Ethyl (triphenylphosphoranylidene)acetate

Base Information

• Chemical Name: Ethyl (triphenylphosphoranylidene)acetate
• CAS No.: 1099-45-2
• Deprecated CAS: 103603-89-0,21382-83-2
• Molecular Formula: C22H21O2P
• Molecular Weight: 348.381
• Hs Code.: 29310095
• European Community (EC) Number: 214-151-7
• NSC Number: 72406
• UNII: WX75SQL8ZF
• DSSTox Substance ID: DTXSID7061485
• Nikkaji Number: J728.507H,J217.213E
• Wikipedia: Triphenylcarbethoxymethylenephosphorane
• Wikidata: Q7843270
• Mol file: 1099-45-2.mol

Synonyms:1099-45-2;(Carbethoxymethylene)triphenylphosphorane;Ethyl (triphenylphosphoranylidene)acetate;Ethyl 2-(triphenylphosphoranylidene)acetate;(Ethoxycarbonylmethylene)triphenylphosphorane;Triphenylcarbethoxymethylenephosphorane;Acetic acid, (triphenylphosphoranylidene)-, ethyl ester;MFCD00009183;Carbethoxytriphenylphosphonium methylide;Carboethoxymethylidenetriphenylphosphorane;Ethyl (triphenylphosphoranilidene)acetate;ethyl (triphenylphosphoranylidene) acetate;ethyl 2-(triphenyl-lambda5-phosphanylidene)acetate;Carbethoxymethylidenetriphenylphosphorane;NSC 72406;WX75SQL8ZF;ethoxycarbonylmethylenetriphenylphosphorane;Phosphorane, (carboxymethylene)triphenyl-, ethyl ester;[(Ethoxycarbonyl)methylene]triphenylphosphorane;(Triphenylphosphoranylidene)acetic Acid Ethyl Ester;EINECS 214-151-7;NSC-72406;Carboethoxymethylenetriphenylphosphorane;Ethyl (triphenylphosphanylidene)acetate;ethyl(triphenylphosphoranylidene)acetate;Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester;((Ethoxycarbonyl)methylene)triphenylphosphorane;((Ethoxycarbonyl)ethylidene)triphenylphosphorane;[(Ethoxycarbonyl)ethylidene]triphenylphosphorane;carbethoxymethylene triphenylphosphorane;NSC-167159;ethyl triphenylphosphoranylidene-acetate;Ethyl (triphenylphosphoranyliden)acetate;Phosphorane, ethyl ester;UNII-WX75SQL8ZF;(TRIPHENYLCARBETHOXYMETHYLENE)PHOSPHORANE;SCHEMBL65066;DTXSID7061485;HMS3886A10;AMY24781;BCP28332;CS-M0973;NSC72406;carbethoxymethylenetriphenylphosphorane;carboethoxymethylentriphenylphosphorane;s5511;(carbethoxymethylene)triphenylphosphine;ethyl triphenylphosphoranylideneacetate;ethyl(triphenylphosphoranyliden)acetate;AKOS005146272;carbethoxymethylene-triphenylphosphorane;carbethoxymethylenetriphenyl phosphorane;carboethoxymethylene triphenylphosphoran;(Carbethoxymethylene)triphenylphosphoran;(carboethoxymethylene)triphenylphosphine;AB00967;CCG-268011;(carbethoxymethylen)-triphenylphosphorane;carbethoxy methylene triphenylphosphorane;carbethoxymethylene triphenyl phosphorane;Carboethoxymethylene triphenylphosphorane;ethoxycarbonylmethylenetriphenylphosphoran;ethyl (triphenylphosphanylidene)-acetate;ethyl 2-triphenylphosphoranylideneacetate;ethyl(triphenyl-phosphoranylidene)acetate;ethyl(triphenylphosphoranylidene)-acetate;(carbethoxy methylene)triphenylphosphorane;(carbethoxymethylene) triphenylphosphorane;(carbethoxymethylene)-triphenylphosphorane;(carbethoxymethylene)triphenyl phosphorane;(carbethoxymethylene)triphenyl-phosphorane;carbethoxy methylene