diphenyl chlorophosphonate

• ChemBase编号: 137349
• 分子式: C12H10ClO3P
• 平均质量: 268.632761
• 单一同位素质量: 268.00560849
• SMILES: c1ccc(cc1)OP(=O)(Oc1ccccc1)Cl
• Canonical SMILES: ClP(=O)(Oc1ccccc1)Oc1ccccc1
• InChI: InChI=1S/C12H10ClO3P/c13-17(14,15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H
• InChIKey: BHIIGRBMZRSDRI-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: diphenyl chlorophosphonate
• IUPAC传统名: diphenyl chlorophosphonate
• 别名: 二苯基氯磷酸酯; 二苯磷酰氯; 氯磷酸二苯酯; Diphenyl chlorophosphate; Diphenyl phosphorochloridate; Diphenyl phosphoryl chloride; Diphenyl chlorophosphate; Diphenyl phosphoryl chloride; Diphenyl phosphorochloridate

登记号

• CAS号: 2524-64-3
• EC号: 219-759-6
• MDL号: MFCD00003030
• Beilstein号: 654130
• PubChem SID: 24861235; 24893614; 162231612
• PubChem CID: 75654

理论计算性质

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 3.8171308
• LogD (pH = 7.4): 3.8171308
• Log P: 3.8171308
• 摩尔折射率: 66.7434 cm^3
• 极化性: 26.448591 Å^3
• 极化表面积: 35.53 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 沸点: 145-147°C/1mm; 314-316 °C/272 mmHg(lit.)
• 闪点: >113 °C; >235.4 °F; 113°C(235°F)
• 密度: 1.296; 1.296 g/mL at 25 °C(lit.)
• 折射率: 1.5500; n20/D 1.55(lit.)
• 蒸汽压: 10 mmHg ( 190 °C)

安全信息

• 保存注意事项: Moisture Sensitive
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C)
• 联合国危险货物编号: 3265; UN3265
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 2; III
• 危险公开号: 34; 34-37
• 安全公开号: 20-26-36/37/39-45-60; 26-36/37/39-45
• TSCA收录: 是
• GHS危险品标识: GHS05
• GHS警示词: Danger
• GHS危险声明: H314; H314-H318
• GHS警示性声明: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• 个人保护装置: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 2

产品相关信息

• 纯度: 96%; 97%; 99%
• 线性分子式: (C6H5O)2POCl

详细说明

Sigma Aldrich - 344249

包装
100, 500 g in glass bottle

Sigma Aldrich - D206555

包装
25, 100 g in glass bottle
Application
保护性丝氨酸1和吡喃糖的磷酸化试剂。2

参考文献

• Diphenylphosphate esters, formed with or without catalysis by DMAP, undergo a variety of transformations:
• Hydrogenolysis of the phenyl groups yields the monophosphate ester of the alcohol. Glycosyl monophosphates have been prepared in this way. Alternatively, treatment of the glycosyl diphenyl phosphate with sodium azide in DMF provides a high yield route to glycosyl azides: Carbohydr. Res., 223, 169 (1992).
• Diphenylphosphate has also been exploited as a good leaving group in the high yield conversion (equivalent to dehydration) of secondary alcohols to olefins by thermal elimination: Synthesis, 1300 (1995). For further information, see Triphenyl phosphate, L08130. Other conversions, generally in the presence of a base such as triethylamine, in which the equivalent of a dehydration step occurs are:
• Aldoximes to nitriles at room temperature: J. Org. Chem., 34, 2805 (1969). Peptide coupling (see Appendix 6), via the mixed carboxyl phosphate anhydride: Chem. Ber., 94, 2644 (1961). Carboxylic acids to anhydrides: Synthesis, 219 (1981). ω-Hydroxy acids to macrolides, promoted by DMAP: J. Org. Chem., 47, 1612 (1982).
• Lithium enolates give enol diphenylphosphates in which the phosphate moiety acts as a leaving group; e.g., ketone enol phosphates have been converted to the corresponding alkene by reaction with organocuprates: Tetrahedron Lett., 4405 (1976). With amides, internal displacement occurs; subsequent reaction with NaN₃ gives azirines: Helv. Chim. Acta, 76, 2830 (1993):
  
• See also Diphenylphosphonic azide, A12124.