triethyl phosphite

• ChemBase编号: 104745
• 分子式: C6H15O3P
• 平均质量: 166.155261
• 单一同位素质量: 166.07588097
• SMILES: CCOP(OCC)OCC
• Canonical SMILES: CCOP(OCC)OCC
• InChI: InChI=1S/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H3
• InChIKey: BDZBKCUKTQZUTL-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: triethyl phosphite
• IUPAC传统名: triethyl phosphite
• 别名: 亚磷酸三乙酯; P(EtO)3; P(OEt)3; Triethyl phosphite; TRIETHYL PHOSPHITE; Triethoxyphosphine; Phosphorous acid triethyl ester

登记号

• CAS号: 122-52-1
• EC号: 204-552-5
• MDL号: MFCD00009084
• Beilstein号: 956578
• PubChem SID: 24889381; 162091936; 24900347
• PubChem CID: 31215
• Chemspider ID: 28956
• 维基百科标题: Triethyl_phosphite

理论计算性质

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 1.9333991
• LogD (pH = 7.4): 1.9334
• Log P: 1.9334
• 摩尔折射率: 42.2225 cm^3
• 极化性: 16.630682 Å^3
• 极化表面积: 27.69 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: organic solvents
• 外观: colorless liquid
• 熔点: -112 °C; -112°C; -70°C
• 沸点: 155-157°C; 156 - 158 °C at 1013 hPa; 156 °C(lit.); 156 °C (57–58 °C/16 mm)
• 闪点: 129.2 °F; 43°C(109°F); 52 °C (closed cup and DIN 51755); 54 °C
• 密度: .954 g/cm^3 at 20 °C; 0.958; 0.969 g/mL; 0.969 g/mL at 25 °C(lit.)
• 折射率: 1.4130; n20/D 1.413; n20/D 1.413(lit.)
• 蒸汽压: 6 hPa at 20 °C
• 作为配体的用途: Reductions

安全信息

• 保存条件: Room Temperature (15-30°C)
• 保存注意事项: Air & Moisture Sensitive
• RTECS编号: TH1130000
• 欧盟危险性物质标志: 易燃性(Flammable) (F); X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2323; UN2323
• 德国WGK号: 1
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 3; III
• 澳大利亚Hazchem: 3Y
• 危险公开号: 10-20-36-43-52/53; 10-22-36/37/38; R:10-22-36
• 安全公开号: 16-26-36; 24-26-36/37-61; S:9-16-26-29-36/37/39
• 欧盟危险货物分类: F1
• 欧盟危险识别号(EUHIN): 3B
• 美国ERG指导号: 129
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Warning
• 主要危害: toxic
• GHS危险声明: H226-H302-H315-H319-H332-H335; H226-H332-H319-H317-H402-H412
• GHS警示性声明: P261-P305 + P351 + P338; P280H-P262-P273-P305+P351+P338
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2323 3/PG 3

产品相关信息

• 纯度: ≥95.0% (GC); 95+%; 98%
• 级别: purum
• 杂质: ≤1% triethyl phosphate and diethyl phosphite
• 线性分子式: (C2H5O)3P

详细说明

MP Biomedicals - 02157015

NOT FOR EXPORT

Sigma Aldrich - T61204

Application
Used as a reducing agent; can react with electrophiles to form phosphonates or phosphates; forms a stable complex with copper(I) iodide.
包装
4 L in glass bottle
5, 100, 500 mL in glass bottle

Sigma Aldrich - 90540

Other Notes
该亚磷酸酯的活性低于三苯基膦，但所得产物中的非对映体比例更好1,2

参考文献

• Reaction with acyl halides yields acylphosphonate esters, borohydride reduction of which gives aldehydes: Chem. Ber., 103, 2984 (1970).
• Precursor of phosphonate esters by the Arbuzov reaction. See also Triisopropyl phosphite, A15247. The Arbuzov isomerization to diethyl ethanephosphonate can be induced by a trace of iodine: Synth. Commun., 20, 239 (1990). For reviews of the Arbuzov reaction, see: Org. React., 6, 273 (1951); Chem. Rev., 71, 317 (1971); 81, 415 (1981).
• Reducing agent: o-nitrobenzylidineaniline gives 2-phenylindazole: Org. Synth. Coll., 5, 941 (1973). For a review of the phosphite reduction of aromatic nitro compounds to heterocycles, see: Synthesis, 11 (1969). Reaction with ?-nitro styrenes forms 3-phenyl-2-substituted indoles in good yields: J. Org. Chem., 57, 6508 (1992).
• Use in a modified Staudinger reaction provides a useful one-pot conversion of an alkyl bromide to an amine via the azide: Synthesis, 202 (1985):
  
• For reviews of the Staudinger reaction, see: Tetrahedron, 37, 437 (1981); 48, 353 (1992).