2-ブロモピリジン
2-ブロモピリジン · 2ブロモピリジン · 2‐ブロモピリジン · 2-ピリジルブロミド · (2-ピリジル)ブロミド · 2-ピリジニルブロミド · -Bromopyridine · Pyridine,2-bromo-
識別子と物理属性
| CAS No. | 109-04-6 |
|---|---|
| 分子式 | C5H4BrN |
| 平均分子量 | 158 g/mol |
| 単同位体質量 | 156.95271123 g/mol |
| SMILES | Brc1ccccn1 |
| InChIKey | IMRWILPUOVGIMU-UHFFFAOYSA-N |
| PubChem CID | 7973 |
| ChEMBL | CHEMBL331374 |
| ChEBI | CHEBI:51574 |
| EC No. | 203-641-6 |
| DTXSID | DTXSID6051564 |
| 現地名 | 2-ブロモピリジン |
化学・物理的性質
| XLogP | 1.4 |
|---|---|
| 極性表面積 | 12.9 |
| 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 | 0 |
| 重原子数 | 7 |
| 形式電荷 | 0 |
| 複雑度 | 56 |
| 物質分類 | Nitrogen Compounds -> Pyridines |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| LogP（分配係数） | 1.42 |
| 蒸気圧 | 1.0 [mmHg] |
| Physical Description | Colorless oily liquid[EPA - PPRTV] Pale yellow or colorless liquid[Alfa Aesar MSDS] |
| 融点 | 193°C |
| 沸点 | 192-194 °C (lit.) |
| 密度 | 1.657 g/mL at 25 °C (lit.) |
| 屈折率 | n20/D 1.572(lit.) |
| 引火点 | 130 °F |
| 貯蔵条件 | Keep in dark place,Sealed in dry,Room Temperature |
| 溶解度 | 20g/リットル水とわずかに混和する。 |
| 外観・状態 | 液体 |
| pKa（酸解離定数） | pK1: 0.71(+1) (25°C) |
| 色 | 無色透明～淡褐色 |
| BRN | 105789 |
| ヘンリー定数 | 1.3×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 誘電率 | 24.02 |
| 安定性 | 安定。可燃性。強力な酸化剤、強酸、酸塩化物とは相容れない。 |
| InChI | 1S/C5H4BrN/c6-5-3-1-2-4-7-5/h1-4H |
| InChIKey | IMRWILPUOVGIMU-UHFFFAOYSA-N |
| SMILES | Brc1ccccn1 |
| LogP（分配係数） | 1.42 |
| CAS データベース | 109-04-6(CAS DataBase Reference) |
| NISTの化学物質情報 | Pyridine, 2-bromo-(109-04-6) |
| EPAの化学物質情報 | Pyridine, 2-bromo- (109-04-6) |
化学的特性
light yellow oily or dark red liquid. miscible with ethanol, ether, benzene and pyridine, still soluble in water.
安全性と法規制
| GHS 分類 | DangerH226 (16.7%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 60 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: Pyridine, 2-bromo-Status: Active Update: 16-06-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/186202-Bromopyridine: HSNO Approval: HSR006014 Approved with controls |
| 有害性の概要 | A skin and strong eye irritantToxic by ingestionHighly toxic by skin absorption[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Flam. Liq. 3 (16.7%) |
| Toxicity Data | LC50 (rat) < 200,000 mg/m3/1hr |
| EPA Provisional Peer-Reviewed Toxicity Values | 2-BromopyridinePDF Document2011 |
| F | 8 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | US3850000 |
| 輸送番号（UN） | UN 2929 6.1/PG 2 |
| 税関コード | 29333999 |
| 危険文句（R） | 10-24/25-36/37/38-23/24/25-20/21/22 |
| 消防法 | 危-4-2-III |
| 危険表示 | T,Xn,F |
| hazard_note | Toxic |
| 安全措置（S） | 16-36/37-45-38-36/37/39-28A-26 |
| 危険等級 | 6.1Acute Tox. 2 DermalAcute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 包装等級 | II |
| 貯蔵分類 | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
用途
用途
有機合成原料。
使用
2-Bromopyridine is a 2-halogenated pyridine used in the preparation of a variety of biologically active compounds such as antimalarial agents and beta-adrenoceptor agonist.
製法・合成法
製造方法
2-Bromopyridine is synthesized from 2-aminopyridine by bromination. In industrial production, hydrobromic acid (over 48%) is first cooled to below 0°C, 2-aminopyridine is slowly added, and then liquid bromine is added dropwise in a salt bath under freezing, and the rate of addition is to control the reaction temperature below -5°C appropriate. After adding, add sodium nitrite aqueous solution dropwise, control the reaction temperature to be below 0°C, stir for 20-30min, dropwise add 50% sodium hydroxide solution, extract the reaction solution with ether, wash with water, dry with anhydrous sodium sulfate, filter, and recover Diethyl ether, the residue was distilled under reduced pressure, and the 88°C-94°C/3333Pa fraction was collected to obtain the finished product of 2-bromopyridine with a yield of 83.8%.
純化方法
Dry 2-bromopyridine over KOH for several days, then distil it from CaO under reduced pressure, and taking the middle fraction. [Beilstein 20/5 V 422.]