Triisopropyl phosphite Chemical Properties

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 Information

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)

MSDS

• Language:English Provider:Phosphorous acid tris(1-methylethyl) ester
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Triisopropyl phosphite Usage And Synthesis

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.

It can also be used as an alternative to triphenylphosphine in Mitsunobu reaction to facilitate the isolation of products.

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.]

Triisopropyl phosphite(116-17-6)Related Product Information

• Isopropyl palmitate
• BUTYL OLEATE
• Tri(4-isopropylphenyl) phosphate
• N,N-Diisopropylethylamine
• Isopropyl salicylate
• Triisopropyl borate
• Orthophosphorus acid
• Lithium diisopropylamide
• Diisopropyl phosphite
• Methyl acrylate
• Phosphorus
• Isopropyl myristate
• Triisopropylsilane
• Titanium tetraisopropanolate
• Dimethyl succinate
• Olibanum oil
• Tris(trimethylsilyl)phosphate
• Isopropyl acetate