Triethyl Phosphite - Materials / Alfa Chemistry

NAVIGATION

Triethyl Phosphite

PRICE INQUIRY

Catalog Number

ACMA00017208

Product Name

Triethyl Phosphite

Category

Polymers; PVC Stabilizers

Description

Triethyl phosphite appears as a clear colorless liquid with a strong foul odor. Flash point 130°F. Less dense than water and insoluble in water. Vapors heavier than air.;COLOURLESS LIQUID.

IUPAC Name

triethyl phosphite

Molecular Weight

166.16g/mol

Molecular Formula

C6H15O3P;C6H15O3P

Canonical SMILES

CCOP(OCC)OCC

InChI

InChI=1S/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H3

InChI Key

BDZBKCUKTQZUTL-UHFFFAOYSA-N

Boiling Point

311 °F at 760 mm Hg (USCG, 1999);157.9 °C;157.9 °C;157-159 °C

Melting Point

-112 °C

Flash Point

115 °F (USCG, 1999);54 °C (129 °F) - closed cup;54 °C c.c.

Density

0.969 (USCG, 1999);0.9629 g at 20 °C;Relative density (water = 1): 0.97

Solubility

Soluble in alcohol, ether;Solubility in water: reaction

Application

Triethyl phosphite serves multiple purposes in the field of chemistry due to its versatile chemical properties. It is primarily utilized as a ligand in organometallic chemistry and has a significant role as a reagent in organic synthesis. Beyond these applications, triethyl phosphite is pivotal in 31P NMR spectroscopy, where it is used as a reference to the phosphoric acid standard. Its reducing capabilities are exploited for synthesizing compounds like 2-phenylindazole from o-nitrobenzylidineaniline, and it can react with electrophiles to form phosphonates. It is effective in forming stable complexes, such as with copper(I) iodide, and is integral to modified Staudinger reactions, which convert alkyl bromides to amines through azides. Triethyl phosphite is also crucial in synthesizing 3-phenyl-2-substituted indoles via its reaction with beta-nitro styrenes, a process beneficial in creating phosphonate reagents for advanced studies. For example, it facilitates the preparation of diethyl 3-alkoxycarbonyl-2-propenylphosphonates with yields ranging from 72-91% when reacting with methyl or ethyl 4-bromocrotonates at elevated temperatures. It similarly aids in producing other specialized phosphonates through its reactions with various substrates under specific conditions, showcasing its valuable role in synthetic organic chemistry.

Color/Form

Colorless liquid

Complexity

55.7

Covalently-Bonded Unit Count

EC Number

204-552-5

Exact Mass

166.075881g/mol

Formal Charge

Heavy Atom Count

ICSC Number

0684

MeSH Entry Terms

triethyl phosphite;triethyl phosphite, (32)P-labeled

Monoisotopic Mass

166.075881g/mol

NSC Number

5284

Odor

Pungent odor;Characteristic, obnoxious phosphite odor

Other Experimental

Decomposes when dissolved in water;Hydroxy radical reaction rate constant = 5.8X10-11 cu cm/molec-sec at 25 °C (est)[Hydroxy radical reaction rate constant = 5.8X10-11 cu cm/molec-sec at 25 °C (estimated)

Refractive Index

Index of refraction: 1.4127 at 20 °C/D

Rotatable Bond Count

RTECS Number

TH1130000

Stability

Stable under recommended storage conditions.

UNII

6B2R04S55G

UN Number

2323;2323;2323;2323

Vapor Pressure