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Methyl iodide
ヨードメタン · ヨードメチル · メチルヨージド · よう化メチル · ハロン-10001 · ヨードメタン ヨウ化メチル ヨウ化物 · 沃化メチル · ヨードメタン よう化メチル
識別子と物理属性
| CAS No. | 74-88-4 |
|---|---|
| 分子式 | CH3I |
| 平均分子量 | 141.939 g/mol |
| 単同位体質量 | 141.9279481 g/mol |
| SMILES | CI |
| InChIKey | INQOMBQAUSQDDS-UHFFFAOYSA-N |
| PubChem CID | 6328 |
| ChEMBL | CHEMBL115849 |
| ChEBI | CHEBI:39282 |
| EC No. | 200-819-5 |
| DTXSID | DTXSID0024187 |
| 現地名 | ヨードメタン |
化学・物理的性質
| XLogP | 1.5 |
|---|---|
| 極性表面積 | 0 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 0 |
| 回転可能結合数 | 0 |
| 重原子数 | 2 |
| 形式電荷 | 0 |
| 複雑度 | 2 |
| 物質分類 | Hazardous Air Pollutants (HAPs)Toxic Gases & Vapors -> Other Toxic Gases & Vapors |
| SpringerMaterials Properties | Dunham energy parameter |
| 農薬 | Pesticide -> EPA IRISVolatile Organic Compound (VOC) (Pesticide/Volatile Organic Compound (VOC)) |
| LogP（分配係数） | log Kow= 1.51 |
| 臭い | Pungent, ether-like odor.甘い、空気のような匂い (利用可能な閾値データなし)不適切な警告プロパティ |
| 密度 | 2.279 at 68 °F (USCG, 1999) - Denser than waterwill sink2.28 @ 20 °C/4 °CDENSITY OF SATURATED AIR: 3.04 (AIR= 1)Relative density (water = 1): 2.32.2789 @ 20°C2.28 g/mL at 25 °C(lit.) |
| Viscosity | 0.606 cP at 0 °C, 0.424 cP at 40 °C.0.18 mm²/s at 40 °C |
| Color/Form | Colorless, transparent liquid (turns brown on exposure to light) |
| 溶解度 | 10 to 50 mg/mL at 64 °F (NTP, 1992)Miscible with alcohol, ether.Sol in acetoneSOL IN CARBON TETRACHLORIDE1.39X10+4 mg/l at 20 °C in waterSolubility in water, g/100ml at 20 °C: 1.4水：20℃で可溶14g/L14g/L（20℃） |
| 沸点 | 108.3 °F at 760 mmHg (NTP, 1992)42.5 °C109 °F42.43 °C @760 [mm Hg]41-43 °C |
| Decomposition | IODIDE & HYDROGEN IODIDE MAY BE RELEASED WHEN METHYL IODIDE UNDERGOES THERMAL DECOMPOSITION (270 °C). |
| 融点 | -87.6 °F (NTP, 1992)-66.5 °C-88 °F-66.4 °C−64(lit.) |
| 蒸気密度 | 4.89 (vs air) |
| 蒸気圧 | 24.09 psi ( 55 °C) |
| 屈折率 | n20/D 1.530 |
| 引火点 | −18 °F |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 液体 |
| 比重 | 2.280 |
| 色 | クリア |
| pH | 5.2 (H2O, 25℃) |
| 爆発限界 | 8.5-66% (v/v) |
| 比熱容量 | Cp(liquid): 0.89 J/(g·K)Cp(gas): 0.31 J/(g·K), at 25℃ |
| Merck | 14,6087 |
| BRN | 969135 |
| ヘンリー定数 | 5.06 at 21 °C (Gan and Yates, 1996) |
| 誘電率 | 7.0(20℃) |
| 安定性 | 光に敏感 |
| InChI | 1S/CH3I/c1-2/h1H3 |
| InChIKey | INQOMBQAUSQDDS-UHFFFAOYSA-N |
| SMILES | CI |
| LogP（分配係数） | 1.510 |
| CAS データベース | 74-88-4(CAS DataBase Reference) |
| NISTの化学物質情報 | Methyl iodide(74-88-4) |
| EPAの化学物質情報 | Methyl iodide (74-88-4) |
化学的特性
light yellow to light pink liquid
安全性と法規制
| GHS 分類 | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P203, P261, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P317, P318, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.4% (1 of 264) of reports.H226 (42.8%): Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| Hazards Identification | Toxic/poison by inhalation (TIH/PIH) |
| 規制情報 | Chemical: Methane, iodo-Hazard Traits - CarcinogenicityNeurotoxicityRespiratory ToxicityMethane, iodo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methane, iodo- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 03-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/12834Iodomethane: HSNO Approval: HSR003006 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| その他の安全情報 | IMAP assessments - Methane, iodo-: Human health tier II assessment |
| 輸送ラベル（DOT） | Poison Inhalation Hazard |
| 火災危険 | Special Hazards of Combustion Products: Toxic and irritating gases are generated when exposed to fire or heat.· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.Not combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 火災の可能性 | Iodomethane is not flammable. |
| 健康有害性 | Inhalation of vapor causes lung congestion and pulmonary edema. Higher concentrations causes rapid narcosis and death. Contact with liquid irritates eyes and burns skin. (USCG, 1999)· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin. |
