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Butyl-triphenyl-phosphanium bromide is a quaternary phosphonium salt that is widely recognized for its role as a phase transfer catalyst in organic synthesis. It is characterized by its white crystalline solid form and its solubility in polar solvents such as water and methanol. butyl-triphenyl-phosphanium bromide is distinguished by its capacity to facilitate the transfer of organic and inorganic reagents between immiscible phases, thereby enhancing the efficiency and selectivity of various chemical reactions.

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  • 22949-84-4 Structure
  • Basic information

    1. Product Name: butyl-triphenyl-phosphanium bromide
    2. Synonyms: butyl-triphenyl-phosphanium bromide;butyltriphenylphosphonium
    3. CAS NO:22949-84-4
    4. Molecular Formula: C22H24P*I
    5. Molecular Weight: 446.31
    6. EINECS: 918-205-7
    7. Product Categories: N/A
    8. Mol File: 22949-84-4.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: butyl-triphenyl-phosphanium bromide(CAS DataBase Reference)
    10. NIST Chemistry Reference: butyl-triphenyl-phosphanium bromide(22949-84-4)
    11. EPA Substance Registry System: butyl-triphenyl-phosphanium bromide(22949-84-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 22949-84-4(Hazardous Substances Data)

22949-84-4 Usage

Uses

Used in Organic Synthesis:
Butyl-triphenyl-phosphanium bromide is used as a phase transfer catalyst for enhancing the efficiency and selectivity of organic reactions. Its ability to transfer reagents between immiscible phases is particularly beneficial in reactions that require the interaction of water-soluble and organic-soluble reactants.
Used in Williamson Ether Synthesis:
In the Williamson ether synthesis, butyl-triphenyl-phosphanium bromide is employed as a phase transfer catalyst to facilitate the nucleophilic substitution of alkoxide ions with alkyl halides, leading to the formation of ethers.
Used in Wittig Reaction:
Butyl-triphenyl-phosphanium bromide is utilized as a phase transfer catalyst in the Wittig reaction, which is a method for the synthesis of alkenes from aldehydes or ketones. Its role in this reaction is to improve the reaction conditions and increase the yield of the desired alkene products.
Used in Nucleophilic Substitution Reactions:
In nucleophilic substitution reactions, butyl-triphenyl-phosphanium bromide is used as a phase transfer catalyst to promote the reaction between nucleophiles and electrophiles, which are often found in different phases. This catalyst helps to bring the reactants into contact, thereby increasing the reaction rate and selectivity.
Used in the Pharmaceutical Industry:
Butyl-triphenyl-phosphanium bromide is used as a phase transfer catalyst in the synthesis of various pharmaceutical compounds. Its ability to improve reaction efficiency and selectivity is particularly valuable in the production of complex organic molecules that are used as active pharmaceutical ingredients.
Used in the Fine Chemicals Industry:
In the fine chemicals industry, butyl-triphenyl-phosphanium bromide is used as a phase transfer catalyst for the synthesis of high-value organic compounds, such as fragrances, dyes, and specialty chemicals. Its application in these processes helps to improve the overall yield and purity of the final products.

Check Digit Verification of cas no

The CAS Registry Mumber 22949-84-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,9,4 and 9 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 22949-84:
(7*2)+(6*2)+(5*9)+(4*4)+(3*9)+(2*8)+(1*4)=134
134 % 10 = 4
So 22949-84-4 is a valid CAS Registry Number.
InChI:InChI=1/C22H24P/c1-2-3-19-23(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22/h4-18H,2-3,19H2,1H3/q+1

22949-84-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name butyl(triphenyl)phosphanium,iodide

1.2 Other means of identification

Product number -
Other names Butyltriphenylphosphonium iodide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:22949-84-4 SDS

22949-84-4Relevant articles and documents

Monitoring and Modulating mtDNA G-Quadruplex Dynamics Reveal Its Close Relationship to Cell Glycolysis

Chen, Shuo-Bin,Chen, Xiu-Cai,Dai, Jing,Huang, Zhi-Shu,Luo, Wen-Hua,Shao, Wen,Tan, Jia-Heng,Tang, Gui-Xue,Zeng, Shu-Tang

supporting information, p. 20779 - 20791 (2021/12/14)

