ChemicalBook > CAS DataBase List > IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER

IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER

Product Name
IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER
CAS No.
39028-27-8
Chemical Name
IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER
Synonyms
SIA;SIA Crosslinker;NHS IODOACETATE;N-IodoacetoxysucciniMide;Succinimidyl iodoacetate;N-SUCCINIMIDYL IODOACETATE;SIA (succinimidyl iodoacetate);N-Succinimidyl Iodoacetate >N-SucciniMidyl iodoacetate(SIA);N-Succinimidyl Iodoacetate, 95+%
CBNumber
CB9364435
Molecular Formula
C6H6INO4
Formula Weight
283.02
MOL File
39028-27-8.mol
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IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER Property

Melting point:
148°C
Boiling point:
315.6±44.0 °C(Predicted)
Density 
2.11±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMF: 50 mg/mL
form 
powder
color 
White to Off-White
InChI
InChI=1S/C6H6INO4/c7-3-6(11)12-8-4(9)1-2-5(8)10/h1-3H2
InChIKey
VRDGQQTWSGDXCU-UHFFFAOYSA-N
SMILES
C(ON1C(=O)CCC1=O)(=O)CI
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
HS Code 
29251900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

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

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
I9760
Product name
Iodoacetic acid N-hydroxysuccinimide ester
Purity
powder
Packaging
50mg
Price
$219.1
Updated
2025/07/31
Sigma-Aldrich
Product number
I9760
Product name
Iodoacetic acid N-hydroxysuccinimide ester
Purity
powder
Packaging
100mg
Price
$317.8
Updated
2025/07/31
TCI Chemical
Product number
S0844
Product name
N-Succinimidyl Iodoacetate
Purity
>95.0%(N)
Packaging
100mg
Price
$212
Updated
2025/07/31
TRC
Product number
S690290
Product name
N-Succinimidyl Iodoacetate
Packaging
50mg
Price
$80
Updated
2021/12/16
Chem-Impex
Product number
22998
Product name
Succinimidyliodoacetate,≥98%(HPLC)
Purity
≥98%(HPLC)
Packaging
100MG
Price
$69.89
Updated
2021/12/16
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IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER Chemical Properties,Usage,Production

Description

SIA Crosslinker is a non-cleavable, water-soluble crosslinker containig an NHS ester and an iodine group. The NHS ester is reactive toward amines while the iodine reacts with thiol groups.

Chemical Properties

White Solid

Uses

A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. Spacer Arm: 1.5 Angstroms

Uses

forms water soluble carboxylate derivatives

Uses

A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. Spacer Arm: 1.5 Angstroms

reaction suitability

reagent type: cross-linking reagent

Biological Activity

SIA Crosslinker is a non-cleavable ADC linker that can be used to synthesize antibody drug conjugates (ADCs).

Synthesis

6066-82-6

64-69-7

39028-27-8

N-hydroxysuccinimide (12.6 mmol) and dicyclohexylcarbodiimide (20.3 mmol) were dissolved in an appropriate amount of solvent at 0 °C, followed by the addition of iodoacetic acid (6 mmol). The reaction mixture was gradually warmed up to room temperature with continuous stirring for 4 hours. For the synthesis of compound VIa, maleic anhydride (10 mmol) was pre-reacted with β-alanine in N,N-dimethylformamide for 1 hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure and the crude product was dissolved in dichloromethane and washed with water. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated to dryness. The residue was purified by recrystallization to afford the target product succinimidyl iodoacetate (VIb) in 30% yield. The structure of the product was confirmed by 1H NMR (CDCl3) and 13C NMR (CDCl3): 1H NMR (CDCl3) δppm: 2.87 (2H, s), 3.96 (1H, s); 13C NMR (CDCl3) δppm: -12.47 (1C, s) 25.85 (2C, s) 164.78 (1C, s) 168.78 (2C, s).

in vitro

ADCs are comprised of an antibody to which is attached an ADC cytotoxin through an ADC linker.

References

[1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 32, p. 7777 - 7791
[2] Patent: US2013/273581, 2013, A1. Location in patent: Page/Page column 0092; 0111-0112; 0114
[3] Farmaco, 1992, vol. 47, # 11, p. 1367 - 1383

IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER 39028-27-8
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER 39028-27-8
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-08
Career Henan Chemical Co
Product
IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER 39028-27-8
Price
US $6.60/KG
Min. Order
1KG
Purity
97%-99%
Supply Ability
1kg-1000kg
Release date
2019-12-26

39028-27-8, IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTERRelated Search:


  • N-HydroxysucciniMide Iodoacetic Acid Ester
  • N-IodoacetoxysucciniMide
  • Iodoacetic Acid N-Succinimidyl Ester N-(Iodoacetoxy)succinimide
  • 2,5-Pyrrolidinedione, 1-[(iodoacetyl)oxy]-
  • N-SucciniMidyl iodoacetate(SIA)
  • SIA
  • N-HYDROXYSUCCINIMIDYL IODOACETATE
  • NHS IODOACETATE
  • N-SUCCINIMIDYL IODOACETATE
  • SIA Crosslinker
  • Iodoacetic acid N-hydroxysuccinimide ester powder
  • 2,5-Dioxopyrrolidin-1-yl 2-iodoacetate
  • IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER
  • Succinimidyl iodoacetate
  • SIA (succinimidyl iodoacetate)
  • 2-Iodoacetate N-Succinimidyl Ester
  • N-Succinimidyl Iodoacetate &gt
  • Acetic acid, 2-iodo-, 2,5-dioxo-1-pyrrolidinyl ester
  • Iodoacetic Acid N-Succinimidyl Ester
  • N-Succinimidyl Iodoacetate, 95+%
  • Iodoacetic acid <i>N</i>-hydroxysuccinimide ester
  • 39028-27-8
  • C6H6INO4
  • C6H6NO4I
  • BioChemical
  • Crosslinking
  • Heterobifunctional Cross-Linking Reagents
  • Proteomics and Protein Expression
  • Protein Modification
  • Proteomics
  • MTS and Sulfhydryl Active Reagents
  • Heterobifunctional Crosslinker
  • heteroXlink
  • Cross Linking Reagents
  • MTS & Sulfhydryl Active Reagents
  • Active Esters/AdditivesProtein Modification
  • Active Esters/AdditivesSynthetic Reagents
  • Coupling
  • Crosslinking
  • Heterobifunctional Cross-Linking Reagents
  • Peptide Synthesis