ДИБЕНЗИЛФОСФИТ

Description

Dibenzylphosphite is a diester of phosphorous acid, an H-phosphonate with two benzyl groups at the oxygen atoms. Belongs to the class of dialkyl phosphites, contains a mobile hydrogen atom at phosphorus (P-H bond), due to which it enters into the Arbuzov reaction, Abramov reaction and addition to aldehydes, ketones and imines. It is used as a reagent for the growth of organophosphorus fragments and as a building block in the synthesis of phosphonates and phosphonites.

Basic Attributes

• CAS No.: 538-60-3
• Chemical formula: C14H15O3P
• Molecular weight: 262.24
• Exact weight: 262.07600
• EU number: 241-226-1
• HS code: 2920901900
• PSA Specifications: 52.28000
• XLogP3: 3.63920

Physico-chemical characteristics

• Density: 1.187 g/ml at 25 °C (according to literature data)
• Boiling point: 110–120 °C with a residual pressure of 0.01 mmHg. Art.
• Flash point: above 230°F (about 110°C)
• Refractive index: n20/D 1.555 (according to literature data)
• Storage conditions: 2–8 °C

Synonyms

NSC49746, AURORAKA-1209, O,O'-dibenzylphosphine (obsolete name), bis(benzyl)hydrophosphite, phosphonic acid dibenzyl ester, phosphorous dibenzyl ester, bis(phenylmethyl)hydrophosphite.

Scope of application

Dibenzyl phosphite is used as an intermediate product in fine organic synthesis - for the preparation of phosphonates, phosphonites and protected phosphate derivatives, including nucleotide and glycosidic chemistry, where benzyl groups are convenient for subsequent hydrogenolytic deprotection. Serves as a raw material for fire retardants and stabilizer additives based on organophosphates, as well as a precursor ligand in the production of P,O-chelating compounds for catalysis. In analytical practice it appears as a reference substance for the control of related dibenzylphosphonates.

Safety Information

WGK Germany: 3 (hazardous for water bodies). The compound belongs to organophosphorus esters with a P-H bond - it is sensitive to oxidation by atmospheric oxygen and hydrolysis, therefore cold storage conditions are regulated.

Storage and transportation conditions

Store in the original sealed container at a temperature of 2–8 °C, in the refrigerator, away from sources of moisture and strong oxidizing agents. The room is dry, ventilated, protected from direct light. When working, use gloves and safety glasses, avoid inhaling vapors when heated to boiling point under vacuum. Transport in thermally insulated containers that prevent temperature increases above the specified range.

More about reactivity

Unlike fully substituted trialkyl phosphites, dibenzyl phosphite retains the ability to undergo a tautomeric transition between the trivalent P(III)-H form and the tetravalent P(V)=O form, which makes it a convenient partner for the hydrophosphorylation reactions of unsaturated compounds and the synthesis of unsymmetrical phosphonates through intermediate deprotonation with a strong base followed by alkylation of the resulting phosphite anion. Benzyl protecting groups are resistant to most conditions of organic synthesis, except catalytic hydrogenation, which allows multi-step sequences without loss of the phosphorus moiety and deprotection at the final stage under mild conditions that do not affect other functional groups of the molecule.