2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid

HCID 319935

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Basic information

CAS: 25021-08-3
Standard SMILES: O=C(O)CN1C(=O)C=CC1=O
InChIKey: GBKPNGVKZQBPCZ-UHFFFAOYSA-N
Molecular formula: C6H5NO4
Average molar mass: 155.11 g/mol
Monoisotopic mass: 155.02185764

Names & identifiers

Preferred name: 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid
IUPAC: 2-(2,5-dioxopyrrol-1-yl)acetic acid
English name: 2-Maleimido acetic acid
Molecular formula: C6H5NO4
Molecular weight: 155.11

Names & synonyms

2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acidRefChem:452115607-487-425021-08-32-Maleimido acetic acid2-(2,5-dioxopyrrol-1-yl)acetic acid2-Maleimidoacetic acidMaleimidoacetic AcidMFCD004572542,5-Dihydro-2,5-dioxo-1H-pyrrole-1-acetic AcidMLS003107259(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid

Show more names

N-MaleoylglycineN-MaleiMidoglycineN,N-maleoyl-glycine2-maleimide acetic acidN-(CarboxyMethyl)MaleiMide2-MALEIMIDO ACETIC ACID 97%

2-Maleimidoaceticacid2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-acetic Acid; N-(Carboxymethyl)maleimide; N-Maleimidoglycine; N-Maleoylglycine; NSC 266055;N-maleyl glycine1H-Pyrrole-1-acetic acid, 2,5-dihydro-2,5-dioxo-NSC266055NSC 2660552,5-dihydro-2,5-dioxopyrrol-1-ylacetic acidSCHEMBL515800

Database identifiers

CAS: 25021-08-3
PubChem CID: 319935
DTXSID: DTXSID40313040
ChEMBL: CHEMBL1878916
EC Number: 607-487-4
Nikkaji: J654.141K

Properties

Computed structural properties

XLogP: -0.1
Topological polar surface area: 74.7 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 11
Formal charge: 0
Complexity: 237

Physicochemical properties

Melting point: 114 °C · 114 °C(Solv: chloroform (67-66-3))
Boiling point: 376.7 · 376.7±25.0 °C(Predicted)
Density: 1.578 · 1.578±0.06 g/cm3(Predicted)
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2-8°C
solubility: soluble in DMSO, Methanol
form: powder to crystal
pka: 3.31 · 3.31±0.10(Predicted)
color: White to Almost white
InChI: InChI=1S/C6H5NO4/c8-4-1-2-5(9)7(4)3-6(10)11/h1-2H,3H2,(H,10,11)
InChIKey: GBKPNGVKZQBPCZ-UHFFFAOYSA-N
SMILES: N1(CC(O)=O)C(=O)C=CC1=O
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302+H312+H332-H315-H319-H335
Precautionary statements: 261 · P261-P280-P305+P351+P338
HS Code: 2925.19 · 2925.19.4200

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (50%)；Skin Irrit. 2 (100%)；Eye Irrit. 2A (100%)；STOT SE 3 (50%)

Safety data

hs_code: 2925.19.4200
Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302+H312+H332-H315-H319-H335
Precautionary statements: P261-P280-P305+P351+P338

Chemistry & industry

Applications · 1 item

UsesMaleimidoacetic Acid (CAS# 25021-08-3) is a heterocyclic organic compound that has a variety of uses in organic synthesis. It contains both a maleimide and carboxylic acid functional group, making it a versatile reagent for coupling reactions with amine-containing compounds.