4-Acetoxy-2-azetidinone

Product Name: 4-Acetoxy-2-azetidinone
CAS No.: 28562-53-0
Chemical Name: 4-Acetoxy-2-azetidinone
Synonyms: 4-Oxo-2-azetidinyl acetate;4-ACETOXY-2-AZETIDINONE;3-Acetoxy-3-propanelactam;4-Acetyloxyazetidin-2-one;4-OXOAZETIDIN-2-YLACETATE;2-oxoazetidinium 4-acetate;4-ACETOXY-2-AZETIDINONE(4-AA);2-Azetidinone, 4-(acetyloxy)-;4-Acetoxy-2-azetidinone - [A15221];Acetic acid 4-oxo-2-azetidinyl ester
CBNumber: CB8672313
Molecular Formula: C5H7NO3
Formula Weight: 129.11
MOL File: 28562-53-0.mol

More

Less

4-Acetoxy-2-azetidinone Property

Melting point:: 38-40 °C (lit.)
Boiling point:: 239.15°C (rough estimate)
Density: 1.3816 (rough estimate)
refractive index: 1.4220 (estimate)
Flash point:: >230 °F
storage temp.: 2-8°C
solubility: formic acid: soluble50mg/mL, clear, yellow-orange
pka: 13.41±0.40(Predicted)
form: solid
Appearance: Light yellow to orange Solid
BRN: 1524738
InChI: InChI=1S/C5H7NO3/c1-3(7)9-5-2-4(8)6-5/h5H,2H2,1H3,(H,6,8)
InChIKey: OEYMQQDJCUHKQS-UHFFFAOYSA-N
SMILES: N1C(OC(C)=O)CC1=O
CAS DataBase Reference: 28562-53-0(CAS DataBase Reference)
NIST Chemistry Reference: 4-Acetoxy-2-azetidinone(28562-53-0)

More

Less

Safety

Hazard Codes: C
Risk Statements: 34-43
Safety Statements: 26-36/37/39-45
RIDADR: UN 1759 8/PG 2
WGK Germany: 3
HazardClass: 8
PackingGroup: III

More

Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More

Less

N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 272159
Product name: 4-Acetoxy-2-azetidinone
Purity: 98%
Packaging: 1g
Price: $125
Updated: 2023/01/07

Sigma-Aldrich

Product number: 272159
Product name: 4-Acetoxy-2-azetidinone
Purity: 98%
Packaging: 5g
Price: $300
Updated: 2023/01/07

TRC

Product number: A187958
Product name: 4-Acetoxy-2-azetidinone
Packaging: 100mg
Price: $75
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FA30790
Product name: 4-Acetoxy-2-azetidinone
Packaging: 1g
Price: $80
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: APN0000239
Product name: 4-ACETOXY AZETIDIN-2-ONE
Purity: 95.00%
Packaging: 1G
Price: $155.4
Updated: 2021/12/16

More

Less

4-Acetoxy-2-azetidinone Chemical Properties,Usage,Production

Chemical Properties

White crystalline powder

Uses

4-Acetoxy-2-azetidinone was used in the synthesis of derivatized cyclopentenes in high regio- and diastereoselectivity. It was also used as a heterocyclic synthon for antibiotic and anti-inflammatory agents.

Synthesis Reference(s)

Journal of the American Chemical Society, 112, p. 7820, 1990 DOI: 10.1021/ja00177a067
Tetrahedron Letters, 29, p. 1409, 1988 DOI: 10.1016/S0040-4039(00)80310-X

Synthesis

108-05-4

1189-71-5

28562-53-0

The reaction of chlorosulfonyl isocyanate (1.0 mL, 11 mmol) with vinyl acetate (5.0 mL, 54 mmol) in anhydrous dichloromethane for 2 h at 0 °C afforded 4-acetoxy-2-azetidinone (Compound 9, 0.50 g, 35% yield). The spectral data of compound 9 was in agreement with the results reported in the literature.

Purification Methods

Dissolve it in CHCl3, dry (MgSO4) concentrate at 40o/70mm, or better at room temperature to avoid decomposition. Wash and stir the residual oil with hexane by decantation and discard the wash. Dry the oil at high vacuum when it should solidify, m 34o. It can be distilled at high vacuum, 80-82o/10-3mm, but this results in extensive losses. The purity can be checked by TLC using Merck Silica Gel F254 and eluting with EtOAc. The azetidinone has RF 0.38 (typical impurities have RF 0.67). The spots can be detected by the TDM spray. This is prepared from (A) 2.5g 4,4'-tetramethyldiaminodiphenylmethane (TDM) in 10mL AcOH and diluted with 50mL of H2O, (B) 5g KI in 100mL of H2O and (C) 0.3g ninhydrin in 10mL of AcOH and 90mL of H2O. The spray is prepared by mixing (A) and (B) with 1.5mL of (C) and stored in a brown bottle. [Clau et al. Justus Liebigs Ann Chem 539 1974, Michel et al. Org Synth 65 135 1987, Beilstein 21/12 V 4.]

References

[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 17, p. 2055 - 2068
[2] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 10, p. 2990 - 2994
[3] Journal of Organic Chemistry, 2008, vol. 73, # 13, p. 5015 - 5021
[4] Synthesis, 1987, # 3, p. 324
[5] Patent: US8859183, 2014, B2. Location in patent: Paragraph 0258-0261

4-Acetoxy-2-azetidinone Preparation Products And Raw materials

Raw materials

Preparation Products

More

Less

4-Acetoxy-2-azetidinone Suppliers

Canada 1 China 118 Europe 2 Germany 3 India 4 Switzerland 1 United Kingdom 11 United States 23 Global 163

Alchem Pharmtech,Inc.