| 有害性の概要 | Methyl iodide is used as an intermediate in the manufacture of some pharmaceuticals and pesticides, in methylation processes, and in the field of microscopy. In humans, acute (short-term) exposure to methyl iodide by inhalation may depress the central nervous system (CNS), irritate the lungs and skin, and affect the kidneys. Massive acute inhalation exposure to methyl iodide has led to pulmonary edema. Acute inhalation exposure of humans to methyl iodide has resulted in nausea, vomiting, vertigo, ataxia, slurred speech, drowsiness, skin blistering, and eye irritation. Chronic (long-term) exposure of humans to methyl iodide by inhalation may affect the CNS and cause skin burns. EPA has not classified methyl iodide for potential carcinogenicity.Liquid causes second degree burns after contact for a few minutes. [CHRIS] Corrosive to skin[Quick CPC] In animal feeding studies, methyl iodide is hepatotoxic, ten times as acutely toxic as carbon tetrachloride. After an industrial accident, an exposed chemical plant worker developed symptoms of central nervous system poisoning and died. [ACGIH] Inhalation can cause pulmonary edema, CNS depression, and death[CAMEO] A lachrymator[CHEMINFO] It is an acute pulmonary irritant that can cause chronic neurological symptoms after a heavy dermal exposure. [Reference #1] |
| 輸送番号・ガイド（DOT） | 2644 151 |
| 反応性グループ | Halogenated Organic Compounds |
| EC 分類 | Symbol: TR: 21-23/25-37/38-40S: (1/2)-36/37-38-45 |
| UN 分類 | UN Hazard Class: 6.1UN Pack Group: I |
| 消火 | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:In case of fire in the surroundings, use appropriate extinguishing media. In case of fire: keep drums, etc., cool by spraying with water. |
| 応急処置措置 | Fresh air, rest. Refer immediately for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Do NOT induce vomiting. Give a slurry of activated charcoal in water to drink. Refer immediately for medical attention. |
| 漏出応急措置 | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. |
| 応急処置 | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.General First Aid:(General first aid procedures) |
| 安全保管 | Provision to contain effluent from fire extinguishing. Separated from strong oxidants and food and feedstuffs. Well closed. Ventilation along the floor. Store in an area without drain or sewer access. |
| 暴露管理・個人防護 | · Wear positive pressure self-contained breathing apparatus (SCBA).TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016]. |
| 消火手順 | Self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive-pressure mode.If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself dose not burn or burns with difficulty.) Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources. |
| 保管条件 | Keep containers closed and store in a dark place.... MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS DUE TO CONTACT WITH HEAT, MOISTURE, ACID, OR ACID FUMES, SHOULD BE STORED IN COOL, WELL-VENTILATED PLACE, OUT OF DIRECT RAYS OF SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD & SHOULD BE PERIODICALLY INSPECTED & MONITORED. |
| 清掃方法 | 1. VENTILATE AREA OF SPILL OR LEAK. 2. COLLECT FOR RECLAMATION OR ABSORB IN VERMICULITE, DRY SAND, EARTH, OR SIMILAR MATERIAL./In laboratory/ absorb the spills with paper towels, or like materials. Place in hood to evaporate. Dispose by burning the towel. |
| 非火災時の漏出対応 | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| 処分方法 | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U138, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. |
| 漏出処分 | Evacuate danger area! Consult an expert! Personal protection: self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Cancer Sites | [in animals: lung, kidney & forestomach tumors] |
| 相互作用 | ... SYNERGIZES TOXICITY OF FENITROTHION ELEVEN FOLD & DICHLOROVOS TWO FOLD /IN MOUSE LIVER/.S-Methyl-N-acetylpenicillamine, S-methylthiol, and S-methylcysteine, as well as iodomethane decreased biliary excretion of methylmercury markedly. Excretion of sulfhydryl in bile was not influenced by S-methylcysteine, S-methylthiol, S-methyl-N-acetylpenicillamine or a low dose of iodomethane (0.5 mmol/kg). This indicated that coupling of methylmercury to glutathione in the liver before biliary excretion was glutathione S-transferase-dependent reaction and the methylthiols tested, or metabolites of these compounds were likely to be inhibitors of S-transferase. The effect of S-methylcysteine and low doses of iodomethane (1 mmol/kg) seem to deplete the liver of reduced glutathione through S-methylation as illustrated by decreased biliary excretion of sulfhydryl. |
