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398489-26-4

Basic Information
CAS No.: 398489-26-4
Name: tert-Butyl 3-oxoazetidine-1-carboxylate
Article Data: 37
Molecular Structure:
Molecular Structure of 398489-26-4 (tert-Butyl 3-oxoazetidine-1-carboxylate)
Formula: C8H13NO3
Molecular Weight: 171.196
Synonyms: 1-Azetidinecarboxylicacid, 3-oxo-, 1,1-dimethylethyl ester;1-(tert-Butoxycarbonyl)-3-oxoazetidine;1-tert-Butoxycarbonyl-3-azetidinone;3-Oxoazetidine-1-carboxylic acid tert-butyl ester;tert-Butyl3-oxoazetidine-1-carboxylate;
EINECS: 627-725-0
Density: 1.174 g/cm3
Melting Point: 49-52 °C
Boiling Point: 251.3 °C at 760 mmHg
Flash Point: 105.8 °C
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-37/38-41
Safety: 26-39
PSA: 46.61000
LogP: 0.74410
Synthetic route
141699-55-0

tert-butyl 3-hydroxyazetidine-1-carboxylate

398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide In acetonitrile at 0 - 20℃; for 18h; Inert atmosphere; Molecular sieve;99%
With 1-methyl-1H-imidazole; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 4,4'-Dimethoxy-2,2'-bipyridin; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen In acetonitrile at 20℃; for 0.5h; Time;98%
With pyridine-SO3 complex; triethylamine In dimethyl sulfoxide at 10 - 20℃; Inert atmosphere;95%
20599-01-3

1,3-dibromoacetone ethylene glycol

4248-19-5

tert-butyl carbamate

398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane at 50℃; for 16h; Reagent/catalyst; Solvent; Temperature;92%

1-tert-butoxycarbonyl-3,3-dimethoxyazetidine

398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
With citric acid In water; ethyl acetate at 20 - 40℃;85.4%
24424-99-5

di-tert-butyl dicarbonate

3,3-dimethoxyazetidine

398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 10 - 40℃;80.2%
24424-99-5

di-tert-butyl dicarbonate

398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / tetrahydrofuran / 1 h / 20 °C
2: triethylamine / sulfur trioxide pyridine complex / chloroform; dimethyl sulfoxide / 4 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / 1,4-dioxane; water / 15 h / 20 °C
2: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 15 h / -78 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / ethanol / 16 h / 0 - 20 °C
2: pyridine-SO3 complex; triethylamine / dimethyl sulfoxide / 10 - 20 °C / Inert atmosphere
View Scheme
141699-55-0

tert-butyl 3-hydroxyazetidine-1-carboxylate

A

398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

B

172096-95-6

1,1-dimethylethyl 5-oxo-3-oxazolidinecarboxylate

Conditions
ConditionsYield
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium hydrogencarbonate; potassium bromide In dichloromethane; water at -10 - -5℃; Temperature;
801290-71-1

methylene-carbamic acid tert-butyl ester

398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trichlorophosphate / diethyl ether / Inert atmosphere; Schlenk technique; Reflux
2: zinc; acetic acid / 7 h / 20 - 80 °C / Inert atmosphere; Schlenk technique
View Scheme

C8H11Cl2NO3

398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
With acetic acid; zinc at 20 - 80℃; for 7h; Inert atmosphere; Schlenk technique;
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

124-40-3

dimethyl amine

792970-55-9

tert-butyl 3-(dimethylamino)azetidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: tert-butyl 3-oxoazetidine-1-carboxylate; dimethyl amine With hydrogen; acetic acid; palladium 10% on activated carbon In tetrahydrofuran; methanol at 20℃; for 14h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
100%
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

1779-49-3

Methyltriphenylphosphonium bromide

934664-41-2

3-methylene-azetidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: potassium tert-butylate; Methyltriphenylphosphonium bromide In diethyl ether at 20℃; for 1h;
Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In diethyl ether at 35℃; for 2h;
100%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In diethyl ether at 20℃; for 1h;
Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In diethyl ether at 35℃; for 2h;
100%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In diethyl ether at 20℃; for 1h;
Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In diethyl ether at 35℃; for 2h;
100%
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    Product Name: tert-Butyl 3-oxoazetidine-1-carboxylate CAS: 398489-26-4 MF: C8H13NO3 MW: 171.19 EINECS: 627-725-0 Mol File: 398489-26-4.mol tert-Butyl 3-oxoazetidine-1-carboxylate Structure tert-Butyl 3-oxoazetidine-1-carboxylate C

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Chemistry

The molecular structure of 1-Boc-3-azetidinone (CAS NO.398489-26-4):

IUPAC Name: tert-butyl 3-oxoazetidine-1-carboxylate
Empirical Formula: C8H13NO3
Molecular Weight: 171.1937
H bond acceptors: 4
H bond donors: 0
Freely Rotating Bonds: 2
Polar Surface Area: 46.61Å2
Molar Refractivity: 42.34 cm3
Molar Volume: 145.7 cm3
Index of Refraction: 1.492
Surface Tension: 43.4 dyne/cm
Density: 1.174 g/cm3
Flash Point: 105.8 °C
Enthalpy of Vaporization: 48.87 kJ/mol
Boiling Point: 251.3 °C at 760 mmHg
Vapour Pressure: 0.0206 mmHg at 25°C
Melting point: 49-52°C
Storage temp: Store under inert gas
Sensitive: Moisture Sensitive/Stench
Product Categories: pharmacetical; Heterocycles series; Azetidine; Ring Systems
SMILES: O=C1CN(C(=O)OC(C)(C)C)C1
InChI: InChI=1/C8H13NO3/c1-8(2,3)12-7(11)9-4-6(10)5-9/h4-5H2,1-3H3

Safety Profile

Hazard Codes: IrritantXi,HarmfulXn
Risk Statements: 22-37/38-41 
R22:Harmful if swallowed. 
R37/38:Irritating to respiratory system and skin. 
R41:Risk of serious damage to the eyes.
Safety Statements: 26-39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S39:Wear eye / face protection.
Hazard Note: Irritant
HazardClass: Irritant

Specification

 1-Boc-3-azetidinone  , its cas register number is 398489-26-4. It also can be called 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% and so on.