IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER

Base Information

• Chemical Name: IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER
• CAS No.: 39028-27-8
• Molecular Formula: C6H6INO4
• Molecular Weight: 283.022
• Hs Code.: 29251900
• European Community (EC) Number: 636-792-5
• DSSTox Substance ID: DTXSID40391202
• Nikkaji Number: J875.367I
• Wikidata: Q72483281
• Mol file: 39028-27-8.mol

Synonyms:2,5-Pyrrolidinedione,1-[(iodoacetyl)oxy]- (9CI);N-Hydroxysuccinimide iodoacetate;N-Hydroxysuccinimide iodoacetic acid ester;N-Hydroxysuccinimidyl iodoacetate;N-Iodoacetoxysuccinimide;SIA;SIA (crosslinking agent);

Chemical Property of IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 0.000433mmHg at 25°C
• Melting Point: 148 °C
• Refractive Index: 1.614
• Boiling Point: 315.6 °C at 760 mmHg
• Flash Point: 144.7 °C
• PSA: 63.68000
• Density: 2.11 g/cm³
• LogP: -0.03350
• Storage Temp.: −20°C
• Solubility.: DMF: 50 mg/mL
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 282.93416
• Heavy Atom Count: 12
• Complexity: 224

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Succinimidyl Iodoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)CI
• 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.
• Uses: A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. Spacer Arm: 1.5 Angstroms forms water soluble carboxylate derivatives A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. Spacer Arm: 1.5 Angstroms

Technology Process of IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER

There total 2 articles about IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + Iodoacetic acid (64-69-7) → N-hydroxy-succinimide-(2-iodo)acetate (39028-27-8)

Guidance literature:

With diisopropyl-carbodiimide; In ethyl acetate; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1039/c6ob01080f

Reference yield:

→ N-hydroxy-succinimide-(2-iodo)acetate (39028-27-8)

Guidance literature:

N-Hydroxysuccinimid, Iodessigsaeure;

Reference yield: 90.0%

N-hydroxy-succinimide-(2-iodo)acetate (39028-27-8) + 1-(N-benzyloxycarbonyl-3-iodo-L-tyrosyl)-hydrazine (79677-63-7) → 1-(N-benzyloxycarbonyl-3-iodo-L-tyrosyl)-2-iodoacetylhydrazine

Guidance literature:

In N,N-dimethyl-formamide; for 0.5h; Ambient temperature;

DOI:10.1016/0223-5234(93)90147-7

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

Iodoacetic acid

Downstream raw materials:

1-(N-carbobenzyloxy-L-alanyl-L-alanyl-L-phenylalanyl)-2-iodoacetyl hydrazine

N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^ε-(iodoacetyl)-L-lysine

C₇₅H₉₉IN₂₆O₁₃

C₂₁H₂₉IN₄O₈

Refernces

• 1、 Lizzul-Jurse, Antoine,Bailly, Laetitia,Hubert-Roux, Marie,Afonso, Carlos,Renard, Pierre-Yves,Sabot, Cyrille. "Readily functionalizable phosphonium-tagged fluorescent coumarins for enhanced detection of conjugates by mass spectrometry". supporting information. p. 7777 - 7791. Retrieved 2016/08/24.
• 2、 Bartolucci,Cellai,Di Filippo,Segre,Brufani,Filocamo,Bianco,Guiso,Brizzi,Benedetto,Di Caro,Elia. "Rifamycins as inhibitors of retroviral reverse transcriptase from M-MuLV, RAV-2, and HIV-1". . p. 1367 - 1383. Retrieved 2007/10/02.