The mitochondrial DNA G-quadruplex (mtDNA G4) is a potential regulatory element for the regulation of mitochondrial functions; however, its relevance and specific roles in diseases remain largely unknown. Here, we engineered a set of chemical probes, incl

Organic phosphine salt and optical physical property regulation and control method and application thereof (by machine translation)

-

Paragraph 0070-0072, (2020/05/30)

The invention discloses an organic phosphine salt and an optical physical property regulation and control method and application, of the compound, with different alkyl chain lengths through an ion exchange reaction; to obtain the organic phosphine salt, with different alkyl chain lengths through the ion exchange reaction to control the photophysical property (Cl, Br, I), of the compound by using alkyl, chain length and heavy atom, after, ultraviolet irradiation to achieve information, encryption application 300 nm. (by machine translation)

Quaternary Phosphorus-Induced Iodocuprate(I)-Based Hybrids: Water Stabilities, Tunable Luminescence and Photocurrent Responses

Zhang, Wen-Ting,Liu, Jian-Zhi,Liu, Jing-Bo,Song, Kai-Yue,Li, Yi,Chen, Zhi-Rong,Li, Hao-Hong,Jiang, Rong

supporting information, p. 4234 - 4244 (2018/10/15)

Four (triphenyl)phosphonium-based quaternary phosphorus salts with different substituents (varying from methyl to n-butyl) were selected to be structural directed agents (SDAs) to construct four iodocuprate(I) hybrids via solution method, i.e., [(PPh3Me)(Cu3I4)]n (1), [(PPh3Et)(Cu3I4)]n (2), (PPh3iPr)2(Cu2I4) (3), [(PPh3nBu)(Cu3I4)]n (4). The inorganic iodocuprates in 1, 2 and 4 are 1-D (Cu3I4)nn– chains constructed from Cu5I11 units, but (Cu2I4)2– in 3 is a di-nuclear cluster. Interestingly, the strength of Cu···Cu and π–π stacking interactions are weakened with the lengthening of alkyl groups on P-atom. The best water stability of 4 can be ascribed to the better hydrophobicity of n-butyl group, which deters the dispersing of organic and inorganic moieties and as a result, inhibit hydrolysis reaction. Furthermore, all compounds exhibit typical reversible luminescent thermochromic behaviors, among which 4 exhibits blue emission and the quenching of higher energy (HE) zone in 1 and 2 are led by strong π–π stacking interactions. Besides, effective and repeatable photocurrent responses can be detected in these compounds. In all, by systematically introducing alkyl groups into (triphenyl)phosphonium as SDAs to prepare hybrid iodocuprates, we can find that the longer alkyl groups can achieve stronger tunable PL materials with enhanced water stabilities.

ALKENES AS ALKYNE EQUIVALENTS IN RADICAL CASCADES TERMINATED BY FRAGMENTATIONS

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Paragraph 0153; 0154, (2016/12/22)

Disclosed are methods for rerouting radical cascade cyclizations by using alkenes as alkyne equivalents. The reaction sequence is initiated by a novel 1,2 stannyl shift which achieves chemo- and regioselectivity in the process. The radical “hopping” leads to the formation of the radical center necessary for the sequence of selective cyclizations and fragmentations to follow. In the last step of the cascade, the elimination of a rationally designed radical leaving group via β-C—C bond scission aromatizes the product without the need for external oxidant. The Bu3Sn moiety, which is installed during the reaction sequence, allows further functionalization of the product via facile reactions with electrophiles as well as Stille and Suzuki cross-coupling reactions. This selective radical transformation opens a new approach for the controlled transformation of enynes into extended polycyclic structures of tunable dimensions.

Double C-H amination by consecutive SET oxidations

Evoniuk, Christopher J.,Hill, Sean P.,Hanson, Kenneth,Alabugin, Igor V.

supporting information, p. 7138 - 7141 (2016/06/09)

A new method for intramolecular C-H oxidative amination is based on a FeCl3-mediated oxidative reaction of anilines with activated sp3 C-H bonds. The amino group plays multiple roles in the reaction cascade: (1) as the activating group in single-electron-transfer (SET) oxidation process, (2) as a directing group in benzylic/allylic C-H activation at a remote position, and (3) internal nucleophile trapping reactive intermediates formed from the C-H activation steps. These multielectron oxidation reactions proceed with catalytic amounts of Fe(iii) and inexpensive reagents.

