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Triethyl phosphite

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Identification
Molecular formula
P(OCH2CH3)3
CAS number
122-52-1
IUPAC name
triethyl phosphite
State
State
Triethyl phosphite is a liquid at room temperature. It is commonly used in organic synthesis as a reagent in various chemical reactions.
Melting point (Celsius)
-112.80
Melting point (Kelvin)
160.35
Boiling point (Celsius)
156.00
Boiling point (Kelvin)
429.15
General information
Molecular weight
166.16g/mol
Molar mass
166.1570g/mol
Density
0.9625g/cm3
Appearence
Triethyl phosphite is a transparent, colorless liquid. It may exhibit a faint characteristic odor associated with organophosphorus compounds.
Comment on solubility

Solubility of Triethyl Phosphite

Triethyl phosphite (C6H15O4P) is known for its intriguing solubility properties. Being an organophosphorus compound, its solubility is influenced by both its chemical structure and the polar nature of its functional groups. Here are some key points regarding its solubility:

  • Soluble in Organic Solvents: Triethyl phosphite is highly soluble in various organic solvents, such as ether, acetone, and benzene, primarily due to its non-polar ethyl groups which enhance its compatibility with non-polar solvents.
  • Limited Solubility in Water: This compound exhibits limited solubility in water, primarily because of the hydrophobic ethyl groups that resist interacting with water molecules.
  • Hydrolysis Potential: While its solubility in water is low, triethyl phosphite can undergo hydrolysis, leading to products that may have higher solubility in aqueous solutions.
  • Solubility Variance: The solubility can vary significantly depending on temperature and the presence of other solutes, which may influence the interactions in solution.

In conclusion, while triethyl phosphite shows a strong affinity for organic solvating environments, its solubility in water is rather modest. Understanding these solubility characteristics is crucial for its applications in synthetic chemistry and as a reagent in various chemical processes.

Interesting facts

Interesting Facts about Triethyl Phosphite

Triethyl phosphite is a fascinating compound with a variety of applications and properties that intrigue both chemists and industry professionals alike. Here are some notable facts about this versatile phosphite ester:

  • Versatile Reagent: Triethyl phosphite is commonly used as a reagent in organic synthesis, particularly in phosphorus chemistry. It serves as a source of phosphorus for the preparation of various phosphorus-containing compounds.
  • Role in the Synthesis of Organophosphorus Compounds: This compound plays a critical role in the synthesis of organophosphorus compounds, which are significant in agriculture, pharmaceuticals, and material science.
  • Applications in Catalysis: It is utilized in catalytic reactions, such as the generation of phosphorus ylide, which can be used in the Wittig reaction—a key transformation in organic synthesis.
  • Toxicity Considerations: While triethyl phosphite has many valuable applications, chemists must handle it with care due to its potential toxicity and the need for proper safety protocols.
  • Hydrolysis Sensitivity: One of the interesting characteristics of triethyl phosphite is its sensitivity to hydrolysis, leading to the formation of phosphonic acids, which are also crucial in various biochemical processes.

In summary, triethyl phosphite is not just another chemical compound; it embodies significant roles in both academic research and practical applications. Its diverse functionalities make it an invaluable asset in synthetic organic chemistry.

Synonyms
TRIETHYL PHOSPHITE
122-52-1
Triethoxyphosphine
Phosphorous acid, triethyl ester
Ethyl phosphite, (EtO)3P
Fosforyn trojetylowy
DTXSID2026991
6B2R04S55G
NSC-5284
TRIS(ETHOXY)PHOSPHINE
DTXCID506991
RefChem:191514
204-552-5
triethylphosphite
Phosphorous Acid Triethyl Ester
Triethoxyphosphine-d15
P(OEt)3
(C2H5O)3P
147672-00-2
MFCD00009084
Fosforyn trojetylowy [Czech]
CAS-122-52-1
HSDB 895
NSC 5284
EINECS 204-552-5
UN2323
BRN 0956578
UNII-6B2R04S55G
AI3-15624
Phosphorus ether
triethyl-phosphite
tri ethyl phosphite
Triethyl phosphite, 98%
(EtO)3P
EC 204-552-5
SCHEMBL6102
4-01-00-01333 (Beilstein Handbook Reference)
SCHEMBL9538650
TRIETHYL PHOSPHITE [MI]
CHEMBL3186349
SCHEMBL16346372
P(OC2H5)3
NSC5284
TRIETHYL PHOSPHITE [HSDB]
XFA67200
Tox21_201603
Tox21_303083
AKOS000119964
UN 2323
NCGC00164018-01
NCGC00164018-02
NCGC00257080-01
NCGC00259152-01
BP-31214
NS00004886
T0430
Triethyl phosphite, purum, >=95.0% (GC)
A804911
A937097
Q414714
Triethyl phosphite [UN2323] [Flammable liquid]
Triethyl phosphite 100 microg/mL in Acetonitrile
InChI=1/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H
Ethyl phosphite, (EtO)3P (7CI); Ethyl phosphite, Et3PO3 (4CI); NSC 5284; Triethoxyphosphine; Tris(ethoxy)phosphine