Cyclopropyltriphenylphosphonium bromide

Base Information

• Chemical Name: Cyclopropyltriphenylphosphonium bromide
• CAS No.: 14114-05-7
• Molecular Formula: C21H20BrP
• Molecular Weight: 383.268
• Hs Code.: 29319090
• European Community (EC) Number: 237-970-1
• NSC Number: 110599
• DSSTox Substance ID: DTXSID40931001
• Mol file: 14114-05-7.mol

Synonyms:Cyclopropyltriphenylphosphonium bromide;14114-05-7;NSC 110599;EINECS 237-970-1;cyclopropyl(triphenyl)phosphanium;bromide;Phosphonium, cyclopropyltriphenyl-, bromide;Phosphonium, cyclopropyltriphenyl-, bromide (1:1);MFCD00011872;cyclopropyl(triphenyl)phosphanium bromide;Phosphonium,cyclopropyltriphenyl-, bromide (1:1);SCHEMBL1082615;DTXSID40931001;XMPWFKHMCNRJCL-UHFFFAOYSA-M;GEO-00894;NSC110599;AKOS005216619;cyclopropyl triphenylphosphonium bromide;cyclopropyl-triphenylphosphonium bromide;cyclopropyltriphenyl-phosphonium bromide;NSC-110599;Triphenyl-cyclopropylphosphonium bromide;cyclopropyl(triphenyl)phosphonium bromide;SY112004;CS-0031381;FT-0604895;Phosphonium,cyclopropyltriphenyl-,bromide(1:1);A853172;J-007466

Chemical Property of Cyclopropyltriphenylphosphonium bromide

Chemical Property:

• Appearance/Colour: white to slightly yellowish crystalline powder
• Melting Point: 178-181 °C(lit.)
• PSA: 13.59000
• LogP: 1.14690
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Hygroscopic
• Water Solubility.: Soluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 382.04860
• Heavy Atom Count: 23
• Complexity: 295

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cyclopropyltriphenylphosphonium bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC1[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.[Br-]
• Uses: Cyclopropyltriphenylphosphonium bromide has cytotoxic activity against the growth of tissue culture cells originating from human epidermoid carcinoma of the nasopharynx (KB). It is commonly used as a Wittig reagent. Used for electrolytic polarization of ZnStudied for potential antitumor activityReactant for synthesis of:Keto halides for sequential azidation and intramolecular Schmidt reactionsCycloporpylidenemethylarylethynynesDipeptides containing azabicyclo[3.1.0]hexaneReactant for hydroalkynylation

Technology Process of Cyclopropyltriphenylphosphonium bromide

There total 7 articles about Cyclopropyltriphenylphosphonium bromide 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: 91.0%

3-bromopropyltriphenylphosphonium bromide (3607-17-8) → cyclopropyltriphenylphosphonium bromide (14114-05-7)

Guidance literature:

With sodium hydroxide; In water; 2 h, reflux; 12 h, room temp.;

DOI:10.1016/S0040-4020(01)86961-1

Reference yield: 76.0%

vinyltriphenylphosphonium bromide (5044-52-0) + (dimethylamino)methylphenylsulfoxonium tetrafluoroborate → cyclopropyltriphenylphosphonium bromide (14114-05-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 2h; Heating;

DOI:10.1246/bcsj.68.2313

Reference yield: 36.4%

triphenylphosphine (603-35-0) + 1,3-dibromo-propane (109-64-8) → cyclopropyltriphenylphosphonium bromide (14114-05-7)

Guidance literature:

In xylene; at 130 ℃; for 24h;

DOI:10.1021/ja00072a014

upstream raw materials:

3-bromopropyltriphenylphosphonium bromide

(2-oxotetrahydro-3-furanyl)triphenylphosphonium bromide

triphenylphosphine

1,3-dibromo-propane

Downstream raw materials:

(Methylcyclopropylmethylene)cyclopropane

cyclopropylidenecyclohexane

cyclopropyldiphenylphosphine oxide

1-(2-t-butyldimethylsiloxy-4-methylphenyl)-1-cyclopropylideneethane

Refernces

• 1、 González, Jorge A.,López, Fernando,Mascare?as, José Luis,Nevado, Cristina,Verdugo, Felipe. "[C^N]-Alkenyl Gold(III) Complexes by Proximal Ring-Opening of (2-Pyridyl)alkylidenecyclopropanes: Mechanistic Insights". . p. 20049 - 20054. Retrieved 2020.
• 2、 Okuma, Kentaro,Ikari, Komei,Ono, Masaaki,Sato, Yasunari,Kuge, Seiji,et al.. "Reaction of Vinylphosphonium Salts with Sulfoxonium Ylides. Synthesis of Cyclopropylphosphonium Salts". . p. 2313 - 2318. Retrieved 1995.
• 3、 Yao, Bangben,Li, Yong,Liang, Zunjun,Zhang, Yuhong. "Ni-catalyzed intramolecular cycloaddition of methylenecyclopropanes to alkynes". supporting information; experimental part. p. 640 - 643. Retrieved 2011/04/16.