Triisopropyl phosphite Property

Boiling point:

63-64 °C11 mm Hg(lit.)

Density 

0.844 g/mL at 25 °C(lit.)

vapor pressure 

<2 mm Hg ( 20 °C)

refractive index 

n20/D 1.411(lit.)

Flash point:

154 °F

storage temp. 

-20°C

form 

Liquid

Specific Gravity

0.844

color 

Clear

Water Solubility 

Insoluble

Sensitive 

Moisture Sensitive

BRN 

1701528

LogP

2

CAS DataBase Reference

116-17-6(CAS DataBase Reference)

NIST Chemistry Reference

Phosphorous acid, tris(1-methylethyl) ester(116-17-6)

EPA Substance Registry System

Phosphorous acid, tris(1-methylethyl) ester (116-17-6)

Safety

Hazard Codes 

T,F

Risk Statements 

25-38-68

Safety Statements 

37-46-45-36/37

RIDADR 

UN 3278 6.1/PG 3

WGK Germany 

3

RTECS 

TH2800000

F 

1-10

Hazard Note 

Toxic/Flammable/Moisture Sensitive/

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29209090

Hazardous Substances Data

116-17-6(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

Precautionary statements

P302+P352IF ON SKIN: wash with plenty of soap and water.

Triisopropyl phosphite Chemical Properties,Usage,Production

Chemical Properties

Colorless liquid; characteristic odor. Miscible with most common organic solvents; insoluble in water; hydrolyzes slowly in water; exposure to air should be minimum; high thermal stability. Combustible.

Uses

Triisopropyl phosphite can be used as a reactant:

• With Ru-based indenylidene complexes to form 1^st generation complexes for metathesis reactions.
• In Perkow-type reaction to synthesize compounds containing polarized carbon-carbon double bonds.
• For the synthesis of phosphonohydrazines by reacting with arylamines and isoamyl nitrite.

Uses

Intermediate for insecticides, component of vinyl stabilizers, lubricant additive, specialty solvent.

Synthesis

A solution of 180.3 g (3 mol) of anhydrous isopropyl alcohol and 447 g (477 ml, 3 mol) of freshly distilled diethylaniline in 1 l of dry petroleum ether (b.p. 40–60°) is placed in a 3-l three-necked flask fitted with a sealed stirrer, an efficient reflux condenser, and a 500-ml dropping funnel, which is charged with a solution of 137.5 g (87.5 ml, 1 mol) of freshly distilled phosphorus trichloride in 400 ml of dry petroleum ether (b.p. 40–60°). The flask is cooled in a cold-water bath. With vigorous stirring, the phosphorus trichloride solution is introduced at such a rate that the mixture boils gently towards the end of the addition. After the addition, which requires about 30 minutes, the mixture is heated under gentle reflux for about 1 hour with stirring. The suspension, containing a copious precipitate of diethylaniline hydrochloride, is then cooled and filtered with suction through a sintered glass funnel. The cake of the amine salt is well compressed and washed with five 100-ml. portions of dry petroleum ether (b.p. 40–60°). The filtrate and washings are combined and concentrated by distillation at water-bath temperature through a 75-cm. Vigreux column. The residue is transferred to a pear-shaped flask and distilled under a water-pump vacuum through a 75-cm. Vigreux column. After a small fore-run, the product Triisopropyl phosphite is collected. It has the following properties: b.p. 43.5°/1.0 mm; nD25 1.4080; d417 0.917.

Purification Methods

Distil it from sodium, under vacuum, through a column packed with glass helices. (This removes any dialkyl phosphonate.) [Ford-Moore & Williams J Chem Soc 1465 1947, Arbuzov Chem Ber 38 1171 1905, see Verkade & Coskren in Organo Phosphorus Compound (Kosolapoff & Maier eds) Wiley Vol 2 pp 1-187 1972, Beilstein 1 IV 1476.]