DL-2-メチル-1-ブタノール (合成)
DL-2-メチル-1-ブタノール (合成) · 2-メチル-1-ブタノール · 活性アミルアルコール · 2-メチルブタン-1-オール · 2-メチルブチルアルコール · sec-ブチルカルビノール · 光学活性アミルアルコール · 2-メチルブタノール
識別子と物理属性
| CAS No. | 137-32-6 |
|---|---|
| 分子式 | C5H12O |
| 平均分子量 | 88.15 g/mol |
| 単同位体質量 | 88.088815 g/mol |
| SMILES | CCC(C)CO |
| InChIKey | QPRQEDXDYOZYLA-UHFFFAOYSA-N |
| PubChem CID | 8723 |
| ChEMBL | CHEMBL451923 |
| ChEBI | CHEBI:48945 |
| EC No. | 205-289-9 |
| DTXSID | DTXSID5027069 |
| 現地名 | DL-2-メチル-1-ブタノール (合成) |
化学・物理的性質
| XLogP | 1.2 |
|---|---|
| 極性表面積 | 20.2 |
| 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 | 2 |
| 重原子数 | 6 |
| 形式電荷 | 0 |
| 複雑度 | 27.1 |
| 脂質 | Fatty Acyls [FA] -> Fatty alcohols [FA05] |
| Solvents | Solvents -> Alcohols (<C12) |
| 香料 | Fragrance Ingredient (2-Methylbutanol) -> IFRA transparency List |
| LogP（分配係数） | log Kow= 1.29 (measured)1.2901.3/1.4 |
| 食品添加物 | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 密度 | 0.816 @ 20 °C/4 °CRelative density (water = 1): 0.80.815-0.8200.819 g/mL at 20 °C(lit.) |
| 香味料 | EU Flavoring substances |
| Color/Form | COLORLESS LIQ |
| 溶解度 | MISCIBLE WITH ALC & ETHERSol in acetoneWater solubility: 30,000 mg/l : 25 °CSolubility in water, g/100ml at 25 °C: 3.0 (moderate)Very slightly soluble in water50% soluble in heptane, triacetinsoluble (in ethanol)水: わずかに溶ける3.6g/a00g at 30°C3.6g/100mL(30℃) |
| 引火点 | 50 °C122 °F (50 °C) (OPEN CUP)50 °C o.c.110 °F |
| 沸点 | 128 °C @ 760 MM HG128.00 to 130.00 °C. @ 760.00 mm Hg130 °C130 °C mm Hg(lit.) |
| 融点 | FREEZING POINT: LESS THAN -70 °C−70 °C(lit.) |
| 比旋光度 | -0.1~+0.1°(20℃/D)(neat) |
| 蒸気密度 | 3 (vs air) |
| 蒸気圧 | 3 mm Hg ( 20 °C) |
| 屈折率 | n20/D 1.411 |
| FEMA | 3998 | (+/-)-2-METHYL-1-BUTANOL |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 液体 |
| pKa（酸解離定数） | 15.24±0.10(Predicted) |
| 色 | 無色透明～ごくわずかに黄色 |
| pH | 7 (H2O) |
| 臭い | 100.00%で。エーテル的なフーゼル アルコール性 脂肪分が多い 脂っこい ワインっぽい ウィスキー 革っぽい ココア |
| においのタイプ | エーテル的な |
| 由来生物 | synthetic |
| 爆発限界 | 1.2-10.3%(V) |
| Merck | 14,6030 |
| JECFA Number | 1199 |
| BRN | 1718810 |
| ヘンリー定数 | 7.6×10-1 mol/(m3Pa) at 25℃, Brockbank (2013) |
| 主な用途 | フレーバーそして香料 |
| 化粧品成分の機能 | 香料 |
| InChI | 1S/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3 |
| InChIKey | QPRQEDXDYOZYLA-UHFFFAOYSA-N |
| SMILES | CCC(C)CO |
| LogP（分配係数） | 1.22 |
| 表面張力 | 24.09mN/m at 293.15K |
| CAS データベース | 137-32-6(CAS DataBase Reference) |
| NISTの化学物質情報 | 1-Butanol, 2-methyl-(137-32-6) |
| EPAの化学物質情報 | 2-Methyl-1-butanol (137-32-6) |
化学的特性
(+/–)2-Methyl-1-butanol has a cooked, roasted aroma with fruity or alcoholic undernotes.