Tel: 8485655694
Email: sales@alchempharmtech.com
Country: United States
ProdList: 63687
Advantage: 58

Aladdin Scientific

Tel
Email: tp@aladdinsci.com
Country: United States
ProdList: 52923
Advantage: 58

Aceschem Inc.

Tel: +1-817863-6948 +1-（817）863-6948
Email: sales@aceschem.com
Country: United States
ProdList: 19632
Advantage: 58

Synthonix Inc

Tel: --
Fax: --
Email: info@synthonix.com
Country: United States
ProdList: 6872
Advantage: 58

Tractus USA LLC

Tel: --
Fax: --
Country: United States
ProdList: 227
Advantage: 60

3B Scientific Corporation

Tel: --
Fax: --
Email: sales@3bsc.com
Country: United States
ProdList: 6962
Advantage: 56

Waterstone Technology, LLC

Tel: --
Fax: --
Email: sales@waterstonetech.com
Country: United States
ProdList: 6786
Advantage: 30

Alichem Inc.

Tel: --
Fax: --
Email: sales@alichem.com
Country: United States
ProdList: 6167
Advantage: 58

Chemphtec Corporation

Tel: --
Fax: --
Email: fo@chemphtec.com
Country: United States
ProdList: 2181
Advantage: 58

MilliporeSigma (Sigma-Aldrich Corp.)

Tel: --
Fax: --
Email: @sial.com
Country: United States
ProdList: 5414
Advantage: 58

JR MediChem LLC

Tel: --
Fax: --
Email: sales@jrmedichem.com
Country: United States
ProdList: 86
Advantage: 0

SynInnova Laboratories Inc.

Tel: --
Fax: --
Email: sales@syninnova.com
Country: United States
ProdList: 491
Advantage: 50

OChem Incorporation

Tel: --
Fax: --
Email: sales@ocheminc.com
Country: United States
ProdList: 6501
Advantage: 60

Combi-Blocks Inc.

Tel: --
Fax: --
Email: sales@combi-blocks.com
Country: United States
ProdList: 6618
Advantage: 69

Riedel-de Haen AG

Tel: --
Fax: --
Country: United States
ProdList: 6773
Advantage: 87

Matrix Scientific

Tel: --
Fax: --
Email: sales@matrixscientific.com
Country: United States
ProdList: 6632
Advantage: 80

Anvia Chemicals, LLC

Tel: --
Fax: --
Email: sales@anviachem.com
Country: United States
ProdList: 3933
Advantage: 0

Labseeker Inc

Tel: --
Fax: --
Email: marketing@labseeker.com
Country: United States
ProdList: 1495
Advantage: 55

Ivy Fine Chemicals

Tel: --
Fax: --
Email: sales@ivychem.com
Country: United States
ProdList: 6493
Advantage: 58

AK Scientific, Inc.

Tel: --
Fax: --
Email: sales@aksci.com
Country: United States
ProdList: 6347
Advantage: 65

HONEST JOY HOLDINGS LIMITED

Tel: --
Fax: --
Email: sales@honestjoy.cn
Country: United States
ProdList: 6675
Advantage: 54

3B Scientific Corporation

Tel: --
Fax: --
Email: sales@3bsc.com
Country: United States
ProdList: 6718
Advantage: 47

APAC Pharmaceutical, LLC

Tel: --
Fax: --
Email: sales@apacpharma.com
Country: United States
ProdList: 6322
Advantage: 38

More

Less

View Lastest Price from 4-Acetoxy-2-azetidinone manufacturers

Henan Aochuang Chemical Co.,Ltd.

Product: 4-Acetoxy-2-azetidinone 28562-53-0
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1ton
Release date: 2022-10-14

Career Henan Chemical Co

Product: 4-Acetoxy-2-azetidinone 28562-53-0
Price: US $7.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: JD 794
Release date: 2019-09-02

28562-53-0, 4-Acetoxy-2-azetidinoneRelated Search:

2-Azetidinone (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one Acetoxyacetyl chloride Sodium triacetoxyborohydride Acetoxyacetic acid Silicon tetraacetate 4-BROMOMETHYLBIPHENYL 4-Aminopyrimidine 4-BroMo-3-Methyl-7-azaindole 4-Bromoindole (3R,4R)-4-ACETOXY-3-[(3R)-1-(BUTYLDIMETHYL-SILYOXY)-ETHYL]-2-AZETIDIONE Cyclobutanone 4-BENZOYLOXY-2-AZETIDINONE Acetoxy 4-Acetoxy-2-azetidinone

2-Azetidinone, 4-(acetyloxy)-

4-Oxo-2-azetidinyl acetate

4-ACETOXY-2-AZETIDINONE

3-Acetoxy-3-propanelactam

2-oxoazetidinium 4-acetate

4-OXOAZETIDIN-2-YLACETATE

4-ACETOXY-2-AZETIDINONE(4-AA)

4-Acetyloxyazetidin-2-one

Acetic acid 2-oxoazetidin-4-yl ester

Acetic acid 4-oxo-2-azetidinyl ester

acetic acid (2-oxo-1-azetidinyl) ester

4-Acetoxy-2-azetidinone - [A15221]

28562-53-0

C5H7NO312911

Lactams

Organic Building Blocks

Building Blocks

Carbonyl Compounds

Lactams

Organic Building Blocks

Ring Systems