ChemicalBook > CAS DataBase List > 2-Iodoacetamide

2-Iodoacetamide

Product Name
2-Iodoacetamide
CAS No.
144-48-9
Chemical Name
2-Iodoacetamide
Synonyms
IODOACETAMIDE;IAM;IODACETAMIDE;Surauto;usafd-1;USAF d-1;2-Iodacetamid;Iodoethanamide;2-iodo-acetamid;2-IODOACETAMIDE
CBNumber
CB4760867
Molecular Formula
C2H4INO
Formula Weight
184.96
MOL File
144-48-9.mol
More
Less

2-Iodoacetamide Property

Melting point:
92-95 °C(lit.)
Boiling point:
297.1±23.0 °C(Predicted)
Density 
2.1103 (estimate)
storage temp. 
2-8°C
solubility 
Soluble in water, dimethyl formamide and ethanol. Slightly soluble in methanol.
form 
crystalline
pka
15.16±0.40(Predicted)
color 
White to pale yellow or beige
Water Solubility 
H2O: 0.5M at 20°C, clear, colorless
Sensitive 
Light Sensitive
BRN 
1739080
Stability:
Stable, but light sensitive. Incompatible with strong oxidizing agents, strong bases, reducing agents, acids.
InChIKey
PGLTVOMIXTUURA-UHFFFAOYSA-N
CAS DataBase Reference
144-48-9(CAS DataBase Reference)
NIST Chemistry Reference
Alpha-iodo acetamide(144-48-9)
EPA Substance Registry System
2-Iodoacetamide (144-48-9)
More
Less

Safety

Hazard Codes 
T
Risk Statements 
25-42/43-43-36/37/38-53
Safety Statements 
22-36/37-45-37/39-26-24
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
AC4200000
F 
8-10-21
TSCA 
T
HazardClass 
6.1
PackingGroup 
III
HS Code 
29241900
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

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

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.04744
Product name
2-Iodoacetamide
Purity
for synthesis
Packaging
25g
Price
$73.2
Updated
2024/03/01
Sigma-Aldrich
Product number
8.04744
Product name
2-Iodoacetamide
Purity
for synthesis
Packaging
100g
Price
$233
Updated
2024/03/01
Sigma-Aldrich
Product number
A3221
Product name
Iodoacetamide
Purity
Single use vial of 56 mg
Packaging
10vials
Price
$97.9
Updated
2024/03/01
Sigma-Aldrich
Product number
8.04744
Product name
2-Iodoacetamide
Purity
for synthesis
Packaging
1kg
Price
$1500
Updated
2024/03/01
Sigma-Aldrich
Product number
8.04744
Product name
2-Iodoacetamide
Purity
for synthesis
Packaging
2.5kg
Price
$3550
Updated
2024/03/01
More
Less

2-Iodoacetamide Chemical Properties,Usage,Production

Chemical Properties

White solid in amber, foil sealed microtubes. Soluble in hot water, easily soluble in ethanol.

Uses

2-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.

Application

Alkylating agent used in peptide mapping because it covalently binds with the thiols in cysteine to prevent disulfide bond formation 2-Iodoacetamide is used as an electrophile for covalent modification of nucleophilic residues on proteins such as cysteine, methionine and histidine. It is used to bind with thiol group of cysteine, thereby it protects the formation disulfide bonds. It is involved as an inhibitor of deubiquitinase enzymes (DUBs). Further, it acts as an alkylating sulfhydryl reagent.

Biological Activity

Iodoacetamide acts as an alkylating reagent for cysteine residues in peptide sequencing. 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 inhibiting ribonuclease.

Synthesis

2-Iodoacetamide is synthesized by reacting chloroacetamide with sodium iodide. The chloroacetamide, anhydrous acetone, and anhydrous sodium iodide were refluxed on the bath for 15h. Cool to room temperature, filter out sodium chloride, recover acetone, pour into ice water of sodium bisulfate after a little cooling, and then neutralize to pH 6 with saturated sodium sulfate solution. Cool to crystallize and filter to obtain crude product. The crude product is recrystallized with water to obtain the finished product.

Purification Methods

Crystallise it from water or CCl4. It is used for tagging proteins. [Gurd Methods Enzymol 25 424 1972, Beilstein 2 IV 536.]

Preparation and handling

Alkylation Procedure
Iodoacetamide is unstable and light-sensitive. Prepare solutions immediately before use and perform alkylation in the dark. If iodoacetamide is present in limiting quantities and a slightly alkaline pH, cysteine modification will be the exclusive reaction. Excess iodoacetamide or non-buffered iodoacetamide reagent can also alkylate amines (lysine, N-termini), thioethers (methionine), imidazoles (histidine) and carboxylates (aspartate, glutamate).
1. Add 5 μl of 2% SDS and 45 μl of 200 mM ammonium bicarbonate (pH 8.0) to 20-100 μg of protein sample. Adjust volume to 100 μl with ultrapure water.
2. Add 5 μl of 200 mM Tris(2-carboxyethyl) phosphine hydrochloride (TCEP.HCl, Product No. 20490) and incubate sample at 55°C for 1 hour.
3. Immediately before use, dissolve one tube of iodoacetamide (9.3 mg) with 132 μl of 200 mM ammonium bicarbonate (pH 8.0) to make 375 mM iodoacetamide. Protect solution from light.
4. Add 5 μl of the 375 mM iodoacetamide to the sample and incubate for 30 minutes protected from light.
5. Proceed to proteolytic digestion before MS analysis or other processing.

