ジブチルアミン
ジブチルアミン · 1,1'-イミノビスブタン · N-ブチルブタン-1-アミン · N-ブチル-1-ブタンアミン · n-ジブチルアミン · ジ-N-ブチルアミン · N,N-ジ-N-ブチルアミン · ジ‐N‐ブチルアミン
識別子と物理属性
| CAS No. | 111-92-2 |
|---|---|
| 分子式 | C8H19N |
| 平均分子量 | 129.24 g/mol |
| 単同位体質量 | 129.15174961 g/mol |
| SMILES | CCCCNCCCC |
| InChIKey | JQVDAXLFBXTEQA-UHFFFAOYSA-N |
| PubChem CID | 8148 |
| ChEMBL | CHEMBL3184528 |
| EC No. | 203-921-8 |
| DTXSID | DTXSID7024952 |
| 現地名 | ジブチルアミン |
化学・物理的性質
| XLogP | 2.8 |
|---|---|
| 極性表面積 | 12 |
| 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 | 6 |
| 重原子数 | 9 |
| 形式電荷 | 0 |
| 複雑度 | 37.8 |
| 物質分類 | Nitrogen Compounds -> Amines, AliphaticCorrosives |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| 農薬 | Environmental transformation -> Pesticide transformation products (metabolite, successor) |
| LogP（分配係数） | log Kow= 2.832.68 |
| 臭い | AMMONIA-LIKE ODOR弱いアンモニア。 |
| 密度 | 0.759 at 68 °F (USCG, 1999) - Less dense than waterwill float0.7601 @ 20 °C/4 °CDensity (at 20 °C): 0.76 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.010.7613 @ 20°C0.767 g/mL at 25 °C(lit.) |
| Color/Form | LiquidColorless |
| 溶解度 | Soluble (NTP, 1992)Sol in alcoholVery sol in ether and ethanolsol in acetone3500 mg/l in water @ 25 °CSolubility in water, g/100ml: 0.35 (slightly soluble)水：20℃で可溶3.8g/L4.05g/L（25℃） |
| 引火点 | 125 °F (NTP, 1992)57 °C57 °C (open cup)51.6 °C (open cup)47 °C106 °F |
| 沸点 | 318 to 320 °F at 760 mmHg (NTP, 1992)159-160 °C159 °C159.6 °C @760 [mm Hg]159 °C(lit.) |
| Decomposition | When heated to decomp it emits toxic fumes of /nitrogen oxides/.Products of decomposition include carbon monoxide, carbon dioxide, hydrocarbons, & oxides of nitrogen as well as amine vapors. |
| 融点 | -76 to -74 °F (NTP, 1992)-60 to -59 °C-61.9 °C−62 °C(lit.) |
| 蒸気密度 | 4.46 (vs air) |
| 蒸気圧 | 1.9 mm Hg ( 20 °C) |
| 屈折率 | n20/D 1.417(lit.) |
| 貯蔵条件 | Store below +30°C. |
| pKa（酸解離定数） | 11.25(at 21℃) |
| 外観・状態 | 液体 |
| 色 | 白い |
| pH | 11.1 (1g/l, H2O, 20℃) |
| 爆発限界 | 0.6-6.8%(V) |
| 比熱容量 | Cp(liquid): 2.27 J/(g·K), at 25℃ |
| Merck | 14,3032 |
| BRN | 506001 |
| ヘンリー定数 | 1.3×10-1 mol/(m3Pa) at 25℃, Brockbank (2013) |
| 誘電率 | 3.0(20℃) |
| 安定性 | 安定。可燃性。強力な酸化剤、最も一般的な金属、強酸とは相容れない。空気と爆発性混合物を形成する可能性があります。 |
| InChI | 1S/C8H19N/c1-3-5-7-9-8-6-4-2/h9H,3-8H2,1-2H3 |
| InChIKey | JQVDAXLFBXTEQA-UHFFFAOYSA-N |
| SMILES | CCCCNCCCC |
| LogP（分配係数） | 2.1 at 23℃ |
| CAS データベース | 111-92-2(CAS DataBase Reference) |
| NISTの化学物質情報 | 1-Butanamine, N-butyl-(111-92-2) |
| EPAの化学物質情報 | Dibutylamine (111-92-2) |
化学的特性
Dibutylamine is a colorless liquid with an odor of ammonia.
