Iodoacetamide

HCID 3727CAS 144-48-9

Basic information

Standard SMILES
NC(=O)CI
InChIKey
PGLTVOMIXTUURA-UHFFFAOYSA-N
Molecular formula
C2H4INO
Average molar mass
184.96 g/mol
Monoisotopic mass
184.93376175

Overview

Iodoacetamide is a sulfhydryl alkylating reagent that forms covalent bonds with the thiol group of cysteines so the protein or peptide no longer forms disulfide bonds.

Names & identifiers

Preferred name
Iodoacetamide
IUPAC
2-iodoacetamide
English name
2-Iodoacetamide
Molecular formula
C2H4INO
Molecular weight
184.96

Names & synonyms

2-Iodoacetamideiodoacetamide144-48-9SurautoACETAMIDE, 2-IODO-MonoiodoacetamideDTXSID9020742N-(3-Methoxy-4-butoxybenzyl)thiobarbituric acidZRH8M27S79NSC-9581DTXCID10742RefChem:389075
Show more names
IAMIODACETAMIDEusafd-12-IodacetamidIodoethanamide2-iodo-acetamid
205-630-1USAF D-1MFCD00008028CCRIS 7710.alpha.-IodoacetamideAI3-518412-Iodo-acetamidealpha-Iodoacetamide

Database identifiers

CAS
144-48-9
PubChem CID
3727
DTXSID
DTXSID9020742
ChEMBL
CHEMBL276727
UNII
ZRH8M27S79
EC Number
205-630-1
Nikkaji
J3.270K

Properties

Computed structural properties

XLogP
-0.2
Topological polar surface area
43.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
5

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds
SpringerMaterials PropertiesSchoenflies notation
LogP-0.19
Vapor Pressure0.00506 [mmHg]
Physical DescriptionCrystalline solid; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
92 · 92-95 °C(lit.)
Boiling point
297.1 · 297.1±23.0 °C(Predicted)
Density
2.1103 · 2.1103 (estimate)
storage temp.
2 · 2-8°C
solubility
Soluble in water, dimethyl formamide and ethanol. Slightly soluble in methanol.
form
crystalline

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (99%): Toxic if swallowed [Danger Acute toxicity, oral]

P233, P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P316, P302+P352, P304+P340, P321, P330, P333+P317, P342+P316, P362+P364, P403, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 192 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Acetamide, 2-iodo-

2-Iodoacetamide: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 item

Causes ulceration or bleeding from the stomach and other GI changes in 74-week intermittent oral studies of rats; [RTECS] May cause irritation; May cause skin and respiratory sensitization; Toxic by ingestion; [Sigma-Aldrich MSDS] See Chloroacetamide.

Hazard Classes and CategoriesAcute Tox. 3 (99%)

Toxicology

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.

Safety data

F
8-10-21
wgk
3
tsca
TSCA listed
rtecs
AC4200000
ridadr
UN 2811 6.1/PG 3
hs_code
29241900

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Highly reactive chemicals that introduce alkyl radicals into biologically active molecules and thereby prevent their proper functioning. Many are used as antineoplastic agents, but most are very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. They have also been used as components in poison gases.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Uses & manufacturing

UsesAn alkylating sulfhydryl reagent with action similar to iodoacetate; [ChemIDplus]
General Manufacturing InformationAcetamide, 2-iodo-: ACTIVE
Applications · 1 item

Uses2-Iodoacetamide is an alkylating reagent for cysteine residues in peptide sequencing. Its actions are similar to those of iodoacetate. By virtue of reaction with cysteine, it is an irreversible inhibitor of enzymes with cysteine at the active site. It reacts much more slowly with histidine residues, but that activity is responsible for inhibition of ribonuclease.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Related reactions

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Linked notes

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