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DIIODOMETHANE
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  • Name DIIODOMETHANE
  • EINECS200-841-5
  • CAS No. 75-11-6
  • Density3.238 g/cm3
  • PSA0.00000
  • LogP1.81390
  • Solubilitywater: 14 g/L (20 °C)
  • Melting Point6 °C
  • FormulaCH2I2
  • Boiling Point182 °C at 760 mmHg
  • Molecular Weight267.836
  • Flash Point76.6 °C
  • Transport InformationN/A
  • Appearancelight yellow or gold liquid with chloroform-like odour
  • Safety26-37/39
  • Risk Codes36/37/38
  • Molecular Structure
    Molecular Structure of 75-11-6 (Diiodomethane)
  • Hazard SymbolsIrritantXi
  • SynonymsIrritantXi
  • Article Data67

DIIODOMETHANE Synthetic route

75-77-4

chloro-trimethyl-silane

75-47-8

iodoform

A

75-11-6

diiodomethane

B

128530-64-3

trimethylsilyltriiodomethane

Conditions
ConditionsYield
With hexaethylphosphoric triamide In diethyl ether at 20℃; for 1h;A n/a
B 40%
75-47-8

iodoform

A

75-11-6

diiodomethane

B

594-04-7

dichloroiodomethane

C

638-73-3

chlorodiiodomethane

Conditions
ConditionsYield
With mercury dichloride at 130℃; for 2h; Substitution; Title compound not separated from byproducts;A 1%
B 1%
C 30%
75-77-4

chloro-trimethyl-silane

75-47-8

iodoform

A

75-11-6

diiodomethane

B

18178-59-1

(E)-1,2-bis(trimethylsilyl)ethene

C

29955-07-5

(diiodomethyl)trimethylsilane

Conditions
ConditionsYield
With manganese In tetrahydrofuran at 25℃; for 1h; Product distribution; Further Variations:; Solvents;A 3%
B 3%
C 21%
186581-53-3, 908094-01-9

diazomethane

75-11-6

diiodomethane

Conditions
ConditionsYield
With diethyl ether; iodine
75-47-8

iodoform

141-52-6

sodium ethanolate

A

75-11-6

diiodomethane

B

53103-75-6

2-ethoxypropionic acid

C

79-10-7

acrylic acid

75-47-8

iodoform

127-09-3

sodium acetate

75-11-6

diiodomethane

Conditions
ConditionsYield
With ethanol
75-47-8

iodoform

75-11-6

diiodomethane

Conditions
ConditionsYield
at 140 - 150℃;
With iodine at 140 - 150℃;
With sodium ethanolate
75-09-2

dichloromethane

75-11-6

diiodomethane

Conditions
ConditionsYield
With acetone; sodium iodide
With sodium iodide; benzyl alcohol at 125℃;
67-66-3

chloroform

75-11-6

diiodomethane

Conditions
ConditionsYield
With hydrogen iodide at 125℃;
64-69-7

Iodoacetic acid

75-11-6

diiodomethane

Conditions
ConditionsYield
Electrolysis;
With potassium peroxomonosulphate; water at 85℃;

DIIODOMETHANE Chemical Properties

Diiodomethane's Molecular formula: CH2I2
Molar mass: 267.84 g/mol
Appearance: Light yellow to gold liquid with chloroform-like odour
Density: 3.325 g/cm3
Melting point: 6 °C, 279 K, 43 °F
Boiling point: 181 °C (358 °F)
Solubility in water: 14 g/l at 20 °C
Flash point: 113 °C
Diiodomethane is light yellow to gold  liquid halomethane soluble in ether and alcohol, but insoluble in water.
Diiodomethane has a relatively high refractive index of 1.741. Fresh diiodomethane is a colorless liquid. However, exposure to light causes it to slowly decompose and liberate iodine, which colours it brownish.

DIIODOMETHANE Uses

Diiodomethane is used with its high specific gravity for the separation of minerals or for determination of specific gravity of mineral particles.
Diiodomethane is also used as a solvent and can be a reaction intermediate in the Simmons-Smith reaction, ect.

DIIODOMETHANE Production

Diiodomethane is commercially available. It may also be prepared by reducing iodoform with sodium arsenite:
        CHI3 + Na3AsO3 + NaOH → CH2I2 + NaI + Na3AsO4

DIIODOMETHANE Toxicity Data With Reference

1.   

orl-cld LDLo:2778 µL/kg:BAH,PUL

   AEMED3    Annals of Emergency Medicine. 19 (1990),1171.
2.   

ipr-rat LD50:403 mg/kg

   34ZIAG    Toxicology of Drugs and Chemicals ,Deichmann, W.B.,New York, NY.: Academic Press, Inc.,1969,756.
3.   

ipr-mus LD50:467 mg/kg

   34ZIAG    Toxicology of Drugs and Chemicals ,Deichmann, W.B.,New York, NY.: Academic Press, Inc.,1969,756.
4.   

scu-mus LD50:830 mg/kg

   TXAPA9    Toxicology and Applied Pharmacology. 4 (1962),354.

DIIODOMETHANE Consensus Reports

Reported in EPA TSCA Inventory.

DIIODOMETHANE Safety Profile

Moderately toxic by intraperitoneal and subcutaneous routes. Probably an irritant and narcotic in high concentration. Human systemic effects: acute pulmonary edema, somnolence. Potentially explosive reaction with diethyl zinc + alkenes. Violent reaction with copper-zinc alloys + ether. Forms very shock-sensitive explosive mixtures with potassium, potassium-sodium alloys, and lithium. When heated to decomposition it emits toxic fumes of I−. See also IODIDES.
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