triphenyl phosphorane;carboethoxy-methylenetriphenyl phosphorane;ethyl 2-(triphenylphosphanylidene)acetate;(carbethoxymethylidene)triphenylphosphorane;(carboethoxy-methylene)triphenylphosphorane;(carboethoxymethylene) triphenylphosphorane;(carboethoxymethylene)-triphenylphosphorane;(carboethoxymethylene)triphenylphospho-rane;(carboethoxyrnethylene)triphenylphosphorane;AS-12884;Carboethoxymethylidene triphenylphosphorane;ethyl (triphenylphosphoranylidene)-acetate;SY003933;(carbethoxymethylene) triphenyl-phosphorane;(carbethoxymethylene)-triphenyl phosphorane;(carbethoxymethylene)-triphenyl-phosphorane;Ethoxycarbonyl(triphenylphosphonio)methanide;ethoxycarbonylmethylene triphenylphosphorane;ethoxycarbonylmethylene-triphenylphosphorane;ethoxycarbonylmethylidenetriphenylphosphorane;ethyl 2-tri(phenyl)phosphoranylideneacetate;(carbethoxy methylene)-triphenyl phosphorane;(ethoxycarbonylmethylen)-triphenylphosphorane;Ethoxycarbonylmethylene triphenyl phosphorane;ethoxycarbonylmethylene-triphenyl-phosphorane;(ethoxycarbonylmethylene)-triphenylphosphorane;ethoxycarbonyl-methylene-triphenyl-phosphorane;ethyl 2-(triphenyl phosphoranylidene)acetate;ethyl 2-(triphenylphosphoranylidene)-acetate;FT-0623464;T1944;(ethoxy-carbonylmethylene)-triphenylphosphorane;(ethoxycarbonylmethylene)-triphenyl-phosphorane;EN300-19609;(2-Ethoxy-2-oxoethylidene)triphenylphosphorane;(Carbethoxymethylene)triphenylphosphorane, 95%;(ethoxycarbonyl methylene) triphenyl phosphorane;[(ethoxycarbonyl)methylene]triphenyl phosphorane;Ethyl(triphenyl-lambda5-phosphanylidene)acetate;triphenylphosphoranylideneacetic acid ethyl ester;(CARBOETHOXYMETHYLENE)TRIPHENYLPHOSPHORANE;(triphenylphosphanylidene)acetic acid ethyl ester;Ethyl (triphenyl-lambda5-phosphanylidene)acetate;triphenylphosphoranylidene acetic acid ethyl ester;(triphenyl-phosphanylidene)acetic acid ethyl ester;A802115;triphenyl-phosphoranylidene acetic acid ethyl ester;(triphenyl phosphoranylidene)acetic acid ethyl ester;(triphenyl-phosphanylidene)-acetic acid ethyl ester;(triphenylphosphoranylidene)-acetic acid ethyl ester;Q7843270;W-111711;(triphenyl-phosphoranylidene)-acetic acid ethyl ester;2-(triphenylphosphoranylidene)acetic acid ethyl ester;(Triphenyl-I>>5-phosphanylidene)-acetic acid ethyl ester;Z104474440;(triphenyl-lambda-5-phosphanylidene)acetic acid ethyl ester;(triphenyl-lambda5-phosphanylidene)acetic acid ethyl ester;(TRIPHENYL-LAMBDA5-PHOSPHANYLIDENE)-ACETIC ACID ETHYL ESTER

Chemical Property of Ethyl (triphenylphosphoranylidene)acetate

Chemical Property:

• Appearance/Colour: white or slight yellow powder
• Vapor Pressure: 9.18E-10mmHg at 25°C
• Melting Point: 125-127ºC
• Refractive Index: 1.6
• Boiling Point: 490.4 ºC at 760 mmHg
• Flash Point: 263.5 ºC
• PSA: 36.11000
• Density: 1.15 g/cm³
• LogP: 3.34580
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Chloroform, THF
• Water Solubility.: Insoluble
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 348.12791691
• Heavy Atom Count: 25
• Complexity: 414

