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Basic Information
| CAS No.: | 75-11-6 |
|---|---|
| Name: | Diiodomethane |
| Article Data: | 67 |
| Molecular Structure: | |
|
|
|
| Formula: | CH2I2 |
| Molecular Weight: | 267.836 |
| Synonyms: | Methylene diiodide;Methylene iodide;NSC 35804; |
| EINECS: | 200-841-5 |
| Density: | 3.238 g/cm3 |
| Melting Point: | 6 °C |
| Boiling Point: | 182 °C at 760 mmHg |
| Flash Point: | 76.6 °C |
| Solubility: | water: 14 g/L (20 °C) |
| Appearance: | light yellow or gold liquid with chloroform-like odour |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-37/39 |
| PSA: | 0.00000 |
| LogP: | 1.81390 |
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Synthetic route
- 75-77-4
chloro-trimethyl-silane
- 75-47-8
iodoform
A
- 75-11-6
diiodomethane
B
- 128530-64-3
trimethylsilyltriiodomethane
Conditions
| Conditions | Yield |
|---|---|
| With hexaethylphosphoric triamide In diethyl ether at 20℃; for 1h; | A n/a B 40% |
...Expand
Conditions
| Conditions | Yield |
|---|---|
| With mercury dichloride at 130℃; for 2h; Substitution; Title compound not separated from byproducts; | A 1% B 1% C 30% |
...Expand
- 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
| Conditions | Yield |
|---|---|
| With manganese In tetrahydrofuran at 25℃; for 1h; Product distribution; Further Variations:; Solvents; | A 3% B 3% C 21% |
...Expand
- 186581-53-3, 908094-01-9
diazomethane
- 75-11-6
diiodomethane
Conditions
| Conditions | Yield |
|---|---|
| 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
...Expand
Conditions
| Conditions | Yield |
|---|---|
| With ethanol |
Conditions
| Conditions | Yield |
|---|---|
| at 140 - 150℃; | |
| With iodine at 140 - 150℃; | |
| With sodium ethanolate |
Conditions
| Conditions | Yield |
|---|---|
| With acetone; sodium iodide | |
| With sodium iodide; benzyl alcohol at 125℃; |
Conditions
| Conditions | Yield |
|---|---|
| With hydrogen iodide at 125℃; |
Conditions
| Conditions | Yield |
|---|---|
| Electrolysis; | |
| With potassium peroxomonosulphate; water at 85℃; |
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Diiodomethane
Chemistry
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.
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.
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.
Production
Diiodomethane is commercially available. It may also be prepared by reducing iodoform with sodium arsenite:
CHI3 + Na3AsO3 + NaOH → CH2I2 + NaI + Na3AsO4
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. |
Consensus Reports
Reported in EPA TSCA Inventory.
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.