Vinyltrimethylsilane

HCID 79102CAS 754-05-2

Basic information

Standard SMILES
C=C[Si](C)(C)C
InChIKey
GCSJLQSCSDMKTP-UHFFFAOYSA-N
Molecular formula
C5H12Si
Average molar mass
100.23 g/mol
Monoisotopic mass
100.07082691

Overview

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)

Names & identifiers

Preferred name
Vinyltrimethylsilane
IUPAC
ethenyl(trimethyl)silane
English name
Vinyltrimethylsilane
Molecular formula
C5H12Si
Molecular weight
100.23

Names & synonyms

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

Database identifiers

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

Properties

Computed structural properties

Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
6

Experimental & physicochemical properties

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

Liquid

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

Physicochemical properties

Melting point
-132 °C · -132°C
Boiling point
55 °C · 55 °C (lit.)
Density
0.684 g/mL · 0.684 g/mL at 25 °C (lit.)
vapor pressure
4.44 psi · 4.44 psi ( 20 °C)
refractive index
20 · n20/D 1.391(lit.)
Flash point
-30 °C · <-30 °C

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Regulatory Information · 4 items

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 item

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%)

Safety & protection

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

Toxicology

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 item

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 item

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).

Safety data

PPE
Eyeshields, Faceshields, Gloves
wgk
1
tsca
TSCA listed
ridadr
UN 1993 3/PG 1
hs_code
29319090
risk_code
11-22-36/37/38-40

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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)

Uses & manufacturing

Uses · 3 items

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 items

Computer and Electronic Product Manufacturing

Silane, ethenyltrimethyl-: ACTIVE

Applications · 3 items

UsesVinyltrimethylsilane is used in semiconductor processing. It is involved in the Preparation of silyl-ethers by Rh(I) catalysis. Further, it is used in the preparation of trimethylsilylethyl sulfoxides which in the presence of fluoride ion generate sulfenate nucleophiles.

UsesPreparation of silyl-ethers by Rh(I) catalysis.1

UsesVinyltrimethylsilane 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.

Preparation methods

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

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
温州共赢化学有限公司+86-0086-577-64498589 +86-15355981851 · [email protected]

Related reactions

29 records

Linked notes

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