트라이에틸실레인
트라이에틸실레인 · Et3SiH · Triethylsilyl · Triethylsilyl hydride · PDFF · Silane, triethyl- · Triethylsilicon hydride · NSC 93579
식별자 및 물리적 특성
| CAS No. | 617-86-7 |
|---|---|
| 분자식 | C6H16Si |
| 평균 분자량 | 116.28 g/mol |
| 단동위원소 질량 | 116.10212704 g/mol |
| SMILES | CC[SiH](CC)CC |
| InChIKey | AQRLNPVMDITEJU-UHFFFAOYSA-N |
| PubChem CID | 12052 |
| ChEBI | CHEBI:188370 |
| EC No. | 210-535-3 |
| DTXSID | DTXSID20870702 |
| 현지명 | 트라이에틸실레인 |
화학 및 물리적 성질
| 극성 표면적 | 0 |
|---|---|
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 0 |
| 회전 가능 결합 수 | 3 |
| 무거운 원자 수 | 7 |
| 형식 전하 | 0 |
| 복잡도 | 25.7 |
| 물질 분류 | Metals -> Metalloid Compounds (Silicon) |
| SpringerMaterials Properties | Schoenflies notation |
| 증기압 | 42.9 [mmHg]>1 hPa (20 °C) |
| Physical Description | Colorless liquid with a mild odor like garlic[Merck Index] |
| 녹는점 | -157°C |
| 끓는 점 | 107-108 °C (lit.) |
| 밀도 | 0.728 g/mL at 25 °C (lit.) |
| 굴절률 | n20/D 1.412(lit.) |
| 인화점 | 25 °F |
| 저장 조건 | Store below +30°C. |
| 용해도 | 물에 불용성탄화수소, 할로겐화 탄화수소 및 에테르 유기 화합물에 용해됩니다. |
| 물리적 상태 | 액체 |
| 색상 | 무색의 |
| 비중 | 0.728 |
| 용해도 | 물과 섞일 수 있습니다. |
| BRN | 1098278 |
| 안정성 | 안정적이지만 습기에 민감합니다. 가연성이 높습니다. 물, 산, 염기와 접촉하면 인화성이 높은 가스(수소)를 생성합니다. |
| InChI | 1S/C6H16Si/c1-4-7(5-2)6-3/h7H,4-6H2,1-3H3 |
| InChIKey | AQRLNPVMDITEJU-UHFFFAOYSA-N |
| SMILES | CC[SiH](CC)CC |
| LogP(분배 계수) | 3.6 at 20℃ |
| NIST | Silane, triethyl-(617-86-7) |
| EPA | Triethylsilane (617-86-7) |
화학적 성질
Clear liquid
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 0.7% (1 of 143) of reports.DangerH225 (99.3%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P273, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 143 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Chemical: Silane, triethyl-Status: Active Update: 21-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/22521Triethylsilane: Does not have an individual approval but may be used under an appropriate group standard |
| 유해성 요약 | An irritant[Merck Index] A skin, respiratory tract, and strong eye irritant[Alfa Aesar MSDS] See Silicon tetrahydride. See Tetramethylsilane and Diethylsilane. |
| Hazard Classes and Categories | Flam. Liq. 2 (99.3%) |
| 수질 위해 등급(WGK) | 1 |
| TSCA 등재 상태 | TSCA listed |
| 운송 번호(UN) | UN 1993 3/PG 2 |
| 관세 코드 | 29310095 |
| 위험 문구(R) | 11-36/37/38-52/53 |
| 위험 표시 | F,Xi |
| 안전 문구(S) | 9-16-29-33-37/39-26-61 |
| 포장분류 | II |
| 위험 등급 | 3Eye Irrit. 2Flam. Liq. 2Skin Irrit. 2STOT SE 3 |
| 기존화학 물질 | KE-34232 |
| F 고인화성물질 | 10-21 |
| 저장 분류 | 3 - Flammable liquids |
용도
개요
Triethylsilane is a useful versatile reductant since it has a active hydride. It can be used for mediated the palladium-catalyzed dehalogenation reaction of alkyl or aryl halides, the reduction of primary, secondary, and tertiary chlorides, bromides, and iodides catalyzed by iridium, as well as efficient reduction of multiple bonds, azides, imines, and nitro groups, as well as benzyl group and allyl group deprotection. It is also specifically for the hydrosilation of olefins to give alkyl silanes. It is also the catalyst for synthesis of a spiro-oxindole blocker of Nav1.7 for the treatment of pain, redox initiated cationic polymerization and Beckmann rearrangement of cyclododecanone oxime as well as regioselective reductive coupling of enones and allenes.
용도
Triethylsilane is a trialkylsilicon hydride used in the synthesis of alkylsilanes via hydrosilation of olefins. It acts as a reducing agent in the reduction of 2-chromanols, since it has an active hydride. It acts as a catalyst for redox initiated cationic polymerization, regioselective reductive coupling of enones and allenes, and Beckmann rearrangement of cyclododecanone oxime. It is associated with trifluoroacetic acid and involved in the selective reduction of alkenes.
제조 및 합성 방법
생산 방법
A synthetic method of triethylsilane comprises the following steps: reacting sodium hydride with trimethyl borate to prepare trimethoxy sodium borohydride; adding triethylchlorosilane to trimethoxy sodium monohydroborate to react to obtain triethylsilane.To a 500ml reaction flask, 20g (0.5mol) of 60% sodium hydride and 80g of anhydrous tetrahydrofuran were added. Stirring and cooling to 0-10 ℃ under the protection of nitrogen, the mixture was then maintained under nitrogen protection, stirred, and the liquid temperature at 0-10 ℃, and dropwise added 57.2g (0.55mol) of trimethyl borate. After the dropwise addition, the temperature was kept at 0-10 ℃ and stirred for 1 hour.Maintaining the nitrogen protection, stirring and liquid temperature of the reaction liquid at 0-10 ℃, and then dropwise adding 67.7g (0.45mol) of triethylchlorosilane. After the dropwise addition, continuously keep the temperature at 0-10 ℃ and stir for 1 hour. The reaction solution was then filtered at room temperature. Rectifying the filtrate at normal pressure and collecting fractions with the boiling range of 109-110 ℃ as triethylsilane to obtain 46.1g of triethylsilane, which yields 88.2%. 45-64 ℃: a mixed solution of trimethyl borate and tetrahydrofuran; 64-109 ℃:a mixture of tetrahydrofuran and a small triethylsilane.