4-Oxoazetidine-2-carboxylic acid

HCID 3488064

Notes Reactions

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Basic information

CAS: 98019-65-9
Standard SMILES: O=C1CC(C(=O)O)N1
InChIKey: YSPMLLKKKHCTBN-UHFFFAOYSA-N
Molecular formula: C4H5NO3
Average molar mass: 115.09 g/mol
Monoisotopic mass: 115.02694302

Names & identifiers

Preferred name: 4-Oxoazetidine-2-carboxylic acid
IUPAC: 4-oxoazetidine-2-carboxylic acid
English name: 4-Oxoazetidine-2-carboxylic acid
Molecular formula: C4H5NO3
Molecular weight: 115.09

Names & synonyms

4-oxoazetidine-2-carboxylic AcidRefChem:526202869-806-54-oxo-2-azetidinecarboxylic acid98019-65-94-Oxo-azetidine-2-carboxylic acidMFCD007981602-Azetidinecarboxylic acid, 4-oxo-4-carboxy-2-azetidinone4-Carboxyazetidin-2-one4-carboxyazetidine-2-oneSCHEMBL690090

Show more names

(2R)-2-azetidinone-4-carboxylic acid

4-oxo-2-azetidinecarboxylicacid4-hydroxycarbonylazetidine-2-oneDTXSID80392950YSPMLLKKKHCTBN-UHFFFAOYSA-NAKOS006227845CS-W019929PB21715PB27000

Database identifiers

CAS: 98019-65-9
PubChem CID: 3488064
DTXSID: DTXSID80392950
EC Number: 869-806-5

Properties

Computed structural properties

XLogP: -1.1
Topological polar surface area: 66.4 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 1
Heavy atoms: 8
Formal charge: 0
Complexity: 142

Physicochemical properties

Boiling point: 489.4 · 489.4±38.0 °C(Predicted)
Density: 1.519 · 1.519±0.06 g/cm3(Predicted)
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2-8°C
pka: 3.19 · 3.19±0.20(Predicted)
Appearance: White to off-white Solid
InChI: InChI=1S/C4H5NO3/c6-3-1-2(5-3)4(7)8/h2H,1H2,(H,5,6)(H,7,8)
InChIKey: YSPMLLKKKHCTBN-UHFFFAOYSA-N
SMILES: N1C(=O)CC1C(O)=O
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H319
Precautionary statements: 305 · P305+P351+P338
HazardClass: IRRITANT

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2A (100%)；STOT SE 3 (100%)

Safety data

Signal word: Warning
Symbol(GHS): GHS07
hazard_class: IRRITANT
Hazard statements: H302-H319
Precautionary statements: P305+P351+P338

Chemistry & industry

Applications · 1 item

Description4-Oxoazetidine-2-carboxylic acid may be interpreted as a cyclic mimetic of the amino acid Asp. Due to the high reactivity of the four-membered ring, this molecule can serve as an “electrophilic trap” in reactions with nucleophiles. 4-oxoazetidine-2-carboxylic acid can be used as a building block for developing enzyme inhibitors, particularly protease inhibitors. It undergoes coupling reactions with amino acids and oligopeptide esters. Following desilylation of the amino acid residue and deprotection, free β-lactam peptides are obtained[1].