CAS 75-11-6|diiodomethane|diiodomethane|DIIODOMETHANE|Diiodomethane 98+%|Methylene diiodide|Diiodomethane|碘化亚甲基|Methylene iodide|二碘甲烷

General Information

Structure

Molecular Formula

CH₂I₂

Molecular Mass

267.83552

Exact Mass

267.82459606

Charge

InChI

InChI=1S/CH2I2/c2-1-3/h1H2

InChIKey

NZZFYRREKKOMAT-UHFFFAOYSA-N

Canonic Smiles

ICI

Isomeric Smiles

ICI

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

2.4811857

LogD (pH = 7.4)

2.4811857

Log P

2.4811857

Molar Refractivity

32.2147

Polarizability

13.44563

Polar Surface Area

0.0

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

diiodomethane

IUPAC Traditional name

diiodomethane

Synonyms

DIIODOMETHANEMethylene diiodideDiiodomethane 98+%碘化亚甲基二碘甲烷Methylene iodideDiiodomethane

Names and Identifiers

Registration numbers

EC Number

CAS Number

Beilstein Number

MDL Number

Merck Index

PubChem SID

MeSH Name

Wikipedia Title

PubChem CID

Chemspider ID

Registration numbers

Properties

Safety Information

Toxic/Harmful/Irritant/Light Sensitive/Keep Cold

Light Sensitive

R:36/37/38

R22,R36/37/38

22-36/37/38

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Apollo Scientific

OR17001

Stabilised with copper

MP Biomedicals

05212020

MP Biomedicals Rare Chemical collection

Wikipedia

Diiodomethane

Sigma Aldrich

158429

Packaging
25, 100, 500 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Molecule Details

References

PubChem Literature

From Data Sources

• The combination with Zinc-copper couple, L09811, generates ICH₂ZnI, the reagent for the classical Simmons-Smith cyclopropanation of alkenes: J. Am. Chem. Soc., 80, 5323 (1958); examples: Org. Synth. Coll., 5, 85 (1973). Review: Org. React., 20, 1 (1973). Alternative systems include Zn powder/ Cu(I) halide: J. Org. Chem., 35, 2057 (1970); ultrasound irradiation: Tetrahedron Lett., 23, 2729 (1982), thermal activation: Synth. Commun., 22, 2801 (1992), or catalytic TMS-Cl: J. Org. Chem., 59, 2671 (1994) with ordinary zinc; or Zn/Ag couple: Tetrahedron Lett., 4593 (1972); 3327 (1974). Other reagents include trialkylaluminums: J. Org. Chem., 50, 4412 (1985): Org. Synth. Coll., 8, 321 (1993) and the most widely-used modification, diethylzinc: Tetrahedron, 24, 53 (1968); J. Org. Chem., 42, 3031 (1977); for use in the ring-expansion of ketones, see: Org. Synth. Coll., 6, 327 (1988). For use of a boronic acid-derived chiral dioxaborolane ligand in enantioselective cyclopropanantion, see: Tetrahedron Lett., 37, 7925 (1996); Org. Synth., 76, 86 (1998):

• Selective ortho-methylation of phenols can be brought about by a one-pot method utilizing Et₂Zn/ CH₂I₂ modification: Tetrahedron Lett., 30, 5215 (1989).

• Allylic bromides are converted to homoallylic iodides by the Simmons-Smith reagent in the presence of CuI.2LiI in THF: J. Org. Chem., 54, 5202 (1989).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

diiodomethane

IUPAC Traditional name

diiodomethane

Synonyms

DIIODOMETHANEMethylene diiodideDiiodomethane 98+%碘化亚甲基二碘甲烷Methylene iodideDiiodomethane

Registration numbers

EC Number

CAS Number

Beilstein Number

MDL Number

Merck Index

PubChem SID

MeSH Name

Wikipedia Title

PubChem CID

Chemspider ID

Molecule Details

OR17001

Stabilised with copper

MP Biomedicals

05212020

MP Biomedicals Rare Chemical collection

Wikipedia

Diiodomethane

Sigma Aldrich

158429

Packaging
25, 100, 500 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

References

PubChem Literature

From Data Sources

• Selective ortho-methylation of phenols can be brought about by a one-pot method utilizing Et₂Zn/ CH₂I₂ modification: Tetrahedron Lett., 30, 5215 (1989).

• Allylic bromides are converted to homoallylic iodides by the Simmons-Smith reagent in the presence of CuI.2LiI in THF: J. Org. Chem., 54, 5202 (1989).

Bioactivity

PubChem BioAssay

Properties

Safety Information

Toxic/Harmful/Irritant/Light Sensitive/Keep Cold

Light Sensitive

R:36/37/38

R22,R36/37/38

22-36/37/38

Molecule

ID:78031