Tributyl phosphite

Base Information

• Chemical Name: Tributyl phosphite
• CAS No.: 102-85-2
• Molecular Formula: C12H27 O3 P
• Molecular Weight: 250.318
• Hs Code.: 29209085
• European Community (EC) Number: 203-061-3
• NSC Number: 2675
• UNII: 498030B4AD
• DSSTox Substance ID: DTXSID7051474
• Nikkaji Number: J3.232H
• Wikidata: Q27259245
• RXCUI: 2399030
• Mol file: 102-85-2.mol

Synonyms:TBPi cpd;tributyl phosphite

Chemical Property of Tributyl phosphite

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 0.013mmHg at 25°C
• Melting Point: -80 °C
• Refractive Index: n20/D 1.431(lit.)
• Boiling Point: 125 °C
• Flash Point: 121.1°C
• PSA: 41.28000
• Density: g/cm³
• LogP: 4.66340
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 12
• Exact Mass: 250.16978172
• Heavy Atom Count: 16
• Complexity: 110

Purity/Quality:

98% ^*data from raw suppliers

Tributyl phosphite ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 21-34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phosphite Compounds
• Canonical SMILES: CCCCOP(OCCCC)OCCCC
• General Description: Tributyl phosphite (TBP) is a trialkyl phosphite that reacts readily with sulfenyl chlorides, including alkyl and aromatic variants, to form monothiophosphoric acid esters. The reaction proceeds rapidly, even at low temperatures, via nucleophilic displacement of chloride with concurrent elimination of alkyl chloride. TBP demonstrates reactivity comparable to or exceeding that of acyl halides, which are known for exothermic reactions with tertiary phosphites. The resulting thioester derivatives, particularly those with chloro substituents, have been explored for their potential applications in cancer chemotherapy as mustard analogs.

Technology Process of Tributyl phosphite

There total 20 articles about Tributyl phosphite which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.0%

O,O-dibutyl (tributoxymethyl)phosphonate → tri-n-butyl phosphite (102-85-2) + Dibutyl carbonate (542-52-9)

Guidance literature:

With boron trifluoride diethyl etherate; under 8 Torr; Heating;

Reference yield: 71.0%

O,O-dibutyl (tributoxymethyl)phosphonate → tri-n-butyl phosphite (102-85-2)

Guidance literature:

With boron trifluoride diethyl etherate; under 8 Torr; Heating;

DOI:10.1002/hc.21024

Reference yield: 69.0%

butan-1-ol (71-36-3) → tri-n-butyl phosphite (102-85-2)

Guidance literature:

With potassium phosphate; tetrahexylammonium chloride; phosphorus trichloride; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1002/hc.20438

upstream raw materials:

pyridine

butyl dichlorophosphite

butan-1-ol

triphenyl phosphite

Downstream raw materials:

dibutyl butylphosphonate

n-Butyl chloride

dibutyl chlorophosphate

O,O-dibutyl O-(2,2-dichlorovinyl) phosphate

Refernces

The Reaction of Sulfenyl Chlorides with Trialkyl Phosphites1

10.1021/ja01606a062

The study investigates the reaction of sulfenyl chlorides with trialkyl phosphites, resulting in the formation of esters of monothiophosphoric acid. Various alkyl and aromatic sulfenyl chlorides, such as methanesulfenyl chloride, benzenesulfenyl chloride, and p-chloroethanesulfenyl chloride, were reacted with triethyl phosphite, tri-n-propyl phosphite, and tri-n-butyl phosphite. The reactions were rapid, even at Dry Ice temperatures, indicating a nucleophilic displacement of chloride accompanied by the elimination of alkyl chloride. The study also compared the reactivity of these sulfenyl chlorides with that of sulfur monochloride and noted that the sulfenyl chlorides reacted at least as readily as acyl halides, which are known to react exothermally with tertiary phosphites. The compounds synthesized were used for biological testing in cancer chemotherapy studies, with particular interest in the 6-chloro thioester as a potential mustard analog.