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四臭化炭素
四臭化炭素 · テトラブロモメタン · テトラブロムメタン · 四臭化炭素, vacuum sublimed (99.998%-C) PURATREM · CBr4 · TETRABROMOMETHANE · PERBROMOMETHANE · TETRABROMOETHANE
識別子と物理属性
| CAS No. | 558-13-4 |
|---|---|
| 分子式 | CBr4 |
| 平均分子量 | 331.63 g/mol |
| 単同位体質量 | 327.6733484 g/mol |
| SMILES | BrC(Br)(Br)Br |
| InChIKey | HJUGFYREWKUQJT-UHFFFAOYSA-N |
| PubChem CID | 11205 |
| ChEBI | CHEBI:47875 |
| EC No. | 209-189-6 |
| DTXSID | DTXSID8060327 |
| 現地名 | 四臭化炭素 |
化学・物理的性質
| XLogP | 3.4 |
|---|---|
| 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 | 5 |
| 形式電荷 | 0 |
| 複雑度 | 19.1 |
| Solvents | Solvents -> Brominated Solvents |
| SpringerMaterials Properties | Schoenflies notation |
| LogP（分配係数） | log Kow= 3.42 |
| 臭い | Slight odor.Lacrymator |
| 密度 | 3.42 (NIOSH, 2024) - Denser than waterwill sink2.9608 @ 100 °C/4 °CRelative density (water = 1): 3.423,42 g/cm3 |
| Color/Form | Colorless, monoclinic tabletsColorless crystalsColorless to yellow-brown crystals. |
| 溶解度 | 0.02 % (NIOSH, 2024)Sol in alcohol, ether, chloroformSoluble in ethanol, chloroform, and ethyl ether.In water, 0.024 g/100 ml @ 30 °CSolubility in water: none0.02%soluble in Chloroform不溶性 |
| 沸点 | 374 °F at 760 mmHg (NIOSH, 2024)189.5 °C190 °C190 °C(lit.) |
| Decomposition | When heated to decomp it emits toxic fumes of /hydrogen bromide/. |
| 融点 | 194 °F (NIOSH, 2024)90.1 °C90 °C88-90 °C(lit.) |
| 蒸気密度 | 11.4Relative vapor density (air = 1): 11.4 |
| 蒸気圧 | 40 mmHg at 205 °F (NIOSH, 2024)0.72 [mmHg]0.72 mm Hg @ 25 °CVapor pressure, kPa at 96 °C: 5.3340 mmHg at 205 °F(205 °F): 40 mmHg40 mm Hg ( 96 °C) |
| 屈折率 | 1.5942 |
| 引火点 | 190°C |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 結晶性固体 |
| 色 | ホワイトからオフホワイト |
| 比熱容量 | Cp(crystal): 0.44 J/(g·K)Cp(gas): 0.28 J/(g·K), at 25℃ |
| BRN | 1732799 |
| ヘンリー定数 | 2.0×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 誘電率 | 7(22.0℃) |
| InChI | 1S/CBr4/c2-1(3,4)5 |
| InChIKey | HJUGFYREWKUQJT-UHFFFAOYSA-N |
| SMILES | BrC(Br)(Br)Br |
| CAS データベース | 558-13-4(CAS DataBase Reference) |
| NISTの化学物質情報 | Carbon tetrabromide(558-13-4) |
| EPAの化学物質情報 | Carbon tetrabromide (558-13-4) |
化学的特性
Carbon tetrabromide, is a colorless powder, white crystalline solid, or yellow-brown crystals. Slight odor
安全性と法規制
| GHS 分類 | DangerH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 111 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302: Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 規制情報 | Chemical: Methane, tetrabromo-Carbon tetrabromide: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:· 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 | Not flammable by standard tests in air |
| 健康有害性 | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin. |
| 有害性の概要 | In an acute study of mice, carbon tetrabromide was determined to be 2.2 times more toxic to the liver than carbon tetrachloride. It causes significant eye irritation (tearing) in workers even at lower exposure levels. [ACGIH] A lachrymator[HSDB] Inhalation of high concentrations can cause CNS depressionCauses corrosive burns to eyes [ICSC] |
| 輸送番号・ガイド（DOT） | 2516 151 |
| 反応性グループ | Halogenated Organic Compounds |
| UN 分類 | UN Hazard Class: 6.1UN Pack Group: III |
| Reactivity Profile | CARBON TETRABROMIDE is incompatible with the following: Strong oxidizers, hexacyclohexyldilead, lithium (NIOSH, 2024). |
| 大気基準 | This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Carbon tetrabromide is produced, as an intermediate or a final product, by process units covered under this subpart. |
| Chemical Dangers | Decomposes on heating. This produces toxic and corrosive fumes. Reacts with alkali metals. This generates explosion hazard. |
| 消火 | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:In case of fire in the surroundings, use appropriate extinguishing media. |
| 応急処置措置 | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. 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. Refer 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 | Excerpt from NIOSH Pocket Guide for Carbon tetrabromide:General First Aid:(General first aid procedures) |
| 安全保管 | Well closed. |
| 暴露管理・個人防護 | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| 清掃方法 | Collect on paper and evaporate on a glass dish in a hood. Burn the paper. |
