2-Oxetanone supplier | CasNO.57-57-8

Name
2-Oxetanone
EINECS 200-340-1
CAS No. 57-57-8
Article Data39
CAS DataBase
Density 1.231 g/cm³
Solubility 37 g/100 mL in water
Melting Point -33 °C(lit.)
Formula C₃H₄O₂
Boiling Point 161.999 °C at 760 mmHg
Molecular Weight 72.0636
Flash Point 35.01 °C
Transport Information UN 3382 6.1/PG 1
Appearance Colorless to light yellow liquid
Safety 53-45-99
Risk Codes 45-26-36/38
Molecular Structure
Hazard Symbols T+
Synonyms Hydracrylicacid, b-lactone (6CI);1,3-Propiolactone;3-Hydroxypropionic acid lactone;3-Propanolide;3-Propiolactone;Betaprone;NSC 21626;Propanoic acid, 3-hydroxy-, b-lactone;Propanolide;Propiolactone;b-Propiolactone;b-Propionolactone;
PSA 26.30000
LogP -0.06670

Synthetic route

: 504-63-2
trimethyleneglycol

: 57-57-8
β-Propiolactone

Conditions

Conditions	Yield
With tetrachloromethane; bis(acetylacetonate)oxovanadium at 100℃; for 1h;	98%
With [RuCl2(PPh3)2(2-PyCH21,3,5-triaza-7-phosphadamantane)].Br; potassium hydroxide In water for 48h; Reagent/catalyst; Schlenk technique; Reflux; Inert atmosphere; Green chemistry;	95%

: 5009-27-8
cyclopropanone

: 57-57-8
β-Propiolactone

Conditions

Conditions	Yield
With oxygen; benzaldehyde; nickel(II) iodide; Dowex 50W; iron(II) In 1,2-dichloro-ethane at 20℃; for 15h; Baeyer-Villiger oxidation;	94%

: 75-21-8
oxirane

: 201230-82-2
carbon monoxide

A: 57-57-8
β-Propiolactone

B: 75-07-0
acetaldehyde

Conditions

Conditions	Yield
Hexamethylbenzene; [(C1TPP)Al][Co(CO)4] In tetrahydrofuran at -78 - 60℃; under 10343.2 Torr; for 3h; Product distribution / selectivity; Molecular sieve; Inert atmosphere;	A 92% B 5%
[(C1TPP)Al][Co(CO)4] In sulfolane at -78 - 80℃; under 31029.7 Torr; Product distribution / selectivity; Inert atmosphere;	A 46.8% B 7.9%
With Hexamethylbenzene; [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)][tetracarbonylcobaltate] In tetrahydrofuran at 60℃; under 10343.2 Torr; for 3h; Catalytic behavior; Pressure; Reagent/catalyst; Solvent; Temperature; Glovebox; Inert atmosphere;	A 92 %Spectr. B 5 %Spectr.

...Expand

: 590-92-1
3-Bromopropionic acid

: 57-57-8
β-Propiolactone

Conditions

Conditions	Yield
With P(MeNCH2CH2)3N In acetonitrile at 25℃; for 0.0833333h;	90%

: 75-21-8
oxirane

: 201230-82-2
carbon monoxide

A: 108-30-5
succinic acid anhydride

B: 57-57-8
β-Propiolactone

Conditions

Conditions	Yield
Hexamethylbenzene; [(C1TPP)Al][Co(CO)4] In tetrahydrofuran at -78 - 60℃; under 31029.7 Torr; for 3h; Product distribution / selectivity; Molecular sieve; Inert atmosphere;	A 8% B 88%
Hexamethylbenzene; [(C1TPP)Al][Co(CO)4] In tetrahydrofuran at -78 - 60℃; under 31029.7 Torr; for 3h; Product distribution / selectivity; Molecular sieve; Inert atmosphere;	A 13% B 81%
With Hexamethylbenzene; [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)][tetracarbonylcobaltate] In tetrahydrofuran at 60℃; under 31029.7 Torr; for 3h; Glovebox; Inert atmosphere;	A 8 %Spectr. B 88 %Spectr.

