2-Azetidinone supplier | CasNO.930-21-2

Name
2-Azetidinone
EINECS
CAS No. 930-21-2
Article Data58
CAS DataBase
Density 1.119 g/cm³
Solubility
Melting Point 74-76 °C(lit.)
Formula C₃H₅NO
Boiling Point 222.434 °C at 760 mmHg
Molecular Weight 71.0788
Flash Point 151.536 °C
Transport Information UN 3263 8/PG 2
Appearance Colorless solid
Safety 26-36/37/39-45
Risk Codes 34
Molecular Structure
Hazard Symbols C
Synonyms 2-Azetidone;Propiolactam;b-Alanine,lactam;b-Propiolactam;
PSA 29.10000
LogP -0.16490

Synthetic route

: 17392-83-5
(R)-Methyl lactate

: 930-21-2
2-azetidinone

Conditions

Conditions	Yield
Stage #1: (R)-Methyl lactate With dmap; triethyl phosphite at 2 - 20℃; for 5.66667h; Stage #2: With sodium hydroxide at 55℃; for 1.5h; Temperature;	95.6%

: 107-95-9
3-amino propanoic acid

: 930-21-2
2-azetidinone

Conditions

Conditions	Yield
With triphenylphosphine In acetonitrile for 4.5h; Heating;	80%
With sodium hydrogencarbonate; methanesulfonyl chloride In acetonitrile at 80℃;	36%
With 2,2'-dipyridyldisulphide; triphenylphosphine In acetonitrile for 5h; Heating;	0.44 g
In toluene at 90℃; Inert atmosphere; Green chemistry;

: 130065-29-1
amino-azetidinone

: 930-21-2
2-azetidinone

Conditions

Conditions	Yield
With N-nitrosodiphenylamine In benzene for 3h; Heating;	61%

: 110967-04-9
1-isopropylazetidin-2-one

A: 930-21-2
2-azetidinone

B: 51599-74-7
1-acetylazetidin-2-one

Conditions

Conditions	Yield
With ruthenium(IV) oxide; sodium periodate In ethyl acetate for 24h; Ambient temperature;	A 35% B 42%

: 2679-13-2
1-methylazetidine-2-one

: 930-21-2
2-azetidinone

Conditions

Conditions	Yield
With ruthenium(IV) oxide; sodium periodate In ethyl acetate for 72h; Ambient temperature;	36%

: 4138-35-6
methyl 3-aminopropanoate

: 930-21-2
2-azetidinone

Conditions

Conditions	Yield
With triisobutylaluminum In diethyl ether at 45 - 50℃; for 15h;	28%

: 60-29-7
diethyl ether

: 924-73-2
3-amino-propionic acid ethyl ester

: 925-90-6
ethylmagnesium bromide

: 930-21-2
2-azetidinone

...Expand

: 924-73-2
3-amino-propionic acid ethyl ester

: 925-90-6
ethylmagnesium bromide

: 930-21-2
2-azetidinone

Conditions

Conditions	Yield
With diethyl ether anschliessend Behandeln mit wss.Ammoniumchlorid-Loesung;

: 28562-53-0
4-acetoxy azetidinone

: 930-21-2
2-azetidinone

Conditions

Conditions	Yield
With sodium tetrahydroborate; acidic Amberlite resin 1.) ethanol, 0 deg C, 1 h; 2.) 0.5 h, 0 deg C; Yield given. Multistep reaction;
With potassium borohydride In water
With sodium borohydrid; sodium chloride In water; pentane	8.7 g (61%)
In Potassium borohydride; dichloromethane; water

: 115946-47-9
1-[(4-methylphenyl)sulfonyl]azetidin-2-one

: 930-21-2
2-azetidinone

Conditions

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide at 20℃; Hg-cathode, Et4NClO4;	89 % Chromat.

