化工社化工社 化学情報印刷レポート · 研究参考用
ヒドロキシアゾベンゼン
4-(フェニルアゾ)フェノール · p-フェニルアゾフェノール · ブラシラジナオイルイエローO · 4-フェニルアゾフェノール · ソルベントイエロー7 · 4-ヒドロキシアゾベンゼン · 1,4-ベンゾキノンモノフェニルヒドラゾン · アゾベンゼン-4-オール
識別子と物理属性
| CAS No. | 1689-82-3 |
|---|---|
| 分子式 | C12H10N2O |
| 平均分子量 | 198.22 g/mol |
| 単同位体質量 | 198.07931294 g/mol |
| SMILES | Oc1ccc(N=Nc2ccccc2)cc1 |
| InChIKey | BEYOBVMPDRKTNR-UHFFFAOYSA-N |
| PubChem CID | 15529 |
| ChEMBL | CHEMBL1525953 |
| ChEBI | CHEBI:82475 |
| EC No. | 216-880-6 |
| DTXSID | DTXSID3022160 |
| 現地名 | ヒドロキシアゾベンゼン |
化学・物理的性質
| XLogP | 3.7 |
|---|---|
| 極性表面積 | 45 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 2 |
| 重原子数 | 15 |
| 形式電荷 | 0 |
| 複雑度 | 204 |
| 物質分類 | Dyes -> Azo Dyes |
| LogP（分配係数） | 3.18 |
| Color/Form | YELLOW LEAVES FROM BENZENE, ORANGE PRISMS FROM ALC |
| 溶解度 | INSOL IN WATERVERY SOL IN ALC & ETHERSOL IN BENZENE, CONCN SULFURIC ACID & DIL ALKALI (YELLOW)Soluble in acetone, ethanol, benzene and etherIn water, 90 mg/l @ 20 °C4.7 [ug/mL] (The mean of the results at pH 7.4)DMSO、メタノールアセトン、エタノール、ベンゼン、エーテルに可溶。水に不溶。 |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 沸点 | 220-230 °C @ 20 MM HG SLIGHT DECOMP230°C/20mmHg(lit.) |
| 融点 | 155-157 °C150-152 °C(lit.) |
| 蒸気圧 | 0.00000023 [mmHg]2.31X10-7 mm Hg @ 25 °C |
| Physical Description | Yellow or orange solid[HSDB] Deep yellow powder[MSDSonline] |
| Ionization Efficiency | Positive2.992.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Dissociation Constants | pKa= 8.2 (conjugate acid) |
| 密度 | 1.1447 (rough estimate) |
| 屈折率 | 1.6330 (estimate) |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 微結晶性粉末 |
| pKa（酸解離定数） | 8.93±0.13(Predicted) |
| 色 | 茶色 |
| BRN | 957567 |
| ヘンリー定数 | 1.5×104 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 主な用途 | 診断アッセイの製造血液学組織学 |
| InChI | 1S/C12H10N2O/c15-12-8-6-11(7-9-12)14-13-10-4-2-1-3-5-10/h1-9,15H/b14-13+ |
| InChIKey | BEYOBVMPDRKTNR-BUHFOSPRSA-N |
| SMILES | Oc1ccc(cc1)\N=N\c2ccccc2 |
| CAS データベース | 1689-82-3(CAS DataBase Reference) |
| EPAの化学物質情報 | p-Phenylazophenol (1689-82-3) |
化学的特性
BROWN FINE CRYSTALLINE POWDER
安全性と法規制
| GHS 分類 | WarningH315 (97.8%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Phenol, 4-(phenylazo)- |
| 有害性の概要 | Intraperitoneal LD50 (mouse) = 75 mg/kg[HSDB] An irritantMay cause injury to skin and eyes[MSDSonline] |
| Hazard Classes and Categories | Skin Irrit. 2 (97.8%) |
| 生態毒性値 | LC50 Pimephales promelas (fathead minnow) 110 (1.07-1.13) mg/l 72 hr, wt 100 mg, flow-through bioassay, dissolved oxygen 7.4 (4.6-8.8) mg/l, water hardness 44.9 (42.4-46.6) mg/l as CaCO3, pH 6.9-7.7, alkalinity 42.9 (39.6-61.4) mg/l CaCO3, temp: 26.4 +/- 1.4 °C, Purity 90%+LC50 Pimephales promelas (fathead minnow) 1.09 (1.05-1.13) mg/l 96 hr, wt 100 mg, flow-through bioassay, dissolved oxygen 7.4 (4.6-8.8) mg/l, water hardness 44.9 (42.4-46.6) mg/l as CaCO3, pH 6.9-7.7, alkalinity 42.9 (39.6-61.4) mg/l CaCO3, temp: 26.4 +/- 1.4 °C, Purity 90%+ |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3200(SRC), determined from a structure estimation method(2), indicates that 4-hydroxyazobenzene is expected to have slight mobility in soil(SRC). The pKa of 4-hydroxyazobenzene is 8.2, indicating that the undissociated form will exist in neutral and acidic soils. In basic soils, the anion form will predominate and is expected to have higher mobility than the undissociated species. Volatilization of 4-hydroxyazobenzene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.7X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 2.31X10-7 mm Hg(3), and water solubility, 90 mg/l(4). 