クロロ酢酸
クロロ酢酸 · モノクロロ酢酸 · クロロ酢酸標準原液 · モノクロル酢酸 · モノクロロ酢酸(クロロ酢酸) · クロロ酢酸, 1000 µg/mL in MtBE · モノクロロ酢酸, 60 µg/mL in MtBE · クロロエタン酸
識別子と物理属性
| CAS No. | 79-11-8 |
|---|---|
| 分子式 | C2H3ClO2 |
| 平均分子量 | 94.5 g/mol |
| 単同位体質量 | 93.98215702 g/mol |
| SMILES | O=C(O)CCl |
| InChIKey | FOCAUTSVDIKZOP-UHFFFAOYSA-N |
| PubChem CID | 300 |
| ChEMBL | CHEMBL14090 |
| ChEBI | CHEBI:27869 |
| EC No. | 201-178-4 |
| DTXSID | DTXSID4020901 |
| 現地名 | クロロ酢酸 |
化学・物理的性質
| XLogP | 0.2 |
|---|---|
| 極性表面積 | 37.3 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 5 |
| 形式電荷 | 0 |
| 複雑度 | 42.9 |
| 物質分類 | Hazardous Air Pollutants (HAPs)Other Classes -> Organic AcidsCorrosives |
| 医薬品 | Pharmaceuticals |
| 脂質 | Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Halogenated fatty acids [FA0109] |
| 化粧品 | Cosmetics ingredient -> Preservative/Stabilizer |
| SpringerMaterials Properties | Moessbauer quadrupole effect |
| LogP（分配係数） | log Kow = 0.220.34 |
| 臭い | Strong vinegar-like odor浸透する焦げ臭い |
| 食品添加物 | ANTIMICROBIAL AGENT -> FDA Substance added to food |
| 密度 | 1.4043 at 104 °F (EPA, 1998) - Denser than waterwill sink1.328 (USCG, 1999) - Denser than water1.58 at 20 °C/20 °C (solid)Density: 1.4043 g/cu cm at 40 °CDensity: 1.3703 at 65 °C/4 °C (liquid)Density (at 20 °C): 1.58 g/cm³ |
| Color/Form | Monoclinic prismsColorless or white deliquescent crystalsColorless to light-brownish crystalsColorless, hygroscopic, crystalline solid, which occurs in monoclinically prismatic structures ... |
| 溶解度 | greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)In water, 8.58X10+5 mg/L at 25 °CSoluble in ethanol, diethyl ether, benzene, chloroformslightly soluble in carbon tetrachloride... good solubility in methanol, acetone, diethyl ether, and ethanol, but is only sparingly soluble in hydrocarbons and chlorinated hydrocarbons.858 mg/mL at 25 °CSolubility in water at 20 °C: very goodメタノール、アセトン、エーテル、ベンゼン、クロロホルム、エタノールに可溶。溶ける |
| Corrosivity | ...extremely corrosive and will cause serious chemical burns. |
| 融点 | 60-63 °C (lit.) |
| 沸点 | 189 °C (lit.) |
| 蒸気密度 | 3.26 (vs air) |
| 蒸気圧 | 0.75 mm Hg ( 20 °C) |
| 屈折率 | 1.4330 |
| 引火点 | 126°C |
| 貯蔵条件 | Store below +30°C. |
| pKa（酸解離定数） | 2.85(at 25℃) |
| 外観・状態 | 液体 |
| 色 | 白い |
| pH | <1 (20°C, 800g/L in H2O) |
| 爆発限界 | 8% |
| 比熱容量 | Cp(gas): 0.83 J/(g·K), at 25℃ |
| Merck | 14,2112 |
| BRN | 605438 |
| Specific Activity | 5-10 Ci/mmol |
| ヘンリー定数 | 1.1×103 mol/(m3Pa) at 25℃, Burkholder et al. (2019) |
| 誘電率 | 12.3(60℃) |
| 安定性 | 安定。潮解性。強塩基、アルカリ、最も一般的な金属、強力な酸化剤とは相容れない。 |
| 化粧品成分の機能 | 角質溶解性 |
| InChI | 1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5) |
| InChIKey | FOCAUTSVDIKZOP-UHFFFAOYSA-N |
| SMILES | OC(=O)CCl |
| LogP（分配係数） | 0.49 at 20℃ |
| CAS データベース | 79-11-8(CAS DataBase Reference) |
| NISTの化学物質情報 | Acetic acid, chloro-(79-11-8) |
| EPAの化学物質情報 | Chloroacetic acid (79-11-8) |
| ECETOC JACC REPORT | Chloroacetic acid (79-11-8) |
化学的特性
Chloroacetic acid is a colorless to white crystalline solid. It has a strong vinegar-like odor and an Odor Threshold of 0.15 milligram per cubic meter.
