基本情報
- 標準SMILES
C=C[Si](C)(C)C- InChIKey
GCSJLQSCSDMKTP-UHFFFAOYSA-N- 分子式
- C5H12Si
- 平均分子量
- 100.23 g/mol
- 単同位体質量
- 100.07082691
概要
Nysted reagent is a chemical compound containing zinc. It is used for the olefination of ketones and aldehydes. Zinc is a metallic element with the atomic number 30. It is found in nature most often as the mineral sphalerite. Though excess zinc in harmful, in smaller amounts it is an essential element for life, as it is a cofactor for over 300 enzymes and is found in just as many transcription factors. (L48, L49, L536)
名称と識別子
- 優先名称
- Vinyltrimethylsilane
- IUPAC
- ethenyl(trimethyl)silane
- 現地名
- ビニルトリメチルシラン
- 英語名
- Vinyltrimethylsilane
- 分子式
- C5H12Si
- 分子量
- 100.23
名称と別名
名称をさらに表示
データベース識別子
- CAS
754-05-2- PubChem CID
- 79102
- DTXSID
DTXSID1061071- UNII
- H5HJ2RET1N
- EC Number
- 212-042-9
- Nikkaji
- J120.971J
物性
構造計算による物性
- 極性表面積
- 0 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 0
- 回転可能結合数
- 1
- 重原子数
- 6
- 形式電荷
- 0
- 複雑度
- 49.4
実験および物理化学的性質
Physical Description
Liquid
Clear liquid with an unpleasant odor; [Air Products MSDS]
物理化学的性質
- 融点
- -132 °C · -132°C
- 沸点
- 55 °C · 55 °C (lit.)
- 比重(密度)
- 0.684 g/mL · 0.684 g/mL at 25 °C (lit.)
- 蒸気圧
- 4.44 psi · 4.44 psi ( 20 °C)
- 屈折率
- 20 · n20/D 1.391(lit.)
- 闪点
- -30 °C · <-30 °C
- 貯蔵温度
- 2 · Inert atmosphere,2-8°C
- 溶解性
- テトラヒドロフラン、ジエチルエーテル、ベンゼン、ジクロロメタンと混和します。
- 外見
- 液体
- 比重
- 0.6903 · 0.6903
- 色
- Colorless to Almost colorless
- BRN
- 956572 · 956572
- InChI
- 1S/C5H12Si/c1-5-6(2,3)4/h5H,1H2,2-4H3
- InChIKey
- GCSJLQSCSDMKTP-UHFFFAOYSA-N
- SMILES
- C[Si](C)(C)C=C
- CAS データベース
- 754 · 754-05-2(CAS DataBase Reference)
- NISTの化学物質情報
- Silane, ethenyltrimethyl-(754-05-2)
- EPAの化学物質情報
- Silane, ethenyltrimethyl- (754-05-2)
化学的性質
化学的特性clear colourless liquid
安全と法規制
GHS分類
GHS Classification
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 73 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Chemical: Silane, ethenyltrimethyl-
Silane, ethenyltrimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Silane, ethenyltrimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 26-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21677
Trimethylvinylsilane: HSNO Approval: HSR006887 Approved with controls
Hazards Summary
Flammable; A mild irritant; May decompose to form flammable or explosive mixtures with air; Lethal-dose study of rats at 2,000 mg/kg produced diarrhea on the day of administration and no deaths; Lethal-concentration study of rats at 20,030 mg/m3 (4,886 ppm) caused no clinical signs of toxicity or irritation and no deaths; [Air Products MSDS] May contain up to 3% tetrahydrofuran (with BHT inhibitor) as residual impurity of production; Highly flammable; An irritant; Harmful by ingestion; Targets kidneys, liver, and CNS; [Aldrich MSDS]
安全と保護具
毒性情報
Toxicity Summary
Anaemia results from the excessive absorption of zinc suppressing copper and iron absorption, most likely through competitive binding of intestinal mucosal cells. Unbalanced levels of copper and zinc binding to Cu,Zn-superoxide dismutase has been linked to amyotrophic lateral sclerosis (ALS). Stomach acid dissolves metallic zinc to give corrosive zinc chloride, which can cause damage to the stomach lining. Metal fume fever is thought to be an immune response to inhaled zinc. (L48, L49, A49)
Signs and Symptoms
Ingestion of large doses of zinc causes stomach cramps, nausea, and vomiting. Acute inhalation of large amounts of zinc causes metal fume fever, which is characterized by chills, fever, headache, weakness, dryness of the nose and throat, chest pain, and coughing. Dermal contact with zinc results in skin irritation. (L49)
