| Identification | More | [Name]
3-tert-Butoxy-3-oxopropanoic acid | [CAS]
40052-13-9 | [Synonyms]
MALONIC ACID MONO-TERT-BUTYL ESTER
MONO-TERT-BUTYL MALONATE
TERT-BUTYL MALONATE
3-(tert-Butoxy)-3-oxopropanoic acid
Propanedioic acid mono(1,1-dimethylethyl) ester
tert-Butyl hydrogen malonate, 97% | [EINECS(EC#)]
628-204-0 | [Molecular Formula]
C7H12O4 | [MDL Number]
MFCD00191886 | [Molecular Weight]
160.17 | [MOL File]
40052-13-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
19-20 °C (lit.) | [Boiling point ]
90 °C/2 mmHg (lit.) | [density ]
1.04 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.426(lit.)
| [Fp ]
195 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Soluble in ethanol. | [form ]
Liquid | [pka]
2.92±0.32(Predicted) | [color ]
Clear colorless | [BRN ]
1765457 | [InChI]
InChI=1S/C7H12O4/c1-7(2,3)11-6(10)4-5(8)9/h4H2,1-3H3,(H,8,9) | [InChIKey]
NGGGZUAEOKRHMA-UHFFFAOYSA-N | [SMILES]
C(OC(C)(C)C)(=O)CC(O)=O | [CAS DataBase Reference]
40052-13-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS06 | [Signal word ]
Danger | [Hazard statements ]
H314-H330 | [Precautionary statements ]
P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338 | [Hazard Codes ]
T | [Risk Statements ]
R26:Very Toxic by inhalation.
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2922 8/PG 3
| [WGK Germany ]
3
| [REACH Registrations]
Active | [HazardClass ]
8, 6.1 | [PackingGroup ]
Ⅲ | [HS Code ]
29171900 | [Storage Class]
6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | [Hazard Classifications]
Acute Tox. 2 Inhalation
Skin Corr. 1B |
| Hazard Information | Back Directory | [Chemical Properties]
Clear light yellow liquid | [Uses]
tert-Butyl hydrogen malonate may be used in the preparation of dendritic precursor to asymmetric methanofullerenes, hapten-3,6-(O,S-dimethylthiophosphoramido)-6-oxohexanoic acid, hapten-4,3-(O,S-dimethylthiophosphoramido)-3-oxopropanoic acid. | [General Description]
Mono-tert-Butyl malonates is an ester. It is reported to be an aminoacylase inhibitor. Preparation of mono-tert-Butyl malonates has been described. | [Synthesis]
1. Malonic acid (5.0 g, 48 mmol) and tert-butanol (1.8 mL, 19 mmol) were dissolved in 150 mL of acetonitrile (ACN) under nitrogen protection and stirred at room temperature.
2. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC, 9.2 g, 48 mmol) was added and the reaction was continued for 30 minutes at room temperature under nitrogen atmosphere.
3. After completion of the reaction, acetonitrile was removed by distillation under reduced pressure.
4. The residue was dissolved in 200 mL of ether and back-extracted with two 50 mL portions of saturated sodium bicarbonate (NaHCO3) solution.
5. The aqueous phases were combined and acidified to pH 2 with 1N sodium bisulfate solution.
6. Extract the acidified aqueous phase with three 200 mL portions of dichloromethane (DCM) and combine the organic phases.
7. Wash the combined organic phases with water and saturated saline in turn, and then dry with anhydrous sodium sulfate.
8. Dichloromethane was removed by pressure-reduced distillation to give monotert-butyl malonate as a white solid product in 76% (2.3 g) yield. 9.
9. The product was characterized by 1H NMR (CDCl3, 400 MHz): δ 3.28 (s, 2H), 1.42 (s, 9H); 13C NMR (CDCl3, 100 MHz): δ 168.5, 162.1, 83.5, 39.7, 27.9, 27.8, 25.6. | [References]
[1] Journal of Organic Chemistry, 2018, vol. 83, # 3, p. 1116 - 1133
[2] Patent: WO2018/144880, 2018, A1. Location in patent: Paragraph 72-73
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 17, p. 5273 - 5281
[4] Patent: US2006/211634, 2006, A1. Location in patent: Page/Page column 15
[5] Organic and Biomolecular Chemistry, 2008, vol. 6, # 19, p. 3561 - 3572 |
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