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2,6-ジクロロ安息香酸
2,6-ジクロロ安息香酸 · ２，６ジクロロ安息香酸 · 2,6‐ジクロロ安息香酸 · AI3-33337 · NSC 76599 · CCRIS 8610 · BRN 0973858 · 2,6-Dichlorobe
識別子と物理属性
| CAS No. | 50-30-6 |
|---|---|
| 分子式 | C7H4Cl2O2 |
| 平均分子量 | 191.01 g/mol |
| 単同位体質量 | 189.95883473 g/mol |
| SMILES | O=C(O)c1c(Cl)cccc1Cl |
| InChIKey | MRUDNSFOFOQZDA-UHFFFAOYSA-N |
| PubChem CID | 5758 |
| ChEMBL | CHEMBL114828 |
| ChEBI | CHEBI:48623 |
| EC No. | 200-025-9 |
| DTXSID | DTXSID0024979 |
| 現地名 | 2,6-ジクロロ安息香酸 |
化学・物理的性質
| XLogP | 2.2 |
|---|---|
| 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 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 151 |
| SpringerMaterials Properties | Nuclear quadrupole resonance spectroscopy |
| 溶解度 | 1 to 10 mg/mL at 66 °F (NTP, 1992)14g/リットル19℃で0.1～1g/100mL |
| 沸点 | Sublimes (NTP, 1992)273.68°C (rough estimate) |
| 融点 | 291 °F (NTP, 1992)139-142 °C (lit.) |
| Physical Description | 2,6-dichlorobenzoic acid appears as needles (from ethanol) or white solid. (NTP, 1992) |
| 密度 | 1.4410 (rough estimate) |
| 屈折率 | 1.4590 (estimate) |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| pKa（酸解離定数） | 1.69±0.10(Predicted) |
| 外観・状態 | 微結晶性粉末 |
| 色 | 白からベージュ |
| BRN | 973858 |
| 安定性 | 安定。強力な酸化剤とは相容れない。 |
| InChI | 1S/C7H4Cl2O2/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3H,(H,10,11) |
| InChIKey | MRUDNSFOFOQZDA-UHFFFAOYSA-N |
| SMILES | OC(=O)c1c(Cl)cccc1Cl |
| CAS データベース | 50-30-6(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzoic acid, 2,6-dichloro-(50-30-6) |
| EPAの化学物質情報 | Benzoic acid, 2,6-dichloro- (50-30-6) |
化学的特性
white to off-white crystalline powder
安全性と法規制
| GHS 分類 | WarningH315 (98.1%): 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 53 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Benzoic acid, 2,6-dichloro-PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.2,6-Dichlorobenzoic 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 irritation. |
| 反応性グループ | Acids, Carboxylic |
| Reactivity Profile | 2,6-DICHLOROBENZOIC ACID is a halogenated 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. |
| Air and Water Reactions | Slightly soluble in water. |
| Hazard Classes and Categories | Skin Irrit. 2 (98.1%) |
| 消火 | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (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 stored, weighed and diluted, wear an 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) |
| Acute Toxicity Link | Chemical: 2,6-DICHLOROBENZOIC ACID |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | DG7000000 |
| 税関コード | 29163900 |
| 危険文句（R） | 36/37/38 |
| 化審法 | (3)-1410, (3)-1424 |
| 危険表示 | Xi |
| 安全措置（S） | 26-36-24/25-37/39 |
| 危険等級 | IRRITANTEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
使用
2,6-Dichlorobenzoic Acid is an di-halogenated benzoic acid derivative and is used in the synthesis of Lux-S enzyme inhibitor.
製法・合成法
製造方法
2,6-Dichlorobenzoic Acid can be prepared through several synthetic routes. One common method is the chlorination of benzoic acid in the presence of a catalyst such as phosphorus pentachloride or thionyl chloride. The reaction takes place under reflux in anhydrous conditions, resulting in the substitution of two chlorine atoms at positions 2 and 6 of the benzene ring. The resulting product is then isolated and purified through recrystallization from a suitable solvent. Another method involves the chlorination of the methyl ester of 2,6-dichlorobenzoic acid, followed by hydrolysis to yield the desired compound. Alternatively, it can also be synthesized through the oxidation of 2,6-dichlorotoluene using potassium permanganate or other oxidizing agents.
純化方法
Crystallise the acid from EtOH and sublime it in vacuo.[Beilstein 9 IV 1005.] 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.]