triethyl phosphite

• ChemBase ID: 104745
• Molecular Formular: C6H15O3P
• Molecular Mass: 166.155261
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: triethyl phosphite
• IUPAC Traditional name: triethyl phosphite
• Synonyms: P(EtO)3; P(OEt)3; Triethyl phosphite; TRIETHYL PHOSPHITE; Triethoxyphosphine; Phosphorous acid triethyl ester; 亚磷酸三乙酯

Database IDs

• CAS Number: 122-52-1
• EC Number: 204-552-5
• MDL Number: MFCD00009084
• Beilstein Number: 956578
• PubChem SID: 24889381; 162091936; 24900347
• PubChem CID: 31215
• Chemspider ID: 28956
• Wikipedia Title: Triethyl_phosphite

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.9333991
• LogD (pH = 7.4): 1.9334
• Log P: 1.9334
• Molar Refractivity: 42.2225 cm^3
• Polarizability: 16.630682 Å^3
• Polar Surface Area: 27.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: organic solvents
• Apperance: colorless liquid
• Melting Point: -112 °C; -112°C; -70°C
• Boiling Point: 155-157°C; 156 - 158 °C at 1013 hPa; 156 °C(lit.); 156 °C (57–58 °C/16 mm)
• Flash Point: 129.2 °F; 43°C(109°F); 52 °C (closed cup and DIN 51755); 54 °C
• Density: .954 g/cm^3 at 20 °C; 0.958; 0.969 g/mL; 0.969 g/mL at 25 °C(lit.)
• Refractive Index: 1.4130; n20/D 1.413; n20/D 1.413(lit.)
• Vapor Pressure: 6 hPa at 20 °C
• Ligand For: Reductions

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Air & Moisture Sensitive
• RTECS: TH1130000
• European Hazard Symbols: Flammable (F); X; Harmful (Xn)
• UN Number: 2323; UN2323
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 3; III
• Australian Hazchem: 3Y
• Risk Statements: 10-20-36-43-52/53; 10-22-36/37/38; R:10-22-36
• Safety Statements: 16-26-36; 24-26-36/37-61; S:9-16-26-29-36/37/39
• EU Classification: F1
• EU Hazard Identification Number: 3B
• Emergency Response Guidebook(ERG) Number: 129
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• Main Hazard: toxic
• GHS Hazard statements: H226-H302-H315-H319-H332-H335; H226-H332-H319-H317-H402-H412
• GHS Precautionary statements: P261-P305 + P351 + P338; P280H-P262-P273-P305+P351+P338
• Personal Protective Equipment: 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

Product Information

• Purity: ≥95.0% (GC); 95+%; 98%
• Grade: purum
• Impurities: ≤1% triethyl phosphate and diethyl phosphite
• Linear Formula: (C2H5O)3P

DETAILS

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.
Packaging
4 L in glass bottle
5, 100, 500 mL in glass bottle

Sigma Aldrich - 90540

Other Notes
This phosphite is less reactive than triphenylphosphine but can lead to a more favorable diastereomer ratio in products1,2

REFERENCES

• 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).