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ブロモ酢酸エチル
ブロモ酢酸エチル · 3-メチルベンゼンスルホン酸 · α-ブロモ酢酸エチル · エチル=ブロモアセタート · ブロム酢酸エチル · m-トルエンスルホン酸 · アントール · 2-ブロモ酢酸エチル
識別子と物理属性
| CAS No. | 105-36-2 |
|---|---|
| 分子式 | C4H7BrO2 |
| 平均分子量 | 167 g/mol |
| 単同位体質量 | 165.96294156 g/mol |
| SMILES | CCOC(=O)CBr |
| InChIKey | PQJJJMRNHATNKG-UHFFFAOYSA-N |
| PubChem CID | 7748 |
| ChEMBL | CHEMBL1085948 |
| EC No. | 203-290-9 |
| DTXSID | DTXSID4020587 |
| 現地名 | ブロモ酢酸エチル |
化学・物理的性質
| XLogP | 1.3 |
|---|---|
| 極性表面積 | 26.3 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 3 |
| 重原子数 | 7 |
| 形式電荷 | 0 |
| 複雑度 | 62.7 |
| 物質分類 | Other Classes -> Halogenated EstersFlammable agents - 2nd degree |
| SpringerMaterials Properties | Diamagnetic susceptibility |
| LogP（分配係数） | log Kow= 1.12 |
| 臭い | Pungent odor刺激臭 |
| 密度 | 1.5032 @ 20 °C/20 °C1.5032 @ 20°C1.506 g/mL at 25 °C(lit.) |
| Color/Form | Clear colorless liquid |
| 溶解度 | Insoluble in water, soluble in acetone, miscible in ethanol and ethyl ether.Sol in benzene and alcoholMiscible in oxygenated and aromatic solvents水：不溶エタノール、アセトン、ベンゼン、エチルエーテルと混和します。水と混和しない。 |
| 引火点 | 48 °C118 °F (48 °C) (CLOSED CUP) |
| 沸点 | 168.5 °C158.8 °C @760 [mm Hg]159 °C(lit.) |
| Decomposition | When heated to decomposition ... it emits highly toxic fumes of /hydrogen bromide/. |
| 蒸気密度 | 5.8 (Air= 1)5.8 (vs air) |
| 蒸気圧 | 3.37 [mmHg]2.6 [mm Hg] @25 °C2.6 mm Hg ( 25 °C) |
| 融点 | -38 °C |
| 屈折率 | n20/D 1.451(lit.) |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 液体 |
| 色 | クリア |
| 比重 | 1.506 |
| BRN | 506456 |
| ヘンリー定数 | 3.7×10-1 mol/(m3Pa) at 25℃, HSDB (2015) |
| 誘電率 | 9.75 |
| 安定性 | 安定。可燃性。強力な酸化剤、水、強酸とは相容れない。 |
| InChI | 1S/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3 |
| InChIKey | PQJJJMRNHATNKG-UHFFFAOYSA-N |
| SMILES | BrCC(=O)OCC |
| CAS データベース | 105-36-2(CAS DataBase Reference) |
| NISTの化学物質情報 | Acetic acid, bromo-, ethyl ester(105-36-2) |
| EPAの化学物質情報 | Acetic acid, 2-bromo-, ethyl ester (105-36-2) |
化学的特性
Ethyl bromoacetate is a clear, colorless to light-yellow liquid and has a pungent odor. It is miscible with ethanol, ether, benzene and with other oxygenated and aromatic solvents, insoluble in water and partially decomposed by water.
安全性と法規制
| GHS 分類 | DangerH300: Fatal if swallowed [Danger Acute toxicity, oral]P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.6% (1 of 164) of reports.H226 (93.3%): Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| 規制情報 | Chemical: Acetic acid, bromo-, ethyl esterStatus: Active Update: 17-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/18025Restricted substance: Ethyl bromoacetateEthyl bromoacetate: HSNO Approval: HSR004469 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 - Acetic acid, bromo-, ethyl ester: Human health tier I assessment |
| 輸送ラベル（DOT） | Poison Flammable Liquid |
| 火災危険 | Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. |
| 火災の可能性 | Flammable liquid when exposed to heat, flame, and oxidizers. |
| 健康有害性 | Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:· TOXIC and/or CORROSIVEinhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. |
| 有害性の概要 | A skin, eye, and mucous membrane irritantContact with liquid can cause corneal burns[HSDB] A lachrymator and a strong skin irritant[CAMEO] Highly toxic[Quick CPC] A lachrymator--exposure to 8 ppm for more than 1 minute is unbearable[CHEMINFO] Inhalation of high concentrations may produce acute pneumonitis and pulmonary edema[MSDSonline] See Ethyl chloroacetate. |
| 輸送番号・ガイド（DOT） | 1603 155 |
| 反応性グループ | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| Special Reports | TOXICOLOGICAL ASPECTS OF IRRITATING AGENTS ETHYLBROMOACETATE. A REVIEW.[HOLMBERG BBIOLOGICAL ASPECTS OF CHEMICAL & BIOLOGICAL WEAPONSAMBIO 4(5-6) 211 (1975)] |
| Reactivity Profile | ETHYL BROMOACETATE is a halogenated ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. |
| DOT Emergency Guidelines | /GUIDE 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water./GUIDE 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Health: TOXICinhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution./GUIDE 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas./GUIDE 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLYit is not effective in spill situations where direct contact with the substance is possible.For more DOT Emergency Guidelines (Complete) data for ETHYL 2-BROMOACETATE (8 total), please visit the HSDB record page. |
| 消火 | Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: |
| 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.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| 応急処置 | Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:General First Aid: |
| 暴露管理・個人防護 | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| 消火手順 | To fight fire, use water as a fire blanket. |
