2-ピコリン
2-ピコリン · 2-メチルピリジン · α-メチルピリジン · α-ピコリン · 2メチルピリジン · 2-ピコリン(α-〃) · Α‐ピコリン · Α-ピコリン(2-)

識別子と物理属性
| CAS No. | 109-06-8 |
|---|---|
| 分子式 | C6H7N |
| 平均分子量 | 93.13 g/mol |
| 単同位体質量 | 93.05784922 g/mol |
| SMILES | Cc1ccccn1 |
| InChIKey | BSKHPKMHTQYZBB-UHFFFAOYSA-N |
| PubChem CID | 7975 |
| ChEMBL | CHEMBL15732 |
| ChEBI | CHEBI:50415 |
| EC No. | 203-643-7 |
| DTXSID | DTXSID9021899 |
| 現地名 | 2-ピコリン |
化学・物理的性質
| XLogP | 1.1 |
|---|---|
| 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 | 52.1 |
| 物質分類 | Nitrogen Compounds -> PyridinesFlammable agents - 2nd degreeFlammable agents - 3rd degree |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| pH | /SRP/: Weak base8.5 (100g/l, H2O, 20℃) |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| LogP(分配係数) | log Kow = 1.11 |
| 臭い | Strong unpleasant odor不快 |
| 密度 | 0.944 at 68 °F (USCG, 1999) - Less dense than waterwill float0.9443 at 20 °C/4 °CRelative density (water = 1): 0.950.950 @ 15°C0.942-0.946 at 20 °C 0.943 g/mL at 25 °C (lit.) |
| 香味料 | EU Flavoring substances |
| Color/Form | Colorless liquid |
| 溶解度 | greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)Miscible in water at 20 °CVery sol in acetoneMiscible with alcohol, etherSolubility in water: miscibleH2O: 自由に溶ける混和性 |
| 引火点 | 97 °F (NTP, 1992)26 °C102 °F (39 °C)(Open cup)26 °C c.c.79 °F |
| 沸点 | 262 to 264 °F at 760 mmHg (NTP, 1992)129.4 °C128-129 °C129 °C @760 [mm Hg]128-129 °C (lit.) |
| 融点 | -70 °C (lit.) |
| 蒸気密度 | 3.2 (vs air) |
| 蒸気圧 | 10 mm Hg ( 24.4 °C) |
| 屈折率 | n20/D 1.500(lit.) |
| 貯蔵条件 | Store below +30°C. |
| pKa(酸解離定数) | 5.97(at 20℃) |
| 外観・状態 | 液体 |
| 色 | 澄んだ薄黄色 |
| においのタイプ | 湿った |
| 爆発限界 | 1.4-8.6%(V) |
| 比熱容量 | Cp(liquid): 1.7 J/(g·K), at 25℃ |
| Merck | 14,7400 |
| BRN | 104581 |
| ヘンリー定数 | 9.8×10-1 mol/(m3Pa) at 25℃, Brockbank (2013) |
| 誘電率 | 9.8000000000000007 |
| 安定性 | 安定。可燃性。強酸化剤、硫酸、酸、金属、硫酸鉄(II)、過酸化水素とは相容れない。吸湿性。 |
| InChI | 1S/C6H7N/c1-6-4-2-3-5-7-6/h2-5H,1H3 |
| InChIKey | BSKHPKMHTQYZBB-UHFFFAOYSA-N |
| SMILES | Cc1ccccn1 |
| LogP(分配係数) | 1.11 at 20℃ |
| CAS データベース | 109-06-8(CAS DataBase Reference) |
| NISTの化学物質情報 | Pyridine, 2-methyl-(109-06-8) |
| EPAの化学物質情報 | 2-Methylpyridine (109-06-8) |
化学的特性
colourless to yellow liquid with an unpleasant smell
安全性と法規制
| GHS 分類 | WarningH226: Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P317, P319, P321, P330, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 2.7% (11 of 409) of reports.DangerH226 (97.3%): Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| 規制情報 | Chemical: Pyridine, 2-methyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Pyridine, 2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pyridine, 2-methyl- 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: 17-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/176852-Methylpyridine: Does not have an individual approval but may be used under an appropriate group standardThe 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) | Flammable Liquid |
| 火災危険 | Special Hazards of Combustion Products: When heated to decompo- sition, emits toxic fumes of cyanide.Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 26 °C explosive vapour/air mixtures may be formed. |
| 火災の可能性 | Moderate fire riskFlammable liquid when exposed to heat or flame. |
| 健康有害性 | INHALATION, INGESTION OR SKIN ABSORPTION: Narcosis, headache, nausea, giddiness, vomiting. EYES: Severe irritation. SKIN: Causes burns. INGESTION: Irritation and gastric upset. (USCG, 1999) |
| 有害性の概要 | May cause first degree burns after short exposure and second degree burns after longer contactLiver and kidney injury after chronic exposure have been reported. [CHRIS] See Pyridine.A corrosive substance that can cause injury to the skin, eyes, and respiratory tract |
