Йодоэтан

Description

Iodoethane (ethyl iodide) is an iodoalcane, ethane with one iodine atom. A colorless or pale yellow, sometimes pinkish liquid with a characteristic odor, darkens in the light. The main purpose is as an ethylating agent in organic synthesis: the C-I bond breaks easily, and the ethyl group is transferred to the nucleophile. With magnesium it gives the Grignard reagent - ethylmagnesium iodide. Chemically stable, but incompatible with strong bases, magnesium and strong oxidizing agents; light, moisture and air cause discoloration and darkening. Commercial lots are stabilized with copper or silver.

Basic Attributes

• CAS No.: 75-03-6
• Chemical formula: C2H5I
• Molecular Weight: 155.97
• Exact weight: 155.97; monoisotopic mass 155.94360
• EU number: 200-833-1
• BRN: 505934
• UNII: 59PO05D39L
• ICSC number (chemical safety card): 0479
• SNB number: 8825
• TSCA: TSCA listed
• DSSTox ID: DTXSID9058783
• HS code: 2903 39 80
• Number of heavy atoms: 3; difficulty 2.8; covalently linked units 1; structure canonized

Physico-chemical characteristics

• Appearance: transparent liquid from colorless to pale yellow or pink
• Odor: weak, characteristic
• Density: 1.95 g/ml at 25 °C (lit.)
• Vapor Density: 5.38 (by air)
• Melting point: −108 °C
• Boiling point: 69–73 °C (lit.)
• Flash point: 53°C
• Refractive index: n20/D 1.513 (lit.)
• Solubility in water: 4 g/l at 20 °C
• Steam pressure: 100 mm Hg. Art. at 18 °C
• Henry's law constant: 1.4 × 10⁻³ mol/(m³·Pa) at 25 °C, Burkholder et al. (2019)
• PSA Features: 0
• XLogP3: 2.0 (on another card 2.1)

Methods of obtaining

The main way is the interaction of ethanol with phosphorus triiodide, which is produced directly in the reactor. Technical ethanol and red phosphorus are loaded into the apparatus, heated under reflux in a water bath, and iodine is slowly introduced. After the loading is completed, boiling is continued for about 3 hours, then the reaction mass is distilled, the crude yellow product is washed and dried. The second route is the addition of hydrogen iodide to ethylene.

Scope of application

• ethylating agent in fine organic synthesis - introduction of an ethyl group into a molecule
• preparation of ethylmagnesium iodide (Grignard reagent)
• synthesis of 1-ethyl-3-nitro-2-phenylindole
• hydrogen radical promoter
• additives for paints and coatings
• production of plastics and resins

A separate area of ​​application is physicochemical research: the interaction of iodoethane with the Pt(111) surface was studied by thermal desorption and X-ray photoelectron spectroscopy, the microwave spectrum of the molecule was recorded, the dynamics of gas-phase photolysis was studied by resonance Raman spectroscopy, and the thermodynamic characteristics in the ideal gas state were described.

Toxicity and exposure

• Intraperitoneal, LD50 rat: 330 mg/kg; intraperitoneal, mouse LD50: 560 mg/kg
• Toxicity class: highly toxic substance
• Hazard statements: toxic by inhalation and absorption through the skin, acts like a narcotic in high concentrations
• Routes of exposure: inhalation of vapors, skin, ingestion
• Effects of short-term exposure: irritation of eyes, skin and respiratory tract, effects on the central nervous system up to loss of consciousness
• Symptoms: confusion, cough, drowsiness, dizziness, shortness of breath, sore throat, redness, pain, loss of consciousness
• Inhalation risk: The rate at which evaporation reaches harmful concentrations in air at 20°C has not been determined.
• Metabolism: a known metabolite in humans is ethylglutathione.

Fire danger

• Flammable liquid; Explosive vapor-air mixtures are possible at temperatures above 61 °C
• Open flame and heat lead to ignition; Decomposes when exposed to high temperatures or contact with water and oxidizing agents to form toxic iodide gas
• Steam is heavier than air and accumulates at the bottom of the room
• Extinguishing media: sprayed water, powder, foam, carbon dioxide; Cool burning barrels with water
• Fire regime: prohibition of open flames, sparks and smoking; above 61 °C - closed ventilation system and explosion-proof electrical equipment

GHS classification and safety precautions

• Signal word: "Danger"; H226 (13.93%): flammable liquid and vapor
• Reason: Aggregated GHS information from 122 companies for 14 notifications to the ECHA C and L register
• Packaging level: III; hazard category 6.1; transport codes 2922; RIDADR 2922
• WGK Germany: 3
• Hazard class code: Xn, T; tags: Xn, T
• Safety instructions: 23-26-36/37-45-37/39-16-36/37/39-27
• RTECS number: KI4750000
• Precautions: P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P272, P280, P285, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P304+P341, P305+P351+P338, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
• Protective equipment: respirator with a filter for organic gases and vapors for concentration in the air; protective gloves and clothing; goggles or face shield in combination with respiratory protection; ventilation or local suction

Storage and disposal of spills

The warehouse is ventilated, low-temperature and dry, fire-resistant, temperature below +30 °C. Keep away from strong bases, oxidizing agents and food additives. In the event of a spill, remove all sources of ignition, collect the liquid in closed containers, absorb the remainder with sand or an inert sorbent, then transfer it for disposal according to local regulations.

First aid

If inhaled - fresh air, rest, semi-sitting position, artificial respiration if necessary, call a doctor. In case of contact with skin, rinse with plenty of water or take a shower and seek medical help. In case of contact with eyes, rinse with plenty of water for several minutes, remove contact lenses if possible, then consult a doctor.