| 標的器官 | Eyes, skin, respiratory system, central nervous system |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 14(SRC), determined from a structure estimation method(2), indicates that methyl iodide should have very high mobility in soil(SRC). Volatilization of methyl iodide from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 0.00526 atm-cu m/mole at 25 °C(3). The potential for volatilization of methyl iodide from dry soil surfaces may exist based upon a vapor pressure of 405 mm Hg(4). Cumulative volatilization losses of methyl iodide, applied at 30 cm, from 60-cm soil columns packed with a sandy loam soil ranged from 94% when the soil was untarped to 75% with a high-barrier tarp(5). Volatilization losses were significantly lower, 38% and 53%, from soils high in organic matter and capable of rapidly degrading the chemical. Ten days after methyl iodide was applied to field plots (30 cm depth) covered with a polyethylene film, methyl iodide was detected at most depths(5). It was concluded that should the water table be shallow and the degradation rate in soil low, methyl iodide may leach into ground water(5). Methyl iodide abiotically degrades in soil by hydrolysis and reaction with chloride ions, HS- and other nucleophiles(6). The half-life of methyl iodide in soils that were rich in organic matter was 9-13 days, while in a sandy loam soil it was 42-63 days. The organic-rich soils were thought to contain more nucleophiles with which methyl iodide could react(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 14(SRC), determined from an estimation method(2), indicates that methyl iodide is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 0.00526 atm-cu m/mole at 25 °C(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1.3 hours and 4.8 days, respectively(SRC). Methyl iodide hydrolyses slowly in water with a half-life of 110-251 days at 20-25 °C(8,9). It reacts with chloride ions in seawater in which its half-life is 20 and 58 days at 19.2 and 10.8 °C, respectively(8). According to a classification scheme(5), an estimated BCF of 2.9(SRC), from its log Kow of 1.51(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low.ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl iodide, which has a vapor pressure of 405 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl iodide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 220 days(SRC), from its rate constant of 7.20X10-14 cu cm/molecule-sec at 25 °C(3). However the major loss process for methyl iodide in the atmosphere is direct photolysis. The half-life of this reaction is 2.8-5.5 days(3,4). Physical removal of methyl iodide from air may occur via wet deposition since methyl iodide is relatively soluble in water(SRC). |
| 有害作用 | Neurotoxin - Other CNS neurotoxin |
| 暴露経路 | The substance can be absorbed into the body by inhalation of its vapour and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contact |
| Signs and Symptoms | Cough. Sore throat. Nausea. Vomiting. Diarrhoea. Headache. Dizziness. Drowsiness. Weakness. Convulsions. Confusion. Death Symptoms may be delayed.Redness. Pain.See Inhalation.irritation eyes, skin, respiratory systemnausea, vomitingdizziness, ataxiaslurred speech, drowsinessdermatitis[potential occupational carcinogen] |
| Effluent Concentrations | Methyl iodide was detected (conc not reported) in air samples collected above a hazardous waste site in NJ(1)its presence is likely the result of volatile emissions from the site(1). |
| ICSC Environmental Data | The substance is very toxic to aquatic organisms. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal. |
| EPA IRIS Information | Methyl iodide |