: 1-trityl-azetidin-2-one

: 930-21-2
2-azetidinone

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane; water at 20℃;

: (2-oxoazetidin-1-yl)methyl benzoate

A: 930-21-2
2-azetidinone

B: 344930-61-6
N-hydroxymethylazetidin-2-one

Conditions

Conditions	Yield
With hydrogenchloride; sodium perchlorate In water at 25℃; pH=2; Kinetics; Further Variations:; Reagents; Temperatures; Solvents; pH-values;

: (2-oxoazetidin-1-yl)methyl phenylacetate

A: 930-21-2
2-azetidinone

B: 344930-61-6
N-hydroxymethylazetidin-2-one

Conditions

Conditions	Yield
With hydrogenchloride; sodium perchlorate In water at 25℃; pH=2; Kinetics; Further Variations:; Reagents; pH-values; Solvents;

: (2-oxoazetidin-1-yl)methyl 2-methoxybenzoate

A: 930-21-2
2-azetidinone

B: 344930-61-6
N-hydroxymethylazetidin-2-one

Conditions

Conditions	Yield
With hydrogenchloride; sodium perchlorate In water at 25℃; pH=2; Kinetics; Further Variations:; Reagents; pH-values; Solvents;

: (2-oxoazetidin-1-yl)methyl 4-methoxybenzoate

A: 930-21-2
2-azetidinone

B: 344930-61-6
N-hydroxymethylazetidin-2-one

Conditions

Conditions	Yield
With hydrogenchloride; sodium perchlorate In water at 25℃; pH=2; Kinetics; Further Variations:; Reagents; pH-values; Solvents;

: (2-oxoazetidin-1-yl)methyl (E)-cinnamate

A: 930-21-2
2-azetidinone

B: 344930-61-6
N-hydroxymethylazetidin-2-one

Conditions

Conditions	Yield
With hydrogenchloride; sodium perchlorate In water at 25℃; pH=2; Kinetics; Further Variations:; Reagents; pH-values; Solvents;

: (2-oxoazetidin-1-yl)methyl 3-chlorobenzoate

A: 930-21-2
2-azetidinone

B: 344930-61-6
N-hydroxymethylazetidin-2-one

Conditions

Conditions	Yield
With hydrogenchloride; sodium perchlorate In water at 25℃; pH=2; Kinetics; Further Variations:; Reagents; pH-values; Solvents;

: (2-oxoazetidin-1-yl)methyl 4-nitrobenzoate

A: 930-21-2
2-azetidinone

B: 344930-61-6
N-hydroxymethylazetidin-2-one

Conditions

Conditions	Yield
With hydrogenchloride; sodium perchlorate In water at 25℃; pH=2; Kinetics; Further Variations:; Reagents; pH-values; Solvents;

: 2-ethoxy-2-oxo-1-(2-oxoazetidin-1-yl)ethyl benzoate

A: 930-21-2
2-azetidinone

B: 701910-95-4
ethyl 2-hydroxy-2-(2-oxo-azetidin-1-yl)acetate

Conditions

Conditions	Yield
With hydrogenchloride; sodium perchlorate In water at 25℃; pH=2; Kinetics; Further Variations:; Reagents; pH-values; Solvents; Temperatures;

: (3-amino-propionyloxymethylene)-dimethyl-ammonium; chloride

: 930-21-2
2-azetidinone

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;

: 873073-30-4
1-(4-chlorobenzoyl)-1-azetidin-2-one

A: 930-21-2
2-azetidinone

B: 4641-33-2
4-chlorobenzoate ion

Conditions

Conditions	Yield
With sodium hydroxide; potassium chloride In water; acetonitrile at 30℃; Kinetics;

: 873073-29-1
1-(4-methoxybenzoyl)-1-azetidin-2-one

A: 930-21-2
2-azetidinone

B: 16285-97-5
p-methoxybenzoate(1-)

Conditions

Conditions	Yield
With sodium hydroxide; potassium chloride In water; acetonitrile at 30℃; Kinetics;

: 873073-31-5
1-(4-nitrobenzoyl)-1-azetidin-2-one

A: 930-21-2
2-azetidinone

B: 2906-29-8
4-nitrobenzoate

Conditions

Conditions	Yield
With sodium hydroxide; potassium chloride In water; acetonitrile at 30℃; Kinetics;