安全性と法規制
| GHS 分類 | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P361+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)H301+H311+H331 (17.1%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P361+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| 規制情報 | Chemical: Acetic acid, chloro-Hazard Traits - DermatotoxicityNeurotoxicityOcular ToxicityRespiratory ToxicityAcetic acid, 2-chloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetic acid, 2-chloro- 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: 08-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15187Chloroacetic acid: HSNO Approval: HSR003030 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, chloro-: Human health tier II assessment |
| 輸送ラベル（DOT） | Poison Corrosive |
| 火災危険 | When heated to decomposition, it emits highly toxic fumes of phosgene and chlorides. Water may cause frothing if it gets below surface of the liquid and turns to steam. Flammable/poisonous gases may accumulate in tanks and hopper cars. Some of these materials may ignite combustibles, e.g., wood, paper, oil. It is corrosive to metals. Avoid heating. (EPA, 1998)Special Hazards of Combustion Products: Toxic gases, such as hydrogen chloride, phosgene and carbon monoxide, may be generated. (USCG, 1999)· Combustible material: may burn but does not ignite readily. |
用途
解説
酢酸の塩素置換体に相当し，その程度によって異なる3種類のものがある．一般にはモノクロロ酢酸をさす．【Ⅰ】モノクロロ酢酸：C2H3ClO2(94.50)．CH2ClCOOH．酢酸を少量の硫黄，ヨウ素などの存在下で塩素化するか，トリクロロエテンを硫酸で処理すると得られる．無色の潮解性結晶．d20201.58．3種類の形があり，それぞれの融点はα形：63 ℃，β形：55～56 ℃，γ形：50 ℃．沸点189 ℃，104 ℃(2.66 kPa)．水，エタノール，ベンゼン，クロロホルム，エーテルに可溶．水溶液は酢酸より強酸である．pKa 2.85，Ka 1.55×10－2(25 ℃)．アンモニアと反応してグリシンに，またシアン化カリウムと反応してシアン酢酸になる．種々の有機合成の原料になる．[CAS 79-11-8]【Ⅱ】ジクロロ酢酸：C2H2Cl2O2(128.95)．CHCl2COOH．モノクロロ酢酸を塩素化すると得られる．液体．融点9.7 ℃，沸点193～194 ℃，102 ℃(2.6 kPa)．d204"1.563．水，エタノール，エーテルに易溶．加水分解するとグリオキシル酸になる．刺激臭を有する．[CAS 79-43-6]【Ⅲ】トリクロロ酢酸：C2HCl3O2(163.39)．CCl3COOH．クロラールを硝酸酸化するか，ジクロロ酢酸をさらに塩素化すると得られる．無色の潮解性結晶．融点57～58 ℃，沸点197 ℃，142 ℃(3.3 kPa)．d204"1.629．水，エタノール，エーテルに易溶．モノクロロ酢酸，ジクロロ酢酸より強酸である．pH 1.2．希アルカリで加水分解されてクロロホルムと二酸化炭素になる．また，濃アルカリではギ酸になる．腐食剤，角質溶解剤などのほか，生体のリン酸化合物，タンパク質，脂質などの分画分析に用いられる．強い腐食性を有する．[CAS 76-03-9] 三者とも皮膚，粘膜などをおかすのでとくに注意が必要である．森北出版「化学辞典（第2版）
用途
除草剤、医薬品原料、有機合成用
用途
カルボキシメチルセルロース原料、2,4-ジシクロフェノキシ酢酸原料、チオグリコール酸及び両性界面活性剤原料 (NITE初期リスク評価書)
用途
有機合成原料。
用途
有機合成原料(医薬、農薬、可塑剤、香料等)。
説明
Chloroacetic acid (CAA) is a monohalogenated acetic acid (m-HAA) that is used as a photosensitizing agent and in industrial synthesis of certain organic chemicals such as indigoid dyes. The m-HAAs are a major class of drinking water disinfection by-products during chlorination of drinking water.
使用
Chloroacetic acid behaves as a very strong monobasic acid and is used as a strong acid catalyst for diverse reactions. The Cl function can be displaced in base-catalyzed reactions.
一般的な説明
Chloroacetic acid, solution is a colorless solution of the white crystalline solid. The acid concentration can be up to 80%.It is used in manufacturing dyes and in medicine. Chloroacetic acid is toxic by inhalation, ingestion and skin contact. Chloroacetic acid is corrosive to metals and tissue. Chloroacetic acid is used as an herbicide, preservative and bacteriostat.
製法・合成法
調製方法
Chloroacetic acid can be synthesized by the radical chlorination of acetic acid, treatment of trichloroethylene with concentrated H2SO4, oxidation of 1,2-dichloroethane or chloroacetaldehyde, amine displacement from glycine, or chlorination of ketene.
合成方法
氷酢酸に赤リンなどの存在下で塩素を作用させて合成する。
純化方法
Crystallise the acid from CHCl3, CCl4, *benzene or water. Dry it over P2O5 or conc H2SO4 in a vacuum desiccator. Further purification is by distillation from MgSO4, and by fractional crystallisation from the melt. Store it under vacuum or under dry N2. [Bernasconi et al. J Am Chem Soc 107 3621 1985, Beilstein 2 IV 474.]