安全データ
- wgk
- 1
- tsca
- TSCA listed
- ridadr
- UN 1993 3/PG 1
- hs_code
- 29319090
- risk_code
- 11-22-36/37/38-40
- 化審法
- (2)-4007
- 消防法
- 危-4-1-II
- hazard_code
- F,Xn
- safety_code
- 16-26-33-36-36/37/39-36/37
- hazard_class
- 3
- packing_group
- II
- Hazard Classifications
- Carc. 2Eye Irrit. 2Flam. Liq. 2Skin Irrit. 2
- ストレージクラス
- 3 - Flammable liquids
化学と産業
薬理情報
Metabolism/Metabolites
Zinc can enter the body through the lungs, skin, and gastrointestinal tract. Intestinal absorption of zinc is controlled by zinc carrier protein CRIP. Zinc also binds to metallothioneins, which help prevent absorption of excess zinc. Zinc is widely distributed and found in all tissues and tissues fluids, concentrating in the liver, gastrointestinal tract, kidney, skin, lung, brain, heart, and pancreas. In the bloodstream zinc is found bound to carbonic anhydrase in erythrocytes, as well as bound to albumin, _2-macroglobulin, and amino acids in the the plasma. Albumin and amino acid bound zinc can diffuse across tissue membranes. Zinc is excreted in the urine and faeces. (L49)
用途と製造
Uses
Used in semiconductor processing; [Air Products MSDS]
Semiconductor Manufacturing [Category: Industry]
Nysted reagent is used for the olefination of ketones and aldehydes. (L536)
General Manufacturing Information
Computer and Electronic Product Manufacturing
Silane, ethenyltrimethyl-: ACTIVE
応用分野
使用Vinyltrimethylsilane is ethylene equivalent in electrophilic substitution reactions; precursor to 3-trimethylsilyl-3-buten-2-one, a methyl vinyl ketone surrogate for Robinson annulations; homologation of aldehydes to α,β-unsaturated aldehydes. It takes part in the reactions of Synthesis of Vinyl Aryl Sulfides, Synthesis of 3-Triethylsilyl-3-buten-2-one, Synthesis of α,β-Unsaturated Primary Amides, Synthesis of α,β-Unsaturated Aldehydes, Synthesis of Bicyclopentenones, Synthesis of 1-Chlorocyclopropene, Radical Addition Reactions of Vinyltrimethylsilane, Reaction of Vinyltrimethylsilane with 2-Azaallylanions, Regioselective Hydroesterification of Vinyltrimethylsilane, 3 + 2 Cycloaddition of Vinyltrimethylsilane with Nitrones, Addition of α-Iodo-α,α-Difluoroketones to Vinyltrimethylsilane, Addition of α-Iodosulfones to Vinyltrimethylsilane, Titanium-mediated Formation of Trimethylsilylcyclopropanols, β-Trimethylsilyl Ketones and Cyclopropenes, Hydrogen Acceptor Catalyst in the Conversion of Alcohols to Hydrogenated Wittig Adducts, Formation of 2-Trimethylsilylaziridines, Formation of Sulfonyl Chlorides, Improved Synthesis of 2-Trimethylsilylethylsulfonyl Chloride, Formation of an Iron Carbonyl Trienone Complex, Synthesis of 2-Phenyl-2-Trimethylsilylethanol, Synthesis of 2-Vinylanilines, Decarbonylative Vinylation of an Aromatic Ester, Asymmetric Epoxidation of Vinyltrimethylsilane, Direct Silylation of Heteroarylcarbonyl Compounds, Trimethylsilylation of Vinylboronates, etc.
調製方法
製造方法Prepared in 67–91% yield from vinylmagnesium bromide and chlorotrimethylsilane in THF.
純化方法If the 1H NMR spectrum shows impurities, then dissolve it in Et2O, wash it with aqueous NH4Cl solution, dry over CaCl2, filter, evaporate and distil it at atmospheric pressure in an inert atmosphere. It is used as a co-polymer and may polymerise in the presence of free radicals. It is soluble in CH2Cl2. [Nagel & Post J Org Chem 17 1379 1952, Beilstein 4 IV 3922.]
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