| Identification | Back Directory | [Name]
ETHYL 2-(TRIMETHYLSILYLMETHYL)ACRYLATE | [CAS]
74976-84-4 | [Synonyms]
2-Ethoxycarbonylallyltrimethylsilane
ETHYL 2-(TRIMETHYLSILYLMETHYL)ACRYLATE
ETHYL 2-(TRIMETHYLSILYLMETHYL)PROPENOATE
2-(TRIMETHYLSILYLMETHYL)ACRYLIC ACID ETHYL ESTER
2-Propenoic acid, 2-[(trimethylsilyl)methyl]-, ethyl ester
2-(Trimethylsilylmethyl)acrylic acid ethyl ester, Ethyl 2-(trimethylsilylmethyl)propenoate | [Molecular Formula]
C9H18O2Si | [MDL Number]
MFCD00075508 | [MOL File]
74976-84-4.mol | [Molecular Weight]
186.32 |
| Chemical Properties | Back Directory | [Boiling point ]
70-72 °C/10 mmHg (lit.) | [density ]
0.897 g/mL at 25 °C (lit.) | [refractive index ]
n20/D 1.438(lit.) | [Fp ]
140 °F | [storage temp. ]
2-8°C | [form ]
liquid | [BRN ]
4658894 | [InChI]
1S/C9H18O2Si/c1-6-11-9(10)8(2)7-12(3,4)5/h2,6-7H2,1,3-5H3 | [InChIKey]
HSEYTIDQGJXPIF-UHFFFAOYSA-N | [SMILES]
CCOC(=O)C(=C)C[Si](C)(C)C |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-36 | [RIDADR ]
1993 | [WGK Germany ]
3 | [F ]
10-21 | [HazardClass ]
3.2 | [PackingGroup ]
III | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
2-Ethoxycarbonylallyltrimethylsilane is used for 2-ethoxycarbonylallylation of aldehydes and acetals; the allylation products are useful precursors to α-
methylene-γ-butyrolactones; precursor of allyl cation equivalents for [3 + 2] and [3 + 4] cycloadditions. | [Preparation]
Preparative Methods of 2-Ethoxycarbonylallyltrimethylsilane: a three-step synthesis from Diethyl Malonate has been reported. t-Butyl and
trimethylsilyl esters are also prepared by this method. Syntheses from ethyl diethylphosphonoacetate and
ethyl α-bromoacrylate also have been reported, but the simplest procedure involves the reaction of
ethoxalyl chloride with two equivalents of Trimethylsilylmethylmagnesium Chloride followed by
treatment with Thionyl Chloride (53% yield). The CeIII-mediated reaction of
trimethylsilylmethylmagnesium chloride with Diethyl Oxalate is also reported to give 2-
ethoxycarbonylallyltrimethylsilane in 45% yield. | [storage]
2-Ethoxycarbonylallyltrimethylsilane can be stored in a glass bottle. |
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