diethyl (cyanomethyl)phosphonate

• ChemBase编号: 91244
• 分子式: C6H12NO3P
• 平均质量: 177.138141
• 单一同位素质量: 177.05547988
• SMILES: P(=O)(CC#N)(OCC)OCC
• Canonical SMILES: CCOP(=O)(CC#N)OCC
• InChI: InChI=1S/C6H12NO3P/c1-3-9-11(8,6-5-7)10-4-2/h3-4,6H2,1-2H3
• InChIKey: KWMBADTWRIGGGG-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: diethyl (cyanomethyl)phosphonate
• IUPAC传统名: diethyl cyanomethylphosphonate
• 别名: 氰甲基磷酸二乙酯; 二乙基氰甲基磷酸酯; 氰甲基膦酸二乙酯; 氰甲基膦酸二乙酯; 二乙基氰甲基磷酸酯; Diethyl phosphonoacetonitrile; (Diethylphosphono)acetonitrile; (Diethoxyphosphoryl)acetonitrile; Diethyl (cyanomethyl)phosphonate 98%; Cyanomethylphosphonic acid diethyl ester; Diethyl cyanomethylphosphonate; (Diethoxyphosphinyl)acetonitrile; Diethyl Cyanomethanephosphonate; O,O-Diethyl (Cyanomethyl)phosphonate; NSC 407826; Diethyl Cyanomethylphosphonate; P-(Cyanomethyl)phosphonic Acid Diethyl Ester; (Cyanomethyl)diethoxyphosphine Oxide; (Diethylphosphono)acetonitrile; DIETHYL CYANOMETHYL PHOSPHATE; diethyl (cyanomethyl)phosphonate

登记号

• CAS号: 2537-48-6
• EC号: 219-806-0
• MDL号: MFCD00001893
• Beilstein号: 1772981
• PubChem SID: 162077948; 24894272
• PubChem CID: 75676

理论计算性质

• Acid pKa: 12.055647
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 0.17517574
• LogD (pH = 7.4): 0.17516631
• Log P: 0.17517588
• 摩尔折射率: 41.0751 cm^3
• 极化性: 16.410683 Å^3
• 极化表面积: 59.32 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Dichloromethane; Ethyl Acetate; Tetrahydrofuran
• 外观: Clear Oil
• 沸点: 101-102 °C/0.4 mmHg(lit.); 101-102°C/0.4mm; 132-135°C/1.2mm
• 闪点: >110°C(230°F); 113 °C; 113°C; 235.4 °F
• 密度: 1.094; 1.095; 1.095 g/mL at 25 °C(lit.)
• 折射率: 1.4330; n20/D 1.434; n20/D 1.434(lit.)

安全信息

• 保存注意事项: Corrosive/Irritant
• 欧盟危险性物质标志: X; 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 1760; UN3278
• 德国WGK号: 3
• 联合国危险货物等级: 6.1; 8
• 联合国危险货物包装类别(PG): 2; III
• 危险公开号: 20/21/22-36/38; 38
• 安全公开号: 26-28; 9-23-26-36/37
• TSCA收录: 否
• GHS危险品标识: GHS06; GHS07
• GHS警示词: Warning
• GHS危险声明: H315; H331-H302-H312-H315-H319
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1760 8/PG 2
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98.0% (GC); 98%; 98+%
• 级别: purum
• 线性分子式: NCCH2PO(OC2H5)2

详细说明

MP Biomedicals - 05206945

MP Biomedicals Rare Chemical collection

Sigma Aldrich - D91705

包装
10, 50 g in glass bottle

Sigma Aldrich - 28503

Other Notes
1Horner-Wittig 试剂

Toronto Research Chemicals - D444165

Wittig reagent.

参考文献

• Laine, D., et al.: J. Med. Chem., 52, 5241 (2009)
• Nakao, A., et al.: Bioorg. Med. Chem. Lett., 19, 4607 (2009)
• Arakawa, Y., et al.: Chem. Pharm. Bull., 57, 167 (2009)
• The active methylene group can be monoalkylated under phase transfer conditions with alkyl iodides or allylic or benzylic bromides: Synthesis, 516 (1975). Use of alumina as base leads predominantly to the Knoevenagel product rather than the Wadsworth-Emmons: Tetrahedron, 41, 1259 (1985).
• Horner-Wadsworth-Emmons olefination converts carbonyl compounds to substituted acrylonitriles: J. Am. Chem. Soc., 83, 1733 (1961); J. Org. Chem., 30, 505 (1965). LiOH has been found to be an effective base for this reaction: Tetrahedron Lett., 44, 1333 (2003). See Appendix 1. See also 3-Coumaranone, A10202.