...Expand

: 463-51-4
Ketene

: 50-00-0
formaldehyd

: 57-57-8
β-Propiolactone

Conditions

Conditions	Yield
With aluminium trichloride; zinc(II) chloride In acetone	75%
With acetone; zinc(II) chloride
With β-Propiolactone

: 75-21-8
oxirane

: 201230-82-2
carbon monoxide

: 57-57-8
β-Propiolactone

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; [bis(triphenylphospine)nitrogen(1+)][Co(CO)4] In N,N-dimethyl-formamide at 80℃; under 46544.6 Torr; for 24h;	44%
Hexamethylbenzene; [(C1TPP)Al][Co(CO)4] In tetrahydrofuran at -78 - 30℃; under 31029.7 Torr; for 3h; Product distribution / selectivity; Molecular sieve; Inert atmosphere;	44%
With trimethylaluminum; dicobalt octacarbonyl In diethylene glycol dimethyl ether; toluene at 75℃; under 45004.5 Torr; for 5h;

: 463-51-4
Ketene

: 50-00-0
formaldehyd

: 60-29-7
diethyl ether

: 57-57-8
β-Propiolactone

Conditions

Conditions	Yield
in Gegenwart verschiedener Katalysatoren;

...Expand

: 463-51-4
Ketene

: 50-00-0
formaldehyd

: 78-40-0
triethyl phosphate

: 57-57-8
β-Propiolactone

...Expand

: 463-51-4
Ketene

: 50-00-0
formaldehyd

: 109-63-7
trifluoroborane diethyl ether

: 57-57-8
β-Propiolactone

...Expand

: 2-chloropropionate anion

: 57-57-8
β-Propiolactone

Conditions

Conditions	Yield
With base In water; dimethyl sulfoxide at 34℃;
In water; dimethyl sulfoxide at 34℃; Rate constant; Mechanism;

β-iodo-propionate sodium: β-iodo-propionate sodium

: 57-57-8
β-Propiolactone

Conditions

Conditions	Yield
With silver nitrate

: 463-51-4
Ketene

: 50-00-0
formaldehyd

HgCl2: HgCl2

: 57-57-8
β-Propiolactone

...Expand

: 463-51-4
Ketene

: 50-00-0
formaldehyd

liquid propiolactone: liquid propiolactone

: 57-57-8
β-Propiolactone

Conditions

Conditions	Yield
in Gegenwart verschiedener Katalysatoren;

...Expand

: 463-51-4
Ketene

: 50-00-0
formaldehyd

Al2O3: Al2O3

SiO2: SiO2

: 57-57-8
β-Propiolactone

...Expand

: 463-51-4
Ketene

: 50-00-0
formaldehyd

: 7446-70-0
aluminium trichloride

ZnCl2: ZnCl2

: 57-57-8
β-Propiolactone

...Expand

: 463-51-4
Ketene

: 50-00-0
formaldehyd

: 60-29-7
diethyl ether

ZnCl2: ZnCl2

: 57-57-8
β-Propiolactone

...Expand

: 463-51-4
Ketene

: 50-00-0
formaldehyd

: 7446-70-0
aluminium trichloride

: 60-29-7
diethyl ether

ZnCl2: ZnCl2

: 57-57-8
β-Propiolactone

...Expand

: 463-51-4
Ketene

: 50-00-0
formaldehyd

Zn(ClO4)2: Zn(ClO4)2

: 57-57-8
β-Propiolactone

...Expand

: 7732-18-5
water

: 77545-96-1
sodium-3-iodopropionate

: silver nitrate

: 57-57-8
β-Propiolactone

...Expand

: 107-95-9
3-amino propanoic acid

: 57-57-8
β-Propiolactone

Conditions

Conditions	Yield
With sodium dihydrogenphosphate; sodium perchlorate; sodium nitrite at 24.84℃; pH=3.00; Kinetics;

: 56-86-0
L-glutamic acid

A: 541-59-3
maleiimide

B: 123-56-8
Succinimide

C: 109-97-7
pyrrole

D: 57-57-8
β-Propiolactone

E: 108-99-6
3-Methylpyridine

F: 64-17-5
ethanol

G: 64-19-7
acetic acid

H: 107-13-1
acrylonitrile

I: 3680-71-5
7-deazahypoxanthine

J: 75-05-8
acetonitrile

K: 107-12-0
propiononitrile

Conditions

Conditions	Yield
With oxygen at 400℃; under 760.051 Torr; for 5.55556E-05h; Temperature; Inert atmosphere; Pyrolysis; Gas phase; Flow reactor;

...Expand

: 75-21-8
oxirane

: 201230-82-2
carbon monoxide

A: 108-30-5
succinic acid anhydride

B: 57-57-8
β-Propiolactone

C: 75-07-0
acetaldehyde

Conditions

Conditions	Yield
With [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)bis(tetrahydrofuran)][tetracarbonylcobaltate] at 80℃; under 31029.7 Torr; for 4h; Catalytic behavior; Glovebox; Inert atmosphere;	A 50.8 %Spectr. B 23.6 %Spectr. C 5.5 %Spectr.

