81867-37-0

Basic information

• Product Name: benzyl iodoacetate
• Synonyms: Iodoacetic acid phenylmethyl ester;Nsc21800;benzyl 2-iodoacetate;benzyl iodoacetate;Iodoacetic acid benzyl ester
• CAS NO: 81867-37-0
• Molecular Formula: C₉H₉IO₂
• Molecular Weight: 276.07103
• EINECS: 279-839-1
• Mol File: 81867-37-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 302.6°Cat760mmHg
• Flash Point: 136.8°C
• Appearance: /
• Density: 1.714g/cm³
• Vapor Pressure: 0.000977mmHg at 25°C
• Refractive Index: 1.601
• CAS DataBase Reference: benzyl iodoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl iodoacetate(81867-37-0)
• EPA Substance Registry System: benzyl iodoacetate(81867-37-0)

Safety Data

• Hazardous Substances Data: 81867-37-0(Hazardous Substances Data)

Usage

General Description

Benzyl iodoacetate is an organic compound that is commonly used as a reagent in organic synthesis. It is a colorless to pale yellow liquid with a pungent odor, and is highly reactive due to the presence of the iodine atom. Benzyl iodoacetate is used as an alkylating agent, allowing it to introduce the benzyl group to a variety of organic compounds. It is also used in the synthesis of pharmaceuticals and other organic chemicals. However, benzyl iodoacetate can be hazardous if not handled properly, as it can cause irritation to the skin, eyes, and respiratory system, and may be harmful if ingested or inhaled. As such, it is important to use proper safety precautions when working with this compound.

InChI:InChI=1/C9H9IO2/c10-6-9(11)12-7-8-4-2-1-3-5-8/h1-5H,6-7H2

Upstream product

• 5437-45-6 Benzyl bromoacetate 
• 140-18-1 Benzyl chloroacetate 

Downstream Products

• 95305-61-6 (S)-2-[Benzyloxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-propionic acid benzyl ester 
• 148146-94-5 C₅₂H₇₇NO₁₄ 
• 113882-48-7 pent-4-enoic acid benzyl ester 
• 86170-45-8 benzyl 3-butenoate 
• 330944-30-4 benzyl 4-methyl-3-pentenoate 
• 927175-32-4 allyl 6-O-benzyl-4-O-benzyloxycarbonylmethyl-3-O-((R)-3-benzyloxytetradecanoyl)-2-deoxy-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 
• 637337-13-4 (R)-3-((R)-2-{[(benzyloxy)carbonyl]methyl}-4-[(tert-butoxy)carbonyl]-1-oxobutyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 637337-12-3 (R)-3-((R)-2-{[(benzyloxy)carbonyl]methyl}-3-[(tert-butoxy)carbonyl]-1-oxopropyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 127949-59-1 (S)-1-[(benzyloxycarbonyl)methyl]-3-tert-butoxycarbonylaminoazetidin-2-one 

Relevant articles and documents

Methyl Radical Initiated Kharasch and Related Reactions

An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-tert-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive methyl radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N2) or volatile (acetone and methyl halide) thereby facilitating greatly product purification by either flash column chromatography or distillation. In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 minutes under normal atmosphere) and a low excess of the radical precursor reagent (2 equivalents) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-tert-butyl peroxyoxalate (DTBPO) is also demonstrated as alternative source of tert-butoxyl radicals to initiate these reactions under identical conditions which gives gaseous by-products (CO2). (Figure presented.).

FeCl2-mediated Nucleophilic Chlorination of Iodoalkanes Accelerated by Phenanthroline Ligand

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Tuning the interactions between electron spins in fullerene-based triad systems

A series of six fullerene-linker-fullerene triads have been prepared by the stepwise addition of the fullerene cages to bridging moieties thus allowing the systematic variation of fullerene cage (C60 or C70) and linker (oxalate, acetate or terephthalate) and enabling precise control over the inter-fullerene separation. The fullerene triads exhibit good solubility in common organic solvents, have linear geometries and are diastereomerically pure. Cyclic voltammetric measurements demonstrate the excellent electron accepting capacity of all triads, with up to 6 electrons taken up per molecule in the potential range between -2.3 and 0.2 V (vs Fc+/Fc). No significant electronic interactions between fullerene cages are observed in the ground state indicating that the individual properties of each C60 or C 70 cage are retained within the triads. The electron-electron interactions in the electrochemically generated dianions of these triads, with one electron per fullerene cage were studied by EPR spectroscopy. The nature of electron-electron coupling observed at 77 K can be described as an equilibrium between doublet and triplet state biradicals which depends on the inter-fullerene spacing. The shorter oxalate-bridged triads exhibit stronger spin-spin coupling with triplet character, while in the longer terephthalate-bridged triads the intramolecular spin-spin coupling is significantly reduced.