질량 | 192.02787162 g/mol |
| SMILES | CCOC(=O)C1SCCCS1 |
| InChIKey | ANEDZEVDORCLPM-UHFFFAOYSA-N |
| PubChem CID | 88552 |
| EC No. | 243-838-4 |
| DTXSID | DTXSID50174427 |
화학 및 물리적 성질
| XLogP | 2.1 |
|---|---|
| 극성 표면적 | 76.9 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 3 |
| 무거운 원자 수 | 11 |
| 형식 전하 | 0 |
| 복잡도 | 132 |
| 녹는점 | 19-21°C |
| 끓는 점 | 75-77 °C/0.2 mmHg (lit.) |
| 밀도 | 1.22 g/mL at 25 °C (lit.) |
| 굴절률 | n20/D 1.539(lit.) |
| 인화점 | 130 °F |
| 저장 조건 | Keep in dark place,Sealed in dry,Room Temperature |
| 물리적 상태 | 투명한 액체 |
| 색상 | Colorless to Light yellow to Light orange |
| 용해도 | 물과 약간 섞임. |
| BRN | 1424352 |
| InChI | InChI=1S/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3 |
| InChIKey | ANEDZEVDORCLPM-UHFFFAOYSA-N |
| SMILES | S1CCCSC1C(OCC)=O |
| NIST | Ethyl 1,3-dithiane-2-carboxylate(20462-00-4) |
화학적 성질
clear yellowish liquid
안전 및 규제
| GHS 분류 | WarningH226 (100%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 44 reports by companies from 2 notifications to the ECHA C&L Inventory. |
|---|---|
| 규제 정보 | Chemical: 1,3-Dithiane-2-carboxylic acid, ethyl esterEthyl 1,3-dithiane-2-carboxylate: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Flam. Liq. 3 (100%) |
| 수질 위해 등급(WGK) | 3 |
| 운송 번호(UN) | UN 3272 3/PG 3 |
| 관세 코드 | 29349990 |
| 위험 문구(R) | 10 |
| 안전 문구(S) | 26-36/37/39-45 |
| 포장분류 | III |
| 위험 등급 | 3Flam. Liq. 3 |
| F 고인화성물질 | 9-13 |
| 저장 분류 | 3 - Flammable liquids |
용도
용도
Ethyl 1,3-dithiane-2-carboxylate is used in syn-selective aldol reactions. It undergoes asymmetric oxidation to give trans bis-sulfoxide. It is used to generate carbanon, which finds application in the preparation of alfa- keto esters.
일반 설명
Ethyl 1,3-dithiane-2-carboxylate is an α-keto acid equivalent and bulky equivalent of acetate. It participates in syn-selective aldol reactions. It can be prepared from the reaction of ethyl diethoxyacetate and 1,3-propanedithiol in the presence of BF3/Et2O. Asymmetric oxidation of ethyl 1,3-dithiane-2-carboxylate by Modena protocol has been reported to afford trans bis-sulfoxide in 60% yield. Carbanion from ethyl 1,3-dithiane-2-carboxylate may be employed for the preparation of α-keto esters.
제조 및 합성 방법
제조 방법
To a solution of BF3. Et2O (57.5 mL, 0.454 mmol) in CHC13 (180 mL) heated at reflux was added dropwise, over a 1h period, a solution of 1,3-propanedithiol (22.7 mL, 0.227 mmol), followed by ethyl diethoxyacetate (40 g, 0.227 mmol) in CHCl3 (40 mL). The resulting mixture was heated for 30 minutes, and then cooled to rt. The cooled solution was washed 2 times with water, once with saturated aqueous NaHC03, and then re-washed with water. The combined organic phases were dried over MgS04, then evaporated to give 41 g (94%) of Ethyl 1,3-dithiane-2-carboxylate as a yellow oi. Yield: 94%