: 69689-45-8
N-benzoyl-β-lactam

A: 930-21-2
2-azetidinone

B: 766-76-7
benzoate

Conditions

Conditions	Yield
With sodium hydroxide; potassium chloride In water; acetonitrile at 30℃; Kinetics; Further Variations:; pH-values; Solvents; Temperatures;

: S-1,3-benzothiazol-2-yl 3-aminopropanethioate

: 930-21-2
2-azetidinone

Conditions

Conditions	Yield
With triethylamine In dichloromethane

: C10H14NO3PS2*C6H15N

: 930-21-2
2-azetidinone

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 25 - 30℃;

: 930-21-2
2-azetidinone

: 924-44-7
glyoxylic acid ethyl ester

: 701910-95-4
ethyl 2-hydroxy-2-(2-oxo-azetidin-1-yl)acetate

Conditions

Conditions	Yield
In toluene for 3h; Heating;	100%

: 930-21-2
2-azetidinone

: 868047-80-7
1-bromo-5-(tert-butyl)-2-methoxy-3-nitrobenzene

: 868047-81-8
1-(5-tert-butyl-2-methoxy-3-nitro-phenyl)-azetidin-2-one

Conditions

Conditions	Yield
With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 100℃; for 20h;	100%

: 930-21-2
2-azetidinone

: 98-03-3
thiophene-2-carbaldehyde

: 1394836-02-2
1-(thiophene-2-carbonyl)azatedin-2-one

Conditions

Conditions	Yield
With Shvo's Catalyst In toluene at 100℃; for 24h; Inert atmosphere;	99%

: 930-21-2
2-azetidinone

: 504-88-1
3-nitropropionic acid

Conditions

Conditions	Yield
With methyltrifluoromethyldioxirane In water at 0℃; for 0.5h;	99%

: 930-21-2
2-azetidinone

: 99-97-8
Dimethyl-p-toluidine

: C12H16N2O

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; acetic acid In acetonitrile at 60℃; for 3h; Electrochemical reaction; Inert atmosphere;	99%

: 930-21-2
2-azetidinone

: 728-87-0
4,4'-Dimethoxybenzhydrol

: N-(4,4'-dimethoxybenzhydryl)azetidin-2-one

Conditions

Conditions	Yield
With sulfuric acid In acetic acid at 20℃; for 18h;	98%

: 930-21-2
2-azetidinone

: 57913-41-4
2-phenylethyl chloroformate

: 1-(phenethyloxycarbonyl)azetidin-2-one

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 1.75h;	98%

: 930-21-2
2-azetidinone

: 76-05-1
trifluoroacetic acid

: 71-43-2
benzene

: 3-amino-1-phenyl-propan-1-one trifluoromethylsulfonate

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 20℃;	98%

...Expand

: 930-21-2
2-azetidinone

: 1309362-40-0
1-heptyl-3-iodoquinolin-4(1H)-one

: 1309362-56-8
1-heptyl-3-(2-oxoazetidin-1-yl)quinolin-4(1H)-one

Conditions

Conditions	Yield
With copper; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 135℃; for 1h; Ullmann type reaction; Inert atmosphere;	97%

: 930-21-2
2-azetidinone

: 3173-56-6
benzyl isothiocyanate

: N-benzyl-2-oxoazetidine-1-carboxamide

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane for 24h; Heating;	96%
With triethylamine In dichloromethane at 20℃;	66%
With triethylamine In dichloromethane at 35℃; for 0.166667h; Microwave irradiation; Inert atmosphere;

: 930-21-2
2-azetidinone

: 766-85-8
3-methoxy-1-iodobenzene

: 61999-50-6
N-(3-methoxyphenyl)azetidin-2-one

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate In toluene at 18 - 140℃; for 20h; Goldberg-Buchwald cross-coupling; Inert atmosphere; Sealed;	96%

