bis(4-methoxyphenyl)-1,3,2λ5,4λ5-dithiadiphosphetane-2,4-dithione

• ChemBase编号: 90001
• 分子式: C14H14O2P2S4
• 平均质量: 404.467282
• 单一同位素质量: 403.93518695
• SMILES: S1P(=S)(c2ccc(cc2)OC)SP1(=S)c1ccc(cc1)OC
• Canonical SMILES: COc1ccc(cc1)P1(=S)SP(=S)(S1)c1ccc(cc1)OC
• InChI: InChI=1S/C14H14O2P2S4/c1-15-11-3-7-13(8-4-11)17(19)21-18(20,22-17)14-9-5-12(16-2)6-10-14/h3-10H,1-2H3
• InChIKey: CFHGBZLNZZVTAY-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: bis(4-methoxyphenyl)-1,3,2λ^5,4λ^5-dithiadiphosphetane-2,4-dithione; bis(4-methoxyphenyl)-1,3,2$l^{5},4$l^{5}-dithiadiphosphetane-2,4-dithione
• IUPAC传统名: lawesson's reagent
• 别名: 4-甲氧基苯基硫代磷环二(硫代酸酐); Lawesson 试剂; 劳氏试剂; 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide; 2,4-Bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane; 2,4-Bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide; 4-Methoxyphenylthiophosphoric cyclic di(thioanhydride); Lawesson reagent; Lawesson Reagent; 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulphide; 2,4-Bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane 97%; LR; Lawesson's reagent; Lawesson's Reagent; 2,4-bis(4-METHOXYPHENYL)-1,3-DITHIA-2-4-DIPHOSPHETANE 2,4-DISULFIDE; Lawesson reagent; 4-Methoxyphenylthionophosphine sulfide dimer; Lawesson's Reagent

登记号

• CAS号: 19172-47-5
• EC号: 242-855-4
• MDL号: MFCD00005171
• Beilstein号: 1024888
• 默克索引号: 145391
• PubChem SID: 24874849; 162076856; 24853631
• PubChem CID: 87949
• Chemspider ID: 79346
• 维基百科标题: Lawesson's_reagent

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 5.2936
• LogD (pH = 7.4): 5.2936
• Log P: 5.2936
• 摩尔折射率: 104.6542 cm^3
• 极化性: 43.731716 Å^3
• 极化表面积: 18.46 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Insoluble in water
• 外观: Slightly yellow powder
• 熔点: 221-225°C; 228 - 231 °C; 228-230 °C; 228-230 °C(lit.); 228-230°C
• 密度: , solid

安全信息

• 保存条件: Room Temperature (15-30°C), Desiccate, Store Under Nitrogen
• 保存注意事项: Moisture Sensitive; Toxic/Highly Flammable/Store under Nitrogen/Moisture Sensitive
• 欧盟危险性物质标志: 易燃性(Flammable) (F); Harmful (XN); Irritant; X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: UN3134
• 德国WGK号: 3
• 联合国危险货物等级: 4.3
• 联合国危险货物包装类别(PG): III
• 危险公开号: 15/29; 15/29 20/21/22; 15/29-20/22-36/37/38; R:22
• 安全公开号: 22 45 7/8; 7/8-43; 7/8-9-26-33-36/37-43; S:36/37/39
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS06
• GHS警示词: Danger
• GHS危险声明: H261; H331-H302-H315-H319-H335-H261
• GHS警示性声明: P231 + P232-P422; P231+P232-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 欧盟补充危害声明: Contact with water liberates toxic gas.

产品相关信息

• 纯度: ≥98.0% (S); 97%
• 级别: purum
• Empirical Formula (Hill Notation): C14H14O2P2S4

详细说明

MP Biomedicals - 02155434

(Lawesson's Reagent)

Sigma Aldrich - 227439

Application
近来用于室温下原位生成 tropothione 并使用二烯亲合体捕集的硫杂化试剂。1
包装
10, 25, 100 g in glass bottle

Sigma Aldrich - 61750

Other Notes
目前所知的最有效硫杂化反应试剂，用于羧酰胺、酮、内酯和亚胺、内酰胺、3-氧代羧基衍生物（酰胺、酯和腈）以及硫代-S-酯的硫杂化反应1；寡肽的选择性硫化反应2,3；关于 LR 的综述4,5

参考文献

• Powerful thionation agent used for the replacement of the carbonyl oxygen of ketones, amides and esters, by sulfur: Bull. Soc. Chim. Belg., 87, 223, 229, 293, 299, 525 (1978); Tetrahedron, 35, 1339, 2433 (1979). Review: Tetrahedron, 41, 5061 (1985). For conversion of N-methylpyrrolidinone to the thiolactam, see: Org. Synth. Coll., 7, 372 (1990).
• Uracil and its derivatives are thionated selectively at the 4-position: Synthesis, 152 (1988). Peptides give endo-thiopeptides: Tetrahedron, 37, 3635 (1981). Esters, orthoesters, acetals and epoxides give the thio-analogues: Monatsh. Chem., 115, 769 (1984). Used, in combination with 1,1,3,3-Tetramethylthiourea, L13392, for formation of bis-thioesters for subsequent radical coupling as a method of ring formation in Nicolaou's syntheses of hemibrevitoxin B and brevitoxin B: J. Am. Chem. Soc., 115, 3558 (1993); 117, 10227 (1995).
• Reaction with 1,4-diketones gives 2,5-disubstituted thiophenes in high yield: Synthesis, 1061 (1982).
• Reaction with ɑ-diazo ketones has been used to prepare 1,2,3-thiadiazoles: Heterocycles, 19, 241 (1982).
• Benzylic and related alcoholsare converted to the corresponding thiols: J. Chem. Soc., Chem. Commun., 205 (1989); J. Chem. Soc., Perkin 1, 1113 (1993).
• Reacts with N-protected amino acids to give mixed anhydrides, useful in peptide coupling: Tetrahedron, 38, 3267 (1982). See Appendix 6.
• Has also been found to act as an efficient trapping agent for 1,3-dipoles under very mild conditions. Its powerful dipolarophile character allows it to be used as a "1,3-dipole indicator" even with dipoles of low reactivity, the outcome of the reaction being readily verified by ³¹P NMR: J. Org. Chem., 60, 3904 (1995).