| 非火災時の漏出対応 | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| 処分方法 | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| 漏出処分 | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | Respirators may be used when engineering and work practice controls are not technically feasible, when such controls are in the process of being installed, or when they fail and need to be supplemented. Respirators may also be used for operations which require entry into tanks or closed vessels, and in emergency situations. ... Non-impervious clothing which becomes contaminated with bromoform should be removed promptly and not reworn until the bromoform is removed from the clothing. /Bromoform/The worker should wash daily at the end of each work shift.Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises. |
| Isolation and Evacuation | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:Immediate precautionary measure |
| Treatment | EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration. |
| 標的器官 | Eyes, skin, respiratory system, liver, kidneys |
| 健康影響 | Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627) |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 49(SRC), determined from a structure estimation method(2), indicates that tetrabromomethane is expected to have very high mobility in soil(SRC). Volatilization of tetrabromomethane from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 4.9X10-4 atm-cu m/mole(SRC), from its vapor pressure, 0.72 mm Hg(3) and water solubility, 240 mg/l(4). Tetrabromomethane is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.72 mm Hg(4). Based upon the highly halogenated structure of tetrabromomethane, biodegradation is expected to be slow(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 49(SRC), determined from a structure estimation method(2), indicates that tetrabromomethane is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces may occur based on an estimated Henry's Law constant of 4.9X10-4 atm-cu m/mole(SRC), from its vapor pressure, 0.72 mm Hg(4) and water solubility, 240 mg/l(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4.0 hrs and 8.2 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 86(SRC), from its log Kow value of 3.42(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is moderate. Based upon the highly halogenated structure of tetrabromomethane, biodegradation is expected to be slow(9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tetrabromomethane, which has a vapor pressure of 0.72 mm Hg at 30 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. The rate constant for the vapor-phase reaction of tetrabromomethane with photochemically-produced hydroxyl radicals could not be estimated but is expected to be very slow since there are no abstractable hydrogens(3). |
| 有害作用 | Neurotoxin - Acute solvent syndrome |
| 暴露経路 | The substance can be absorbed into the body by inhalation and by ingestion.inhalation, ingestion, skin and/or eye contactOral (L626)inhalation (L626)dermal (L626) |
| 毒性の概要 | Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (L626, L627, A543) |
| Signs and Symptoms | Cough. Drowsiness. Lethargy. Laboured breathing. Shortness of breath. Sore throat.Redness. Pain.Redness. Pain. Blurred vision. Severe deep burns.Abdominal pain. Diarrhoea. Dullness. Sore throat. See Inhalation.irritation eyes, skin, respiratory systemlacrimation (discharge of tears)lung, liver, kidney injuryIn Animals: corneal damageBromine vapour causes irritation and direct damage to the mucous membranes. Symptoms include lacrimation, rhinorrhoea, eye irritation with mucous secretions from the oropharyngeal and upper airways, coughing, dyspnoea, choking, wheezing, epistaxis, and headache. The bromide ion is a central nervous system depressant producing ataxia, slurred speech, tremor, nausea, vomiting, lethargy, dizziness, visual disturbances, unsteadiness, headaches, impaired memory and concentration, disorientation and hallucinations. This is called bromism. (L626, L627) |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc for tetrabromomethane can be estimated to be about 49(SRC). According to a classification scheme(2), this estimated Koc value suggests that tetrabromomethane is expected to have very high mobility in soil. |
