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トリメチルシリルシアニド

Trimethylsilyl cyanide

HCID 82115
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
7677-24-9
標準SMILES
C[Si](C)(C)C#N
InChIKey
LEIMLDGFXIOXMT-UHFFFAOYSA-N
分子式
C4H9NSi
平均分子量
99.21 g/mol
単同位体質量
99.05042582

概要

Trimethylsilyl cyanide is a chemical compound of cyanide. It is used in organic synthesis. (L106)

名称と識別子

優先名称
Trimethylsilyl cyanide
IUPAC
trimethylsilylformonitrile
現地名
トリメチルシリルシアニド
英語名
Trimethylsilyl cyanide
分子式
C4H9NSi
分子量
99.21

名称と別名

Trimethylsilyl cyanide7677-24-9TrimethylsilanecarbonitrileSilanecarbonitrile, trimethyl-TrimethylsilylnitrileTMSCNTrimethylsilylcarbonitrileDTXSID9064766RefChem:899908DTXCID4047915231-657-3Cyanotrimethylsilane
名称をさらに表示
トリメチルシリルシアニドトリメチル(シアノ)シラン(トリメチルシラン)カルボニトリルトリメチルシアノシラントリメチルシランカルボニトリルトリメチルシリルカルボニトリル(トリメチルシリル)シアニドシアノトリメチルシラントリメチルシリル シアニドシアン化トリメチルシリル ケイ素シアン化トリメチルシリル シアノトリメチルシラン ケイ素シアン化トリメチルシリルトリメチルシリルニトリルトリメチルシリルシアナイドtrimethylsilylmethanenitrileDK897TrimethylsilanecarTrimethyl cyanogen
TrimethylsilylcyanidetrimethylsilylformonitriletrimethylcyanosilaneC4H9NSiMFCD00001765trimethylsilane carbonitrileTrimethylsilylCyanide-13C,15NTMS cyanide

データベース識別子

CAS
7677-24-9
PubChem CID
82115
DTXSID
DTXSID9064766
UNII
X7M2DZS7WZ
EC Number
231-657-3
Nikkaji
J81.438E

物性

構造計算による物性補完中

極性表面積
23.8 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
0
重原子数
6
形式電荷
0
複雑度
81.5

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Nitriles
SpringerMaterials Properties29Si nuclear magnetic resonance spectrum
Physical DescriptionColorless liquid; mp = 11-12 deg C; [MSDSonline]

物理化学的性質

融点
8 · 8-11 °C(lit.)
沸点
114 · 114-117 °C(lit.)
比重(密度)
0.793 g/mL · 0.793 g/mL at 20 °C(lit.)
屈折率
20 · n20/D 1.392(lit.)
闪点
34 °F · 34 °F
貯蔵温度
2 · Inert atmosphere,2-8°C
溶解性
有機溶剤と混和します。
外見
液体
比重
0.744 · 0.744
色
黄色
水溶解度
反応する
BRN
1737612 · 1737612
安定性
湿気に敏感
InChIKey
LEIMLDGFXIOXMT-UHFFFAOYSA-N
CAS データベース

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H225 (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.

危険有害性情報

Regulatory Information · 3 件

Chemical: Silanecarbonitrile, trimethyl-

Status: Active Update: 25-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34122

Trimethylsilyl cyanide: HSNO Approval: HSR004750 Approved with controls

Hazards SummaryReacts violently with water; Highly toxic by inhalation, skin absorption, and ingestion; An irritant; [MSDSonline] See NITRILES.
Hazard Classes and CategoriesFlam. Liq. 2 (100%)

毒性情報

Treatment · 1 件

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)

Health Effects · 1 件

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)

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

用途と製造

UsesTrimethylsilyl cyanide is used in organic synthesis. (L106)
General Manufacturing InformationSilanecarbonitrile, trimethyl-: ACTIVE
応用分野 · 3 件

解説シアノトリメチルシラン，trimethylsilyl cyanide．C4H9NSi(99.21)．(CH3)3SiCN．クロロトリメチルシランとシアン化カリウム，あるいはシアン化銀との反応により得られる．無色の液体．沸点117 ℃．d20D0.7834．n26D1.389．引火性がある．有毒．カルボニル化合物に付加し，シアノヒドリンのシリルエーテルを与える．そのほか，アルケンのシアノシリル化，キノンの保護，ニトリル合成など，合成試薬として用いられる．

用途医薬、電子材料。

使用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.