| Medical Surveillance | Physical examination of workers for placement in operations involving possible exposure to these alkylating agents should include consideration of increased personal risk due to cigarette smoking, pregnancy, or treatment with steroids or cytotoxic agents. /Alkylating agents/IN HUMANS EXPOSED TO METHYL IODIDE, SERUM LIPID CONTENT, ESP THE TRIGLYCERIDE CONTENT WAS SHARPLY INCR, WITH NO APPARENT NERVOUS DISORDER. THUS, BLOOD EXAM, ESP SERUM LIPID, & FUNCTIONAL EXAM OF LIVER & KIDNEY, MAY BE USED FOR EARLY DETECTION OF METHYL IODIDE POISONING.Initial Medical Examination: A complete history and physical examination: The purpose is to detect pre-existing conditions that might place the exposed employee at increased risk, and to establish a baseline for future health monitoring. Examination of the central nervous system should be stressed. The skin should be examined for evidence of chronic disorders. Periodic Medical Examination: The aforementioned medical examinations should be repeated on an annual basis. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc for methyl iodide can be estimated to be 14(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl iodide should have very high mobility in soil. The soil/water distribution coefficient of methyl iodide in various soils were (soil, Kd): Greenfield sandy loam, 0.09Linne clay loam, 0.15Carsetas loamy sand, 0.16and potting mix, 0.55(3). |
| RCRA 要件 | U138As stipulated in 40 CFR 261.33, when methyl iodide, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). |
| 大気基準 | Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Methyl iodide is included on this list. |
| CERCLA 報告数量 | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). |
| 清浄水法要件 | Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Halomethanes/ |
| F | 8 |
| 職業暴露区分（OEB） | B |
| 職業暴露限界（OEL） | TWA: 2 ppm (10 mg/m3) [skin] |
| 水環境危害等級（WGK） | 1 |
| 生命健康即時危険濃度 | 100 ppm |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | PA9450000 |
| 輸送番号（UN） | UN 2644 |
| 毒性 | LD50 orally in rats: 76 mg/kgLD50 s.c. in mice: 0.78 mmoles/kg (IARC, 1986) |
| 税関コード | 29033990 |
| 危険文句（R） | 21-23/25-37/38-40-11-39/23/24/25-23/24/25-38-20/22 |
| 化審法 | (2)-42 |
| 安衛法 | 特化則 特定化学物質(特定第2類) 変異原性物質 |
| 危険表示 | T,F,Xn |
| 安全措置（S） | 36/37-38-45-9-24-16-7-60-36/37/39-33-23-20-4 |
| 危険等級 | 6.1Acute Tox. 3 InhalationAcute Tox. 3 OralAcute Tox. 4 DermalAquatic Acute 1Aquatic Chronic 2Carc. 2Eye Dam. 1Flam. Liq. 3Skin Irrit. 2STOT SE 3 |
| 包装等級 | I |
| 毒劇物取締法 | 劇物 |
| 貯蔵分類 | 3 - Flammable liquids |
| 有害物質データ | 74-88-4(Hazardous Substances Data) |
用途
解説
ヨウ化メチル．ヨードメタンともいう．硫酸ジメチルにヨウ化カリウム水溶液を反応させるか，メタノールにヨウ素と赤リンを作用させると得られる．液体．融点－66.5 ℃，沸点42.4 ℃．d2042.279．n20D1.5317．有機溶媒に可溶，水に微溶．多くの第三級アミンと反応して第四級アンモニウム塩を生成するなど，有機合成におけるメチル化剤として用いられる．空気中で光により一部分解して褐色になるので，冷暗所に保有する．光を当てるとヨウ素を遊離して着色する。ヨウ化カリウムの水溶液に硫酸ジメチルを加えれば得られる。メチル化剤として用いられるほか、医薬の発泡剤に用いられることもあるが、皮膚に付着すると炎症をおこし、蒸気を吸入すると神経障害をおこし、かつ習慣性がある。ラットの経口半数致死量（LD50）は体重1キログラム当り20ミリグラム。
用途
有機合成原料、メチル化剤、医薬?農薬(殺虫剤)原料
使用
.Iodomethane is an approved pesticide used to control insects, plant parasitic nematodes, soil borne pathogens and weed seeds.
一般的な説明
A colorless liquid that turns brown on exposure to light. Denser than water. Contact may irritate skin, eyes and mucous membranes. Very toxic by ingestion, inhalation and skin absorption.
使用用途
ヨウ化メチルは、の代替として、殺センチュウを目的とした脂肪族ハロゲン化物の燻蒸剤として主に用いられます。細菌や糸状菌による病害に対する防除効果もあります。 適用作物には、果樹、野菜及び花き等があり、路地及び施設でのメロンやトマトのネコブセンチュウ、倉庫及び天幕でのクリのクリシギゾウムシやクリミガ等に適用可能です。 殺虫効果が得られる理由は、蒸気として土壌、作物又は木材内部に拡散し、塩基性要求核中心と反応すると、ピルビン酸脱水素酵素やコハク酸脱水素酵素などの必須酵素を阻害するためだと考えられています。
製法・合成法
調製方法
Methyl iodide has had very limited use as a chemical intermediate (methylations), and in microscopy because of its high refractive index, as imbedding materials for examining diatoms, and in tests for pyridine. It has been proposed as a fire extinguisher and insecticidal fumigant. It is a product of natural biological processes. Methyl iodide is a currently registered pesticide.
合成方法
ヨウ素とリンにメタノールを反応させ，蒸留精製して製品とする
純化方法
Methyl iodide deteriorates rapidly with liberation of iodine if exposed to light. It is usually purified by shaking with dilute aqueous Na2S2O3 or NaHSO3 until colourless, then washing with water, dilute aqueous Na2CO3, and more water, drying with CaCl2 and distilling. It is stored in a brown bottle away from sunlight in contact with a small amount of mercury, powdered silver or copper. (Prolonged exposure of mercury to methyl iodide forms methylmercuric iodide.) Methyl iodide can be dried further using CaSO4 or P2O5. An alternative purification is by percolation through a column of silica gel or activated alumina, then distillation. The solution can be degassed by using a repeated freeze-pump-thaw cycle. [Beilstein 1 IV 87.]