4- Hydroxyazobenzene is not expected to volatilize from dry soil surfaces(SRC) based on a vapor pressure of 2.31X10-7 mm Hg at 25 °C(3). 4-Hydroxyazobenzene persists in some wastewater treatment systems and degrades in others, which suggest that biodegradation may be an important fate process in soils(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3200(SRC), determined from an estimation method(2), indicates that 4-hydroxyazobenzene is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.7X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 2.31X10-7 mm Hg(4), and water solubility, 90 mg/l(5). The pKa of 8.2(6) indicates that this chemical will exist in the undissociated form in neutral and acidic environments, and as the anion in basic environments. According to a classification scheme(7), an estimated BCF of 10(SRC), derived from an estimated log Kow of 3.6(8), suggests the potential for bioconcentration in aquatic organisms is low. 4-Hydroxyazobenzene persists in some wastewater treatment systems and degrades in others(9), which suggest that biodegradation may be an important process in aquatic environments(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-hydroxyazobenzene, which has a vapor pressure of 2.31X10-7 mm Hg at 25 °C(4), is expected to exist in vapor and particulate phases in the ambient atmosphere. Vapor-phase 4-hydroxyazobenzene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 27 hours(SRC), calculated from its rate constant of 1.4X10-11 cu cm/molecule-sec at 25 °C determined using a structure estimation method(3). Particulate-phase 4-hydroxyazobenzene may be removed from the air by wet and dry deposition(SRC). |
| Soil Adsorption/Mobility | The Koc of 4-hydroxyazobenzene was estimated as 3200(SRC), using an estimated low Kow of 3.6(1) and a regression-derived equation(2). The pKa of 4-hydroxyazobenzene is 8.2(4), indicating that the undissociated form of 4-hydroxyazobenzene will exist in neutral and acidic soils and the anionic form will exist in basic soils. The anionic forms are expected to have higher mobility than the neutral species(SRC). According to a classification scheme(3), the estimated Koc value suggests that the undissociated form of 4-hydroxyazobenzene will be relatively immobile in soils. |
| Natural Pollution Sources | 4-Hydroxyazobenzene is not known to occur in nature(1). |
| Artificial Pollution Sources | 4-Hydroxyazobenzene's production and use in the dye industry(1) may result in its release to the environment through various waste streams. |
| Environmental Biodegradation | A BACTERIUM WHICH DEGRADES AZO DYES WAS ISOLATED FROM A POLLUTED ENVIRONMENT (DRAINAGE DITCHES OF DYE FACTORIES IN THE GIFU DISTRICT, JAPAN), AND IDENTIFIED AS AEROMONAS HYDROPHILA.AEROBIC: 4-Hydroxyazobenzene is considered to be persistent in the environment(1). This study found that the persistence was due to its toxicity to microbial communities. In an Ashland City, Tennessee activated sludge-based microcosm, 4-hydroxyazobenzene was toxic at 500 mg/l concentration over test periods ranging from 6 to 144 hours(1). In an identical test using activated sludge from Nashville, Tennessee, the chemical was slightly oxidized