Trimethylvinylsilan

Vinyltrimethylsilane

HCID 79102CAS 754-05-2

Grundinformationen

Standard-SMILES
C=C[Si](C)(C)C
InChIKey
GCSJLQSCSDMKTP-UHFFFAOYSA-N
Summenformel
C5H12Si
Durchschnittliche Molmasse
100,23 g/mol
Monoisotopische Masse
100,07082691

Überblick

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)

Namen und Bezeichner

Bevorzugter Name
Vinyltrimethylsilane
IUPAC
ethenyl(trimethyl)silane
Lokaler Name
Trimethylvinylsilan
Englischer Name
Vinyltrimethylsilane
Summenformel
C5H12Si
Molmasse
100.23

Namen und Synonyme

Vinyltrimethylsilane754-05-2trimethyl(vinyl)silaneEthenyltrimethylsilaneTrimethylvinylsilaneSilane, ethenyltrimethyl-Nysted Reagent(Trimethylsilyl)ethyleneSilane, trimethylvinyl-ethenyl(trimethyl)silaneVinyl trimethylsilane41114-59-4
Weitere Namen anzeigen
VinyltrimethysilaneDK385CH2=CHSi(CH3)3Trimethylsilyletheneethenyltrimethyl-silansilane,trimethylvinyl-(Trimethylsilyl)ethene
H5HJ2RET1NC5H12SiMFCD00008606EINECS 212-042-9UNII-H5HJ2RET1NNSC 93553NSC-93553s22050

Datenbank-Bezeichner

CAS
754-05-2
PubChem CID
79102
DTXSID
DTXSID1061071
UNII
H5HJ2RET1N
EC Number
212-042-9
Nikkaji
J120.971J

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
1
Schwere Atome
6

Experimentelle und physikochemische Eigenschaften

Chemical ClassesMetals -> Metalloid Compounds (Silicon)
SpringerMaterials Properties29Si nuclear magnetic resonance spectrum
Physical Description · 2 Einträge

Liquid

Clear liquid with an unpleasant odor; [Air Products MSDS]

Physikochemische Eigenschaften

Schmelzpunkt
-132 °C · -132°C
Siedepunkt
55 °C · 55 °C (lit.)
Dichte
0.684 g/mL · 0.684 g/mL at 25 °C (lit.)
Dampfdruck
4.44 psi · 4.44 psi ( 20 °C)
Brechungsindex
20 · n20/D 1.391(lit.)
Flammpunkt
-30 °C · <-30 °C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Regulatory Information · 4 Einträge

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 · 1 Eintrag

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]

Hazard Classes and CategoriesFlam. Liq. 2 (100%)

Sicherheit und Schutzausrüstung

Minimum Risk LevelIntermediate Oral: 0.3 mg/kg/day (L134) Chronic Oral: 0.3 mg/kg/day (L134)

Toxikologische Informationen

TreatmentZinc poisoning is treated symptomatically, often by administering fluids such as water or milk, or with gastric lavage. (L49)
Health EffectsChronic exposure to zinc causes anemia, atazia, lethargy, and decreases the level of good cholesterol in the body. It is also believed to cause pancreatic and reproductive damage. (L49)
Exposure RoutesOral (L49) ; inhalation (L49) ; dermal (L49)
Toxicity Summary · 1 Eintrag

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 · 1 Eintrag

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)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

wgk
1
tsca
TSCA listed
ridadr
UN 1993 3/PG 1
hs_code
29319090
risk_code
11-22-36/37/38-40
hazard_code
F,Xn

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

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)

Verwendung und Herstellung

Uses · 3 Einträge

Used in semiconductor processing; [Air Products MSDS]

Semiconductor Manufacturing [Category: Industry]

Nysted reagent is used for the olefination of ketones and aldehydes. (L536)

U.S. Production2023: <50,000 lb
Industry UsesIntermediate
General Manufacturing Information · 2 Einträge

Computer and Electronic Product Manufacturing

Silane, ethenyltrimethyl-: ACTIVE

Anwendungen · 1 Eintrag

VerwendenVinyltrimethylsilane 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.

Darstellung

synthetischePrepared in 67–91% yield from vinylmagnesium bromide and chlorotrimethylsilane in THF.

Anbieter50 Anbieter

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