methyl 3-[(trimethylsilyl)oxy]but-2-enoate

• ChemBase ID: 134497
• Molecular Formular: C8H16O3Si
• Molecular Mass: 188.29634
• Monoisotopic Mass: 188.0868709
• SMILES: C/C(=C\C(=O)OC)/O[Si](C)(C)C
• Canonical SMILES: COC(=O)/C=C(/O[Si](C)(C)C)\C
• InChI: InChI=1S/C8H16O3Si/c1-7(6-8(9)10-2)11-12(3,4)5/h6H,1-5H3
• InChIKey: OQNKCUVOGBTGDJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 3-[(trimethylsilyl)oxy]but-2-enoate; methyl (2E)-3-[(trimethylsilyl)oxy]but-2-enoate
• IUPAC Traditional name: methyl 3-[(trimethylsilyl)oxy]but-2-enoate; methyl (2E)-3-[(trimethylsilyl)oxy]but-2-enoate
• Synonyms: 3-Trimethylsiloxy-2-butenoic acid methyl ester; Methyl 3-(trimethylsiloxy)crotonate; Methyl acetoacetate enol trimethylsilylether; Methyl 3-trimethylsiloxy-2-butenoate; Methyl 3-(trimethylsilyloxy)crotonate, mixture of cis and trans; 3-(三甲基硅氧基)丁烯酸甲酯; 3-三甲基硅氧基-2-丁烯酸甲基酯; 乙酰乙酸甲酯烯醇三甲基硅基醚; 3-三甲基硅氧基-2-丁烯酸甲酯; 3-(三甲基硅氧基)丁烯酸甲酯，顺式和反式混合物

Database IDs

• CAS Number: 62269-44-7; 26767-00-0
• EC Number: 263-483-9
• MDL Number: MFCD00008457
• Beilstein Number: 2356944
• PubChem SID: 24889698; 162228773; 24853402
• PubChem CID: 6115690

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.9151
• LogD (pH = 7.4): 1.9151
• Log P: 1.9151
• Molar Refractivity: 45.9832 cm^3
• Polarizability: 19.636827 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 43-45 °C/0.3 mmHg(lit.); 57-59 °C/9 mmHg(lit.)
• Flash Point: 138.2 °F; 147.2 °F; 59 °C; 64 °C
• Density: 0.939 g/mL at 25 °C(lit.); 0.966 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.444(lit.); n20/D 1.447

Safety Information

• European Hazard Symbols: Irritant (Xi)
• UN Number: 3272
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 10; 36/37/38
• Safety Statements: 26-36/37/39
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3272 3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ~86% (trans + ~10% cis); 97%
• Grade: technical
• Linear Formula: CH3C[OSi(CH3)3]=CHCO2CH3
• Empirical Formula (Hill Notation): C8H16O3Si

DETAILS

Sigma Aldrich - 92733

Other Notes
Mild and efficient silylating agent1; Starting material to 1-methoxy-1,3-bis(trimethylsiloxy)butadiene; a diene for Diels-Alder reactions and an equivalent of the dianien of methyl acetoacetate2,3,4
Packaging
50 mL in glass bottle

Sigma Aldrich - 223751

Packaging
10 g in glass bottle