| 非火災時の漏出対応 | Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: |
| 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. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Isolation and Evacuation | Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:Immediate precautionary measure |
| Protective Action Criteria (PAC) | 1.2 [mg/m3]13 [mg/m3]79 [mg/m3] |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: |
| Emergency Response Planning Guidelines | · Note: Most foams will react with the material and release corrosive/toxic gases. |
| 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. |
| 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 12(SRC), determined from a log Kow of 1.12(2) and a regression-derived equation(3), indicates that ethyl 2-bromoacetate is expected to have very high mobility in soil(SRC). Volatilization of ethyl 2-bromoacetate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.70X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of ethyl 2-bromoacetate from dry soil surfaces may exist based upon an estimated vapor pressure of 3.37 mm Hg(5). A base-catalyzed second-order hydrolysis rate constant of 11 L/mole-sec(SRC) was estimated using a structure estimation method(6)this corresponds to half-lives of 8 days and 18 hours at pH values of 7 and 8, respectively(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of 1.12(2) and a regression-derived equation(3), indicates that ethyl 2-bromoacetate is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.70X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 17 hr and 12 days, respectively(SRC). A base-catalyzed second-order hydrolysis rate constant of 11 L/mole-sec(SRC) was estimated using a structure estimation method(7)this corresponds to half-lives of 8 days and 18 hours at pH values of 7 and 8, respectively(7). According to a classification scheme(5), an estimated BCF of 1(SRC), from its log Kow(2) and a regression-derived equation(6), 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), ethyl 2-bromoacetate, which has an estimated vapor pressure of 3.37 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl 2-bromoacetate 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 14 days(SRC), calculated from its rate constant of 1.2X10-12 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3). |
| 有害作用 | Dermatotoxin - Skin burns. |
| 暴露経路 | Oral (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 | Bromine 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 | The Koc of ethyl 2-bromoacetate is estimated as 12(SRC), using a log Kow of 1.12(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that ethyl 2-bromoacetate is expected to have very high mobility in soil. |
| Human Toxicity Excerpts | VAPORS ARE IRRITANT TO ALL MUCOUS MEMBRANES, ESP TO EYES, & ARE UNBEARABLE FOR MORE THAN A MIN AT CONCN OF 8 PPM IN AIR. EXPOSURE OF HUMAN EYES TO HIGH CONCN OF VAPOR FROM TEAR GAS SHELLS HAS CAUSED CORNEAL EDEMA WITH WRINKLING OF DESCEMET'S MEMBRANE, BUT IN MOST PATIENTS THE EYES...RETURNED TO NORMAL.DIRECT CONTACT WITH LIQUID...HAS CAUSED PERMANENT CORNEAL SCARRING & OPACIFICATION.TOXIC BY INGESTION, INHALATION, & SKIN ABSORPTION. |
| Artificial Pollution Sources | Ethyl 2-bromoacetate's production and use as a chemical intermediate and reactant in the synthesis of an analgesic(1) may result in its release to the environment through various waste streams. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Environmental Bioconcentration | An estimated BCF of 1 was calculated for ethyl 2-bromoacetate(SRC), using a log Kow of 1.12(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low. |
| F | 19 |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | AF6000000 |
| 輸送番号（UN） | UN 1603 |
| 税関コード | 29159080 |
| 危険文句（R） | 26/27/28 |
| 化審法 | (2)-2636 |
| 消防法 | 危-4-2-III |
| 危険表示 | T+ |
| 安全措置（S） | 26-45-7/9-1/2 |
| 危険等級 | 6.1Acute Tox. 1 DermalAcute Tox. 2 InhalationAcute Tox. 2 OralFlam. Liq. 3 |
| 包装等級 | II |
| 毒劇物取締法 | 毒物 |
| 貯蔵分類 | 3 - Flammable liquids |
| 有害物質データ | 105-36-2(Hazardous Substances Data) |
用途
用途
農薬中間体、有機合成原料
用途
有機合成原料。
一般的な説明
Ethyl bromoacetate appears as a clear, colorless liquid. A lachrymator. Toxic by ingestion, inhalation and skin absorption; a strong irritant of the skin. Insoluble in water and soluble in alcohol, benzene, and ether. Specific gravity of 1.5.
製法・合成法
製造方法
Ethyl bromoacetate is commonly synthesized by sulfuric acid catalyzed esterification of monobromoacetic acid (MBAA). After reaction completion, excess acid is washed out and the product purified via distillation under reduced pressure if necessary (Stenger, 1978; Korhonen, 1984).
純化方法
Wash the ester with saturated aqueous Na2CO3 (three times), 50% aqueous CaCl2 (three times) and saturated aqueous NaCl (twice). Dry with MgSO4, CaCl2 or CaCO3, and distil it. [Beilstein 2 IV 527.] LACHRYMATORY.