: 930-21-2
2-azetidinone

: 696-62-8
para-iodoanisole

: 7661-29-2
1-(4-methoxyphenyl)-2-azetidinone

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate In toluene at 18 - 140℃; for 20h; Goldberg-Buchwald cross-coupling; Inert atmosphere; Sealed;	96%
With D-glucose; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; copper(ll) bromide; sodium t-butanolate In water at 50℃; Inert atmosphere;	79%

: 930-21-2
2-azetidinone

: 98-01-1
furfural

: 1394836-03-3
1-(2-furoyl)azatedin-2-one

Conditions

Conditions	Yield
With Shvo's Catalyst In toluene at 100℃; for 24h; Inert atmosphere;	96%

: 930-21-2
2-azetidinone

: 108-86-1
bromobenzene

: 5099-95-6
1-phenylazetidin-2-one

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 16h; Arylation;	95%
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 16h;	93%
With 1,1'-bis(diphenylphosphino)ferrocene; sodium t-butanolate; palladium diacetate In toluene at 120℃; for 48h; Phenylation;	20%

: 930-21-2
2-azetidinone

: 22445-41-6
3,5-dimethylphenyl iodide

: N-(3,5-dimethylphenyl)-2-azetidinone

Conditions

Conditions	Yield
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane at 110℃; for 23h;	95%
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane; dodecane at 110℃; for 23h;	95%

: 930-21-2
2-azetidinone

: 3959-05-5
2-bromobenzylamine

: 2,3,5,6-tetrahydro-1H-benzo[b][1,5]diazocin-4-one

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate In toluene at 110℃; for 24h;	95%

: 930-21-2
2-azetidinone

: 100-66-3
methoxybenzene

: 76-05-1
trifluoroacetic acid

: 3-amino-1-(4-methoxy-phenyl)-propan-1-one trifluoromethylsulfonate

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 20℃;	95%

...Expand

: 930-21-2
2-azetidinone

: ethyl acetate n-hexane

: 22445-41-6
3,5-dimethylphenyl iodide

: N-(3,5-dimethylphenyl)-2-azetidinone

Conditions

Conditions	Yield
	95%

...Expand

: 930-21-2
2-azetidinone

: 625-99-0
3-iodochlorobenzene

: 76227-98-0
1-(3-chlorophenyl)-azetidin-2-one

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate In toluene at 18 - 140℃; for 20h; Goldberg-Buchwald cross-coupling; Inert atmosphere; Sealed;	95%

: 930-21-2
2-azetidinone

: 1-benzyl-3-cyclohexyl-5-iodo-4-phenyl-1H-pyrazolo-[3,4-b]pyridine

: 1-(1-benzyl-3-cyclohexyl-4-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)azetidin-2-one

Conditions

Conditions	Yield
With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In 1,4-dioxane at 110℃; for 24h; Inert atmosphere;	95%

: 930-21-2
2-azetidinone

: 79-21-0
peracetic acid

: 28562-53-0
4-acetoxy azetidinone

Conditions

Conditions	Yield
With Ru-carbon; sodium acetate; acetic acid In ethyl acetate for 2.5h; Ambient temperature;	94%

: 930-21-2
2-azetidinone

: 106-39-8
bromochlorobenzene

: 7661-27-0
N-(4'-chlorophenyl)-2-azetidinone

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 18h; Arylation;	94%

: 930-21-2
2-azetidinone

: 18162-48-6
tert-butyldimethylsilyl chloride

: 117505-49-4
1-tert-butyldimethylsilylazetidin-2-one

Conditions

Conditions	Yield
With triethylamine at 0℃; for 1h;	93%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;	90%
With triethylamine In N,N-dimethyl-formamide at 0℃; for 0.5h;	61%

: 930-21-2
2-azetidinone

: 501-53-1
benzyl chloroformate

: 1-(benzyloxycarbonyl)azetidin-2-one

Conditions

Conditions	Yield
Stage #1: 2-azetidinone With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: benzyl chloroformate In tetrahydrofuran at -78 - 20℃; for 6h; Inert atmosphere;	93%
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 1.75h;	75%

