4-ピコリン
4-ピコリン · 4-メチルピリジン · γ-ピコリン · γピコリン · ４メチルピリジン · 4-ピコリン(γ-〃) · Γ‐ピコリン · Γ-ピコリン(4-)
識別子と物理属性
| CAS No. | 108-89-4 |
|---|---|
| 分子式 | C6H7N |
| 平均分子量 | 93.13 g/mol |
| 単同位体質量 | 93.05784922 g/mol |
| SMILES | Cc1ccncc1 |
| InChIKey | FKNQCJSGGFJEIZ-UHFFFAOYSA-N |
| PubChem CID | 7963 |
| ChEMBL | CHEMBL15544 |
| ChEBI | CHEBI:32547 |
| EC No. | 203-626-4 |
| DTXSID | DTXSID4021892 |
| 現地名 | 4-ピコリン |
化学・物理的性質
| XLogP | 1.2 |
|---|---|
| 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 | 46.1 |
| 物質分類 | Nitrogen Compounds -> Pyridines |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| LogP（分配係数） | log Kow = 1.22 |
| 臭い | Obnoxious, sweetish odor不快、甘い |
| 密度 | 0.9548 at 68 °F (NTP, 1992) - Less dense than waterwill float0.9548 g/cu cm at 20 °CRelative density (water = 1): 0.960.957 g/mL at 25 °C (lit.) |
| 香味料 | EU Flavoring substances |
| Color/Form | Colorless liquid |
| 溶解度 | Miscible with water at 20 °CSoluble in alcohol, etherSoluble in acetone, carbon tetrachlorideSolubility in water: miscibleアルコール: 可溶(lit.)溶ける |
| 引火点 | 134 °F (NTP, 1992)57 °C134 °F (57 °C) (Open cup)39 °C (102 °F) (Closed cup)57 °C o.c. |
| 沸点 | 292.8 °F at 760 mmHg (NTP, 1992)145 °C at 760 mm Hg144-145 °C145 °C (lit.) |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitrogen oxides/. |
| 融点 | 38.5 °F (NTP, 1992)3.68 °C3.7 °C2.4 °C (lit.) |
| 蒸気密度 | 3.2 (vs air) |
| 蒸気圧 | 4 mm Hg ( 20 °C) |
| 屈折率 | n20/D 1.504(lit.) |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 液体 |
| pKa（酸解離定数） | 6.02(at 20℃) |
| 色 | クリアライトイエロー |
| 爆発限界 | 1.3-8.7%(V) |
| 比熱容量 | Cp(liquid): 1.71 J/(g·K), at 25℃ |
| Merck | 14,7402 |
| BRN | 104586 |
| ヘンリー定数 | 1.6×100 mol/(m3Pa) at 25℃, Brockbank (2013) |
| 誘電率 | 12.279999999999999 |
| InChI | 1S/C6H7N/c1-6-2-4-7-5-3-6/h2-5H,1H3 |
| InChIKey | FKNQCJSGGFJEIZ-UHFFFAOYSA-N |
| SMILES | Cc1ccncc1 |
| LogP（分配係数） | 1.22 at 25℃ |
| CAS データベース | 108-89-4(CAS DataBase Reference) |
| NISTの化学物質情報 | Pyridine, 4-methyl-(108-89-4) |
| EPAの化学物質情報 | 4-Methylpyridine (108-89-4) |
化学的特性
4-Methylpyridine is a Colorless to light yellow liquid with an obnoxious, sweetish odor. soluble in water, ethanol and ether.
