요오드트리메틸실란

요오드트리메틸실란 · 요오드트리메틸실란(IODOTRIMETHYLSILANE) · TRIMETHYLSILYL IODIDE · TMIS · TRIMETHYLIODOSILANE · TMS iodide · CT3610 · IodotrimethyL

https://huagongshe.com/ko/chemical/85247

식별자 및 물리적 특성

CAS No.	16029-98-4
분자식	C3H9ISi
평균 분자량	200.09 g/mol
단동위원소 질량	199.95182482 g/mol
SMILES	C[Si](C)(C)I
InChIKey	CSRZQMIRAZTJOY-UHFFFAOYSA-N
PubChem CID	85247
EC No.	240-171-0
DTXSID	DTXSID4065997
현지명	요오드트리메틸실란

화학 및 물리적 성질

극성 표면적	0
수소 결합 공여자 수	0
수소 결합 수용자 수	0
회전 가능 결합 수	0
무거운 원자 수	5
형식 전하	0
복잡도	28.4
물질 분류	Metals -> Metalloid Compounds (Silicon)
SpringerMaterials Properties	29Si nuclear magnetic resonance spectrum
Physical Description	Clear light brown liquid[Sigma-Aldrich MSDS]
녹는점	<0°C
끓는 점	106 °C(lit.)
밀도	1.406 g/mL at 25 °C(lit.)
굴절률	n20/D 1.471(lit.)
인화점	−25 °F
저장 조건	-20°C
용해도	물과 반응
물리적 상태	액체
비중	1.47
색상	무색~붉은색 투명
용해도	물과 반응
BRN	1731136
안정성	Moisture Sensitive (Reactive)
InChI	1S/C3H9ISi/c1-5(2,3)4/h1-3H3
InChIKey	CSRZQMIRAZTJOY-UHFFFAOYSA-N
SMILES	C[Si](C)(C)I
NIST	Iodotrimethylsilane(16029-98-4)
EPA	Silane, iodotrimethyl- (16029-98-4)

화학적 성질

Straw liquid

안전 및 규제

GHS 분류	DangerH225 (98.4%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 62 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
규제 정보	Chemical: Silane, iodotrimethyl-Status: Active Update: 23-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24465Iodotrimethylsilane: Does not have an individual approval but may be used under an appropriate group standard
유해성 요약	Reacts violently with waterCauses burnsInhalation may cause corrosive injuries to upper respiratory tract and lungs[Sigma-Aldrich MSDS] See Silicon tetraiodide.
Hazard Classes and Categories	Flam. Liq. 2 (98.4%)
유해 작용	Dermatotoxin - Skin burns.
수질 위해 등급(WGK)	3
TSCA 등재 상태	TSCA listed
운송 번호(UN)	UN 2924 3/PG 2
관세 코드	29310095
위험 문구(R)	11-14-34
위험 표시	F,C
안전 문구(S)	16-26-36/37/39-43-45-25
포장분류	II
위험 등급	3Eye Dam. 1Flam. Liq. 2Skin Corr. 1B
기존화학 물질	KE-21044
F 고인화성물질	8-21
저장 분류	3 - Flammable liquids

용도

Iodotrimethylsilane is used for the introduction of trimethylsilyl group in organic synthesis. It is also useful for gas chromatography analysis by converting alcohol into a silyl ether derivative, thereby making it more volatile than the original molecule.Iodotrimethylsilane is a highly efficient reagent for the cleavage of ethers, esters, carbamates, ketals, and lactones. It is also used for the introduction of TMS groups, such as TMS enol ethers, and is a key reagent for the selective removal of N-Cbz groups in the presence of a trimethyltin moiety.This reagent has recently been reported to convert allyl and benzyl phosphotriesters to the corresponding iodides.

일반 설명

Iodotrimethylsilane is a multipurpose reagent used in various organic reactions. It is used for the dealkylation of few compounds like lactones, ethers, acetals, and carbamates and trimethylsilylating agent for the synthesis of silyl imino esters, alkyl and alkenyl silanes, etc. It also acts as a Lewis acid catalyst and as a reducing agent in many organic reactions.

제조 및 합성 방법

제조 방법

Iodotrimethylsilane is prepared by mixing equimolar amounts of chlorotrimethylsilane and sodium iodide in acetonitrile, reduces various benzylic alcohols to the corresponding phenylalkanes. Other have been reported for the preparation of Trimethylsilyl Iodide(TMS-I): chlorotrimethylsilane undergoes halogen exchange with either lithium iodide in CHCl3 or sodium iodide in MeCN, which allows in situ reagent formation. Alternatively, hexamethyldisilane reacts with iodine at 25–61°C to afford TMS-I with no byproducts.