2-(Trimethylsilylmethyl)allyl acetate

HCID 4428347CAS 72047-94-0

Substructure search Find similar structures

Basic information

Standard SMILES: C=C(COC(C)=O)C[Si](C)(C)C
InChIKey: IKQWABMHZKGCLX-UHFFFAOYSA-N
Molecular formula: C9H18O2Si
Average molar mass: 186.32 g/mol
Monoisotopic mass: 186.10760635

Names & identifiers

Preferred name: 2-(Trimethylsilylmethyl)allyl acetate
IUPAC: 2-(trimethylsilylmethyl)prop-2-enyl acetate
English name: 2-(Trimethylsilylmethyl)allyl acetate
Molecular formula: C9H18O2Si
Molecular weight: 186.32

Names & synonyms

72047-94-02-(Trimethylsilylmethyl)allyl acetateDTXSID80403196RefChem:254973DTXCID00354050627-534-22-((Trimethylsilyl)methyl)allyl acetate2-(trimethylsilylmethyl)prop-2-enyl Acetate2-[(Acetoxymethyl)allyl]trimethylsilaneMFCD000751702-Acetoxymethyl-3-(trimethylsilyl)propene2-(Acetoxymethyl)-3-(trimethylsilyl)propene

Show more names

DK875SKL104DKSI084DKFELEX02312-(Acetoxymethyl)allyltrimethyliane2-(ACETOXYMETHYL)ALLYTRIMETHYLSILANE(2-(Ethoxymethyl)allyl)trimethylsilane[2-(ACETOXYMETHYL)ALLYL]TRIMETHYLSILANE

2-[(trimethylsilyl)methyl]prop-2-en-1-yl acetate2-[(Trimethylsilyl)methyl]allyl Acetate2-(TRIMETHYLSILYLMETHYL)ALLYLACETATE2-[(trimethylsilyl)methyl]-2-propen-1-yl acetatetridecaborondiphosphide2-((trimethylsilyl)methyl)-2-propen-1-yl acetate2-((trimethylsilyl)methyl)prop-2-en-1-yl acetate2-(acetoxymethyl)-3-(trimethylsilyl)-1-propene

Database identifiers

CAS: 72047-94-0
PubChem CID: 4428347
DTXSID: DTXSID80403196
EC Number: 627-534-2
Nikkaji: J582.191F

Properties

Computed structural properties

Topological polar surface area: 26.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 5
Heavy atoms: 12
Formal charge: 0
Complexity: 179

Physicochemical properties

Boiling point: 95 °C7 · 95 °C7 mm Hg(lit.)
Density: 0.877 g/mL · 0.877 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.440(lit.)
Flash point: 160 °F · 160 °F
storage temp.: 2 · Inert atmosphere,2-8°C
solubility: Solubility most organic solvents.
form: Liquid
color: Clear colorless
Water Solubility: reacts
BRN: 1933657 · 1933657
InChI: InChI=1S/C9H18O2Si/c1-8(6-11-9(2)10)7-12(3,4)5/h1,6-7H2,2-5H3
InChIKey: IKQWABMHZKGCLX-UHFFFAOYSA-N
SMILES: C(OC(=O)C)C(C[Si](C)(C)C)=C
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38-14
Safety Statements: 26 · 26-36/37/39-37/39
WGK Germany: 3 · 3
HS Code: 29319090 · 29319090

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

wgk: 3
hs_code: 29319090
risk_code: 36/37/38-14
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36/37/39-37/39
Hazard statements: H315-H319-H335
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications

Uses2-[(Acetoxymethyl)allyl]trimethylsilane was used in the cyclopentane synthesis via Pd(0)-catalyzed reactions with 2π acceptors.

Usesprecursor for palladium trimethylenemethane cycloaddition reactions.

Preparation methods

Preparationcommercially available but expensive. Several preparations of (1) or the precursor alcohol (2) have been reported. The simplest involves the direct silylation of methallyl alcohol (eq 1).