트리메칠시아나이드

트라이메틸실릴사이아나이드 · 트리메칠시아나이드 · 트라이메틸실릴 사이아나이드 · TMSCN · TRIMETHYLSILANECARBONITRILE · trimethylsilylformonitrile · CYANOTRIMETHYLSILANE · TRIMETHYLCYANOSILANE

https://huagongshe.com/ko/chemical/82115

식별자 및 물리적 특성

CAS No.	7677-24-9
분자식	C4H9NSi
평균 분자량	99.21 g/mol
단동위원소 질량	99.05042582 g/mol
SMILES	C[Si](C)(C)C#N
InChIKey	LEIMLDGFXIOXMT-UHFFFAOYSA-N
PubChem CID	82115
EC No.	231-657-3
DTXSID	DTXSID9064766
현지명	트리메칠시아나이드

화학 및 물리적 성질

극성 표면적	23.8
수소 결합 공여자 수	0
수소 결합 수용자 수	1
회전 가능 결합 수	0
무거운 원자 수	6
형식 전하	0
복잡도	81.5
물질 분류	Nitrogen Compounds -> Nitriles
SpringerMaterials Properties	29Si nuclear magnetic resonance spectrum
Physical Description	Colorless liquidmp = 11-12 deg C[MSDSonline]
녹는점	8-11 °C(lit.)
끓는 점	114-117 °C(lit.)
밀도	0.793 g/mL at 20 °C(lit.)
굴절률	n20/D 1.392(lit.)
인화점	34 °F
저장 조건	Inert atmosphere,2-8°C
용해도	유기용매와 섞일 수 있음.
물리적 상태	액체
비중	0.744
색상	노란색
용해도	물과 반응
BRN	1737612
안정성	수분에 민감한
InChIKey	LEIMLDGFXIOXMT-UHFFFAOYSA-N
EPA	Silanecarbonitrile, trimethyl- (7677-24-9)

화학적 성질

Trimethylsilyl cyanide (TMSCN) is a commercial reagent used as cyanide source for nucleophilic reactions. It is a clear colorless to yellow liquid, moisture sensitive, with a boiling point of 114–117 °C, which was first synthetized by the reaction of trimethylsilicon halides TMSX and AgCN in 1952.TMSCN is a versatile reagent that can be used in several different reactions, but it is generally used in nucleophilic additions to aldehydes, ketones and imines to form cyanohydrin silyl ethers (Scheme 1a) and α-aminonitriles in Strecker-type reactions (Scheme 1b).Reactions of Trimethylsilyl Cyanide

안전 및 규제

GHS 분류	DangerH225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P303+P361+P353, P304+P340, P316, P320, P321, P330, P361+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 82 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
규제 정보	Chemical: Silanecarbonitrile, trimethyl-Status: Active Update: 25-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34122Trimethylsilyl cyanide: HSNO Approval: HSR004750 Approved with controls
유해성 요약	Reacts violently with waterHighly toxic by inhalation, skin absorption, and ingestionAn irritant[MSDSonline] See NITRILES.
Hazard Classes and Categories	Flam. Liq. 2 (100%)
Treatment	Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)
건강 영향	Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)
유해 작용	Other Poison - Chemical Asphyxiant
노출 경로	Inhalation (L96)oral (L96)dermal (L96)
독성 요약	Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

용도

Reacts with aldehydes and ketones to give cyanohydrin-TMS ethers which can be reduced to β-aminoethyl alcohols.Trimethylsilyl cyanide (TMSCN) participates in carbonyl aminomethylation via α-silyloxy nitriles.TMSCN can be used as a reagent in the:Trimethylsilyl cyanide was used in the second step of an oxidative Michael addition of cyanide anion to Baylis–Hillman adducts. The importance of the addition of cyanide to α,β-unsaturated carbonyl derivatives is that the products can be converted into a variety of compounds including γ-aminobutyric acids. The reaction took place in a liquid ionic medium ([bmim]Br), which was reused several times without losing its activity. The β-cyano carbonyl compounds were obtained with high regioselectivity and yields (>79%).Cyanosilylation of carbonyl compounds using various catalysts.Synthesis of α-aminonitriles by one-pot, three-component Strecker reaction of ketones with various amines using Brønsted acid catalyst.Cyanation of aryl halides using palladium-complex as a catalyst.

제조 및 합성 방법

제조 방법

Trimethylsilyl cyanide, (CH3)3 Si-CN, is obtained by reacting trimethylsilyl chloride with an approximately equimolar amount of an alkali metal cyanide in the absence of water and in the presence of catalytic, sub-stoichiometric amounts of both an alkali metal iodide and N-methylpyrrolidone, at a temperature of from 15°-25° C. Trimethylsilyl cyanide is very toxic. All reactions in this sequence should be carried out in a hood. Preparation of trimethylsilyl cyanide TRIMETHYLSILYL CYANIDE: CYANOSILATION OF p-BENZOQUINONE