diethyl [(diethoxyphosphoryl)methyl]phosphonate

• ChemBase编号: 75008
• 分子式: C9H22O6P2
• 平均质量: 288.214902
• 单一同位素质量: 288.08916168
• SMILES: P(=O)(CP(=O)(OCC)OCC)(OCC)OCC
• Canonical SMILES: CCOP(=O)(CP(=O)(OCC)OCC)OCC
• InChI: InChI=1S/C9H22O6P2/c1-5-12-16(10,13-6-2)9-17(11,14-7-3)15-8-4/h5-9H2,1-4H3
• InChIKey: STJWVOQLJPNAQL-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: diethyl [(diethoxyphosphoryl)methyl]phosphonate
• IUPAC传统名: diethyl (diethoxyphosphoryl)methylphosphonate
• 别名: 亚甲基二磷酸四乙酯; 双(二乙氧基氧膦基)甲烷; 四乙基亚甲基二磷酸酯; 亚甲基二磷酸四乙酯; NSC 133889; Bis(diethoxyphosphinyl)methane; Methylenediphosphonic acid tetraethylester; Tetraethyl methylenediphosphonate; Tetraethyl methanediylbis(phosphonate); Tetraethyl (methylene)bisphosphonate; Methylenediphosphonic acid tetraethyl ester

登记号

• CAS号: 1660-94-2
• EC号: 216-764-5
• MDL号: MFCD00039887
• Beilstein号: 1813241
• PubChem SID: 162039926; 24862057
• PubChem CID: 15455

理论计算性质

• 极化性: 26.840658 Å^3
• 极化表面积: 71.06 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: true
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 1.2342206
• LogD (pH = 7.4): 1.2342206
• Log P: 1.2342206
• 摩尔折射率: 64.8021 cm^3

分子性质

理化性质

• 沸点: 151-153°C/1.2mm; 171-174 °C/11 mmHg(lit.); 171-174°C
• 闪点: >110°C; >110°C(230°F); 110 °C; 230 °F
• 密度: 1.16 g/mL at 25 °C(lit.); 1.162
• 折射率: 1.4400; n20/D 1.442; n20/D 1.442(lit.)

安全信息

• 保存注意事项: Irritant
• RTECS编号: SZ9150000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38; 36/38
• 安全公开号: 26-36; 26-37
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319; H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P280G-P305+P351+P338
• 个人保护装置: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

产品相关信息

• 纯度: ≥97.0% (GC); 97%; 98+%
• 级别: purum
• 线性分子式: CH2[P(O)(OCH2CH3)2]2

详细说明

Sigma Aldrich - 359181

包装
5, 25 mL in glass bottle
Application
Reactant for synthesis of:
• Dual substrate-site inhibitors of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase1
• Unnatural alpha-amino acid derivatives containing gem-biphosphonates2
• Biphenyl sulfonylamino Me bisphosphonic acids as inhibitors of matrix metalloproteinases and bone resorption3
• Lycopene via Wittig-Horner reaction4
• Alkylaminoethylbisphosphinic acids to target farnesyl diphosphate synthase5
• Aromatic bisphosphonates for use as inhibitors of geranylgeranyl diphosphate synthase6Precursor for synthesis of dendritic polyglycerol anions used toward L-selectin inhibition7

Sigma Aldrich - 64256

Other Notes
Horner-Wittig 试剂，用于合成乙烯基磷酸酯8；通过 Horner-Wittig 反应以及加氢反应制备磷酸酯的电子等排体9,10
Application
Reactant for synthesis of:
• Dual substrate-site inhibitors of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase1
• Unnatural alpha-amino acid derivatives containing gem-biphosphonates2
• Biphenyl sulfonylamino Me bisphosphonic acids as inhibitors of matrix metalloproteinases and bone resorption3
• Lycopene via Wittig-Horner reaction4
• Alkylaminoethylbisphosphinic acids to target farnesyl diphosphate synthase5
• Aromatic bisphosphonates for use as inhibitors of geranylgeranyl diphosphate synthase6Precursor for synthesis of dendritic polyglycerol anions used toward L-selectin inhibition7

参考文献

• Reacts with aromatic aldehydes to give styrylphosphonates in a two-phase system, no added phase-transfer catalyst being necessary: Synthesis, 396 (1976). For cleavage of the resulting vinyl phosphonates to ɑ-hydroxyaldehydes, see Osmium(VIII) oxide, 12103.