Precautions

Store in a cool place. Light and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong acids, strong bases, strong oxidizing agents and strong reducing agents.

2-Iodoacetamide Preparation Products And Raw materials

Raw materials

Dry acetone Acetone Chloroacetamide Sodium iodide

Preparation Products

More
Less

2-Iodoacetamide Suppliers

Americas 1 Belgium 1 Canada 1 China 285 Europe 5 Germany 7 India 9 Japan 5 Poland 1 Slovakia 2 South Korea 1 Switzerland 2 United Kingdom 14 United States 43 Global 377
CovaChem, LLC.
Tel
+1815.714.8421 (direct)
Fax
+1815.315.1272
Email
tonynooner@covachem.com
Country
United States
ProdList
89
Advantage
58
TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32165
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
TargetMol Chemicals Inc.
Tel
Email
support@targetmol.com
Country
United States
ProdList
38632
Advantage
58
DeLong Chemicals America
Tel
--
Fax
--
Email
sales@delongchemicals.com
Country
United States
ProdList
529
Advantage
50
RSA Corporation
Tel
--
Fax
--
Email
media@RSAgroup.ca
Country
United States
ProdList
343
Advantage
58
Alichem Inc.
Tel
--
Fax
--
Email
sales@alichem.com
Country
United States
ProdList
6167
Advantage
58
Fine Chem Trading LTD
Tel
--
Fax
--
Email
chemfinder@chemfinder.co.uk
Country
United States
ProdList
1609
Advantage
64
Esprix Technologies
Tel
--
Fax
--
Email
info@esprixtech.com
Country
United States
ProdList
619
Advantage
58
United States Biological
Tel
--
Fax
--
Email
chemicals@usbio.net
Country
United States
ProdList
6214
Advantage
80
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
TCI America
Tel
--
Fax
--
Email
sales@tciamerica.com
Country
United States
ProdList
6909
Advantage
75
Matrix Scientific
Tel
--
Fax
--
Email
sales@matrixscientific.com
Country
United States
ProdList
6632
Advantage
80
AppliChem, LLC
Tel
--
Fax
--
Email
sales@applichem.com
Country
United States
ProdList
169
Advantage
50
TOKU-E Company
Tel
--
Fax
--
Email
info@toku-e.com
Country
United States
ProdList
320
Advantage
50
Acg Chemical
Tel
--
Fax
--
Email
sales@acgchemical.com
Country
United States
ProdList
40
Advantage
50
Waterstone Technology, LLC
Tel
--
Fax
--
Email
sales@waterstonetech.com
Country
United States
ProdList
6786
Advantage
30
Cambridge Isotope Laboratories, Inc.
Tel
--
Fax
--
Email
cilsales@isotope.com
Country
United States
ProdList
6598
Advantage
79
ChemService Inc.
Tel
--
Fax
--
Country
United States
ProdList
6379
Advantage
68
Beta Pharma, Inc.
Tel
--
Fax
--
Email
sales@betapharma.com
Country
United States
ProdList
6226
Advantage
60
Oakwood Products, Inc.
Tel
--
Fax
--
Email
sales@oakwoodchemical.com
Country
United States
ProdList
6193
Advantage
74
Chem-Impex International, Inc.
Tel
--
Fax
--
Country
United States
ProdList
6730
Advantage
64
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6718
Advantage
47
HONEST JOY HOLDINGS LIMITED
Tel
--
Fax
--
Email
sales@honestjoy.cn
Country
United States
ProdList
6675
Advantage
54
Geno Technology, Inc
Tel
--
Fax
--
Email
order@gbiosciences.com
Country
United States
ProdList
38
Advantage
77
Advance Scientific & Chemical
Tel
--
Fax
--
Email
sales@advance-scientific.com
Country
United States
ProdList
6419
Advantage
71
City Chemical LLC
Tel
--
Fax
--
Email
sales@citychemical.com
Country
United States
ProdList
6708
Advantage
72
Roche Applied Science
Tel
--
Fax
--
Email
biochemts.us@roche.com
Country
United States
ProdList
696
Advantage
85
BioWorld
Tel
--
Fax
--
Email
save@bio-WORLD.com
Country
United States
ProdList
148
Advantage
72
Acros Organics USA
Tel
--
Fax
--
Email
eveleth@fisherchem.com
Country
United States
ProdList
3846
Advantage
81
Perkin Elmer Life Sciences Inc.
Tel
--
Fax
--
Email
techsupport@nen.com
Country
United States
ProdList
1296
Advantage
86
Alfa Aesar
Tel
--
Fax
--
Email
tech@alfa.com
Country
United States
ProdList
6814
Advantage
81
City Chemicals Corporation
Tel
--
Fax
--
Country
United States
ProdList
6460
Advantage
72
Amersham Biosciences, Inc.
Tel
--
Fax
--
Country
United States
ProdList
1270
Advantage
85
Research Organics Inc.
Tel
--
Fax
--
Email
info@resorg.com
Country
United States
ProdList
1324
Advantage
72
Eastern Chemical Corp.
Tel
--
Fax
--
Email
eastern@u-g.com
Country
United States
ProdList
2786
Advantage
34
EMD Biosciences, Inc.
Tel
--
Fax
--
Email
technical@calbiochem.com
Country
United States
ProdList
6529
Advantage
66
Spectrum Chemicals & Laboratory Products
Tel
--
Fax
--
Email
sales@spectrumchemical.com
Country
United States
ProdList
6699
Advantage
77
Crescent Chemical Co., Inc.
Tel
--
Fax
--
Email
sales@creschem.com
Country
United States
ProdList
4597
Advantage
68
MP Biomedicals, Inc.
Tel
--
Fax
--
Country
United States
ProdList
6561
Advantage
81
AMRESCO Inc.
Tel
--
Fax
--
Email
info@amresco-inc.com
Country
United States
ProdList
760
Advantage
73
Pfaltz & Bauer, Inc.
Tel
--
Fax
--
Email
sales@pfaltzandbauer.com
Country
United States
ProdList
6828
Advantage
72
More
Less

