| Identification | More | [Name]
TERT-BUTYL PROPIOLATE | [CAS]
13831-03-3 | [Synonyms]
PROPARGYLIC ACID TERT-BUTYL ESTER
PROPIOLIC ACID TERT-BUTYL ESTER
TERT-BUTYL ACETYLENECARBOXYLATE
TERT-BUTYL PROPIOLATE
Propiolicacidbutylester
Propynoic acid tert-butyl ester | [Molecular Formula]
C7H10O2 | [MDL Number]
MFCD00060100 | [Molecular Weight]
126.15 | [MOL File]
13831-03-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
18-20 °C (lit.) | [Boiling point ]
52-53 °C/27 mmHg (lit.) | [density ]
0.919 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.418(lit.)
| [Fp ]
82 °F
| [storage temp. ]
2-8°C
| [form ]
Liquid | [color ]
Clear colorless to yellow | [Sensitive ]
Air Sensitive | [BRN ]
1747175 | [InChI]
InChI=1S/C7H10O2/c1-5-6(8)9-7(2,3)4/h1H,2-4H3 | [InChIKey]
XGTPDIIFEPTULX-UHFFFAOYSA-N | [SMILES]
C(OC(C)(C)C)(=O)C#C | [CAS DataBase Reference]
13831-03-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 3272 3/PG 3
| [WGK Germany ]
3
| [F ]
4.5-10-23 | [HazardClass ]
3.1 | [PackingGroup ]
II | [HS Code ]
29161995 |
| Hazard Information | Back Directory | [Uses]
tert-Butyl propiolate may be used in the preparation of heterocycles, alkaloids, and unsaturated amino acids. | [Uses]
TERT-BUTYL PROPIOLATE is used to prepare heterocycles,1,2 alkaloids,3 and unsaturated amino acids.4
| [General Description]
tert-Butyl propiolate is an ester. It reacts with methimazole to afford tert-butyl (E)-3-(1-methyl-1H-imidazol-2-ylthio) acrylate. Crystallographic data for the lithium enolate of tert-butyl propiolate has been described.. | [Synthesis]
General procedure for the synthesis of tert-butyl propargylate from propargyl acid and tert-butanol: About 60 g of propargyl acid, about 100 g of N,N'-dicyclohexylcarbodiimide, about 10 g of 4-(dimethylamino)pyridine, and about 20 g of tert-butanol were dissolved in tetrahydrofuran, and the reaction was stirred for about 24 hours. Upon completion of the reaction, extraction was carried out with dichloromethane and water. The extracted organic layer was dried with a chemical desiccant and subsequently purified by column chromatography to give about 80 g of tert-butyl propargylate. | [References]
[1] Patent: JP2016/533394, 2016, A. Location in patent: Paragraph 0103
[2] Organic Letters, 2018, vol. 20, # 13, p. 4023 - 4027 |
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