Coupling cyclizations with fragmentations for the preparation of heteroaromatics: Quinolines from o-alkenyl arylisocyanides and boronic acids

Evoniuk, Christopher J.,Ly, Michelle,Alabugin, Igor V.

supporting information, p. 12831 - 12834 (2015/08/06)

Stereoelectronic restrictions on homoallylic ring expansion in alkyne cascades can be overcome by using alkenes as synthetic equivalents of alkynes in reaction cascades that are terminated by C-C bond fragmentation. Implementation of this approach using Mn(iii)-mediated reaction of o-alkenyl isocyanides and boronic acids leads to efficient synthesis of substituted quinolines.

Design of leaving groups in radical C-C fragmentations: Through-bond 2c-3e interactions in self-terminating radical cascades

Mondal, Sayantan,Gold, Brian,Mohamed, Rana K.,Alabugin, Igor V.

supporting information, p. 8664 - 8669 (2014/07/21)

Radical cascades terminated by β-scission of exocyclic C-C bonds allow for the formation of aromatic products. Whereas β-scission is common for weaker bonds, achieving this reactivity for carbon-carbon bonds requires careful design of radical leaving groups. It has now been found that the energetic penalty for breaking a strong σ-bond can be compensated by the gain of aromaticity in the product and by the stabilizing two-center, three-electron "half-bond" present in the radical fragment. Furthermore, through-bond communication of a radical and a lone pair accelerates the fragmentation by selectively stabilizing the transition state. The stereoelectronic design of radical leaving groups leads to a new, convenient route to Sn-functionalized aromatics.

Synthesis of truncated analogues of the iNKT cell agonist, α-galactosyl ceramide (KRN7000), and their biological evaluation

Veerapen, Natacha,Reddington, Faye,Salio, Mariolina,Cerundolo, Vincenzo,Besra, Gurdyal S.

experimental part, p. 221 - 228 (2011/03/17)

Stimulation of iNKT cells by α-galactosyl ceramide (α-GalCer), also known as KRN7000, and its truncated analogue OCH induces both Th1- and Th2-cytokines, with OCH inducing a Th2-cytokine bias. Skewing of the iNKT cells' response towards either a Th1- or Th2-cytokine profile offers potential therapeutic benefits. The length of both the acyl and the sphingosine chains in α-galactosyl ceramides is known to influence the cytokine release profile. We have synthesized analogues of α-GalCer with truncated sphingosine chains for biological evaluation, with particular emphasis on the Th1/Th2 distribution. Starting from a common precursor, d-lyxose, the sphingosine derivatives were synthesised via a straightforward Wittig condensation.

Novel benzothienyl or indole derivatives, preparation and use thereof as inhibitors of prenyl transferase proteins

-

Page 49, (2010/02/08)

The invention concerns compounds of general formula (1), wherein, in particular; W represents H, SO2R5. CO(CH2)nR5, (CH2)nR6, CS(CH2)nR5; X represents S or NH; Y represents (CH2)p, CO, (CH2)pCO, CH═CH—CO; Z represents a hetcrocycle, imidazole, benzimidazole, isoxazole, tetrazole, oxadiazole, thiadazole, pyridine, quinazoline, quinoxaline, quinoline, thiophene; R1 represents COOR6, CONR6R7, CO—NH—CH(R6)—COOR7, CH2NR6R7, CH2OR6, (CH2)pR6, CH═CHR6; R2 represents in particular hydrogen, C1-C10 alkyl, a substituted or unsubstituted phenyl; R5 and R6 represents hydrogen, C1—C6 alkyl; R5 represents a substituted or unsubstituted phenyl or naphthyl; R6 and R7, identical or different, represent hydrogen, C1—C15 alkyl, a hetcrocycle. an aryl; n represents 0 to 10; p represents 1 to 6.

Synthesis and characterization of stilbene derivatives for possible incorporation as smart additives in polymers used as packaging films

Day, Gary M.,Howell, Owen T.,Metzler, Michael R.,Woodgate, Paul D.

, p. 425 - 434 (2007/10/03)

Several series of stilbene derivatives for possible use as smart additives in polymers used as packaging films have been prepared and characterized. Differential scanning calorimetry was performed on some of the stilbenes in order to determine any liquid crystal properties. Those compounds which had multiple phase transitions were also shown to have two liquid crystalline phases according to optical microscopy.

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