View Lastest Price from 2-Iodoacetamide manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
2-Iodoacetamide 144-48-9
Price
US $75.00-20.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-06-03
Shaanxi Dideu Medichem Co. Ltd
Product
2-Iodoacetamide 144-48-9
Price
US $0.00-0.00/KG
Min. Order
5mg
Purity
99% HPLC
Supply Ability
2000tons
Release date
2019-12-30
Hebei Yanxi Chemical Co., Ltd.
Product
2-Iodoacetamide 144-48-9
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20 tons
Release date
2023-11-21

144-48-9, 2-IodoacetamideRelated Search:

Iodobenzene Lead(II) iodide Potassium iodide Cuprous iodide Zinc iodide Cyclopropyl iodide Sodium iodide IODOCYCLOPENTANE Cesium iodide Lithium iodide 5-IODOURIDINE EDANS IODOACETAMIDE 5-Iodouracil 2-Iodoacetamide IODOANTIPYRINE BENZOPHENONE-4-IODOACETAMIDE Acetamide 1,8-I-AEDANS

  • 2-iodo-acetamid
  • Acetamide, 2-iodo-
  • Monoiodoacetamide
  • Surauto
  • USAF d-1
  • usafd-1
  • 2-Iodoacetamide, Stab. With ca 5-8% Water
  • Iodiacetamide[IAM]
  • IAM
  • 2-IodoacetaMide&nbsp
  • IodoacetaMide, 98% 25GR
  • 2-IODOACETAMIDE FOR SYNTHESIS
  • 2-IodoacetaMide, 98.0%(N)
  • IAM, iodoacetamide
  • Iodoacetamide 2-Iodoacetamide
  • Iodoacetamide Vetec(TM) reagent grade, 99%
  • COLUMN HIBIND RNA COLUMNS
  • Iodoacetamide acid
  • IODOACETAMIDE BIOULTRA
  • IODOACETAMIDE, >=99% (NMR), CRYSTALL
  • IODOACETAMIDE, SINGLE USE VIAL OF 56
  • 2-Iodoacetamide, stabilized with &ap:5 to 8% water
  • α-Iodoacetamide - CAS 144-48-9 - Calbiochem
  • ALPHA-IODOACETAMIDE
  • 2-IODOACETAMIDE
  • IODOACETAMIDE
  • 0IODOACETAMIDE CRYSTALLINE
  • ALKYLATING REAGENT, IODOACETAMIDE
  • IODOACETAMIDE SIGMAULTRA
  • 2-Iodoacetamide, 98%, stab. with ca 5-8% water
  • 2-IODOACETAMIDE,CRYSTAL
  • IODACETAMIDE
  • Iodoethanamide
  • 2-Iodoacetamide [for Biochemical Research]
  • Iodoacetamide,98%
  • 2-Iodacetamid
  • Iodoacetamide, 98%, reagent grade
  • 2-Iodoacetamide[forBiochemicalResearch]&gt
  • 2-Iodoacetamide&gt
  • 2-Iodoacetamide ISO 9001：2015 REACH
  • 2-lodoacetamide
  • 144-48-9
  • C2H4INO
  • C2H4I1N1O1
  • ICH2CONH2
  • BioChemical
  • Biochemicals and Reagents
  • A to C
  • Carnitine acetyltransferase
  • Protein Modification
  • Specific Amino Acid Modification
  • Enzymes, Inhibitors, and Substrates
  • Enzyme Inhibitors by Enzyme
  • Enzyme Inhibitors
  • Reagents for cysteine modification
  • Proteomics and Protein Expression
  • Proteomics
  • API intermediates