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p-トルイル酸
p-トルイル酸 · p-トルエン酸 · 4-メチル安息香酸 · p-メチル安息香酸 · 4-メチルベンゼンカルボン酸 · pトルイル酸 · ｐメチル安息香酸 · P‐トルイル酸
識別子と物理属性
| CAS No. | 99-94-5 |
|---|---|
| 分子式 | C8H8O2 |
| 平均分子量 | 136.15 g/mol |
| 単同位体質量 | 136.0524295 g/mol |
| SMILES | Cc1ccc(C(=O)O)cc1 |
| InChIKey | LPNBBFKOUUSUDB-UHFFFAOYSA-N |
| PubChem CID | 7470 |
| ChEMBL | CHEMBL21708 |
| ChEBI | CHEBI:36635 |
| EC No. | 202-803-3 |
| DTXSID | DTXSID6021618 |
| 現地名 | p-トルイル酸 |
化学・物理的性質
| XLogP | 2.3 |
|---|---|
| 極性表面積 | 37.3 |
| 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 | 1 |
| 重原子数 | 10 |
| 形式電荷 | 0 |
| 複雑度 | 123 |
| 物質分類 | Other Classes -> Organic Acids |
| SpringerMaterials Properties | Boiling point |
| LogP（分配係数） | 2.272.43 |
| 溶解度 | less than 1 mg/mL at 66 °F (NTP, 1992)0.34 mg/mL at 25 °C0.3g/l<0.1 g/100 mL で 19 ºC |
| 沸点 | 525 to 527 °F at 760 mmHg (NTP, 1992)274-275 °C (lit.) |
| 融点 | 356 to 360 °F (NTP, 1992)181 °C177-180 °C (lit.) |
| 蒸気圧 | 0.0061 [mmHg]0.02 hPa (70 °C) |
| Physical Description | P-toluic acid is a white powder. Sublimes. (NTP, 1992)Dry PowderWhite solid[CAMEO] White to yellow-brown solid[OECD SIDS] White powder[Alfa Aesar MSDS] |
| 密度 | 1,06 g/cm3 |
| 屈折率 | 1.5120 (estimate) |
| 引火点 | 181°C |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 粉 |
| pKa（酸解離定数） | 4.36(at 25℃) |
| 色 | 白色～やや黄色がかったクリーム色 |
| pH | 3.73(1 mM solution)3.2(10 mM solution)2.69(100 mM solution) |
| 比熱容量 | Cp(crystal): 1.24 J/(g·K), at 25℃ |
| Merck | 14,9535 |
| BRN | 507600 |
| ヘンリー定数 | 2.7×102 mol/(m3Pa) at 25℃, Wang et al. (2017) |
| 安定性 | 安定。強酸化剤、強塩基とは相容れない。 |
| InChI | 1S/C8H8O2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3,(H,9,10) |
| InChIKey | LPNBBFKOUUSUDB-UHFFFAOYSA-N |
| SMILES | Cc1ccc(cc1)C(O)=O |
| LogP（分配係数） | 2.44 |
| CAS データベース | 99-94-5(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzoic acid, 4-methyl-(99-94-5) |
| EPAの化学物質情報 | Benzoic acid, 4-methyl- (99-94-5) |
化学的特性
colourless crystals or white crystalline powder. Slightly soluble in water; soluble in alcohol and ether. Combustible.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 2.8% (5 of 180) of reports.WarningH315 (10.6%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 180 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Benzoic acid, 4-methyl-Benzoic acid, 4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, 4-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: 20-12-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/251264-Methylbenzoic acid: Does not have an individual approval but may be used under an appropriate group standard |
| 火災危険 | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| 健康有害性 | SYMPTOMS: Symptoms of exposure to this compound may include skin and eye irritation. |
| 有害性の概要 | May cause skin and eye irritationHarmful by ingestion, inhalation, and skin absorption[NTP] A skin sensitizer in human volunteers[OECD SIDS] An irritantHarmful by ingestion[Alfa Aesar MSDS] See Methyl 4-methylbenzoate and Phenylacetic acid. |
| 反応性グループ | Acids, Carboxylic |
| Reactivity Profile | P-TOLUIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in waterthose with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactionslike other acids, they often catalyze (increase the rate of) chemical reactions. This chemical is incompatible with strong oxidizers. It is also incompatible with strong bases. (NTP, 1992). |
| Air and Water Reactions | Fine dust dispensed in air in sufficient concentrations, and in the presence of an ignition source is a potential dust explosion hazard. (NTP, 1992). Insoluble in water. |
| Hazard Classes and Categories | Skin Irrit. 2 (10.6%) |
| 消火 | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992) |
| 応急処置 | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| 非火災時の漏出対応 | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| 有害作用 | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| RAIS Toxicity Values | 0.005PPRTV Current0.05 |
| EPA Provisional Peer-Reviewed Toxicity Values | p-Toluic Acid5 x 10^-3 mg/kg-day5 x 10^-2 mg/kg-dayPDF DocumentInadequate information to assess carcinogenic potential2017 |
| Hazard Quotient Level 0.1 or Cancer Risk Level 1E-06 | 3.20e+024.10e+039.00e+011.00e+032.30e-025.00e-03 |
| Hazard Quotient Level 3 or Cancer Risk Level 1E-04 | 9.50e+021.20e+042.70e+021.00e+035.00e-03Volatile |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | XU1575000 |
| 毒性 | LD50 orally in Rabbit: 400 mg/kg |
| 税関コード | 29163900 |
| 危険文句（R） | 22 |
| 化審法 | (3)-1285 |
| 危険表示 | Xn |
| 安全措置（S） | 22-24/25 |
| 自然発火温度 | 570 °C |
| 危険等級 | Skin Sens. 1 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
使用
p-Toluic Acid is used as a reagent in the synthesis of several organic compounds including that of 2-aryl-1,3,4-oxadiazole derivatives which are potential antibacterial agents. Also used in the synthesis of 4-(bromomethyl) benzoic acid.
製法・合成法
純化方法
Crystallise the acid from water, water/EtOH (1:1), MeOH/water or *benzene. [Beilstein 9 IV 1724.] Aromatic acid impurities (to <0.05%) can be removed via the (±)--methylbenzylamine salt as described for 2,4-dichlorobenzoic acid [Ley & Yates Organic Process Research & Development 12 120 2008]. The S-benzylisothiuronium salt has m 164o (from aqueous EtOH).