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Chloroiodomethane
Book chapter

Chloroiodomethane

Sotaro Miyano and Gregory K Friestad
Encyclopedia of Reagents for Organic Synthesis
John Wiley & Sons, Ltd
1995
DOI: 10.1002/047084289X.rc110.pub2

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Abstract

[ 593‐71‐5 ]  CH 2 ClI  (MW 176.38) InChI =  1S/CH2ClI/c2‐1‐3/h1H2 InChIKey =  PJGJQVRXEUVAFT‐UHFFFAOYSA‐N (chloromethylating agent for organozinc, ‐lithium, ‐phosphorus, and ‐transition metal compounds, and alkenes; can generate N,N ‐dimethylmethyleneiminium iodide (Eschenmoser's salt) by reaction with N,N,N ′, N ′‐tetramethylmethylenediamine ) Alternate Name:  CIM. Physical Data:  bp 108–109 °C; d 20 4 2.42 g cm −3 ; n 20 D 1.582. Solubility:  sol ethers, acetone, polyhalomethanes, and benzene. Form Supplied in:  pale yellow oil; commercially available or readily preparable via halogen exchange of dichloromethane with iodide sources. Analysis of Reagent Purity:  NMR (CCl 4 /TMS), δ (ppm) 5.00. Handling, Storage, and Precautions:  should be stored over tin or silver wire in the dark.

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