ベンジジン
ベンジジン · ベンジジンおよび/またはその誘導体類 · ベンジジンおよびその塩類 · ベンジジン及びその塩 · 4,4′‐ベンジジン標準液 · ベンジジン 溶液 · 4,4′-ビ[アニリン] · [1,1'-ビフェニル]-4,4'-ジアミン

識別子と物理属性
| CAS No. | 92-87-5 |
|---|---|
| 分子式 | C12H12N2 |
| 平均分子量 | 184.24 g/mol |
| 単同位体質量 | 184.10004838 g/mol |
| SMILES | Nc1ccc(-c2ccc(N)cc2)cc1 |
| InChIKey | HFACYLZERDEVSX-UHFFFAOYSA-N |
| PubChem CID | 7111 |
| ChEMBL | CHEMBL15901 |
| ChEBI | CHEBI:80495 |
| EC No. | 202-199-1 |
| DTXSID | DTXSID2020137 |
| 現地名 | ベンジジン |
化学・物理的性質
| XLogP | 1.3 |
|---|---|
| 極性表面積 | 52 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 14 |
| 形式電荷 | 0 |
| 複雑度 | 145 |
| 物質分類 | Hazardous Air Pollutants (HAPs)Nitrogen Compounds -> Benzidine and DerivativesCarcinogensSemi-Volatile Organic Compound (SVOC) |
| SpringerMaterials Properties | Chemical structure |
| 農薬 | Pesticide -> EPA IRIS |
| LogP(分配係数) | log Kow= 1.341.53 |
| 密度 | 2.15 at 68 °F (USCG, 1999) - Denser than waterwill sink1.250 @ 20 °C/4 °C1.3 g/cm³1.25 @ 20°C |
| Color/Form | White or slightly-reddish, crystalline powderGrayish-yellow, reddish-gray, or white crystalline powder [Note: Darkens on exposure to air and light]. |
| 溶解度 | less than 1 mg/mL at 72 °F (NTP, 1992)1 g dissolves in 2500 ml cold water1 g dissolves in 107 ml boiling water1 g dissolves in 5 ml boiling alcohol1 g dissolves in 50 ml etherIn water, 322 mg/l @ 25 °C0.322 mg/mL at 25 °CSolubility in water, g/100ml at 25 °C:(54 °F): 0.04%エタノール (USEPA, 1985) およびエーテル (1g/50mL) (Windholz et al., 1983) に可溶難溶性。 <0.1 g/100 mL で 22 ºC |
| 沸点 | 752 °F at 740 mmHg (NTP, 1992)401 °C401 °C @760 [mm Hg]402°C |
| Decomposition | When heated to decomp it emits highly toxic fumes of /nitrogen oxides/. |
| 融点 | 262 °F (NTP, 1992)120 °C127 °C239 °F127-128 °C |
| 蒸気密度 | 6.36 (NTP, 1992) - Heavier than airwill sink (Relative to Air)6.36 (Air = 1)Relative vapor density (air = 1): 6.4 |
| 蒸気圧 | Low (NIOSH, 2024)0.0000009 [mmHg]Based on the specific vapor density value of 6.36 (Sims et al., 1988), the vapor pressure wascalculated to be 0.83 at 20 °C. |
| 屈折率 | 1.6266 (estimate) |
| 引火点 | 11 °C |
| 貯蔵条件 | 2-8°C |
| pKa(酸解離定数) | 4.66(at 30℃) |
| 色 | 灰黄色の結晶性粉末。白色またはわずかに赤みがかった結晶、粉末 |
| Merck | 13,1077 |
| BRN | 742770 |
| ヘンリー定数 | (x 10-11 atmm3/mol): 3.88 at 25 °C (estimated, Howard, 1989) |
| 安定性 | 安定。可燃性。強力な酸化剤とは相容れない。 |
| InChIKey | HFACYLZERDEVSX-UHFFFAOYSA-N |
| CAS データベース | 92-87-5(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzidine(92-87-5) |
| EPAの化学物質情報 | Benzidine (92-87-5) |
化学的特性
Benzidine is a white, grayish-yellow, or slightly reddish crystalline solid or powder. The major use for benzidine is in the production of dyes, especially azo dyes in the leather, textile, and paper industries, as a synthetic precursor in the preparation and manufacture of dyestuffs. It is also used in the manufacture of dyes and rubber, as a reagent, and as a stain in microscopy. It is slightly soluble and slowly changes from a solid to a gas.