...Expand

: 67-56-1
methanol

: 57-57-8
β-Propiolactone

: 6149-41-3
methyl ester (3-hydroxy) propionic acid

Conditions

Conditions	Yield
With sodium methylate at 50℃; for 1h;	100%
With sulfuric acid at 0℃; for 18h;	97%
With sodium methylate In methanol at 50℃; for 1.5h;	90%

: 57-57-8
β-Propiolactone

: 64-19-7
acetic acid

: 4272-12-2
3-acetoxypropionic acid

Conditions

Conditions	Yield
With sulfuric acid at 20℃; for 4h;	100%
With sulfuric acid at 20℃; for 4h;	98.2%
With sulfuric acid for 2h; Ambient temperature;	60%
With sulfuric acid

: 57-57-8
β-Propiolactone

: 2651-43-6
3-hydroxypropionamide

Conditions

Conditions	Yield
With ammonia In water at 0 - 20℃;	100%
With ammonia at 100℃; unter Druck;
With ammonia; water
With ammonia In methanol at 20℃;
With ammonia In tetrahydrofuran at -78 - 3℃; for 2.58h; Sealed tube; regioselective reaction;	66 %Spectr.

: 57-57-8
β-Propiolactone

: 124-41-4
sodium methylate

: 6149-41-3
methyl ester (3-hydroxy) propionic acid

Conditions

Conditions	Yield
In methanol at 50℃; for 4h;	100%
In methanol at 50℃; for 1h;	69%
In methanol at 50℃; for 1h; Inert atmosphere;	39%

: 57-57-8
β-Propiolactone

: 107-11-9
1-amino-2-propene

: 1021495-88-4
C6H11NO2

Conditions

Conditions	Yield
With bis(trifluoromethane)sulfonimide lithium In chloroform at 85℃; for 40h;	100%

: 57-57-8
β-Propiolactone

: 6487-38-3
3-hydroxypropanoic acid sodium salt

Conditions

Conditions	Yield
With water; sodium hydroxide at 20℃; Inert atmosphere;	100%
With sodium hydroxide In water at 20℃;
Stage #1: β-Propiolactone With water Stage #2: With sodium hydroxide pH=9.33;
With water; sodium hydroxide at 20℃; Inert atmosphere;	1 g

: 57-57-8
β-Propiolactone

: 12-methoxydodecylmagnesium bromide

: 78350-13-7
15-methoxypentadecanoic acid

Conditions

Conditions	Yield
With copper(l) iodide; dimethylsulfide In tetrahydrofuran at 0℃; for 3h;	99%

: 57-57-8
β-Propiolactone

: 802294-64-0
propionic acid

Conditions

Conditions	Yield
With palladium 10% on activated carbon; W(OTf)6; hydrogen at 135℃; under 760.051 Torr; for 12h;	99%
With palladium on activated carbon; W(OTf)6; hydrogen In neat (no solvent) at 135℃; under 760.051 Torr; for 12h; Reagent/catalyst;	90 %Chromat.

: 57-57-8
β-Propiolactone

: 625-36-5
2-chloropropionyl chloride

Conditions

Conditions	Yield
With bis(trichloromethyl) carbonate; N,N-dimethylpiperidine-4-carboxamide hydrochloride at 25℃; for 10h; Reagent/catalyst; Large scale;	98%
With phosphorus pentachloride In benzene at 20℃; for 10h; Chlorination;	87%
With tetrachloromethane; sulfuryl dichloride
With tetrachloromethane; phosphorus pentachloride
With thionyl chloride

: 57-57-8
β-Propiolactone

: 865-47-4
potassium tert-butylate

: 1663-39-4
tert-Butyl acrylate

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.25h;	96%

: 57-57-8
β-Propiolactone

: 693-04-9
butyl magnesium bromide

: 111-14-8
oenanthic acid

Conditions

Conditions	Yield
With copper(l) chloride In tetrahydrofuran at -10℃;	95%
With copper(I) bromide at -5℃; for 1h; Mechanism; Product distribution; other solvents, Grignard reagents, catalyst and temperature;

