1732-72-5

Basic information

• Product Name: DI-N-BUTYLPHOSPHINE
• Synonyms: Dibutyl-phosphane;dibutyl-phosphin;dibutyl-Phosphine;DI-N-BUTYLPHOSPHINE
• CAS NO: 1732-72-5
• Molecular Formula: C₈H₁₉P
• Molecular Weight: 146.21
• Mol File: 1732-72-5.mol

Chemical Properties

• Melting Point: 72 °C
• Boiling Point: 186.9 °C at 760 mmHg
• Flash Point: 66.8 °C
• Appearance: /
• Vapor Pressure: 0.89mmHg at 25°C
• CAS DataBase Reference: DI-N-BUTYLPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: DI-N-BUTYLPHOSPHINE(1732-72-5)
• EPA Substance Registry System: DI-N-BUTYLPHOSPHINE(1732-72-5)

Safety Data

• RIDADR: 2845
• HazardClass: 4.2
• PackingGroup: I
• Hazardous Substances Data: 1732-72-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Reactions:
DI-N-BUTYLPHOSPHINE is used as a reagent in various chemical reactions for its ability to promote a multitude of chemical transformations due to its strong electron-donating properties.
Used in Organic Synthesis:
As a catalyst, DI-N-BUTYLPHOSPHINE plays a crucial role in organic synthesis, enhancing the efficiency and selectivity of reactions, which is vital for the production of complex organic molecules.
Used in Pharmaceutical Production:
DI-N-BUTYLPHOSPHINE is utilized in the production of pharmaceuticals, where its unique properties contribute to the synthesis of various medicinal compounds.
Used in Agrochemical Production:
DI-N-BUTYLPHOSPHINE also finds application in the agrochemical industry, aiding in the synthesis of chemicals used in agricultural applications to protect crops and enhance yields.
Used in Homogeneous Catalysis:
DI-N-BUTYLPHOSPHINE is employed in the field of homogeneous catalysis, where it helps to improve the catalytic processes by maintaining the catalyst in the same phase as the reactants.
Used as a Polymer Stabilizer:
In the polymer industry, DI-N-BUTYLPHOSPHINE serves as a stabilizer, contributing to the production of stable polymers with desired properties for various applications.

InChI:InChI=1/C8H19P/c1-3-5-7-9-8-6-4-2/h9H,3-8H2,1-2H3

Upstream product

• 542-69-8 1-iodo-butane 
• 5958-53-2 tetrabutyldiphosphine disulfide 
• 814-29-9 Tributylphosphine oxide 
• 50602-70-5 dibutylphosphinous acid 
• 109-65-9 1-bromo-butane 
• 693-03-8 n-butyl magnesium bromide 
• 4323-64-2 (dibutyl)chlorophosphine 
• 683-16-9 dibutylphosphinic chloride 
• 56660-55-0 ethyl ester of dibutyl phosphinic acid 
• 6372-44-7 (dibutyl)(phenyl)phosphine 
• 7803-51-2 phosphan 
• 109-72-8 n-butyllithium 
• 30148-50-6 bis(trimethylsilyl)phosphonite 
• 15754-54-8 dibutylphosphine oxide 

Downstream Products

• 52773-67-8 1-Dibutylphosphino-2-diphenylphosphinoethan 
• 126337-24-4 (E)-2-Dibutylphosphanyl-4-phenyl-but-3-en-2-ol 
• 126337-26-6 4-Dibutylphosphanyl-4-phenyl-butan-2-one 
• 4141-59-7 1,2-bis(di-n-butylphosphino)-ethane 
• 165131-50-0 1,11-bis<2-(dibutylphosphinoylmethyl)phenoxy>-3,6,9-trioxaundecane 
• 15754-54-8 dibutylphosphine oxide 
• 812697-71-5 2-tert-butoxycarbonylamino-3-dibutylphosphanylmethylsulfanylcarbonyl-propionic acid benzyl ester 
• 97340-47-1 Dibutyl-<α-hydroxy-benzyl>-phosphinsulfid 
• 813-78-5 dimethylphosphoric acid 
• 1110711-01-7 Br^(1-)*C₄₆H₃₈F₁₂P⁽¹⁺⁾ 
• 1402851-47-1 tris{4-[2-(butylphosphoryl)ethyl]benzyl}phosphine oxide 

Relevant articles and documents

Synthesis and reactivity of alkoxy(trimethylsiloxy)phosphines and their derivatives

Convenient procedures for the synthesis of new alkoxy(trimethylsiloxy) phosphines and their derivatives starting from the available alkyl hypophosphites and N-trimethylsilyl succinimide are proposed. Some properties of these new phosphines such as nucleophilic substitution of the trimethylsiloxy group at trivalent phosphorus, the Arbuzov reaction, and addition of PH and POSi fragments to multiple carbon-carbon bonds are presented.

Identification of a four-center intermediate in a Grignard addition reaction to a P-S bond

The reaction between tert-butylmagnesium chloride (or tert-pentylmagnesium chloride) and the particular phosphorus-sulfur bond of a benzothiadiphospholic system showed, for the first time, evidence of formation of intermediates with a four-center structure. The possibility, for the phosphorus atom, to have very stable hypervalent coordinations makes it possible to observe its hypervalent states during the course of a reaction. The benzothiadiphosphole, with its bicyclic folded structure, further stabilizes the hypervalent coordinations thus making the intermediates sufficiently stable to be detected during the course of the reaction by 31P NMR spectroscopy, which revealed the nature and the stability of the species involved in this reaction, carried out also using other Grignard reagents.

