クロロアセトン
クロロアセトン · メチル(クロロメチル)ケトン · 1-クロロプロパン-2-オン · モノクロロアセトン · 1-クロロアセトン · クロロメチルメチルケトン · アセトニルクロリド · 1-クロロ-2-プロパノン
識別子と物理属性
| CAS No. | 78-95-5 |
|---|---|
| 分子式 | C3H5ClO |
| 平均分子量 | 92.52 g/mol |
| 単同位体質量 | 92.00289246 g/mol |
| SMILES | CC(=O)CCl |
| InChIKey | BULLHNJGPPOUOX-UHFFFAOYSA-N |
| PubChem CID | 6571 |
| ChEMBL | CHEMBL1231084 |
| ChEBI | CHEBI:47220 |
| EC No. | 201-161-1 |
| DTXSID | DTXSID0021547 |
| 現地名 | クロロアセトン |
化学・物理的性質
| XLogP | 0.6 |
|---|---|
| 極性表面積 | 17.1 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 1 |
| 重原子数 | 5 |
| 形式電荷 | 0 |
| 複雑度 | 42.2 |
| 物質分類 | Other Classes -> Halogenated KetonesFlammable agents - 3rd degree |
| SpringerMaterials Properties | Schoenflies notation |
| LogP（分配係数） | 0.28 |
| 臭い | Pungent odor |
| 密度 | 1.15 g/cu cm at 20 °CRelative density (water = 1): 1.11.162 @ 20°C1.162 g/mL at 25 °C (lit.) |
| Color/Form | Liquid |
| 溶解度 | Miscible with alcohol, ether and chloroform. Soluble in 10 parts water (wet weight)In water, 8.25X10+4 mg/L, temperature unspecifiedSolubility in water, g/100ml at 20 °C: 10クロロホルム、メタノール（微量）124g/L（20℃） |
| 引火点 | 82 °F40 °C (open cup)35 °C closed cup35 °C c.c. |
| 沸点 | 248 °F (120 ° C)119 °CTurns dark and resinifies on prolonged exposure to lightmay be stabilized by addition of 0.1% H2O or 1% CaCO3. BP: 61 °C at 50 mm Hg20 °C at 12 mm Hg120 °C119 °C @760 [mm Hg]120 °C (lit.) |
| Decomposition | When heated to decomposition it emits highly toxic fumes.It decomposes explosively during distillation. |
| 融点 | -44.5 °CYellow needles from alcoholmp: 124 °C /Chloroacetone 2,4-dihydrophenylhydrazone/-45 °C |
| 蒸気密度 | Relative vapor density (air = 1): 3.2 |
| 蒸気圧 | 42 hPa (20 °C) |
| 屈折率 | n20/D 1.432(lit.) |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 液体 |
| 色 | 澄んだ黄色から黄褐色 |
| 比重 | 1.162 |
| pH | 4.3 (124g/l, H2O, 20°C) |
| 爆発限界 | 3.4%(V) |
| Merck | 14,2114 |
| BRN | 605369 |
| ヘンリー定数 | 5.8×10-1 mol/(m3Pa) at 25℃, Burkholder et al. (2019) |
| 誘電率 | 29.8(20℃) |
| 安定性 | 安定。強酸化剤、強塩基とは相容れない。光に当たると変色することがあります。悪臭。 |
| InChI | 1S/C3H5ClO/c1-3(5)2-4/h2H2,1H3 |
| InChIKey | BULLHNJGPPOUOX-UHFFFAOYSA-N |
| SMILES | CC(=O)CCl |
| LogP（分配係数） | 2.7 at 20℃ |
| CAS データベース | 78-95-5(CAS DataBase Reference) |
| NISTの化学物質情報 | 2-Propanone, 1-chloro-(78-95-5) |
| EPAの化学物質情報 | Chloroacetone (78-95-5) |
化学的特性
colourless to dark yellow liquid
安全性と法規制
| GHS 分類 | DangerH226 (48.1%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 241 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H225: Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| Hazards Identification | Toxic/poison by inhalation (TIH/PIH) |
| 規制情報 | Chemical: 2-Propanone, 1-chloro-2-Propanone, 1-chloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propanone, 1-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: 09-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/32628Chloroacetone: HSNO Approval: HSR002933 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.) |
| 輸送ラベル（DOT） | Poison Inhalation Hazard Flammable Liquid Corrosive |
| 火災危険 | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 35 °C explosive vapour/air mixtures may be formed. |
| 火災の可能性 | Flammable when exposed to heat or flame, or oxidizers. |
| 健康有害性 | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:· TOXICmay be fatal if inhaled, ingested or absorbed through skin. |
| 有害性の概要 | A lacrimator, vesicant, and irritant of the respiratory tractCauses lacrimation at 5 ppm and with continued exposure irritation of the skin and upper respiratory tract, but not pulmonary edema at low, irritating concentrations |
用途
解説
monochloroacetone．C3H5ClO(92.53)．CH2ClCOCH3．クロロアセトン, 塩化カルシウムの存在下，アセトンに塩素を作用させると得られる．融点－44.5 ℃，沸点119 ℃．d164 1.162．水，有機溶媒に易溶．長時間光に当てると着色し，重合する．森北出版「化学辞典（第2版）
用途
有機合成原料。
用途
染料、農薬中間体
用途
クロロアセトン, 催涙性で皮膚に炎症を起こす．カラー写真の発色剤，医薬品，香料に用いられる．また，殺虫剤の合成中間体でもある．
使用
Chloroacetone was used in the synthesis of double-chain nonionic surfactants with an acid decomposition function via acid-catalyzed condensation with fatty alcohols (octyl, decyl and dodecyl). It was also used in the synthesis of meso-tetramethyl tetrakis-(4-phenoxy acetone)calix[4]pyrrole. It can also be used to make dye couplers for color photography and used in the Feist-Benary synthesis of furans.
一般的な説明
A yellow-colored liquid with an irritating pungent odor. Light sensitive, but stabilized with the addition of small amounts of water and/or calcium carbonate. Slightly soluble in water and denser than water. Vapors much heavier than air. Irritates skin and eyes. Very toxic by ingestion or inhalation. Used to make other chemicals. A lachrymator.
製法・合成法
純化方法
Dissolve it in water and shake it repeatedly with small amounts of diethyl ether which extracts, preferentially, 1,1-dichloroacetone present as an impurity. The chloroacetone is then extracted from the aqueous phase using a large amount of diethyl ether, and distilled at slightly reduced pressure. It is dried with CaCl2 and stored at Dry-ice temperature. Alternatively, it was stood over CaSO4, distilled and stored over CaSO4. It is steam volatile. The 2,4-dinitrophenylhydrazone forms yellow needles from EtOH with m 120o or 124o. [Beilstein 1 IV 3215.] LACHRYMATOR with toxic vapour.