1,1-ジフェニルヒドラジン
1,1-ジフェニルヒドラジン · unsym-ジフェニルヒドラジン · α,α-ジフェニルヒドラジン · 1，1ジフェニルヒドラジン · Ai3-23023 · Ccris 4562 · Brn 0957349 · hydrozobenzene
識別子と物理属性
| CAS No. | 530-50-7 |
|---|---|
| 分子式 | C12H12N2 |
| 平均分子量 | 184.24 g/mol |
| 単同位体質量 | 184.10004838 g/mol |
| SMILES | NN(c1ccccc1)c1ccccc1 |
| InChIKey | YHYKLKNNBYLTQY-UHFFFAOYSA-N |
| PubChem CID | 10739 |
| ChEMBL | CHEMBL3301770 |
| EC No. | 208-483-1 |
| DTXSID | DTXSID3043869 |
| 現地名 | 1,1-ジフェニルヒドラジン |
化学・物理的性質
| XLogP | 2.8 |
|---|---|
| 極性表面積 | 29.3 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 2 |
| 重原子数 | 14 |
| 形式電荷 | 0 |
| 複雑度 | 140 |
| 物質分類 | Nitrogen Compounds -> Hydrazines |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| LogP（分配係数） | log Kow = 2.80 |
| 密度 | 1.190 at 16 °C/4 °C1,12 g/cm3 |
| Color/Form | Yellow crystals |
| 溶解度 | SOL IN CONCN SULFURIC ACIDSLIGHTLY SOL IN WATERVery soluble in benzene, ether, ethanol, and chloroform. |
| 沸点 | 220 °C at 40 mm Hg308.2°C (rough estimate) |
| 融点 | 34.5 °Calso stated as 44 °C50.5°C |
| 蒸気圧 | 0.00049 [mmHg]4.9X10-4 mm Hg at 25 °C |
| Heat of Vaporization | 15,940.4 gcal/gmole |
| ヘンリー定数 | Henry's Law constant: 4.1X10-8 atm-cu m/mol at 25 °C /Estimated/ |
| Physical Description | Yellow solid[Merck Index] Liquid[MSDSonline] |
| 屈折率 | 1.6266 (estimate) |
| pKa（酸解離定数） | 3.34±0.10(Predicted) |
| 外観・状態 | powder to lump to clear liquid |
| 色 | White or Colorles to Yellow to Orange |
| Merck | 14,3325 |
| ヘンリー定数 | 2.4×102 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C12H12N2/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,13H2 |
| InChIKey | YHYKLKNNBYLTQY-UHFFFAOYSA-N |
| SMILES | NN(c1ccccc1)c2ccccc2 |
| CAS データベース | 530-50-7(CAS DataBase Reference) |
| EPAの化学物質情報 | 1,1-Diphenylhydrazine (530-50-7) |
安全性と法規制
| GHS 分類 | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 有害性の概要 | Emergency treatment: HydrazinesHydrazines can cause severe eye damage. They can cause seizures, liver injury, hemolysis, and delayed pulmonary edema. [HSDB] May cause irritation[MSDSonline] See Hydrazine. See 1,1-Diphenylhydrazine hydrochloride. |
| TSCA 要件 | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Hydrazine, 1,1-diphenyl- is included on this list. |
| 清浄水法要件 | For the maximum protection of human health from the potential carcinogenic effects of exposure to diphenylhydrazine through ingestion of contaminated water and contaminated aquatic organisms ... the levels which may result in incremented increase of cancer risk over the lifetime are estimated at 1x10-5, 1x10-6, and 1x10-7 the corresponding criteria are: 422 ng/l, 42 ng/l, and 4.2 ng/l respectively. If these estimates are made for consumption of aquatic organisms only, excluding consumption of water, the levels are 5.6 ug/l, 0.56 ug/l, and 0.056 ug/l, respectively. /Diphenylhydrazine/Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Diphenylhydrazine/ |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Explosive Limits and Potential | Interaction, in presence of diluent below 0 °C, with 1,2-diphenylhydrazine caused separation of explosive solids. |
| Skin, Eye, and Respiratory Irritations | Moderate to high concentrations of hydrazine vapors are highly irritating to the eyes, nose and respiratory system. Skin irritation is pronounced with the propellant hydrazines ... /Hydrazine and derivatives/ |
用途
説明
Diphenylhydrazine is a man-made chemical that occurs in two isomeric forms: 1,1-diphenylhydrazine and 1,2-diphenylhdrazine. Diphenylhydrazine is produced by the reduction of nitrobenzene. Little or no information is available for 1,1-diphenylhydrazine. Most toxicological and use data pertain to 1,2-diphenylhydrazine.
使用
Previously, 1,2-diphenylhydrazine was used for producing benzidine that was used in the synthesis of benzidine-based dyes. However, these dyes are no longer produced in the United States. The primary use of 1,2-diphenylhydrazine is in the production of the anti-inflammatory agent phenylbutazone and sulfinpyrazone, a uricosuric agent.
一般的な説明
Yellow crystals. Insoluble in water.
製法・合成法
純化方法
Purify it via the hydrochloride [530-47-2], which has m 165-170o(dec) after crystallization from aqueous EtOH (+ a few drops of HCl) and recover the free base with aqueous NaOH, extract it into Et2O, dry it (KOH), filter, evaporate and distil the residue under a vacuum. The distillate crystallises on cooling. The benzoyl derivative has m 194o (from Me2CO), and the 4-nitrophenyl hydrazone (with the aldehyde) has m 131-132o. [Koga & Anselme J Org Chem 33 3963 1968, Beilstein 15 IV 55.]