シクロヘキシルアミン
シクロヘキシルアミン · シクロヘキサン-1-アミン · ヘキサヒドロアニリン · アミノシクロヘキサン · シクロヘキサンアミン · 1-シクロヘキサンアミン · シクロヘキサン-1-イルアミン · CHA
識別子と物理属性
| CAS No. | 108-91-8 |
|---|---|
| 分子式 | C6H13N |
| 平均分子量 | 99.17 g/mol |
| 単同位体質量 | 99.10479942 g/mol |
| SMILES | NC1CCCCC1 |
| InChIKey | PAFZNILMFXTMIY-UHFFFAOYSA-N |
| PubChem CID | 7965 |
| ChEMBL | CHEMBL1794762 |
| ChEBI | CHEBI:15773 |
| EC No. | 203-629-0 |
| DTXSID | DTXSID1023996 |
| 現地名 | シクロヘキシルアミン |
化学・物理的性質
| XLogP | 1.5 |
|---|---|
| 極性表面積 | 26 |
| 水素結合供与体数 | 1 |
| 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 -> Amines, CyclicCorrosives |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| 化粧品 | AnticorrosiveBuffering |
| pH | STRONG BASE11.5 (100g/l, H2O, 20℃) |
| SpringerMaterials Properties | Boiling point |
| 農薬 | Pesticide -> EPA IRIS |
| LogP（分配係数） | log Kow = 1.49 |
| 臭い | Strong, fishy, amine odor.強い生臭さ |
| 食品添加物 | BOILER WATER ADDITIVE -> FDA Substance added to food |
| 密度 | 0.8647 at 77 °F (EPA, 1998) - Less dense than waterwill float0.8647 @ 25 °C/25 °CRelative density (water = 1): 0.860.870.8647 @25 °C0.867 g/mL at 25 °C(lit.) |
| Viscosity | 2.10 Pa*s at 20 °C |
| Color/Form | Colorless or yellow liquid. |
| 融点 | -17 °C |
| 沸点 | 134 °C(lit.) |
| 蒸気密度 | 3.42 (vs air) |
| 蒸気圧 | 10 mm Hg ( 22 °C) |
| 屈折率 | n20/D 1.459(lit.) |
| 引火点 | 90 °F |
| 貯蔵条件 | Store below +30°C. |
| 溶解度 | 有機溶剤: 混和性 |
| pKa（酸解離定数） | 10.66(at 24℃) |
| 外観・状態 | 液体 |
| 色 | クリア |
| 爆発限界 | 1.6-9.4%(V) |
| 凝固点 | -17.7℃ |
| Merck | 14,2729 |
| BRN | 471175 |
| ヘンリー定数 | 2.2×100 mol/(m3Pa) at 25℃, Brockbank (2013) |
| 誘電率 | 5.3(-21℃) |
| 化粧品成分の機能 | バッファリング防錆剤 |
| InChI | 1S/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2 |
| InChIKey | PAFZNILMFXTMIY-UHFFFAOYSA-N |
| SMILES | NC1CCCCC1 |
| LogP（分配係数） | 3.7 at 25℃ |
| CAS データベース | 108-91-8(CAS DataBase Reference) |
| NISTの化学物質情報 | Cyclohexanamine(108-91-8) |
| EPAの化学物質情報 | Cyclohexylamine (108-91-8) |
化学的特性
Cyclohexylamine is a colorless to yellow liquid (amines, primary aromatic). It has an unpleasant fishy odor. Flammable. It is infinitely miscible with water and conventional organic solvents. With water it forms an azeotrope that contains 44.2 % cyclohexylamine and boils at 96.4℃. Cyclohexylamine can be volatilized with water vapor. It can absorb carbon dioxide in the air and form a white crystalline carbonate. Aqueous solution is alkaline. 0.01% concentration of aqueous solution pH = 10.5. Its vapor and air to form an explosive mixture.
