3-chlorobenzene-1-carboperoxoic acid

• ChemBase编号: 107972
• 分子式: C7H5ClO3
• 平均质量: 172.5658
• 单一同位素质量: 171.9927217
• SMILES: OOC(=O)c1cccc(Cl)c1
• Canonical SMILES: OOC(=O)c1cccc(c1)Cl
• InChI: InChI=1S/C7H5ClO3/c8-6-3-1-2-5(4-6)7(9)11-10/h1-4,10H
• InChIKey: NHQDETIJWKXCTC-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-chlorobenzene-1-carboperoxoic acid
• IUPAC传统名: mcpba
• 别名: 3-氯过氧苯甲酸; 间氯过氧苯甲酸; 3-氯过氧化苯甲酸; 3-Chlorobenzenecarboperoxoic Acid; NSC 97094; m-Chlorobenzoyl Hydroperoxide; m-Chloroperbenzoic Acid; m-Chloroperoxobenzoic Acid; 3-Chloroperbenzoic Acid (Technical Grade, 70-75%, wet with water); 3-Chloroperoxybenzoic acid; 3-Chloroperoxybenzoic acid; 3-Chloroperbenzoic acid; m-Chloroperoxybenzoic acid; m-CHLOROPERBENZOIC ACID; meta-Chloroperoxybenzoic acid; m-Chloroperoxybenzoic acid; meta-Chloroperbenzoic acid; 3-Chloroperbenzoic acid; mCPBA; Meta-Chloroperoxybenzoic acid; 3-Chloroperoxybenzoic acid; 3-Chlorobenzoperoxoic acid

登记号

• CAS号: 937-14-4
• EC号: 213-322-3
• MDL号: MFCD00002127
• Beilstein号: 608317
• PubChem SID: 24855622; 162089126; 24856527
• PubChem CID: 70297
• Chemspider ID: 63480
• 维基百科标题: Meta-Chloroperoxybenzoic_acid

理论计算性质

• Acid pKa: 7.4827013
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 2.3494327
• LogD (pH = 7.4): 2.093771
• Log P: 2.3539097
• 摩尔折射率: 39.756 cm^3
• 极化性: 15.491928 Å^3
• 极化表面积: 46.53 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: Wet White Solid; White powder
• 熔点: 63-67°C (dec.); 64-66°C; 69-71 °C(lit.); 92-94 °C, decomposes; 93°C
• pKa: 7.57

安全信息

• 保存条件: Refrigerator
• RTECS编号: SD9470000
• 欧盟危险性物质标志: 氧化性(Oxidising) (O); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 3106; UN3106
• 德国WGK号: 3
• 联合国危险货物等级: 5.2
• 联合国危险货物包装类别(PG): II
• 危险公开号: 5-8-36/37/38; 5-8-36/37/38-43; R:9-18; R7 R22 R34
• 安全公开号: 17-26-37; 26-36/37; S:13-16-27; S17 S26 S36/37/39 S45
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS03; GHS07
• GHS警示词: Danger
• 主要危害: Oxidizing, corrosive
• GHS危险声明: H242-H272-H315-H319-H335; H242-H315-H317-H319-H335
• GHS警示性声明: P220-P261-P280-P305 + P351 + P338-P410-P411 + P235; P220-P261-P280-P305 + P351 + P338-P410-P412; P221-P210-P305+P351+P338-P405-P410-P501A
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3106 5.2
• 保存温度: 2-8°C

产品相关信息

• 纯度: ~70% (RT); ≤77%; 50-55%, cont. ca 10% 3-chlorobenzoic acid, balance water; 85%; 95+%
• 级别: technical
• 杂质: ~10% 3-chlorobenzoic acid; ~20% water
• 线性分子式: ClC6H4CO3H

详细说明

Sigma Aldrich - 273031

Application
用于使二、三和四取代烯烃环氧化的有效氧化剂。
Other Notes
残留物为 3-氯苯甲酸和水
包装
1 kg in poly bottle
25, 100, 500 g in poly bottle

Sigma Aldrich - 25800

Other Notes
用于烯烃环氧化的试剂1

参考文献

• Reagent for epoxidation of alkenes: J. Org. Chem., 29, 1976 (1964). Dichloromethane has been recommended as solvent for these reactions, since the peracid is soluble, but the by-product, 3-chlorobenzoic acid, is almost insoluble. For high-yield, stereospecific epoxidation in a two-phase, almost neutral system, see: J. Org. Chem., 44, 1351 (1979). For regioselective epoxidation of the more substituted double bond of a diene, see: Org. Synth. Coll., 5, 467 (1973). For epoxidation in aqueous solution followed by in situ hydrolysis to the trans-diol by 10% sulfuric acid, see: Synth. Commun., 19, 1939 (1989).
• Carbonyl compounds undergo the Baeyer-Villiger reaction to give esters or lactones: J. Org. Chem., 29, 2914 (1964). For an extensive review of the Baeyer-Villiger reaction, see: Org. React., 43, 251 (1993).
• Primary aliphatic amines are oxidized to nitro-compounds: J. Org. Chem., 31, 524 (1966). Good yields are obtained in 1,2-dichloroethane solution: J. Org. Chem., 44, 659 (1979); 54, 2869 (1989).
• Sulfides can be oxidized selectively either to sulfoxides or sulfones: Tetrahedron, 22, 1235 (1966); J. Chem. Soc. (C), 2720 (1969); J. Org. Chem., 35, 2106 (1970).
• For the stereospecific oxidation of imines to oxaziridines under phase-transfer conditions, see: Org. Synth. Coll., 8, 546 (1993):
  
• Perfluorooxaziridines have been prepared using acetonitrile as solvent: J. Org. Chem., 58, 4754 (1993).
• For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 664 (2007).
• WARNING: The reagent has been reported to react exothermically with DMF: Org. Process Res. Dev., 6, 159 (2004).