安全性と法規制
| GHS 分類 | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 規制情報 | Chemical: [1,1'-Biphenyl]-4,4'-diamineS - indicates a substance that is identified in a final Significant New Use Rule.Restricted substance: Benzidine[1,1'-Biphenyl]-4,4'-diamine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.The 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 - [1,1'-Biphenyl]-4,4'-diamine: Environment tier I assessment |
| 輸送ラベル(DOT) | Poison |
| 火災危険 | Special Hazards of Combustion Products: Contain highly toxic NOx fumes.· Combustible material: may burn but does not ignite readily.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 火災の可能性 | Benzidine itself does not burn or burns with difficulty. |
| 健康有害性 | Poisonous if inhaled, swallowed or absorbed through skin. May cause contact dermatitis, irritation or sensitization. Ingestion may cause nausea and vomiting. (USCG, 1999)· TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death. |
| 有害性の概要 | Benzidine is a manufactured chemical that does not occur naturally. It is a crystalline solid that may be grayish-yellow, white, or reddish-gray. In the environment, benzidine is found in either its "free" state (as an organic base), or as a salt. Benzidine was used to produce dyes for cloth, paper, and leather. It is no longer produced or used commerically in the U.S.Benzidine is no longer produced in the United States, although benzidine-based dyes may be imported into this country. No information is available on the acute (short-term) effects of benzidine in humans by inhalation exposure but benzidine is considered to be very acutely toxic to humans by ingestion. Chronic (long-term) exposure to benzidine in humans may result in injury to the bladder. Epidemiological studies have shown occupational exposure to benzidine to result in an increased risk of bladder cancer. Animal studies have reported various tumor types at multiple sites from benzidine exposure via oral, inhalation, and injection exposure. EPA has classified benzidine as a Group A, known human carcinogen. |
用途
解説
biphenyl-4,4′-diamine.C12H12N2(184.24).ヒドラゾベンゼンを希硫酸と加熱して,ベンジジン転位させてつくられる.結晶形は3種類あるが,もっとも安定なものは融点128 ℃,沸点400 ℃(98.6 kPa).無色の鱗片状結晶。1845年にロシアのジーニンN.N.Zininがはじめて合成し,62年にドイツのフィティヒR.Fittigがジアミノビフェニル構造であることを証明し,74年に同じくドイツのシュルツG.Schultzが2個のアミノ基がともにパラ位にあることを示して構造が確定した。ニトロベンゼンを還元してヒドラゾベンゼンにしたのち,これに塩酸または硫酸を作用させてベンジジン転位を起こすことによって作られる。直接染料の重要な中間物であったが,発がん性があることがわかり,製造されなくなった.分析試薬として多くの金属および非金属イオンの定性,定量に用いられる.森北出版「化学辞典(第2版)
説明
Benzidine is a white, greyish-yellow, or slightly reddish crystalline solid or powder. The major use for benzidine is in the production of dyes, especially azo dyes in the leather, textile, and paper industries and as a synthetic precursor in the preparation and manufacture of dyestuffs. It is also used in the manufacture of rubber, as a reagent, and as a stain in microscopy. It is slightly soluble and slowly changes from a solid to a gas.
使用
Benzidine was used extensively in the manu facture of dyes. Because of its cancer-causingeffects in humans, its application in dyes hasbeen curtailed. Other uses of this compoundare in chemical analysis: as a reagent for thedetermination of hydrogen peroxide in milkand in the analysis of nicotine. Its hydrochlo ride is used as a reagent to analyze metalsand sulfate.
一般的な説明
A grayish-yellow to grayish-red, crystalline solid. Toxic by ingestion, inhalation, and skin absorption. Combustion produces toxic oxides of nitrogen. Used to make other chemicals and in chemical and biological analysis.
製法・合成法
製造方法
1-Nitrobenzene restore 1,2-Diphenylhydrazineturn with acid rearrangement.
調製方法
Benzidine production is now exclusively for captive consumption and must be carried out in closed systems under stringent workplace controls. Benzidine is used in the synthesisofdyesanddyeintermediates,asahardenerforrubber, and as a laboratory reagent. The rst successful synthetic direct dye was Congo Red, a diazo derivative prepared from benzidinebyBoettigerin1884.Nearlyalldirectdyesareazo products. Congo Red is used in humans intravenously for the medical diagnosis of amyloidosis. The basis for its use is an unexplained afnity for amyloid, which rapidly removes the dye from the blood. It is used medically for the management of profuse capillary hemorrhage such as the one occurring in septicemias and in the terminal phases of leukemia.
純化方法
Its solution in *benzene is decolorized by percolating through two 2-cm columns of activated alumina, then concentrated until benzidine crystallises on cooling. Recrystallise alternately from EtOH and *benzene to constant absorption spectrum [Carlin et al. J Am Chem Soc 73 1002 1951]. It has also been crystallised from hot water (charcoal) and from diethyl ether. Dry it under vacuum in an Abderhalden pistol. Store it in the dark in a stoppered container. CARCINOGENIC. [Beilstein 13 IV 364.]