安全性と法規制
| GHS 分類 | DangerH226: Flammable liquid and vapor [Warning Flammable liquids]P203, P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P318, P321, P330, P362+P364, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)H226 (90.4%): Flammable liquid and vapor [Warning Flammable liquids]P203, P210, P233, P240, P241, P242, P243, P260, P262, P264, P264+P265, P270, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P318, P321, P330, P361+P364, P362+P364, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement) |
|---|---|
| 規制情報 | Chemical: CyclohexanamineCyclohexanamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexanamine 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: 24-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13348Cyclohexanamine: HSNO Approval: HSR001532 Approved with controlsThe 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.) |
| その他の安全情報 | IMAP assessments - Cyclohexanamine: Human health tier II assessment |
| 輸送ラベル（DOT） | Corrosive Flammable Liquid |
| 火災危険 | When heated to decomposition, it emits highly toxic fumes. Vapor may travel a considerable distance to source of ignition and flash back. Toxic oxides of nitrogen are produced during combustion. Nitric acidreacts vigorously with oxiding materials. Stable, avoid physical damage, storage with oxidizing material. (EPA, 1998)· Flammable/combustible material.Flammable. Above 28 °C explosive vapour/air mixtures may be formed. |
| 火災の可能性 | FLAMMABLE LIQUID...Dangerous fire hazard when exposed to heat, flame, or oxidizers. |
| 健康有害性 | This is classified as very toxic -- probable oral lethal dose is 50-500 mg/kg or between 1 teaspoon and 1 ounce for a 70 kg (150 lb.) person. It is considered a nerve poison. This is a weak methemoglobin-forming substance. (EPA, 1998) |
用途
解説
cyclohexanamine．C6H13N(99.18)．シクロヘキシルアミン は，アニリンの高温·高圧還元でつくる．アミン臭のある無色の液体．融点－17.7 ℃，沸点134.5 ℃．d204 0.867．n20D 1.459．水，有機溶媒に可溶．引火点32.2 ℃(開放)．強塩基性．殺虫剤，腐食防止剤，そのほかの化学合成原料として広く用いられる．工業的には有機溶媒，染料の原料として使われる。皮膚から吸収され，毒性を示す。LD50 710 mg/kg(ラット，経口)．森北出版「化学辞典（第2版）
用途
有機合成原料、合成甘味剤原料
用途
ゴム用薬品,清缶剤、染料,顔料,染色助剤、殺虫剤、不凍液、防錆剤
使用
Cyclohexylamine is used in the manufacture of a number of products, including plasticizers, drycleaning soaps, insecticides, and emulsifying agents. It is also used as a corrosion inhibitor and in organic synthesis.
一般的な説明
Cyclohexylamine appears as a clear colorless to yellow liquid with an odor of ammonia. Flash point 90 °F. Irritates the eyes and respiratory system. Skin contact may cause burns. Less dense than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion.
使用用途
シクロヘキシルアミンの主な使用用途は、清缶剤、防錆材、顔料や染料、ゴム用薬品、染色助剤、殺虫剤、不凍液などです。特に印刷インキ工業では、フラッシング助剤として用いられます。 また、シクロヘキシルアミンは有機合成化学的に有用な物質であるため、医薬品などの各種化合物の中間原料としての用途もあります。シクロヘキシルアミンを原料として合成される主な物質には、スルフェンアミド系加硫促進剤、除草剤であるヘキサジノン、 (油よりも粘度の高い半固体状の) 、人工甘味料であるチクロなどがあります。 医薬品では、粘液溶解薬・鎮痛剤・気管支拡張薬などの薬品の原料として用いられる場合が多いです。
製法・合成法
調製方法
Cyclohexylamine is produced by the reaction of ammonia and cyclohexanol at elevated temperature and pressure in the presence of a silica-alumina catalyst (SRI 1985). It is also prepared by a similar process of catalytic hydrogenation of aniline at elevated temperature and pressure. Fractionation of the product of this reaction yields CHA, aniline, and a high-boiling residue containing n-phenylcyclohexylamine and dicyclohexylamine (Carswell and Morrill 1937). In 1982, U.S. production was 4.54 metric tons and 739.3 metric tons were imported into the U.S. (SRI 1985).
純化方法
Dry the amine with CaCl2 or LiAlH4, then distil it from BaO, KOH or Na, under N2. Also purify it by conversion to the hydrochloride (which is crystallised several times from water), then liberation of the amine with alkali and fractional distillation under N2. The hydrochloride has m 205-207o (dioxane/EtOH). [Lycan et al. Org Synth Coll Vol II 319 1943, Beilstein 12 III 10, 12 IV 8.]