| Identification | More | [Name]
tert-Butyl 3-oxoazetidine-1-carboxylate | [CAS]
398489-26-4 | [Synonyms]
1-BOC-3-AZETIDINONE
3-OXO-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
3-OXOAZETIDINE, N-BOC PROTECTED
TERT-BUTYL 3-OXOAZETIDINE-1-CARBOXYLATE
1-Boc-azetidin-3-one
1-TERT-BUTOXYCARBONYL-3-AZETIDINONE
1-N-Boc-3-azetidinone
3-Oxoazetidine, N-BOC protected 95%
1-BOC-3-AZETIDINONE,97%
N-BOC-3-OXOAZETIDINE
1-Azetidinecarboxylic acid, 3-oxo-, 1,1-dimethylethyl ester
1-BOC-3-OXOAZETIDINE | [EINECS(EC#)]
627-725-0 | [Molecular Formula]
C8H13NO3 | [MDL Number]
MFCD01861741 | [Molecular Weight]
171.19 | [MOL File]
398489-26-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
47-51 °C | [Boiling point ]
251.3±33.0 °C(Predicted) | [density ]
1.174±0.06 g/cm3(Predicted) | [Fp ]
102 °C | [storage temp. ]
Store under inert gas | [solubility ]
Chloroform (Sparingly), Dichloromethane (Slightly) | [form ]
Crystalline Powder | [pka]
-1.99±0.20(Predicted) | [color ]
White to off-white | [Sensitive ]
Moisture Sensitive/Stench | [InChI]
InChI=1S/C8H13NO3/c1-8(2,3)12-7(11)9-4-6(10)5-9/h4-5H2,1-3H3 | [InChIKey]
VMKIXWAFFVLJCK-UHFFFAOYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CC(=O)C1 | [CAS DataBase Reference]
398489-26-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H302-H315-H318-H335 | [Precautionary statements ]
P280-P301+P312+P330-P302+P352-P305+P351+P338+P310 | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection . | [RIDADR ]
UN 3335 | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [REACH Registrations]
Inactive | [HazardClass ]
IRRITANT | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White to light brown solid | [Uses]
1-Boc-3-azetidinone can be used for the preparation of antibacterial aminoglycoside analogs.
| [General Description]
tert-Butyl 3-oxoazetidine-1-carboxylate is moisture sensitive and incompatible with oxidizing agents. This chemical can cause skin irritation and severe eye irritation. | [Synthesis]
The traditional preparation method of
tert-Butyl 3-oxoazetidine-1-carboxylate is mainly to oxidize the hydroxyl
on an aza ring into ketone. For example: 3-azetidinium alkoxide, di-tert-butyl dicarbonate and
sodium bicarbonate in dioxane: stirring the mixture of water for 15
hours to obtain 3-hydroxyazetidine-1-carboxylic acid-1, 1-dimethylethyl
ester; dissolving 3-hydroxyazetidine-1-carboxylic acid-1, 1-dimethyl
ethyl ester in ethanedioyl chloride and dichloromethane, adding DMSO and
triethylamine, stirring at room temperature for 15 hours to obtain tert-Butyl 3-oxoazetidine-1-carboxylate.
| [References]
[1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 550 - 555
[2] Journal of the American Chemical Society, 2013, vol. 135, # 42, p. 15742 - 15745
[3] Patent: US2012/35122, 2012, A1. Location in patent: Paragraph 0622; 0623
[4] Patent: WO2013/116236, 2013, A1. Location in patent: Page/Page column 28
[5] Patent: WO2013/169622, 2013, A1. Location in patent: Page/Page column 53; 54 |
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Energy Chemical
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