after six hours, but only 0.1% of the theoretical maximum oxidation occurred(1). After 24 hours, 4.7% of the theoretical maximum was degraded. Similar levels of oxidation were observed when sewage sludges were used from a Franklin, Tennessee sewage treatment plant(1). In contrast, in a study that measured only azo bond cleavage, 90% of the 4-hydroxyazobenzene (at 50 mg/l) was transformed after 20 days in an activated sludge from a Japanese waste-water treatment system(2). The rate constant associated with this transformation was 6.2X10-2/day. |
| Carcinogen Classification | 4-HydroxyazobenzeneGroup 3: Not classifiable as to its carcinogenicity to humansVolume 8: (1975) Some Aromatic Azo Compounds1987 |
| Environmental Bioconcentration | An estimated BCF of 10 was calculated for 4-hydroxyazobenzene(SRC), using an estimated log Kow of 3.6(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low. |
| Volatilization from Water/Soil | The Henry's Law constant for 4-hydroxyazobenzene is estimated as 6.7X10-10 atm-cu m/mole(SRC) from its vapor pressure, 2.31X10-7 mm Hg(1), and water solubility, 90 mg/l(2). This Henry's Law constant indicates that 4-hydroxyazobenzene is expected to be essentially nonvolatile from water surfaces and moist soils(3). 4-Hydroxyazobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 2.31X10-7 mm Hg(1). |
| Non-Human Toxicity Excerpts | NINE ALBINO RATS WERE FED A DIET CONTAINING 4-HYDROXYAZOBENZENE (CONCN NOT GIVEN)4/5 RATS DYING BETWEEN 159-284 DAYS DEVELOPED MULTIPLE PAPILLOMAS OF THE FORESTOMACH /NO REPORTED CONTROLS/.A GROUP OF 12 MALE SPRAGUE-DAWLEY RATS WAS FED A DIET CONTAINING 4-HYDROXYAZOBENZENE @ CONCN OF 53 MG/KG OF DIET FOR 9 MO. NO TUMORS WERE OBSERVED. (ALTHOUGH THE DURATION OF THIS EXPT WAS INADEQUATE, IT WAS NOTED THAT...@ CONCN OF 60 MG/KG OF DIET TO SIMILAR GROUP OF RATS PRODUCED A 100% INCIDENCE OF LIVER TUMORS WITHIN 6 MO) /NO REPORTED CONTROLS/.... REPORTED TO BE NON-MUTAGENIC WHEN TESTED IN DROSOPHILA FOR THE PRODUCTION OF X-LINKED RECESSIVE LETHALS (THE PURITY WAS NOT DEFINED). |
| Evidence for Carcinogenicity | No data are available in humans. Inadequate evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans. |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of 4-hydroxyazobenzene with photochemically-produced hydroxyl radicals has been estimated as 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 27 hours(SRC) at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4-Hydroxyazobenzene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). 4-Hydroxyazobenzene absorbs light at 347 nm(3) and may photolyze in the atmosphere due to absorption in the environmental UV spectrum (>290 nm)(SRC). |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | SM8300000 |
| 輸送番号（UN） | 3234 |
| 税関コード | 29270000 |
| 危険文句（R） | 36/37/38 |
| 化審法 | (5)-3041 |
| 危険表示 | Xi |
| 安全措置（S） | 26-36 |
| 危険等級 | Aquatic Chronic 2 |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 1689-82-3(Hazardous Substances Data) |
用途
解説
4-phenylazophenol．C12H10N2O(198.22)．ヒドロキシアゾベンゼンは，フェノールにベンゼンジアゾニウム塩をアゾカップリングさせると得られる．橙色の柱状晶．融点152 ℃．水に難溶，エタノール，エーテルに可溶．弱い酸性で希アルカリに溶けて黄色を呈し，またアミノ酸と付加物をつくる．還元すればp-アミノフェノールとアニリンになる．森北出版「化学辞典（第2版）
用途
活性アルミナの活性度検定用、クロマトグラフ用標準。
製法・合成法
製造方法
aniline diazotization, and phenol coupling.
純化方法
Crystallise the dye from *benzene or 95% EtOH. [Beilstein 16 II 38, 16 III 86, 16 IV 159.]