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Chemical structure of Chloroidomethane | 593-71-5
CAS: 593-71-5
SKU: S2668
Chloroidomethane | SKU: S2668
synonyms: Chloroiodomethane; Iodochloromethane; Methylene chloroiodide; Chloromethyl iodide; Methane, chloroiodo-
Chemical structure of Chloroidomethane | 593-71-5
Chloroiodomethane (ClCH2I, CH2ClI) is the simplest mixed dihalomethane, with one chlorine and one iodine on a single carbon. It has a molecular weight of 176.38 g/mol and is a very dense liquid (density 2.422 g/mL at 25 °C) that boils at 108–109 °C and has a refractive index of n20/D 1.582. It is supplied at an assay of 97%, stabilised with copper to hold back the liberation of iodine on storage. The two different halogens give the reagent its character. The C–I bond is the weaker and more reactive, so iodide is displaced or exchanged first, leaving a chloromethyl group, and metal–iodine exchange gives halomethyl organometallics. Chloroiodomethane is therefore used as a methylene (CH2) transfer reagent: with diethylzinc it forms the (chloromethyl)zinc carbenoid for Simmons–Smith-type cyclopropanations, and with organolithiums at low temperature it generates chloromethyllithium, which homologates ketones, aldehydes and boronic esters by one carbon. Its photolysis in cryogenic matrices, with recombination of the nascent radical pair, has also been studied in physical chemistry. Chloroiodomethane is toxic if swallowed and irritating to the skin, eyes and airways. Sarchem Labs supplies chloroiodomethane (SKU S2668) for synthesis and research customers, with a Certificate of Analysis and Safety Data Sheet for each lot; laboratory to bulk quantities can be quoted on request.
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Specifications

Boiling Point108–109°C (lit.)
Density2.422 g/mL at 25°C (lit.)
ColorYellow
Linear FormulaClCH2I
Formula Weight176.38
Physical FormClear Liquid at 20°C
Chemical Name or MaterialChloroiodomethane (stabilised with copper)
Molecular Weight176.38 g/mol
SMILES StringClCI
Refractive Indexn20/D 1.582 (lit.)
Assay97%
CAS Number593-71-5
EC Number209-804-8
Empirical FormulaCH2ClI
NACRESNA.22
PubChem Substance ID24854589
UNSPSC Code12352100
MDL NumberMFCD00001078
InChI1S/CH2ClI/c2-1-3/h1H2
InChI KeyPJGJQVRXEUVAFT-UHFFFAOYSA-N
PubChem CID11644
Beilstein/REAXYS Number1730802
Quality Level100
Functional GroupsChloro, iodo
FormLiquid (clear liquid at 20°C)
StabiliserCopper

Applications

No Application Found
One-carbon homologation: with n-butyllithium at low temperature it forms chloromethyllithium, which adds to ketones and aldehydes to give chlorohydrins and epoxides, and to boronic esters for Matteson-type homologation.
Halomethylation: selective displacement of iodide by thiolates, amines, carboxylates and phenoxides introduces a chloromethyl group, a handle for further alkylation.
Photochemistry and spectroscopy: a model dihalomethane for matrix-isolation, photolysis and radical-pair recombination studies.
Analytical reference: a reference halocarbon for GC-MS methods that monitor volatile halogenated compounds.

Product Description

What is Chloroiodomethane?

Chloroiodomethane is a halogenated methane with the formula CH2ClI and a molecular weight of 176.38 g/mol. It is a colourless to pale yellow liquid that darkens slowly in light as traces of iodine form, which is why commercial material is stabilised with copper. It is a different compound from dichloromethane, diiodomethane and bromochloromethane; it is the reagent of choice when the iodide must be the leaving group and the chloride must survive.

Uses of Chloroiodomethane

Chemists buy chloroiodomethane for three jobs: cyclopropanation, one-carbon chain extension and selective halomethylation. In cyclopropanation, the zinc carbenoid from chloroiodomethane and diethylzinc is more reactive than the classical Simmons–Smith reagent from diiodomethane and zinc–copper, and it is widely used for the cyclopropanation of unfunctionalised and allylic alkenes. In homologation, chloromethyllithium adds to carbonyl compounds and boronic esters to extend the carbon chain by one atom.

Buying and Handling Considerations

The grade offered is 97% assay, stabilised with copper. Ask for the Certificate of Analysis of the lot, and tell us if the copper stabiliser must be absent for your chemistry; the copper chip is simply decanted or filtered off before use. Store tightly closed in the dark in a cool place, away from strong bases, oxidisers and reactive metals, and use glass or PTFE equipment. Use a fume hood, chemical-resistant gloves, eye protection and an ABEK respirator filter where vapour may be present.

Safety Information

  • Pictogram / Signal Word: GHS06 (skull and crossbones) | Danger
  • Hazard Statements: H301 (toxic if swallowed), H315 (causes skin irritation), H319 (causes serious eye irritation), H335 (may cause respiratory irritation)
  • Hazard Classification: Acute Tox. 3 Oral, Eye Irrit. 2, Skin Irrit. 2, STOT SE 3 (target organ: respiratory system)
  • Precautionary Statements: P261, P264, P271, P301 + P310, P302 + P352, P305 + P351 + P338
  • Storage Class: 6.1C – Combustible acute toxic Cat. 3 / toxic compounds or compounds which cause chronic effects | WGK: 3 | Flash Point: not applicable
  • PPE: Eyeshields, gloves, type ABEK (EN14387) respirator filter

Toxic if swallowed: do not eat, drink or smoke when using the product, avoid breathing vapour, work in a fume hood and obtain medical attention immediately after any exposure.

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FAQs: Chloroidomethane

It is used as a methylene-transfer reagent: for Simmons–Smith-type cyclopropanation with diethylzinc, for one-carbon homologation via chloromethyllithium, and for selective halomethylation of nucleophiles.

Yes. Chloroiodomethane, iodochloromethane and chloromethyl iodide are the same compound, CAS 593-71-5. The Sarchem Labs product is stabilised with copper.

The formula is CH2ClI, the molecular weight is 176.38 g/mol and the boiling point is 108–109 °C. The density is 2.422 g/mL at 25 °C.

Iodoalkanes slowly release iodine in light, which discolours the liquid and can interfere with organometallic reactions. Copper scavenges the iodine. The copper chip can be removed by decanting or filtering before use.

It is toxic if swallowed (H301) and irritates the skin, eyes and respiratory tract (H315, H319, H335), with the signal word Danger. Use a fume hood, gloves and eye protection.

Keep it tightly closed in the dark in a cool place, away from strong bases, oxidisers and reactive metals.

Yes. For SKU S2668, a Certificate of Analysis and Safety Data Sheet come with each lot, and quotations cover laboratory through bulk quantities.