: 57-57-8
β-Propiolactone

: Triethylammonium-3-methyl-3-phenyl-tiolcarbazat

: 3-(3-Methyl-3-phenyl-carbazoylthio)-propionsaeure

Conditions

Conditions	Yield
In water at 20℃; for 1h;	95%

methylthioglycollate: methylthioglycollate

: 57-57-8
β-Propiolactone

: 93274-67-0
3-(2-methoxy-2-oxoethylsulfanyl)-propanoic acid

Conditions

Conditions	Yield
	94%

: 78569-36-5
(E)-N-(naphthalen-1-yl)-1-phenylmethanimine

: 57-57-8
β-Propiolactone

: 1-(1-naphthyl)-5-ethyl-2-pyrrolidinone

Conditions

Conditions	Yield
nickel(II) iodide; samarium diiodide In tetrahydrofuran for 1h; Addition;	93%

: 52594-52-2
dimethyl(2,2'-bipyridine)platinum(II)

: 57-57-8
β-Propiolactone

: {(methyl)2(CH2CH2C(O)O)(2,2'-bipyridine)platinum}

Conditions

Conditions	Yield
In acetone React. at room temp. for 4 h.; Elem. anal.;	93%
In dichloromethane Kinetics; React. at 25°C.; Rate consts. given.;
In isopropyl alcohol Kinetics; React. at 25°C.; Rate consts. given.;

: 57-57-8
β-Propiolactone

: 5135-39-7
5’-deoxy-5’-(benzylthio)adenosine

: (benzyl)(5’-deoxyadenosyl)-(3-propionate)sulfonium salt

Conditions

Conditions	Yield
With formic acid at 20℃; for 2h; Inert atmosphere;	93%

: 693-03-8
n-butyl magnesium bromide

: 57-57-8
β-Propiolactone

: 111-14-8
oenanthic acid

Conditions

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at -30 - 0℃; for 0.0333333h; Product distribution; Mechanism; further reagents, solvents, temperatures, times, further β-propiolactones and Grignard reagents;	92%
copper(l) chloride In tetrahydrofuran Product distribution; other solvents, catalysts;	90%
copper(l) chloride at 0℃; for 0.25h;	90%
With copper(l) iodide; dimethylsulfide 1) THF, -30 deg C, 30 min; 2) -30 deg C, 1 h, 0 deg C, 1 h; Yield given. Multistep reaction;

: 57-57-8
β-Propiolactone

: 1119-51-3
bromopentene

: 18719-24-9
oct-7-enoic acid

Conditions

Conditions	Yield
Stage #1: bromopentene With magnesium In tetrahydrofuran for 2h; Heating; Stage #2: β-Propiolactone With copper(l) chloride In tetrahydrofuran at 20℃; for 1h;	92%

: 57-57-8
β-Propiolactone

: 100-51-6
benzyl alcohol

: 27912-85-2
3-(benzyloxy)propanoic acid

Conditions

Conditions	Yield
at 75℃; for 24h;	91%

: 57-57-8
β-Propiolactone

: 865-33-8
potassium methanolate

: 292638-85-8
acrylic acid methyl ester

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.25h; Product distribution; other solvent, addition of 18-crown-6, other substrates;	90%
In tetrahydrofuran at 20℃; for 0.25h;	90%

: 57-57-8
β-Propiolactone

: C10H20ClMgO(1-)*Cl(1-)*Mg(2+)

: 7735-38-8
13-hydroxytridecanoic acid

Conditions

Conditions	Yield
dilithium tetrachlorocuprate In tetrahydrofuran at -10℃; for 1h;	90%

: 57-57-8
β-Propiolactone

: 27845-47-2
N-benzylidene ethylamine

: 1-ethyl-5-phenyl-2-pyrrolidinone

Conditions

Conditions	Yield
nickel(II) iodide; samarium diiodide In tetrahydrofuran for 1h; Addition;	90%

: 57-57-8
β-Propiolactone

: 78-93-3
butanone

: 2865-82-9
5-ethyl-5-methyl-dihydro-furan-2-one

Conditions

Conditions	Yield
nickel(II) iodide; samarium diiodide In tetrahydrofuran for 1h; Addition;	90%

: 67-56-1
methanol

: 57-57-8
β-Propiolactone

: 124-41-4
sodium methylate

: 6149-41-3
methyl ester (3-hydroxy) propionic acid

Conditions

Conditions	Yield
at 50℃; for 2h; Inert atmosphere;	90%
Stage #1: methanol; β-Propiolactone; sodium methylate at -78℃; Stage #2: With hydrogenchloride; methanol

