Triethylphosphine

Triethylphosphine Basic information
Product Name:Triethylphosphine
Synonyms:AURORA KA-1111;CYTOP(R) 320;(C2H5)3P;Phosphorus triethyl;tl409;triethylphosphane;Triethyl-phosphane;triethyl-phosphin
CAS:554-70-1
MF:C6H15P
MW:118.16
EINECS:209-068-8
Product Categories:organophosphine ligand;organophosphorus ligand;Organics;Phosphine Ligands;Catalysis and Inorganic Chemistry;Phosphorus Compounds;Tertiary Phosphines
Mol File:554-70-1.mol
Triethylphosphine Structure
Triethylphosphine Chemical Properties
Melting point -88°C
Boiling point 127-128 °C(lit.)
density 0.88 g/mL at 20 °C
refractive index n20/D 1.456(lit.)
Fp 1 °F
form liquid
color colorless
Odorvile, nauseating odor.stench
Water Solubility Insoluble in water.
Sensitive Air & Moisture Sensitive
Merck 14,9675
BRN 969170
InChIKeyRXJKFRMDXUJTEX-UHFFFAOYSA-N
CAS DataBase Reference554-70-1(CAS DataBase Reference)
NIST Chemistry ReferencePhosphine, triethyl-(554-70-1)
EPA Substance Registry SystemPhosphine, triethyl- (554-70-1)
Safety Information
Hazard Codes F,C
Risk Statements 11-34-67-17-40-37-19
Safety Statements 26-36/37/39-45-7/9-33-16
RIDADR UN 2924 3/PG 2
WGK Germany 3
RTECS SZ3400000
10-13-23
TSCA Yes
HazardClass 4.2
PackingGroup I
MSDS Information
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Triethylphosphine English
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ALFA English
Triethylphosphine Usage And Synthesis
Chemical PropertiesColorless Transparent Liquid
UsesIn organic syntheses.
Usessuzuki reaction
UsesTriethylphosphine is used as a ligand for arylation. It is used in organic synthesis.
DefinitionChEBI: Triethylphosphine is a tertiary phosphine.
Safety ProfileHighly flammable liquid. Reactswith oxygen at low temperatures to form an explosiveproduct. When heated to decomposition it emits toxicfumes of POx.
Purification MethodsAll operations should be carried out in an efficient fume cupboard because it is flammable, toxic and has a foul odour. Purify the phosphine by fractional distillation at atmospheric pressure in a stream of dry N2, as it is oxidised by air to the oxide. In 300% excess of CS2 it forms Et3PCS2 (m 118-120o crystallising from MeOH) which decomposes in CCl4 to give Et3PS as a white solid m 94o when recrystallised from EtOH. [Sorettas & Isbell J Org Chem 27 273 1962, Henderson & Streuli J Am Chem Soc 82 5791 1960, pK: Henderson & Streuli J Am Chem Soc 82 5791 1960, see also trimethylphosphine.] Store it in sealed vials under N2. Alternatively, dissolve it in Et2O and shake it with a solution of AgI and KI to form the insoluble complex. Filter off the complex, dry it over P2O5 and the Et3P is regenerated by heating the complex in a tube attached to a vacuum system. [Hewitt & Holliday J Chem Soc 530 1953, Schettas & Isbell J Org Chem 27 2573 1962, Kosolapoff Organophosphorus Compounds, Wiley p 31 1950, Beilstein 4 IV 3431.]
Triethylphosphine Preparation Products And Raw materials
Preparation ProductsAuranofin-->ETHYL ISOCYANIDE-->Benzyltriethylammonium bromide-->BENZYLTRIETHYLPHOSPHONIUM BROMIDE-->TETRAETHYLPHOSPHONIUM HYDROXIDE
TRICYCLOHEXYLPHOSPHINE OXIDE Tributylphosphine Tetrabutylphosphonium bromide TRI-N-PROPYLPHOSPHINE OXIDE Triethylphosphine Trioctylphosphine oxide BORANE-TRIBUTYLPHOSPHINE COMPLEX 98 Tetrabutylphosphonium chloride STEARYLTRIBUTYLPHOSPHONIUM BROMIDE TRIBENZYLPHOSPHINE OXIDE TETRAETHYLPHOSPHONIUM CHLORIDE TRIS[2-(DIPHENYLPHOSPHINO)ETHYL]PHOSPHINE TETRAETHYLPHOSPHONIUM IODIDE TRIETHYLPHOSPHINE OXIDE Cetyltributylphosphonium bromide TRIS(2-CYANOETHYL)PHOSPHINE chloro(triethylphosphine)gol Tricyclohexyl phosphine

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