用途
用途
溶剤、合成樹脂、消毒剤、加硫促進剤原料。
用途
USED IN MANUF, OF 2-VINYLPYRIDINE AND KYC84-K AND PHARMACEUTICALS.溶剤、合成樹脂。溶媒の他、染料、樹脂工業の原料として使われる。
天然物の起源
2-Methylpyridine is released in atmospheric emissions from coal during processing into tar, pitch and coke (Windholz et al 1983; Naizer and Mashek 1974). It is also a byproduct of coal gasification and liquefaction processes (Pellizzori et al 1979; Stuermer et al 1982) and oil shale retorting (Pellizzari et al 1979). It is present in coal and is released in stack emissions (Opresko 1982). 2-Methylpyridine has been identified in effluences from the following industries: timber products, organic chemicals, pharmaceuticals and public waste treatment facilities (Schackleford and Cline 1983). 2-Methylpyridine also is a constituent of tobacco smoke (Brunneman 1978).2-Methylpyridine is biodegradable. A 1 mM solution of 2-methylpyridine exposed in soil microorganism was completely degraded in 14-33 d under aerobic conditions, but not degraded after 97 d in anaerobic conditions (Naik et al 1972).
使用
2-Picoline is used as an intermediate in agrochemicals and pharmaceuticals. It serves as a solvent as well as to prepare dyes and resins. It finds application as a constituent in cigarette smoke, bone oil, coal tar and coke oven emissions. Further, it acts as a precursor of 2-vinylpyridine, picolinic acid and nitrapyrin. It is also employed to study the electron and proton transfer reactions of lumiflavin. In addition, it is used in the synthetic pathway for the preparation of dearomatized, allylated and carbon-hydrogen bond activated pyridine derivatives.
一般的な説明
Colorless liquid with a strong, unpleasant odor. Floats on water. Poisonous vapor is produced.
製法・合成法
調製方法
2-Methylpyridine is synthesized by distillation of coal tar or bone oil or by vapor phase reaction of acetaldehyde and ammonia in a 3:1 ratio followed by isolation of 2-methylpyridine from the reaction mixture (Considine 1974). It also can be synthesized from cyclohexylamine with excess ammonia and ZnCl2 at 350°C, resulting in a 40-50% yield; or prepared from ethylene-mercuric acetate adduct with ammonia water with a 70% yield (Windholz et al 1983). Production in 1977 probably exceeded one million pounds (Opresko 1982).
純化方法
Biddiscombe and Handley [J Chem Soc 1957 1954] steam distilled a boiling solution of the base in 1.2 equivalents of 20% H2SO4 until about 10% of the base had been carried over, along with non-basic impurities. Excess aqueous NaOH is then added to the residue, the free base is separated, dried with solid NaOH and fractionally distilled. 2-Methylpyridine can also be dried with BaO, CaO, CaH2, LiAlH4, sodium or Linde type 5A molecular sieves. An alternative purification is via the ZnCl2 adduct, which is formed by adding 2-methylpyridine (90mL) to a solution of anhydrous ZnCl2 (168g) and 42mL conc HCl in absolute EtOH (200mL). Crystals of the complex are filtered off, recrystallised twice from absolute EtOH (to give m 118.5-119.5o), and the free base is liberated by addition of excess aqueous NaOH. It is steam distilled, and solid NaOH is added to the distillate to form two layers, the upper one of which is then dried with KOH pellets, stored for several days with BaO and fractionally distilled. Instead of ZnCl2, HgCl2 (430g in 2.4L of hot water) can be used. The complex, which separates on cooling, can be dried at 110o and recrystallised from 1% HCl (to m 156-157o). The hydrochloride has m 78-79o, and the picrate has m 165.5o(from EtOH) and 180o(from H2O). [Beilstein 20 III/IV 2679, 20/5 V 464.]