Tetraethyl pyrophosphite
Basic information
- CAS
21646-99-1- Standard SMILES
CCOP(OCC)OP(OCC)OCC- InChIKey
RDXABLXNTVBVML-UHFFFAOYSA-N- Molecular formula
- C8H20O5P2
- Average molar mass
- 258.19 g/mol
- Monoisotopic mass
- 258.07859773
Names & identifiers
- Preferred name
- Tetraethyl pyrophosphite
- IUPAC
- diethoxyphosphanyl diethyl phosphite
- English name
- Tetraethyl pyrophosphite
- Molecular formula
- C8H20O5P2
- Molecular weight
- 258.19
Names & synonyms
Tetraethyl pyrophosphite21646-99-1EINECS 244-494-8DTXSID20176034RefChem:896985DTXCID3098525244-494-8diethoxyphosphanyl diethyl phosphiteTetraethyl diphosphiteEthyl Pyrophosphite; Pyrophosphorous Acid, Tetraethyl Ester; Tetraethyl Diphosphite; Tetraethyl Pyrophosphite; diethoxyphosphanyl diethyl phosphite; EINECS 244-494-8Tetraethyl diphosphite #SCHEMBL6994
Show more names
Diphosphorous acid tetraethyl esterOxybis(diethoxyphosphine)Bis(diethoxyphosphino) etherTetraethyl pyrophosphite 96%iethoxyphosphanyldiethylphosphiteTetraethyl pyrophosphite,93%,tech.TETRAETHYL PYROPHOSPHITE, TECH., 93%Bis(phosphorous acid diethyl)anhydrideOxybis(phosphonous acid diethyl) ester
Tetraethyl pyrophosphite, 96%Diphosphorous acid, tetraethyl esterAR-1H3984AKOS015916079DB-045656NS00051129
Database identifiers
- CAS
21646-99-1- PubChem CID
- 88987
- DTXSID
DTXSID20176034- EC Number
- 244-494-8
- Nikkaji
- J123.409I
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 46.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 10
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 112
Physicochemical properties
- Boiling point
- 79 · 79-81 °C/1 mmHg (lit.)
- Density
- 1.057 g/mL · 1.057 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.434(lit.)
- Flash point
- 230 °F · >230 °F
- solubility
- Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly)
- form
- Oil
- color
- Colourless
- InChI
- 1S/C8H20O5P2/c1-5-9-14(10-6-2)13-15(11-7-3)12-8-4/h5-8H2,1-4H3
- InChIKey
- RDXABLXNTVBVML-UHFFFAOYSA-N
- SMILES
- CCOP(OCC)OP(OCC)OCC
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationHazard Traits - Environmental tox
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 10 - Combustible liquids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
UsesTetraethyl Pyrophosphite is used as a reagent in the preparation of peptides and in the phosphonylation of carbonyl compounds.
UsesThe product can be used as a reagent for peptide synthesis.
Preparation methods
PreparationThe most convenient method involves the reaction of diethyl phosphite with diethyl phosphorochloridite. Diethyl phosphorochloridite (223 g) is added rapidly to a solution of diethyl phosphite (138 g) and triethylamine (101 g) in benzene (200 ml). The mixture is filtered and the benzene removed by distillation at reduced pressure. The product is isolated by further distillation at reduced pressure (79-81 °C/0.15 mmHg) in 41% yield.
Upstream & downstream products
Downstream products
Related reactions
1 records
Compound notes
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