| Identification | Back Directory | [Name]
TERT-BUTYL METHYL MALONATE | [CAS]
42726-73-8 | [Synonyms]
TERT-BUTYL METHYL MA
T-BUTYL METHYL MALONATE
TERT-BUTYL METHYL MALOTE
TERT-BUTYL-(METHYLMALONAT)
TERT-BUTYL METHYL MALONATE
Methyl tert-butyl malonate
tert.-Butyl methylemalonate
tert.-Butyl methyl malonate,95%
tert.-Butyl Methyl Malonate, 95% 5ML
Malonic acid tert-butyl methyl ester
Malonic acid 1-methyl 3-tert-butyl ester
Malonic acid 1-tert-butyl 3-methyl ester
Propanedioic acid 1,1-dimethylethyl methyl ester
Propanedioic acid 1-(1,1-dimethylethyl)3-methyl ester | [EINECS(EC#)]
255-919-1 | [Molecular Formula]
C8H14O4 | [MDL Number]
MFCD00042856 | [MOL File]
42726-73-8.mol | [Molecular Weight]
174.19 |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to slightly yellow liquid | [Melting point ]
-10 °C
| [Boiling point ]
80 °C11 mm Hg(lit.)
| [density ]
1.03 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.415(lit.)
| [Fp ]
175 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Liquid | [pka]
11.83±0.46(Predicted) | [color ]
Clear colorless to slightly yellow | [BRN ]
1772136 | [InChI]
InChI=1S/C8H14O4/c1-8(2,3)12-7(10)5-6(9)11-4/h5H2,1-4H3 | [InChIKey]
XPSYZCWYRWHVCC-UHFFFAOYSA-N | [SMILES]
C(OC(C)(C)C)(=O)CC(OC)=O |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to slightly yellow liquid | [General Description]
tert-Butyl methyl malonate is an ester. Stereospecific Pd(O)-catalyzed addition of tert-butyl methyl malonate to allylic carbonates is reported. | [Synthesis]
To a 200 mL round bottom flask equipped with a magnetic stirrer was added mono-tert-butyl malonate (3.0 g, 18.7 mmol) and methanol (70 mL). To this solution was added hafnium(IV) chloride tetrahydrofuran complex (1:2) (88 mg, 0.19 mmol). The reaction mixture was stirred at room temperature for 48 hours. After completion of the reaction, saturated saline was added to the mixture and extracted with dichloromethane (3 x 70 mL). The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate = 50:50) to afford the target compound tert-butyl methyl malonate (3.0 g, 91% yield) as a colorless oily liquid.1H NMR (400 MHz, CDCl3) δ 3.74 (s, 3H), 3.30 (s, 2H), 1.47 (s, 9H); 13C NMR ( 100 MHz, CDCl3) δ 167.5, 165.8, 82.1, 52.3, 42.7, 27.9; HR-FAB MS m/z calculated value C8H15O4 [M+H]+ 175.0883, measured value 175.0875. | [References]
[1] Tetrahedron Asymmetry, 2015, vol. 26, # 4, p. 214 - 218 |
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