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.)

Flash point:

1 °F

form 

liquid

color 

colorless

Odor

vile, nauseating odor.stench

Water Solubility 

Insoluble in water.

Sensitive 

Air & Moisture Sensitive

Merck 

14,9675

BRN 

969170

InChIKey

RXJKFRMDXUJTEX-UHFFFAOYSA-N

CAS DataBase Reference

554-70-1(CAS DataBase Reference)

NIST Chemistry Reference

Phosphine, triethyl-(554-70-1)

EPA Substance Registry System

Phosphine, 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

F 

10-13-23

TSCA 

Yes

HazardClass 

4.2

PackingGroup 

I

MSDS

• Language:English Provider:Triethylphosphine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Triethylphosphine Usage And Synthesis

Chemical Properties

Colorless Transparent Liquid

Uses

suzuki reaction

Uses

Triethylphosphine is used as a ligand for arylation. It is used in organic synthesis.

Uses

In organic syntheses.

Definition

ChEBI: Triethylphosphine is a tertiary phosphine.

Safety Profile

Highly flammable liquid. Reactswith oxygen at low temperatures to form an explosiveproduct. When heated to decomposition it emits toxicfumes of POx.

Synthesis

Triethylphosphine is prepared most conveniently by the reaction of excess Grignard reagent on phosphorus trichloride or triphenylphosphite.
3CH3CH2MgBr + PCl3 → (CH3CH2)3P + 3MgBrCl
3CH3CH2MgBr + P(OC6H5)3 → P(CH3CH2)3 + 3C6H5-OMgCl

Purification Methods

All 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(554-70-1)Related Product Information

• Tributylphosphine
• Triphenylphosphine
• Triethylaluminum
• Triethylsilane
• Tricyclohexyl phosphine
• Trioctylphosphine oxide
• TRIETHYLPHOSPHINE OXIDE
• TRICYCLOHEXYLPHOSPHINE OXIDE
• Tetrabutylphosphonium chloride
• TRI-N-PROPYLPHOSPHINE OXIDE
• Cetyltributylphosphonium bromide
• Tetrabutylphosphonium bromide
• TRIS[2-(DIPHENYLPHOSPHINO)ETHYL]PHOSPHINE
• TRI-N-BUTYLPHOSPHINE OXIDE
• Triethyl phosphonoacetate
• Fosetyl aluminum
• TRIETHYL PHOSPHONOACETATE
• TRIS(2-CYANOETHYL)PHOSPHINE