1702-42-7

Basic information

• Product Name: METHYLTRIBUTYLPHOSPHONIUM IODIDE
• Synonyms: METHYLTRIBUTYLPHOSPHONIUM IODIDE;METHYLTRI-N-BUTYLPHOSPHONIUM IODIDE;TRIBUTYLMETHYLPHOSPHONIUM IODIDE;HISHICOLIN PX-4MI;M1455;P1,4,4,4I
• CAS NO: 1702-42-7
• Molecular Formula: C₁₃H₃₀P*I
• Molecular Weight: 344.26
• EINECS: 200-144-5
• Product Categories: Phosphonium Salts;Phosphonium Compounds
• Mol File: 1702-42-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 133.5 °C
• Appearance: /
• Solubility: soluble in Methanol
• CAS DataBase Reference: METHYLTRIBUTYLPHOSPHONIUM IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYLTRIBUTYLPHOSPHONIUM IODIDE(1702-42-7)
• EPA Substance Registry System: METHYLTRIBUTYLPHOSPHONIUM IODIDE(1702-42-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 1702-42-7(Hazardous Substances Data)

Usage

General Description

Methyltributylphosphonium iodide is a quaternary ammonium compound with the chemical formula C13H30IP. It is commonly used as a phase-transfer catalyst in organic synthesis, particularly in reactions involving nucleophilic substitutions and alkylations. This chemical is known for its ability to efficiently transfer iodide anions across the lipid bilayer, making it useful in biochemical and pharmaceutical research. Methyltributylphosphonium iodide is a white crystalline solid that is soluble in organic solvents, and it is important to handle it with care due to its toxic and irritant properties.

InChI:InChI=1/C13H30P/c1-5-8-11-14(4,12-9-6-2)13-10-7-3/h5-13H2,1-4H3/q+1

Upstream product

• 74-88-4 methyl iodide 
• 86671-55-8 1,4-bis-(tributylphosphonio)buta-1,3-diene dibromide 
• 998-40-3 tributylphosphine 

Downstream Products

• 86042-82-2 tri-n-butylmethylphosphonium tetrafluoroborate 

Relevant articles and documents

Mechanistic Analysis and Characterization of Intermediates in the Phosphane-Catalyzed Oligomerization of Isocyanates

The mechanism of the oligomerization of aliphatic isocyanates catalyzed by trialkylphosphanes has been studied through low temperature 31P and 15N NMR spectroscopy combined with computational chemistry. A revised mechanism is proposed that contains several (spiro)cyclic pentacoordinate phosphorous intermediates. Previously reported spectroscopic data of a transient intermediate has been reevaluated and assigned to a cyclic intermediate containing a P?N bond by experiments with 15N-labeled isocyanate. 13C, 15N, and 31P NMR shifts that support this assignment have been calculated using quantum chemical methods.

METHOD FOR PRODUCING IONIC LIQUID AND METHOD FOR PRODUCING INTERMEDIATE BODY FOR PRODUCTION OF IONIC LIQUID

PROBLEM TO BE SOLVED: To provide a method for producing an ionic liquid for synthesizing a desired ionic liquid with high purity, and to provide a method for producing an intermediate body for synthesizing the ionic liquid. SOLUTION: A method for producing an ionic liquid which produces a desired ionic liquid Q+Z- formed from cation Q+ and anion Z- includes: a step of purifying a high-melting point intermediate body Q+Y- that is formed from the cation Q+ and the anion Z- and has such a melting point as to be recrystallized, by recrystallization; and a step of obtaining the ionic liquid Q+Z- directly or indirectly from the purified high-melting point intermediate body Q+Y-. A method for producing a strongly acidic intermediate body and a super-hydrophilic intermediate body includes: a step of obtaining a strongly acidic intermediate body or a super-hydrophilic intermediate body from the purified high-melting point intermediate body Q+Y- by a double decomposition precipitation method or obtaining the strongly acidic intermediate body from the purified high-melting point intermediate body Q+Y- by a double decomposition precipitation method, or a step of obtaining the super-hydrophilic intermediate body from the strongly acidic intermediate body by a neutralization method. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2018,JPOandINPIT

Basic hydrolysis of 1,4-bis(triphenylphosphonio)buta-1,3-diene dihalides

Basic hydrolysis of 1,4-bis(triphenylphosphonio)buta-1,3-diene dichloride with 10% NaOH gave isomeric 4-diphenylphosphoryl-4-phenylbut-1(2)-enes and 1-diphenylphosphoryl-1-phenylbuta-1,3-diene, the products of anionotropic migration of a phenyl group from the P atom to the -position. Hydrolysis with Na2CO3 afforded only the diene product. In both cases, triphenylphosphine and triphenylphosphine oxide were isolated as secondary products. Dehydrochlorination of 2-chloro-1,4-bis(triphenylphosphonio) but-2-ene dibromide with triphenylphosphine was proposed as a new convenient route to 1,4-bis(triphenylphosphonio)buta-1,3-diene dibromide.