関連反応

1,368 件
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HRID 7150 の反応式
HRID 7150反応物としてuspto-grants-2006_08
HRID 7694 の反応式
HRID 7694反応物としてuspto-grants-2006_08
HRID 28376 の反応式
HRID 28376反応物としてuspto-grants-2008_09
HRID 44133 の反応式
HRID 44133反応物としてuspto-grants-2013_09
HRID 49912 の反応式
HRID 49912反応物としてuspto-grants-2004_03
HRID 51215 の反応式
HRID 51215反応物としてuspto-grants-2004_03
1 / 171 ページ

化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
7677 · 7677-24-9(CAS DataBase Reference)
EPAの化学物質情報
Silanecarbonitrile, trimethyl- (7677-24-9)
化学的性質 · 1 件

化学的特性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

Adverse EffectsOther Poison - Chemical Asphyxiant
Exposure RoutesInhalation (L96) ; oral (L96) ; dermal (L96)
Toxicity Summary · 1 件

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)

Signs and SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

F
10-21
wgk
3
tsca
TSCA listed
ridadr
UN 3384 6.1/PG 1
hs_code
29310095
risk_code
11-26/27/28-29-50/53
消防法
危-4-1-II
hazard_code
F,T+,T,N
hazard_note
Highly Flammable/Toxic
safety_code
16-36/37/39-45-61-28A-26
hazard_class
6.1
packing_group
II
毒劇物取締法
劇物
調製方法 · 2 件

製造方法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

純化方法The material should have only one sharp signal in the 1H NMR (in CCl4 with CHCl3 as internal standard) : 0.4ppm and IR with max at 2210cm1 [McBride & Beachall J Am Chem Soc 74 5247 1952, Prober J Am Chem Soc 77 3224 1955]; otherwise purify it by fractionating through an 18 x 1/4inch column. [Evers et al. J Am Chem Soc 81 4493 1959.] It has also been carefully distilled using a 60cm vacuum jacketed column. If the volume of sample is small, the cyanide can be chased (in the distillation) with xylene that had been previously distilled over P2O5. It is HIGHLY TOXIC and FLAMMABLE. [Evans et al. J Org Chem 39 914 1974, Beilstein 4 IV 3893.]

上流・下流製品情報

上流原料

アセトニトリル1-メチル-2-ピロリドンヨウ化カリウムクロロトリメチルシランよう化ナトリウムピリジンシアン化カリウム

下流製品

8-ヒドロキシ-2-キノリンカルボン酸4-AMINOMETHYL-PYRIDINE-2-CARBOXYLIC ACID2-シアノイソニコチン酸3-(TERT-BUTOXYCARBONYLAMINO-METHYL)-PYRIDINE-2-CARBOXYLIC ACID3-クロロピラジン-2-カルボニトリル4-メチルピリジン-2-カルボン酸3-フェnオキシベンズアルデヒド シアノhydrin3-クロロ-2-シアノピリジン8‐ヒドロキシキノリン‐2‐カルボニトリル3-AMINOMETHYL-PYRIDINE-2-CARBOXYLIC ACID4-[(TERT-BUTOXYCARBONYLAMINO)METHYL]-2-CYANOPYRIDINEビニルホスホン酸ジエチル(ジエチルアミノ)サルファートリフルオリド2-CYANOPYRIDINE-4-CARBOXALDEHYDEピバロニトリル4-[(tert-ブトキシカルボニルアミノ)メチル]-2-ピリジンカルボン酸β-4,5-dibenzoyl-2-cyano-D-deoxyribrate1-Pyrrolidinecarboxylicacid,2-cyano-,methylester(9CI)4-(HYDROXYMETHYL)PICOLINITRILEETHYL 2-CYANOPYRIDINE-4-CARBOXYLATE7-CHLOROISOQUINOLINE-1-CARBONITRILEMETHYL 7-AMINOTHIENO[2,3-B]PYRAZINE-6-CARBOXYLATE