2-アミノビフェニル
2-アミノビフェニル · ビフェニル-2-アミン · 2-フェニルアニリン · o-アミノビフェニル · 2-アミノ-1,1'-ビフェニル · 1,1'-ビフェニル-2-アミン · [1,1'-ビフェニル]-2-アミン · o-フェニルアニリン
識別子と物理属性
| CAS No. | 90-41-5 |
|---|---|
| 分子式 | C12H11N |
| 平均分子量 | 169.22 g/mol |
| 単同位体質量 | 169.08914935 g/mol |
| SMILES | Nc1ccccc1-c1ccccc1 |
| InChIKey | TWBPWBPGNQWFSJ-UHFFFAOYSA-N |
| PubChem CID | 7015 |
| ChEMBL | CHEMBL296021 |
| ChEBI | CHEBI:232095 |
| EC No. | 201-990-9 |
| DTXSID | DTXSID3030189 |
| 現地名 | 2-アミノビフェニル |
化学・物理的性質
| XLogP | 2.8 |
|---|---|
| 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 | 1 |
| 重原子数 | 13 |
| 形式電荷 | 0 |
| 複雑度 | 149 |
| Polymers | Nitrogen Compounds -> Amines, Polyaromatic |
| SpringerMaterials Properties | Fusion temperature |
| LogP（分配係数） | log Kow = 2.84 @ pH 7 |
| Color/Form | Leaflets (dilute alcohol)Colorless or purplish crystals |
| 溶解度 | less than 0.1 mg/mL at 70 °F (NTP, 1992)Sol in ethanol, ether, benzeneslightly sol in dimethylsulfoxide, petroleum etherInsol in waterクロロホルム（微量）、酢酸エチル（微量）、メタノール（微量）<0.01 g/100 mL で 21 ºC |
| 引火点 | greater than 235 °F (NTP, 1992)Flash point > 113 °C>230 °F |
| 沸点 | 570 °F at 760 mmHg (NTP, 1992)299 °C299 °C(lit.) |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitrogen oxide/. |
| 融点 | 122 to 127 °F (NTP, 1992)51 °C47-50 °C(lit.) |
| 蒸気密度 | 5.8 (NTP, 1992) - Heavier than airwill sink (Relative to Air)5.8 (AIR= 1)5.9 (vs air) |
| 蒸気圧 | 0.000117 [mmHg]1.2X10-4 mm Hg @ 25 °C /Estimated/2 mm Hg ( 140 °C) |
| ヘンリー定数 | Henry's Law constant = 1.5X10-7 atm-m cu/mol @ 25 °C /Estimated/ |
| 密度 | 1.44 |
| 屈折率 | 1.613-1.615 |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 結晶または結晶性粉末 |
| pKa（酸解離定数） | 3.82(at 22℃) |
| 色 | 紫から茶色 |
| BRN | 471874 |
| ヘンリー定数 | 6.6×101 mol/(m3Pa) at 25℃, HSDB (2015) |
| 安定性 | 安定。強力な酸化剤とは相容れない。 |
| InChI | 1S/C12H11N/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9H,13H2 |
| InChIKey | TWBPWBPGNQWFSJ-UHFFFAOYSA-N |
| SMILES | Nc1c(cccc1)c2ccccc2 |
| LogP（分配係数） | 2.84 |
| CAS データベース | 90-41-5(CAS DataBase Reference) |
| NISTの化学物質情報 | [1,1'-Biphenyl]-2-amine(90-41-5) |
| EPAの化学物質情報 | 2-Biphenylamine (90-41-5) |
化学的特性
colourless to purple crystalline solid. Soluble in alcohol, ether and benzene, insoluble in water. Can be volatilized with water vapor. Flash point >110℃.
安全性と法規制
| GHS 分類 | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P273, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 規制情報 | Status: Cease Manufacture Update: 30-05-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/177062-Phenylaniline: Does not have an individual approval but may be used under an appropriate group standard |
| 火災危険 | This chemical is probably combustible. (NTP, 1992) |
| 健康有害性 | SYMPTOMS: Symptoms of exposure to this compound may include irritation. |
| 有害性の概要 | Emergency treatment: Methemoglobinemia[HSDB] May cause irritation[CAMEO] Effects in high-dose animal studies include respiratory depression, coma, hemorrhage, and changes in bone marrow, spleen, and renal tubules[RTECS] Harmful if ingestedSuspected carcinogen[Aldrich MSDS] See Biphenyl. See 4-Aminodiphenyl. |
| 反応性グループ | Amines, Aromatic |
| Special Reports | DHHS/NTPCarcinogenesis Bioassay of 2-Biphenylamine Hydrochloride in F344/N Rats and B6C3F1 Mice (Feed Study) Technical Report Series No. 233 (1982) NIH Publication No. 83-1789 |
| Reactivity Profile | 2-AMINOBIPHENYL neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. |
| Air and Water Reactions | Insoluble in water. |
| NFPA Hazard Classification | 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur. |
用途
用途
カルボニル化合物の蛍光定量試薬、有機合成原料。
説明
2-Aminobiphenyl (2-APB) is an organic compound with the formula C6H5C6H4NH2. It is an amine derivative of biphenyl. It is a colorless solid, although aged samples can appear colored even black. Palladacycles obtained from 2-aminobiphenyl are popular catalysts for cross-coupling.
使用
2-Aminobiphenyl has a mutagenic potency. It is a substrate for UGTs (UDP-glucuronosyltransferases), including UGT1A4, UGT2B13 and UGT2B16.
一般的な説明
2-aminobiphenyl appears as colorless or purplish crystals. (NTP, 1992)
製法・合成法
製造方法
2-Aminodiphenyl is prepared by hydrogenation of 2-nitrobiphenyl.NEW SYNTHESIS OF 2-AMINOBIPHENYLSReflux 2-nitrobiphenyl, ethanol and stannous chloride in a water bath for 3h, recover the ethanol, cool the residue, add 40% liquid alkali to make it strongly alkaline, separate the oil layer, extract the aqueous layer with ether, dry the extract with anhydrous calcium chloride, filter and recover the ether, wash with ethanol to obtain the crude product, then distill the crude product under reduced pressure to obtain 2-aminobiphenyl.
純化方法
Crystallise it from aqueous EtOH (charcoal). [Beilstein 12 IV 3223.]