1-Boc-3-azetidinone supplier | CasNO.398489-26-4

Name
tert-Butyl 3-oxoazetidine-1-carboxylate
EINECS 627-725-0
CAS No. 398489-26-4
Article Data37
CAS DataBase
Density 1.174 g/cm³
Solubility
Melting Point 49-52 °C
Formula C₈H₁₃NO₃
Boiling Point 251.3 °C at 760 mmHg
Molecular Weight 171.196
Flash Point 105.8 °C
Transport Information
Appearance
Safety 26-39
Risk Codes 22-37/38-41
Molecular Structure
Hazard Symbols Xn, Xi
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;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 1223573-23-6
tert-butyl 3-(2-oxomethylene)azetidine-1-carboxylic acid

Conditions

Conditions	Yield
In dichloromethane at 40℃; for 6h;	100%
In dichloromethane at 40℃; for 6h;	100%
In dichloromethane at 40℃;	99%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 1826-67-1
vinyl magnesium bromide

: 398489-51-5
tert-butyl 3-hydroxy-3-vinylazetidine-1-carboxylate

Conditions

Conditions	Yield
In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;	100%
In tetrahydrofuran at -20℃; for 0.5h; Inert atmosphere;	99%
In tetrahydrofuran at -30℃; for 2h; Inert atmosphere;

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1002355-96-5
tert-butyl 3-(2-ethoxy-2-oxoethylidene)azetidine-1-carboxylate

Conditions

Conditions	Yield
In dichloromethane for 6h; Wittig Olefination; Inert atmosphere; Schlenk technique; Reflux;	100%
In dichloromethane at 40℃; for 4h; Cooling with ice;	100%
In dichloromethane at 40℃; for 4.25h; Cooling with ice;	100%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 27784-76-5
tert-butyl diethylphosphonoacetate

: tert-butyl 3-(2-(tert-butoxy)-2-oxoethylidene)azetidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: tert-butyl diethylphosphonoacetate With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran at 0 - 20℃;	100%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 15097-38-8
(carbobenzyloxymethylene)triphenylphosphorane

: tert-butyl 3-(2-benzyloxy-2-oxo-ethylidene)azetidine-1-carboxylic acid

Conditions

Conditions	Yield
In toluene for 2h; Reflux;	100%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 59983-39-0
(S)-1-amino-2-(methoxymethyl)pyrrolidine

: C14H25N3O3

Conditions

Conditions	Yield
at 55℃; for 16h;	100%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 919346-89-7
5-bromo-2,3-dihydro-1H-isoindole hydrochloride

: tert-butyl-3-(5-bromoisoindolin-2-yl)azetidine-1-carboxylate

Conditions

Conditions	Yield
With acetic acid In methanol at 50℃; for 16h;	100%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 2537-48-6
diethyl 1-cyanomethylphosphonate

: 1153949-11-1
3-(cyanomethylene)azetidine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran; mineral oil Product distribution / selectivity;	99%
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran at 0℃; Stage #3: With water In tetrahydrofuran	98%
Stage #1: diethyl 1-cyanomethylphosphonate With potassium tert-butylate In tetrahydrofuran at 0 - 30℃; Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran at 0 - 30℃;	95%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 676-58-4
methylmagnesium chloride

: 1104083-23-9
tert-butyl 3-hydroxy-3-methylazetidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: tert-butyl 3-oxoazetidine-1-carboxylate; methylmagnesium chloride In tetrahydrofuran at 0℃; for 1h; Stage #2: With water; ammonium chloride In tetrahydrofuran	99%
Stage #1: tert-butyl 3-oxoazetidine-1-carboxylate; methylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 6h; Stage #2: With water; ammonium chloride In tetrahydrofuran at 0℃; for 0.166667h;

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 141699-55-0
tert-butyl 3-hydroxyazetidine-1-carboxylate

Conditions

Conditions	Yield
With sodium tetrahydroborate; ethanol for 2h;	99%
With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 6h;	84%
With methanol; sodium tetrahydroborate at 0 - 20℃; for 1h;

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 934664-41-2
3-methylene-azetidine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With potassium tert-butylate; methyl-triphenylphosphonium iodide In diethyl ether at 35℃; for 2h;	99%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 1439-36-7
1-triphenylphosphoranylidene-2-propanone

: tert-butyl 3-acetonylideneazetidine-1-carboxylate

Conditions

Conditions	Yield
In toluene at 70℃; for 2h;	99%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 75-52-5
nitromethane

: 1008526-70-2
3-hydroxy-3-(nitromethyl)azetidin-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With triethylamine In ethanol at 20℃; for 16h; Inert atmosphere;	98%
With triethylamine In ethanol at 20℃; for 16h;	98%
triethylamine In ethanol for 18h;	97%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 1950-68-1
4-methoxybenzenesulfonyl hydrazide

: 1510865-67-4
tert-butyl 3-(2-((4-methoxyphenyl)sulfonyl)hydrazineylidene)azetidine-1-carboxylate

Conditions

Conditions	Yield
In toluene for 2h; Reflux;	98%
In dimethylsulfoxide-d6 at 60℃; Schlenk technique;	73%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 74-88-4
methyl iodide

: 429669-07-8
tert-butyl 3-methoxyazetidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: tert-butyl 3-oxoazetidine-1-carboxylate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	98%

: 503-29-7
azetidine

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: tert-butyl [1,3'-biazetidine]-1'-carboxylate

Conditions

Conditions	Yield
Stage #1: azetidine; tert-butyl 3-oxoazetidine-1-carboxylate With acetic acid In 1,2-dichloro-ethane at 20℃; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 4h;	98%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 925-90-6
ethylmagnesium bromide

: 398489-28-6
tert-butyl 3-ethyl-3-hydroxyazetidine-1-carboxylate

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 5h; Inert atmosphere;	98%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 1942-45-6
4-Octyne

: 1372173-47-1
tert-butyl 3-oxo-4,5-dipropyl-3,6-dihydropyridine-1(2H)-carboxylate

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 6h; Inert atmosphere; regioselective reaction;	97%
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 6h; Glovebox; Inert atmosphere;	97%
With bis(triphenylphosphine)nickel(II) chloride; zinc In acetonitrile at 60℃; for 16h; Catalytic behavior; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere;	95%

1-Boc-3-azetidinone Chemical Properties

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

1-Boc-3-azetidinone Safety Profile

Hazard Codes: Irritant Xi, Harmful Xn
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

1-Boc-3-azetidinone 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.

Product Name

tert-Butyl 3-oxoazetidine-1-carboxylate

Synthetic route

1-Boc-3-azetidinone Chemical Properties

1-Boc-3-azetidinone Safety Profile

1-Boc-3-azetidinone Specification

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