: 930-21-2
2-azetidinone

: 108-88-3
toluene

: 76-05-1
trifluoroacetic acid

: 3-amino-1-(4-methyl-phenyl)-propan-1-one trifluoromethylsulfonate

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 20℃;	93%

...Expand

: 930-21-2
2-azetidinone

: 12080-32-9
dichloro(1,5-cyclooctadiene)platinum(ll)

: 188638-31-5
[Pt(C8H12)(C3H4NO)2]

Conditions

Conditions	Yield
With silver(I) oxide In dichloromethane reflux (4 h); filtration, concn., pptn. with light petroleum, filtration, washing (light petroleum), drying (vac.); elem. anal.;	93%

: 930-21-2
2-azetidinone

: 24424-99-5
di-tert-butyl dicarbonate

: 1140510-99-1
tert-butyl 2-oxoazetidine-1-carboxylate

Conditions

Conditions	Yield
With dmap In acetonitrile at 0 - 20℃; Inert atmosphere;	93%
With dmap In acetonitrile at 0 - 20℃; Inert atmosphere;	90%
With dmap; triethylamine In dichloromethane at 20℃; for 12h; Inert atmosphere;	86%

: 930-21-2
2-azetidinone

: 624-31-7
4-tolyl iodide

: 38560-27-9
N-(4-methylphenyl)azetidin-2-one

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate In toluene at 18 - 140℃; for 20h; Goldberg-Buchwald cross-coupling; Inert atmosphere; Sealed;	93%

: 930-21-2
2-azetidinone

: 66-25-1
hexanal

: 405219-58-1
1-hexanoyl azatedin-2-one

Conditions

Conditions	Yield
With Shvo's Catalyst In toluene at 100℃; for 24h; Inert atmosphere;	93%

2-Azetidinone Chemical Properties

Molecular Structure of 2-Azetidinone (CAS No.930-21-2):

Molecular Formula: C₃H₅NO
Molecular Weight: 71.08
IUPAC Name: Azetidin-2-one
CAS No: 930-21-2
Melting Point: 74-76 ºC
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 0
Polar Surface Area: 20.31 Å²
Index of Refraction: 1.457
Molar Refractivity: 17.31 cm³
Molar Volume: 63.5 cm³
Surface Tension: 34.4 dyne/cm
Density: 1.119 g/cm³
Flash Point: 151.5 °C
Enthalpy of Vaporization: 45.89 kJ/mol
Boiling Point: 222.4 °C at 760 mmHg
Vapour Pressure: 0.102 mmHg at 25°C
Storage Temp.: 2-8°C
Appearance: Colorless solid
Product Categories: Heterocycles series;Ring Systems
Canonical SMILES: C1CNC1=O
InChI: InChI=1S/C3H5NO/c5-3-1-2-4-3/h1-2H2,(H,4,5)
InChIKey: MNFORVFSTILPAW-UHFFFAOYSA-N

2-Azetidinone Safety Profile

Safety Information of 2-Azetidinone (CAS No.930-21-2):
Hazard Codes: Corrosive C
Risk Statements: 34
R34:Causes burns.
Safety Statements: 26-36/37/39-45
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.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 3263 8/PG 2
WGK Germany: 3
Hazard Note: Corrosive/Keep Cold
HazardClass: 8
PackingGroup: III

2-Azetidinone Specification

2-Azetidinone (CAS No.930-21-2), it also can be called 2-Azacyclobutanone ; 2-azetol, 3,4-dihydro- ; Azetidin-2-one . An invention relates to 2-azetidinone compounds in 1981, which have antimicrobial activities, and more particularly, this invention provides new 2-azetidinone compounds, especially ones having various substituted carboxyalkyl radicals at the first position and having various groups at the fourth position of the azetidinone nucleus, which have antimicrobial activities against various pathogenic microorganisms and are useful as antibiotics in treatment for microbial infections in mammal including human being and animals.

Product Name

2-Azetidinone

Synthetic route

2-Azetidinone Chemical Properties

2-Azetidinone Safety Profile

2-Azetidinone Specification

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