安全性と法規制
| GHS 分類 | DangerH226 (36.3%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2020 reports by companies from 32 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H226 (100%): Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| 規制情報 | Chemical: 1-Butanol, 2-methyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)1-Butanol, 2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Butanol, 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: 15-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/120402-Methyl-1-butanol: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| 火災危険 | Flammable. Above 50 °C explosive vapour/air mixtures may be formed. |
| 有害性の概要 | A skin, eye, and respiratory tract irritantMay cause CNS effectsSwallowing the liquid may cause aspiration into the lungs with the risk of chemical pneumonitis. The liquid defats the skin. [ICSC] Safe when used as a flavoring agent[JECFA] In oral lethal dose studies, animals have ataxia and prostration[OECD SIDS] An irritantEffects in high-dose animal studies include spastic paralysis with/without sensory change[MSDSonline]The major hazards encountered in the use and handling of 2-methyl-1-butanol stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal absorption), exposure to this colorless liquid may occur from its use as a solvent, as a frothing agent in ore flotation, in lubricants, plasticizers, oils, and paints, and as a chemical intermediate for diamyldithiophosphates, 2-methyl-1-butylamine, esters, and ethers. Effects from exposure may include irritation of the eyes, skin, and mucous membranes, headache, dizziness, giddiness, nausea, cardiac arrhythmias, or pulmonary edema. In activities and situations where over-exposure may occur, wear a self-contained breathing apparatus. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. This substance must be moderately heated before ignition will occur. If this substance should be involved in a fire, use water to cool the material to below its flash point. |
用途
用途
光学活性アミルグループ導入のため有機合成に使われる。スズメバチやカリバチ、クロスズメバチの誘引剤。果物やワインに含まれる天然アルコールで、ウイスキー様、ワイン様、たまねぎ様の芳香を持ち、加工食品の香料に利用される。
天然物の起源
Reportedly present in over 120 natural food products, including apple, apricot, banana, orange, bilberry, black currant, cranberry, papaya, strawberry, tomato and alcoholic beverages
使用
2-Methyl-1-butanol is a whiskey-scented amyl alcohol that is naturally present in all fruits wine and beer. 2-Methyl-1-butanol is commercially used as a solvent in paints and oils and as flavorant in many processed foods. 2-Methyl-1-butanol has a characteristic redolence, which is thought to account for its active properties as an attractant for hornets and certain wasps, such as yellowjackets, in traps. As a biochemical active ingredient, it has a non-toxic mode of action – targeted pests are killed through physical entrapment.
一般的な説明
S-(-)-2-Methyl-1-butanol is a precursor for the synthesis of chiral liquid crystals. It is a potential new-biofuel.
製法・合成法
調製方法
2-methyl-1-butanol are refined from ethanol production as fusel oil. Isoamyl alcohols are used as solvents for oils, fats, resins, and waxes; in the plastics industry in spinning polyacrylonitrile; and in manufacturing lacquers, chemicals, and pharmaceuticals.
製造方法
Prepared from hydroboration of 2-methyl-1-butene. (–)2-Methyl-1-butanol is isolated by fractional distillation of fusel oil
純化方法
Reflux the butanol with CaO, distil, reflux with magnesium and again fractionally distil it. A small sample of highly purified material is obtained by fractional crystallisation after conversion into a suitable ester such as the trinitrophthalate or the 3-nitrophthalate. The latter is converted to the cinchonine salt in acetone and recrystallised from CHCl3 by adding pentane. The salt is saponified, extracted with ether, and fractionally distilled. [Terry et al. J Chem Eng Data 5 403 1960, Beilstein 1 IV 1666.]