3-ニトロベンズアルデヒド
3-ニトロベンズアルデヒド · 1-ニトロ-3-ホルミルベンゼン · m-ニトロベンズアルデヒド · 1-ホルミル-3-ニトロベンゼン · mニトロベンズアルデヒド · ニトロベンズアルデヒド · 3‐ニトロベンズアルデヒド · M-NITROBENZALDEHYDE
識別子と物理属性
| CAS No. | 99-61-6 |
|---|---|
| 分子式 | C7H5NO3 |
| 平均分子量 | 151.12 g/mol |
| 単同位体質量 | 151.02694302 g/mol |
| SMILES | O=Cc1cccc([N+](=O)[O-])c1 |
| InChIKey | ZETIVVHRRQLWFW-UHFFFAOYSA-N |
| PubChem CID | 7449 |
| ChEMBL | CHEMBL238132 |
| ChEBI | CHEBI:231487 |
| EC No. | 202-772-6 |
| DTXSID | DTXSID8049383 |
| 現地名 | 3-ニトロベンズアルデヒド |
化学・物理的性質
| XLogP | 1.5 |
|---|---|
| 極性表面積 | 62.9 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 1 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 164 |
| 物質分類 | Nitrogen Compounds -> Other Aromatics (Nitrogen) |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP（分配係数） | 1.47 |
| Physical Description | Light yellow powder[MSDSonline] |
| Ionization Efficiency | Positive0.092.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| 融点 | 56 °C |
| 沸点 | 285-290 °C |
| 密度 | 1.2792 |
| 蒸気密度 | 5.21 (vs air) |
| 屈折率 | 1.5800 (estimate) |
| 引火点 | 164°C/23mm |
| 貯蔵条件 | Store below +30°C. |
| 溶解度 | 1.6g/リットル水にわずかに溶ける。 |
| 外観・状態 | 粒状粉末 |
| 色 | 黄色から黄褐色 |
| Merck | 14,6587 |
| BRN | 386795 |
| InChI | 1S/C7H5NO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-5H |
| InChIKey | ZETIVVHRRQLWFW-UHFFFAOYSA-N |
| SMILES | [O-][N+](=O)c1cccc(C=O)c1 |
| LogP（分配係数） | 1.47 |
| CAS データベース | 99-61-6(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzaldehyde, 3-nitro-(99-61-6) |
| EPAの化学物質情報 | Benzaldehyde, 3-nitro- (99-61-6) |
化学的特性
yellowish to yellow-brown granular powder
安全性と法規制
| GHS 分類 | WarningH302 (77.5%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 204 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Benzaldehyde, 3-nitro-Status: Active Update: 08-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/17350Benzaldehyde, 3-nitro-: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | An irritant[MSDSonline] |
| Hazard Classes and Categories | Acute Tox. 4 (77.5%) |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | CU7250000 |
| 輸送番号（UN） | UN3077 |
| 毒性 | LD50 orally in Rabbit: 1075 mg/kg |
| 税関コード | 29130000 |
| 危険文句（R） | 36/37/38-51/53-22 |
| 化審法 | (3)-1181 |
| 消防法 | 危-5-II |
| 危険表示 | Xi |
| hazard_note | Irritant |
| 安全措置（S） | 26-36-24/25-61-37/39-29 |
| 危険等級 | Acute Tox. 4 OralAquatic Chronic 2 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
説明
3-Nitrobenzaldehyde, meta-nitrobenzaldehyde or m-nitrobenzaldehyde is an organic aromatic compound containing a nitro group meta-substituted to an aldehyde. 3-Nitrobenzaldehyde is the primary product obtained via the mono-nitration of benzaldehyde with nitric acid.
使用
3-Nitrobenzaldehyde is a benzaldhyde with a nitro group in the meta position.
製法・合成法
製造方法
89 mL (1.7 mol) concentrated H2SO4 are filled in a 500 mL three-neck flask equipped with an internal thermometer and an addition funnel with pressure balance. Whilst cooling with an ice bath 45 mL (0.95 mol) fuming HNO3 are added carefully under stirring, the temperature must not exceed 10 °C. To this nitrating acid, 10.6 g (10.2 mL, 100 mmol) benzaldehyde are added under further cooling so that the temperature can be constantly kept at 15 °C (about 1 hour). The ice bath is removed and the reaction mixture is stored over night at room temperature.The reaction mixture is poured in a 1 L beaker on 500 g crunched ice, the yellow precipitation is sucked off at 16 hPa over a Buechner funnel and washed with 200 mL of cold water. Crude yield (humid): 14.4 gThe humid crude product is dissolved in 125 mL tert-butyl methyl ether and then shaken out with 125 mL of a 5% NaHCO3 solution. The organic phase is dried over sodium sulfate, filtered and the solvent evaporated at a rotary evaporator. The residue is recrystallized from toluene / petroleumether (60-80 °C) by dissolving it in toluene whilst heating and then adding the double amount of petroleum ether in portions under ice cooling. The crystalllized light yellow 3-nitrobenzaldehyde is sucked off over a Buechner funnel. The product is dried over silica gel in an evacuated desiccator.Yield: 8.0 g (53 mmol, 53%); mp 56 °C
純化方法
Crystallise the aldehyde from water or EtOH/water, then sublime it twice at 2mm pressure at a temperature slightly above its melting point. [Beilstein 7 IV 591.]