N-Iodosuccinimide

Athanor · official

C₄H₄INO₂ · 224.98 g/mol

IUPAC name: 1-iodopyrrolidine-2,5-dione

Also called NIS

Reagents Rings

Open in Athanor

Drawn from its SMILES with RDKit

WarningHarmful if swallowed · Causes skin irritation · Causes serious eye irritation · May cause respiratory irritation

Names and identifiers

IUPAC name: 1-iodopyrrolidine-2,5-dione
Synonyms: NIS, 1-Iodopyrrolidine-2,5-dione, Succiniodimide
+ 35 more
2,5-Pyrrolidinedione, 1-iodo-, 1-iodo-2,5-pyrrolidinedione, 3COS3X3N4P, CHEBI:53204, DTXSID10199550, RefChem:163587, DTXCID70122041, 208-221-6, N-Iodosuccinimide (NIS), MFCD00005512, Succinimide, N-iodo-, UNII-3COS3X3N4P, EINECS 208-221-6, 2,5-Dioxo-1-iodopyrrolidine, BRN 0113917, 1-iodo-pyrrolidine-2,5-dione, 5-21-09-00544 (Beilstein Handbook Reference), 1-iodoazolidine-2,5-dione, C4H4INO2, n-iodo succinimide, 1-iodo-2,5-pyrrolidinedione; NIS; Succiniodimide;, n-iodsuccinimide, N-iodosuccinimid, N-iodosuccinirnide, N-Jod-succinimid, N-iodo-succinimide, N-iodosuccinic acid imide, N-Iodosuccinimide, 95%, N-iodopyrrolidin-2,5-dione, SCHEMBL18779, N-IODOSUCCINIMIDE [MI], HY-ER017, orb2939787, SCHEMBL1058967, STR02991
Molecular formula: C₄H₄INO₂
Empirical formula: C₄H₄INO₂
Molecular weight: 224.98 g/mol
Exact mass: 224.92868
CAS number: 516-12-1
PubChem CID: 120273
Canonical SMILES: C1CC(=O)N(C1=O)I
Isomeric SMILES: C1CC(=O)N(C1=O)I
InChI: InChI=1S/C4H4INO2/c5-6-3(7)1-2-4(6)8/h1-2H2
InChIKey: LQZMLBORDGWNPD-UHFFFAOYSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms: 8
Rings: 1
Aromatic rings: 0
Fraction sp³ carbons (Fsp3): 0.5
H-bond donors: 0
H-bond acceptors: 2
Rotatable bonds: 0
TPSA (Å²): 37.4
Formal charge: 0
XLogP3: -0.2 PubChem
Complexity: 129 PubChem
Stereocenters: None
Double-bond geometry: None specified
Point group: C2v of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

C21.35%
H1.79%
I56.41%
N6.23%
O14.22%

Isotope pattern

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P: 0.49 Crippen (Wildman and Crippen 1999)
log S (water solubility): -1.54 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 3.41 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 224.99
log P ≤ 5 (Crippen): 0.49
H-bond donors ≤ 5: 0
H-bond acceptors ≤ 10: 2

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Warning

Most widely reported: 87 company reports to ECHA. Source [1].

Harmful or irritant

H302Harmful if swallowed (85.1% of reports)
H315Causes skin irritation (90.8% of reports)
H319Causes serious eye irritation (90.8% of reports)
H335May cause respiratory irritation (87.4% of reports)

Precautionary statements: 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, P501

View all classifications (2)

[1] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 8% (7 of 87) of reports.
[1] European Chemicals Agency (ECHA) · 87 reports · WarningH302, H315, H319, H335

Safety data sheets on the supplier’s page: AbaChemScene, Cooke Chemical Co., Ltd, MP Biomedicals.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

[1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
[2]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
·Literature on PubChem

Data last updated 2026-10-14.