A Convenient and Facile Synthesis of Dialkylphosphines

A series of simple dialkylphosphines 2 has been prepared by the thermal disproportionation of dialkylphosphine oxides 1 induced by the R2P(O)Cl/R2PCl system, generated in situ from 1 with a catalytic amount of carbon tetrachloride.

Synthesis and reactivity of substituted α-carbonylphosphonites and their derivatives

Convenient methods for the synthesis of functionalized organophosphorus compounds containing carbonyl groups as well as di- or trialkoxymethyl fragments attached to phosphorus, and their derivatives, starting from the available derivatives of trivalent phosphorus acids, are proposed, and some properties of the new functionalized organophosphorus compounds are presented. So, the alkylation and acylation reaction of (dialkoxymethyl) phosphonites and their analogs have been studied. It is found that the Arbuzov rearrangement of these compounds was accompanied by the phosphorus-carbon bond cleavage with unique retention of the three-coordinate phosphorus.

One-pot synthesis of ultra-branched mixed tetradentate tripodal phosphines and phosphine chalcogenides

Ultra-branched mixed tetradentate tripodal phosphines and phosphine chalcogenides have been synthesized by the exhaustive regioselective addition of secondary phosphines, phosphine sulfides and phosphine selenides to available tris(4-vinylbenzyl)phosphine oxide under free-radical conditions (UV irradiation or AIBN) in good to excellent yields.

High atom-economical one-pot synthesis of secondary phosphines and their borane complexes using recycling phosphorus donor reagent

A general new method for the one-pot preparation of secondary phosphines 11 and in situ generation of their borane complexes 12 is described. This method consists of the sequential addition, at room temperature, of equivalent amounts of R1MgBr and R2MgBr to 1 equiv of the phosphorus atom donor reagent 1. Final treatment with water gives secondary phosphines R 1R2PH (or the corresponding phosphine-borane complexes if treated with BH3·THF) and the end product 6, which can be recycled.

A superior method for the reduction of secondary phosphine oxides

(Chemical Equation Presented) Diisobutylaluminum hydride (DIBAL-H) and triisobutylaluminum have been found to be outstanding reductants for secondary phosphine oxides (SPOs). All classes of SPOs can be readily reduced, including diaryl, arylalkyl, and dialkyl members. Many SPOs can now be reduced at cryogenic temperatures, and conditions for preservation of reducible functional groups have been found. Even the most electron-rich and sterically hindered phosphine oxides can be reduced in a few hours at 50-70°C. This new reduction has distinct advantages over existing technologies.

A METHOD FOR GENERATING SECONDARY PHOSPHINES

This invention provides a method for generating secondary phosphines from secondary phosphine oxides in the presence of a reducing agent, such as diisobutylaluminum hydride (DIBAL-H), triisobutyldialuminoxane, triisobutylaluminum, tetraisobutyldialuminoxane, or another reducing agent comprising: (i) an R1R2AIH moiety, wherein R1 and R2 are each an alkyl species or oxygen, and wherein at least one of R1 or R2 comprises at least 2 carbon atoms, or (ii) an R1R2R3AI moiety, wherein R1, R2, and R3 are not hydrogen, and wherein at least one of R1, R2, and R3 is an alkyl species comprising a β-hydrogen, not including triethylaluminum. Preferred reducing agents for the present invention include: diisobutylaluminum hydride, triisobutyldialiuminoxane, triisobutylaluminum, tetraisobutyldialuminoxane, and combinations thereof.

t-Butyl alcohol-assisted fission of the P-P bonds in red phosphorus with lithium in liquid ammonia. A convenient preparative method for dialkylphosphanes.

Essentially complete fission of the P-P bonds in red phosphorus can be effected by adding one equivalent of t-butylalcohol to a mixture of red P and lithium in liquid ammonia.The reaction has been applied to synthesize some dialkylphosphanes.

Reductive cleavage of the carbon-phosphorus bond with alkali metals. III Reactions of arylalkylphosphines

The reductive cleavage of phenylalkylphosphines Ph2PR, PhPR2 (R = Bu, iPr) with Na/NH3 is unselective; both phenyl and alkyl groups can be cleavaged and Birch reduction may occur.Reaction of Ph2tBuP gives a high yield of diphenylphosphide.Polar groups (CO2Na, SO3Na) at the ω position of primary alkyl groups may lead to an increase in selectivity; Birch reduction is suppressed and a functionalised secondary phosphide is obtained.From diarylbenzyl- and diarylallylphosphines, the benzyl and allyl groups are selectively removed; Ar2PH and ArRPH are formed in high yield after hydrolytic work-up unless the aryl group bears F, CF3 or (CH3)2N substituents.From the reaction mixture of Ph2PCH2Ph we have isolated 1,2-diphenylethane. 2-Methoxyphenyl and 2,6-dimethoxyphenyl groups are selectively removed from Ar2BuP, ArPhBuP and Ar2P(CH2)3PAr2, forming ArBuPH, PhBuPH and ArP(H)(CH2)3(H)PAr, respectively.A double-cleavage reaction of Ar2RP may occur in low yield. 2,6-(dimethoxyphenyl-dibutylphosphine gives dibutylphosphine in moderate yield.When compounds with a 2,6-dimethoxyphenyl moiety are allowed to react with Li/THF, removal of a methyl group leads to novel phosphinophenols.It is concluded that cleavage of alkyl groups R selectively occurs when R radical is relatively stable (tBu, PhCH2> iPr > Bu).