...Expand

: 57-57-8
β-Propiolactone

: 214822-96-5
4-Fluoro-3-hydroxy-benzoic acid methyl ester

: 909407-23-4
3-(2-carboxy-ethoxy)-4-fluoro-benzoic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 4-Fluoro-3-hydroxy-benzoic acid methyl ester With potassium tert-butylate In tetrahydrofuran at 0 - 5℃; for 0.166667h; Stage #2: β-Propiolactone In tetrahydrofuran at 0 - 50℃; for 4h; Stage #3: With hydrogenchloride; water pH=0 - 2;	90%

: 57-57-8
β-Propiolactone

: 124-22-1
n-Dodecylamine

: 1462-54-0
3-(dodecylamino)propanoic acid

Conditions

Conditions	Yield
In acetonitrile	89%
With acetonitrile

2-Oxetanone Chemical Properties

Chemical Name: 2-Oxetanone
IUPAC NAME: Oxetan-2-one
CAS No.: 57-57-8
EINECS: 200-340-1
RTECS: RQ7350000
RTECS Class: Agricultural Chemical and Pesticide ; Tumorigen ; Mutagen
EC Class: Carcinogenic Category 2 ; Very toxic ; Irritant
Molecular Formula: C₃H₄O₂
Molecular Weight: 72.06 g/mol
Melting Point: -33 °C(lit.)
Density: 1.231 g/cm³
Flash Point: 35 °C
Boiling Point: 162 °C at 760 mmHg
Following is the structure of β-Propiolactone (57-57-8):

Product Categories about β-Propiolactone (57-57-8) are Intermediates & Fine Chemicals ; Miscellaneous Reagents ; Pharmaceuticals
The chemical synonymous of β-Propiolactone (57-57-8) are Beta-Hydroxypropionic acid lactone ; Beta-propiolactone ; Beta-propionolactone ; B-propiolactone ; Hydracrylic acid beta-lactone ; Hydracrylic acid lactone ; 2-Oxetanone ; 3-Hydroxypropionic acid lactone

2-Oxetanone Toxicity Data With Reference

1.	slt-dmg-orl 200 mmol/L	ENMUDM Environmental Mutagenesis. 6 (1984),153.
2.	otr-hmn:fbr 28 µmol/L	PNASA6 Proceedings of the National Academy of Sciences of the United States of America. 80 (1983),7219.
3.	ihl-rat LC50:25 ppm/6H	DTLVS* Documentation of Threshold Limit Values for Substances in Workroom Air. 4 (1980),347.
4.	ipr-mus LD50:405 mg/kg	JJIND8 JNCI, Journal of the National Cancer Institute. 62 (1979),911.

2-Oxetanone Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 4 ,1974,p. 259.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program. Community Right-To-Know List. EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory.

2-Oxetanone Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by inhalation. Moderately toxic by intraperitoneal route. An initiator. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:
T+: Very toxic
Risk Statements about β-Propiolactone (57-57-8):
R45 May cause cancer.
R26 Very toxic by inhalation.
R36/38 Irritating to eyes and skin.
Safety Statements about β-Propiolactone (57-57-8):
S53 Avoid exposure - obtain special instructions before use.
S45 In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).
Attentions:
1. Storage: Keep away from sources of ignition. Store in a tightly closed container. Deep freeze (below -20 C). Store protected from light. Store under argon.
2. Handling: Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.

2-Oxetanone Standards and Recommendations

OSHA PEL: OSHA: Carcinogen
ACGIH TLV: TWA 0.5 ppm; Animal Carcinogen
DFG MAK: Animal Carcinogen, Suspected Human Carcinogen

2-Oxetanone Specification

β-Propiolactone (57-57-8) is an organic compound of the lactone family, with a four-membered ring. It is a clear, colorless liquid with a slightly sweet odor, highly soluble in water and miscible with ethanol, acetone, diethyl ether and chloroform.It is a disinfectant and has been used to sterilize blood plasma, vaccines, tissue grafts, surgical instruments, and enzymes.The principal current use of β-Propiolactone is an intermediate in the synthesis of other chemical compounds.

Product Name

2-Oxetanone

Synthetic route

2-Oxetanone Chemical Properties

2-Oxetanone Toxicity Data With Reference

2-Oxetanone Consensus Reports

2-Oxetanone Safety Profile

2-Oxetanone Standards and Recommendations

2-Oxetanone Specification

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