(2-Methoxy-2-oxoethyl)triphenylphosphonium bromide

Base Information

• Chemical Name: (2-Methoxy-2-oxoethyl)triphenylphosphonium bromide
• CAS No.: 1779-58-4
• Molecular Formula: C21H20BrO2P
• Molecular Weight: 415.266
• Hs Code.: 29319019
• European Community (EC) Number: 217-222-0
• NSC Number: 136109
• DSSTox Substance ID: DTXSID00939003
• Mol file: 1779-58-4.mol

Synonyms:1779-58-4;(2-Methoxy-2-oxoethyl)triphenylphosphonium bromide;(Carbomethoxymethyl)triphenylphosphonium bromide;(Methoxycarbonylmethyl)triphenylphosphonium bromide;Carbomethoxymethyl triphenylphosphonium bromide;MFCD00011801;(2-methoxy-2-oxoethyl)-triphenylphosphanium;bromide;Phosphonium, (2-methoxy-2-oxoethyl)triphenyl-, bromide;Phosphonium, (2-methoxy-2-oxoethyl)triphenyl-, bromide (1:1);Methoxycarbonylmethyl(triphenyl)phosphonium Bromide;NSC136109;C21H20O2P.Br;SCHEMBL509486;C21-H20-O2-P.Br;DTXSID00939003;VCWBQLMDSMSVRL-UHFFFAOYSA-M;AKOS015833080;CS-W009695;NSC-136109;SY073667;FT-0623466;M1326;Carbomethoxymethyl(triphenyl)phosphonium Bromide;F14835;(2-Methoxy-2-oxoethyl)triphenylphosphoniumbromide;(carbomethoxymethyl)-triphenylphosphonium bromide;(carbomethoxymethyl)triphenyl phosphonium bromide;(methoxycarbonyl methyl)triphenylphosphonium bromide;[(methoxycarbonyl)methyl]triphenylphosphonium bromide;dodecyl(2-ethoxy-2-oxoethyl)dimethylammoniumbromide;J-011340;(2-methoxy-2-oxo-ethyl)-triphenyl-phosphonium bromide;(2-Methoxy-2-oxoethyl)(triphenyl)phosphanium bromide

Chemical Property of (2-Methoxy-2-oxoethyl)triphenylphosphonium bromide

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 165-170 °C (dec.)(lit.)
• PSA: 39.89000
• LogP: 0.15750
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: Soluble in methanol(almost transparency).
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 414.03843
• Heavy Atom Count: 25
• Complexity: 345

Purity/Quality:

98%, ^*data from raw suppliers

(Methoxycarbonylmethyl)triphenylphosphonium bromide ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
• Uses: (Methoxycarbonylmethyl)triphenylphosphonium bromide is a reactant for the synthesis of GSK-3 inhibitors using the Wittig reaction, substituted furanones for antifungal and cytostatic activities, photochromic dithienylethene derivatives, gem-diiodoalkanes containing allylic alcohols and highly substituted cyclopentenes and brazilanes via Au-catalyzed deoxygenative Nazarov cyclization. As reactant for asymmetric hydrogenation of α,β-unsaturated ester-phosphonates, studies of thermal decomposition of phosphonium alkyl ester salts.

Technology Process of (2-Methoxy-2-oxoethyl)triphenylphosphonium bromide

There total 7 articles about (2-Methoxy-2-oxoethyl)triphenylphosphonium 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: 100.0%

bromoacetic acid methyl ester (96-32-2) + triphenylphosphine (603-35-0) → (methyloxycarbonylmethyl)triphenylphosphonium bromide (1779-58-4)

Guidance literature:

In ethyl acetate; at 20 ℃; for 17h;

DOI:10.1515/znb-2016-0201

Reference yield: 75.0%

2,2-dibromo-indan-1,3-dione (1685-97-8) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → (methyloxycarbonylmethyl)triphenylphosphonium bromide (1779-58-4) + (2-Bromo-1,3-dioxo-indan-2-yl)-(triphenyl-λ5-phosphanylidene)-acetic acid methyl ester (134898-37-6)

Guidance literature:

In benzene; Heating;

Reference yield: 75.0%

[(2-Bromo-1,3-dioxo-indan-2-yl)-methoxycarbonyl-methyl]-triphenyl-phosphonium; bromide (134898-34-3) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → (methyloxycarbonylmethyl)triphenylphosphonium bromide (1779-58-4) + (2-Bromo-1,3-dioxo-indan-2-yl)-(triphenyl-λ5-phosphanylidene)-acetic acid methyl ester (134898-37-6)

Guidance literature:

In benzene; Heating;

upstream raw materials:

bromoacetic acid methyl ester

triphenylphosphine

methyl (triphenylphosphoranylidene)acetate

3,3-dibromo-1,3-diphenyl-1,3-propanedione

Downstream raw materials:

methyl (triphenylphosphoranylidene)acetate

(E)-1-methyl-2-<2-(methoxycarbonyl)ethenyl>pyrrole

3-phenyl-5-[(E)-(methoxycarbonylmethylidene)]-2-furanone

4-Chloro-4,4-difluoro-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid methyl ester

Refernces

• 1、 Villa, Maria-Jesus,Warren, Stuart. "Tandem Conjugate addition of Silylcuprate and Benzenesulfenyl Chloride to Unsaturated Esters: Stereoselective Preparation of anti-3-Dimethylphenylsilyl-2-phenylthio Aldehydes". . p. 1569 - 1572. Retrieved 1994.
• 2、 Mukhtar, Asma,Zaheer, Muhammad,Saeed, Muhammad,Voelter, Wolfgang. "Synthesis of lignin model compound containing a β-O-4 linkage". . p. 119 - 124. Retrieved 2017.
• 3、 Feng, Xiaoming,Hu, Xinyue,Lin, Lili,Wang, Kaixuan,Xu, Chaoran,Zhou, Yuqiao. "Catalytic asymmetric [3+2] cycloaddition of isomünchnones with methyleneindolinones". supporting information. p. 8917 - 8920. Retrieved 2021/09/10.
• 4、 Pitchumani, Venkatachalam,Breugst, Martin,Lupton, David W.. "Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes". supporting information. p. 9413 - 9418. Retrieved 2021/12/09.