化工社化工社 化学情報印刷レポート · 研究参考用
2,3-ジクロロ-1,4-ナフトキノン
2,3-ジクロロ-1,4-ナフトキノン · 2,3-ジクロロナフタレン-1,4-ジオン · フィゴン · フィゴンXL · ジクロン · 2,3-ジクロロ-1,4-ナフタレンジオン · ジクロン【農薬】 · ジクロン標準品
識別子と物理属性
| CAS No. | 117-80-6 |
|---|---|
| 分子式 | C10H4Cl2O2 |
| 平均分子量 | 227.04 g/mol |
| 単同位体質量 | 225.95883473 g/mol |
| SMILES | O=C1C(Cl)=C(Cl)C(=O)c2ccccc21 |
| InChIKey | SVPKNMBRVBMTLB-UHFFFAOYSA-N |
| PubChem CID | 8342 |
| ChEMBL | CHEMBL318782 |
| EC No. | 204-210-5 |
| DTXSID | DTXSID7020425 |
| 現地名 | 2,3-ジクロロ-1,4-ナフトキノン |
化学・物理的性質
| XLogP | 3.4 |
|---|---|
| 極性表面積 | 34.1 |
| 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 | 0 |
| 重原子数 | 14 |
| 形式電荷 | 0 |
| 複雑度 | 301 |
| SpringerMaterials Properties | Fusion temperature |
| 農薬 | FungicidesActive substance -> EU Pesticides database: Not approvedPesticides -> Fungicides |
| Color/Form | Golden yellow needles or leaflets from alcohol. |
| 溶解度 | Slightly sol in alcohol, ether, benzeneAbout 4% in xylene, o-dichlorobenzene. Moderately soluble in acetone, dioxaneIn water, 8.0 mg/Lwater buffered to pH 7.4. /Temp not specified/0.1 mg/L water at 25 °C1.0 mg/L and 7 mg/L (temp not specified)Moderately soluble in ethyl acetate, acetic acid, dimethylformamidesparingly soluble in alcohols0.008g/L |
| 沸点 | Sublimes 527 °F (USCG, 1999)275 °C at 2 mm Hg275 °C (2 mmHg) |
| Decomposition | When heated to decomposition it emits toxic fumes of /hydrogen chloride/. |
| 融点 | 379.4 °F (USCG, 1999)195 °CMelting Point: greater than or equal to 188 °C /Technical Grade/194-197 °C (lit.) |
| 蒸気密度 | 7.8 (Air = 1) |
| 蒸気圧 | 0.0000011 [mmHg]1.1X10-6 mm Hg at 25 °C0Pa at 20℃ |
| Physical Description | Dichlone is a yellow crystalline solid dissolved in a water-emulsifiable liquid carrier. Can cause illness by inhalation, skin absorption and/or ingestion. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Can easily penetrate the soil and contaminate groundwater and nearby streams. Used as a fungicide.Dichlone, [other than liquid] appears as a yellow crystalline solid. It is a wettable powder. Can cause illness by inhalation, skin absorption and/or ingestion. Used as a herbicide.Golden yellow solid[Merck Index] Yellow solid dissolved in water-emulsifiable liquid carrier[CAMEO] Yellow powder[MSDSonline] |
| Stability/Shelf Life | Chemically stable, remains algicidally active in water with pH up to 9 or 10.In the dry state, stable to light and heat. In solution, slowly decomposed by light. Stable in acidic media, but hydrolyzed by alkalis. |
| Other Experimental Properties | In dry state, stable to the light and heatin solution, slowly decomposed by light. Stable in acidic media, but hydrolyzed by alkalis.Vapor concentration: 0.02 mg/L at 100 °CSublimes at greater than 32 °C |
| 密度 | 1.4057 (rough estimate) |
| 屈折率 | 1.5410 (estimate) |
| 引火点 | 275°C/2mm |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 微結晶性粉末 |
| 色 | 黄色 |
| Merck | 14,3045 |
| BRN | 1073511 |
| ヘンリー定数 | 9.7×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C10H4Cl2O2/c11-7-8(12)10(14)6-4-2-1-3-5(6)9(7)13/h1-4H |
| InChIKey | SVPKNMBRVBMTLB-UHFFFAOYSA-N |
| SMILES | ClC1=C(Cl)C(=O)c2ccccc2C1=O |
| LogP（分配係数） | 2.9 at 23℃ |
| CAS データベース | 117-80-6(CAS DataBase Reference) |
| NISTの化学物質情報 | 1,4-Naphthalenedione, 2,3-dichloro-(117-80-6) |
| EPAの化学物質情報 | Dichlone (117-80-6) |
化学的特性
YELLOW FINE CRYSTALLINE POWDER
安全性と法規制
| GHS 分類 | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement) |
|---|---|
| 規制情報 | Chemical: 1,4-Naphthalenedione, 2,3-dichloro-2002/2076Status: Active Update: 26-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/16993Dichlone: HSNO Approval: HSR003966 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 |
| 火災危険 | Special Hazards of Combustion Products: Highly toxic fumes are imminent. (USCG, 1999)Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| 健康有害性 | INHALATION: Irritation to mucous membrane. EYES: Irritation. SKIN: Irritation. INGESTION: Can cause CNS depression. (USCG, 1999)Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| 有害性の概要 | A skin, eye, and mucous membrane irritantIn animal experiments, caused internal bleeding and anemia after feeding 1-3 g/kg[HSDB] A CNS depressant[Merck Index] A skin and eye irritant[eChemPortal: ESIS] |
| 反応性グループ | Ketones |
| Special Reports | USEPA/OPPPESTICIDE REGISTRATION STANDARD--2,3-DICHLORO-1,4-NAPHTHOQUINONE (DICHLONE)REPORTEPA-540/RS-81-001ORDER NO PB81-207383: 125 (1981). REGISTRATION STD FOR DICHLONE AND REQUIREMENTS FOR REGISTERING OR RE-REGISTERING PESTICIDE CONTAINING THE ACTIVE INGREDIENT ARE GIVEN. |
用途
用途
有機合成原料、農薬原料。
用途
除草剤、農業と繊維の殺菌剤。
使用
Fungicide for agriculture and textiles; herbicide.
一般的な説明
2,3-Dichloro-1,4-naphthoquinone is a yellow crystalline solid dissolved in a water-emulsifiable liquid carrier. Can cause illness by inhalation, skin absorption and/or ingestion. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Can easily penetrate the soil and contaminate groundwater and nearby streams. Used as a fungicide.
製法・合成法
合成方法
ナフトキノンを鉄粉や塩化鉄（Ⅲ）を触媒として，塩素で塩素化することにより合成される。
純化方法
Crystallise the quinone from EtOH. [Beilstein 7 IV 2426.]