安全性と法規制
| GHS 分類 | DangerH226: Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P361+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P361+P364, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement) |
|---|---|
| 規制情報 | Chemical: 1-Butanamine, N-butyl-1-Butanamine, N-butyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Butanamine, N-butyl- 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: 01-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/135271-Butanamine, N-butyl-: 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） | Corrosive Flammable Liquid |
| 火災危険 | Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fires. (USCG, 1999)· Flammable/combustible material.Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 47 °C explosive vapour/air mixtures may be formed. Risk of fire and explosion on contact with strong acids or strong oxidizing agents. |
| 火災の可能性 | FLAMMABLE LIQUID WHEN EXPOSED TO HEAT OR FLAME ... . |
| 健康有害性 | Inhalation causes irritation of nose, throat, and lungscoughingnauseaheadache. Ingestion causes irritation of mouth and stomach. Contact with eyes causes irritation. Contact with skin causes irritation and dermatitis. (USCG, 1999) |
用途
用途
界面活性剤?有機ゴム薬品(加硫促進剤)原料,腐食抑制剤 、農薬原料
用途
医薬品中間体、乳化剤
使用
Dibutylamine is a secondary dialkylamine. It is a versatile intermediate with a variety of applications.Dibutylamine is extensively used in palladium-catalyzed cross-coupling with aryl halides to synthesize arylamines, popularly known as Buchwald–Hartwig amination.It can be used in the oxone-mediated annulation of 2-aminobenzamides and 1,2-diaminobenzenes to synthesize 2,3-dihydroquinazolin-4(1H)-ones and 1H-benzimidazoles, respectively.It can also be used in the one-pot multicomponent reactions to synthesize tetra- and penta-substituted polyfunctional dihydropyrroles.Dibutylamine was employed as organocatalyst during the synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates via Knoevenagel, Pinner and phospha-Michael reactions. Di-n-butylamine (Dibutylamine) may be used to investigate the performance of a dry sampler, with an impregnated denuder in series with a glass fibre filter for airborne isocyanates. It was used in the preparation of 1M dibutylammonium phosphate buffer.
一般的な説明
Dibutylamine appears as a yellow-colored liquid with a amine-like odor. Denser than water. Very corrosive, may burn skin, eyes, and mucous membranes. Flash point 125 °F. Combustible. Produce toxic oxides of nitrogen when burned. Used to make other chemicals.
使用用途
ジブチルアミンは、ゴム薬品や腐食抑制剤、界面活性剤として、あるいは医薬品や農薬、染料、鉱物浮選剤、乳化剤の原料などに幅広く利用されています。 1. ゴム薬品 ゴムのにおいて、加硫促進剤として添加されています。原料ゴムに高い弾性を与えるために、硫黄を添加して分子同士を結合させることを加硫と言います。加硫時に加硫促進剤を添加することにより、良質なゴム製品を短時間で安く生産することが可能です。 2. 腐食抑制剤 腐食抑制剤とは、少量の添加により、金属の腐食を著しく防止できる無機または有機薬品です。アミン系の腐食抑制剤は、容易に発生するアンモニウムイオンが金属表面のマイナスに電化した部分を覆い皮膜を形成することで、酸性溶液からの金属の腐食を防止します。
製法・合成法
調製方法
n-Dibutylamine is prepared by two major methods. The first involves passing ammonia and butanol over an alumina or silica catalyst at a temperature of 300-500°C and under pressure. The second method employs passing ammonia, butanol, and hydrogen over a dehydrogenation catalyst. In each instance the resulting mixtures are separated by continuous distillation and extraction (Schweizer et al 1978). n-Dibutylamine can also be prepared from butyl bromide and ammonia or by reaction of butyl chloride and ammonia (HSDB 1989). The amine also is naturally present in food (Neurath et al 1977) and its emissions are produced in soil and sewage. The amine is also found in the expired air of normal, healthy, nonsmoking adults (Krotoszynski et al 1979). N-Nitrosamines and their precursors including n-dibutylamine are present in rubber products in which the accelerators and stabilizers used in the vulcanization process were derived from dialkylamines. Analysis of a single extraction of rubber nipples and baby pacifiers with artificial saliva (containing sodium nitrite) showed n-dibutylamine levels up to 3890 p.p.b. and N-nitrosodibutylamine concentrations as high as 427 p.p.b. (Thompson et al 1984).
純化方法
Dry this strong base with LiAlH4, CaH2 or KOH pellets, filter and distil it from BaO or CaH2. [Beilstein 4 IV 550.]