2-ニトロアニリン
2-ニトロアニリン · アゾイックDC6(ベース) · o-ニトロフェニルアミン · オルト-ニトロアニリン · 2-ニトロベンゼン-1-アミン · 2-アミノ-1-ニトロベンゼン · 2-[オキシラト(オキシ)アミニオ]アニリン · 2-ニトロベンゼンアミン
識別子と物理属性
| CAS No. | 88-74-4 |
|---|---|
| 分子式 | C6H6N2O2 |
| 平均分子量 | 138.12 g/mol |
| 単同位体質量 | 138.04292743 g/mol |
| SMILES | Nc1ccccc1[N+](=O)[O-] |
| InChIKey | DPJCXCZTLWNFOH-UHFFFAOYSA-N |
| PubChem CID | 6946 |
| ChEMBL | CHEMBL274009 |
| EC No. | 201-855-4 |
| DTXSID | DTXSID1025726 |
| 現地名 | 2-ニトロアニリン |
化学・物理的性質
| XLogP | 1.9 |
|---|---|
| 極性表面積 | 71.8 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 0 |
| 重原子数 | 10 |
| 形式電荷 | 0 |
| 複雑度 | 132 |
| 物質分類 | Nitrogen Compounds -> Nitroanilines |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP（分配係数） | log Kow = 1.851.441.62 |
| 臭い | Musty |
| 密度 | 1.44 at 68 °F (USCG, 1999) - Denser than waterwill sink0.9015 at 25 °C/4 °C1.44 g/cm³0.9015 @25 °C1,255 g/cm3 |
| Color/Form | Yellow-orange crystals from boiling waterOrange-red needles |
| 溶解度 | less than 1 mg/mL at 70.7 °F (NTP, 1992)Soluble in ethanolvery soluble in ether, acetone, benzene, chloroformSlightly sol in cold watersol in hot waterIn water, 1.47X10+3 mg/L at 30 °CSolubility in water, g/100ml at 25 °C: 0.126メタノール: 0.1 g/mL、透明1.1g/L(20℃) |
| 引火点 | 335 °F (NTP, 1992)168 °C |
| 沸点 | 543 °F at 760 mmHg (NTP, 1992)284 °C284.5 °C @760 [mm Hg]284 °C (lit.) |
| Decomposition | When heated to decomp it emits toxic fumes of /nitrogen oxides/. |
| 融点 | 160.7 °F (NTP, 1992)71.0 °CHeat of fusion at melting point = 16.1 kJ/mol71 °C72 °C70-73 °C (lit.) |
| 蒸気密度 | 4.77 (NTP, 1992) - Heavier than airwill sink (Relative to Air) |
| 蒸気圧 | 8.1 at 25 °C (Mabey et al., 1982) |
| 屈折率 | 1.6349 (estimate) |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | クリスタルまたはフレーク |
| pKa（酸解離定数） | -0.26(at 25℃) |
| 色 | オレンジからブラウン |
| pH | 6.1 (10g/l, H2O, 20℃)(slurry) |
| 比熱容量 | Cp(crystal): 1.2 J/(g·K), at 25℃ |
| Merck | 14,6582 |
| BRN | 509275 |
| ヘンリー定数 | 5.88 x 10-8 atmm3/mol at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) |
| 安定性 | 安定。酸、酸塩化物、酸無水物、強力な酸化剤、クロロホルメート、ヘキサニトロエタンとは混和しません。 |
| InChI | 1S/C6H6N2O2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H,7H2 |
| InChIKey | DPJCXCZTLWNFOH-UHFFFAOYSA-N |
| SMILES | Nc1ccccc1[N+]([O-])=O |
| LogP（分配係数） | 1.85 at 25℃ |
| CAS データベース | 88-74-4(CAS DataBase Reference) |
| NISTの化学物質情報 | o-Nitroaniline(88-74-4) |
| EPAの化学物質情報 | o-Nitroaniline (88-74-4) |
化学的特性
orange solid
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, P302+P352, P304+P340, P316, P319, 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 0.4% (1 of 227) of reports.H301 (97.4%): Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| 規制情報 | Chemical: Benzenamine, 2-nitro-Benzenamine, 2-nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 2-nitro- 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: 28-06-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/137152-Nitroaniline: Does not have an individual approval but may be used under an appropriate group standard |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire. (USCG, 1999)Combustible. Many reactions may cause fire or explosion. Finely dispersed particles form explosive mixtures in air. |
| 火災の可能性 | SLIGHT, WHEN EXPOSED TO HEAT OR FLAME.COMBUSTIBLE. IN PRESENCE OF MOISTURE CAUSES NITRATION OF ORG MATERIALS & MAY RESULT IN SPONTANEOUS IGNITION.Process errors led to discharge of copious amt of nitrous fumes into glass reinforced plastic ventilation duct above diazotization vessel. On 2 occasions fires were caused in the duct by vigorous reaction of the dinitrogen tetraoxide with nitroaniline dusts in the duct. /Nitroaniline dust/ |
| 健康有害性 | Inhalation or ingestion causes headache, nausea, methemo- globinemia, vomiting, weakness, and stuporcyanosis caused by contact usually develops in 4-6 hrs.prolonged and excessive exposure may also cause liver damage. Contact with eyes or skin causes irritationcontinued exposure may cause same symptoms as inhalation or ingestion. (USCG, 1999) |
| 有害性の概要 | Highly toxicMay be absorbed through skinMay induce methemoglobinemia and cyanosis |
用途
用途
染色中間体
使用
2-Nitroaniline is the main precursor tophenylenediamines, which are converted tobenzimidazoles, a family ofheterocyclesthat are key components in pharmaceuticals.
一般的な説明
Orange solid with a musty odor. Sinks and mixes slowly with water.
製法・合成法
調製方法
2-Chloronitrobenzene is heated with excess (10 mol/mol) strong aqueous ammonia in an autoclave. The temperature is gradually increased to 180 ℃ over 4 h and held there for 5 h more. The pressure builds up to around 4 MPa and is released to an ammonia recycle loop before the product is isolated by filtration and washing. The reaction is extremely exothermic, and too rapid heating or inadequate temperature control can result in a runaway reaction. Because of this hazard, I.G. Farbenindustrie developed a continuous amination unit for amination of chloronitrobenzenes; the process is summarized under 4-nitroaniline.
純化方法
Crystallise the aniline from hot water (charcoal), then from aqueous 50% EtOH, or EtOH, and dry it in a vacuum desiccator. It has also been chromatographed on alumina, then recrystallised from *benzene. [Beilstein 12 IV 1563.]