安全性と法規制
| GHS 分類 | DangerH226: Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P317, 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)This chemical does not meet GHS hazard criteria for 8.2% (36 of 439) of reports.H226 (91.6%): Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| 規制情報 | Chemical: Pyridine, 4-methyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Pyridine, 4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pyridine, 4-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: 03-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/239054-Methylpyridine: Does not have an individual approval but may be used under an appropriate group standard |
| 輸送ラベル（DOT） | Flammable Liquid |
| 火災危険 | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 57 °C explosive vapour/air mixtures may be formed. |
| 火災の可能性 | Moderate fire risk. |
| 健康有害性 | ACUTE/CHRONIC HAZARDS: Moderate fire risk. (NTP, 1992) |
| 有害性の概要 | A corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation of high concentrations can cause unconsciousnessThe liquid defats the skin[ICSC] An irritantCan be absorbed through skin[MSDSonline] An irritant that can cause CNS depressionLiver changes occur in rats exposed to chronic high doses[AIHA] See Pyridine. |
| 反応性グループ | Amines, Phosphines, and Pyridines |
用途
解説
ピリジンに一つのメチル基が置換した化合物．2-メチルピリジン，3-メチルピリジンおよび4-メチルピリジンの3種の異性体があり，それぞれα-，β-およびγ-ピコリンとよばれる．
用途
溶媒、ニコチン酸の製造、 医薬品(イソニコチン酸ヒドラジド)、界面活性剤などの合成原料、溶剤、防水剤などの製造
用途
イソニコチン酸製造原料、医薬、樹脂、染料、加硫促進剤、溶剤などとして用いられる。
天然物の起源
4-Methylpyridine is released by energy-related processes. It is present in coal gassification wastewater (Pellizzari et al 1979), the environment of coke ovens (Naizer and Mashek 1974) and in waters from shale oil waste production (Dobson et al 1985; Hawthorne et al 1985; Leenheer et al 1982). It is also present in coal tar (HSDB, 1988), cigarette smoke (Brunneman et al 1978; IARC 1976) and pyroligneous liquids from woods (Yasuhara and Sugiwara 1987). Methods for the biological treatment of wastewaters containing 4-methylpyridine have been developed (Roubickova 1986) and its movement through (Leenheer and Stuber 1981) and degradation (Sims and Somners 1985) in soils examined.
使用
4-Methylpyridine is used to manufacture isonicotinic acid and derivatives, in waterproofing agents for fabric, and as a solvent for resins, pharmaceuticals, dyestuffs, rubber accelerators, and pesticides. It is also used as a catalyst and curing agent.
一般的な説明
4-methyl pyridine is a colorless moderately volatile liquid. (NTP, 1992)
製法・合成法
調製方法
Currently, 4-methylpyridine is produced by vapor-phase condensation of acetaldehyde and ammonia (3:1) with subsequent isolation of 4-methylpyridine from the reaction mixture. Reactants are exposed to dehydration-dehydrogenation catalysis such as lead oxide, copper oxide on alumina, thorium oxide, zinc oxide or cadmium oxide on silica-alumina, or cadmium fluoride on silica-magnesia at 400-500°C. This results in a 60% yield of 4-methylpyridine which is isolated by fractional distillation (USEPA 1982). Another production method involves the isolation from by-products of coking operations. The crude pyridine extracts come from noncondensable and condensable coke-oven gasses that have been dehydrated and separated by fractional distillation, but only 45% of 4-methylpyridine is obtained (USEPA 1982). 4-Methylpyridine also can be isolated from a dry distillation of bones or coal (Hawley 1977).
純化方法
It can be purified as for 2-methylpyridine. Biddescombe and Handley's method (above) for 3-methylpyridine is also applicable. Lidstone [J Chem Soc 242 1940] purified it via the oxalate (m 137-138o) by heating 100mL of 4-methylpyridine to 80o and adding slowly110g of anhydrous oxalic acid, followed by 150mL of boiling EtOH. After cooling and filtering, the precipitate is washed with a little EtOH, then recrystallised from EtOH, dissolved in the minimum quantity of water and distilled with excess 50% KOH. The distillate is dried with solid KOH and again distilled. Hydrocarbons can be removed from 4-methylpyridine by converting the latter to its hydrochloride, crystallising from EtOH/diethyl ether, regenerating the free base by adding alkali and distilling. As a final purification step, 4-methylpyridine can be fractionally crystallised by partial freezing to effect a separation from 3-methylpyridine. Contamination with 2,6-lutidine is detected by its strong absorption at 270nm. The hydrochloride has m 161o, and the picrate has m 167o(from Me2CO, EtOH or H2O). [Beilstein 20 III/IV 2732, 20/5 V 543.]