| TSCA Test Submissions | Carbon tetrabromide (CAS # 558-13-4) was evaluated for acute oral toxicity in 5 groups of fasted Sprague-Dawley rats (3 male, 2 female rats/group) administered single doses (unspecified) anticipated to produce partial mortality (based on initial range-finding study) in at least 2 groups. Mortality occurred from 24 to 96 hours post-dosing and, according to a method of Berkson, an oral LD50 for carbontetrabromide 60TC (20% in corn oil) was 4,471 mg/kg (fiducial limits: 2,875-6,953 mg/kg). Symptoms included diarrhea, chromodacryorrhea, and lethargy. No further information regarding methods or results was provided.Carbon tetrabromide (CAS # 558-13-4) was evaluated for acute dermal toxicity in 6 rabbits (strain unspecified) administered single occluded applications of 2 g/kg (volume unspecified) upon clipped, intact skin for 24 hours. All rabbits (6/6) died within 2 to 48 hours and signs of toxicity included expression of pain and inability to stand. No further information regarding methods or results was provided. |
| Natural Pollution Sources | Carbon tetrabromide has been isolated from red algae, Asparagopsis toxiformis, found in the ocean near Hawaii. |
| Human Toxicity Excerpts | ACUTE EXPOSURES TO HIGH CONCN CAUSE UPPER RESP IRRITATION & INJURY TO LUNGS, LIVER & KIDNEYS. CHRONIC EXPOSURE EFFECTS @ VERY LOW LEVELS WILL BE ALMOST ENTIRELY LIMITED TO LIVER INJURY. THE MATERIAL IS A POTENT LACHRIMATOR EVEN @ LOW EXPOSURE CONCENTRATIONS.CNS DEPRESSANT IN HIGH CONCN. |
| 職業暴露区分（OEB） | B |
| 職業暴露限界（OEL） | TWA: 0.1 ppm (1.4 mg/m3), STEL: 0.3 ppm (4 mg/m3) |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | FG4725000 |
| 輸送番号（UN） | UN 2516 |
| PRTR法 | 第二種指定化学物質 |
| 税関コード | 29033036 |
| 危険文句（R） | 37/38-41-36-26-52/53-22 |
| 化審法 | (2)-41 |
| 安衛法 | 57,57-2 |
| 危険表示 | Xi,T+,N,Xn |
| 安全措置（S） | 26-36-45-27-24-61 |
| 危険等級 | 6.1Acute Tox. 4 OralEye Dam. 1Skin Irrit. 2STOT SE 3 |
| 包装等級 | III |
| 貯蔵分類 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| 有害物質データ | 558-13-4(Hazardous Substances Data) |
用途
解説
CBr4(331.63)．CHBr3またはCS2に臭化ヨウ素を作用させて得られる．四臭化炭素は，淡黄色の固体で2形がある．α形は単斜晶系．融点90 ℃，沸点189 ℃(やや分解する)．密度2.96 g cm－3(99.5 ℃)．β形は立方晶系結晶．融点94.3 ℃．転移点46.7 ℃．正四面体構造で，原子間距離C-Br0.1942 nm．エタノール，エーテル，クロロホルムに可溶，水に不溶．有機合成の臭素化剤，半導体基板のエッチング剤，写真材料の製造などに用いられる．森北出版「化学辞典（第2版）
用途
有機合成中間体 感光性物質用
用途
有機合成原料、電子工業材料。
説明
Carbon tetrabromide is considered a highly toxic chemical, may be fatal if inhaled, swallowed, or absorbed through skin. It is metabolized in vitro to produce carbon monoxide but the in vivo significance has not been established. Under anaerobic reducing conditions it forms complexes with ferrous cytochrome P450. Carbon monoxide is detected as a metabolic product of the interaction. Carbon tetrabromide’s production and use in organic syntheses may result in its release to the environment through various waste streams. Carbon tetrabromide has been isolated from red algae, Asparagopsis toxiformis, found in the ocean near Hawaii. It was detected in water from treated chlorinated seawater used for drinking at oil platforms. Occupational exposure to carbon tetrabromide may occur through inhalation and dermal contact with this compound at workplaces where it is produced or used. The general population may be exposed to carbon tetrabromide via ingestion of drinking water. Acute exposures to high concentrations may cause upper respiratory tract irritation and injury to lungs, liver (hepatotoxicity) and kidneys (nephrotoxicity). Chronic exposure effects at very low levels will be almost entirely limited to liver injury. It is a potent lachrymator even at low exposure concentrations. Although carbon tetrabromide may release bromine ions during metabolism, clinical bromism is not expected to occur.
使用
Carbon tetrabromide is used to a limited extent as a chemical intermediate. It has been isolated from red algae, Asparagopsis toxiformis, found in the ocean near Hawaii.
一般的な説明
A colorless crystalline solid. Much more dense than water and insoluble in water. Toxic by ingestion. Vapors are narcotic in high concentration. Used to make other chemicals.
製法・合成法
合成方法
ブロモホルムまたは二硫化炭素と臭化ヨウ素の反応から合成される
純化方法
Reactive bromide is removed from CBr4 by refluxing with dilute aqueous Na2CO3, then steam distilling, crystallising from EtOH, and drying in the dark under vacuum. [Sharpe & Walker J Chem Soc 157 1962.] It can be sublimed at 70o and low pressure. [Beilstein 1 IV 85.]