Purity/Quality:

99% ^*data from raw suppliers

(Carbethoxymethylene)triphenylphosphorane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,Xi,Xn
• Statements: 36/37/38-25-20/21/22
• Safety Statements: 22-24/25-45-37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phosphorus Compounds
• Canonical SMILES: CCOC(=O)C=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
• Description: Ethyl (triphenylphosphoranylidene)acetate is a common Wittig reagent in organic synthesis as well as a cholinesterase inhibitor that inhibits both AChE and BChE. It is used in the preparation of indole from o-nitrobenzaldehydes, coumarins from o-hydroxy acetophenone.
• Uses: It acts as an inhibitor and inhibits the activity of cholinesterase. A common Wittig reagent. A cholinesterase inhibitor. (Ethoxycarbonylmethylene)triphenylphosphoran is used as a Wittig reagent in organic synthesis. It is used in the preparation of indole from o-nitrobenzaldehydes, coumarins from o-hydroxy acetophenone. It acts as an inhibitor and inhibits the activity of cholinesterase.

Technology Process of Ethyl (triphenylphosphoranylidene)acetate

There total 44 articles about Ethyl (triphenylphosphoranylidene)acetate 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%

(carbethoxymethyl)triphenylphosphonium bromide (1530-45-6) → ethyl (triphenylphosphoranylidene)acetate (1099-45-2)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 5h;

Reference yield: 99.0%

P-(carboethoxymethyl)triphenylphosphonium cation (42809-80-3) → ethyl (triphenylphosphoranylidene)acetate (1099-45-2)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; at 20 ℃; for 0.5h;

DOI:10.1002/chem.201800313

Reference yield: 89.5%

(ethoxycarbonylmethyl)triphenylphosphonium chloride (17577-28-5) → ethyl (triphenylphosphoranylidene)acetate (1099-45-2)

Guidance literature:

With potassium hydroxide; In water;

DOI:10.1016/j.jorganchem.2006.11.002

upstream raw materials:

diazoacetic acid ethyl ester

triphenylphosphine

sorbic Acid

(2,2-diethoxyvinylidene)triphenylphosphorane

Downstream raw materials:

ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate

(3'E)-15,3',4',15'-tetradehydro-2'-apo-β,ψ-caroten-2'-oic acid methyl ester

3-(5-chloro-2-phenyl-oxazol-4-yl)-acrylic acid ethyl ester

3-(5-oxo-2-phenyl-oxazol-4-ylidene)-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid ethyl ester

Refernces

• 1、 Ball-Jones, Nicolas R.,Badillo, Joseph J.,Tran, Ngon T.,Franz, Annaliese K.. "Catalytic enantioselective carboannulation with allylsilanes". . p. 9462 - 9465. Retrieved 2014.
• 2、 Baktharaman, Sivaraj,Afagh, Nicholas,Vandersteen, Adelle,Yudin, Andrei K.. "Unprotected vinyl aziridines: Facile synthesis and cascade transformations". . p. 240 - 243. Retrieved 2010.
• 3、 Matveeva,Podrugina,Grishin,Pavlova,Zefirov. "Phosphonium-iodonim ylides in nucleophilic substitution reactions". . p. 201 - 206. Retrieved 2007.
• 4、 Balema, Viktor P.,Wiench, Jerzy W.,Pruski, Marek,Pecharsky, Vitalij K.. "Mechanically induced solid-state generation of phosphorus ylides and the solvent-free wittig reaction". . p. 6244 - 6245. Retrieved 2002.
• 5、 Rijn, C. J. M. van,Jesse, W.,Bleijser, J. de,Leyte, J. C.. "Concentration-Dependent Main-Chain Dynamics of Sodium Polyacrylate As Probed by NMR in the Semidilute Regime". . p. 203 - 210. Retrieved 1987.
• 6、 Obi, Grace,Van Heerden, Fanie R.. "Synthesis of 5,6-dehydrokawain and some fluorinated analogues". . p. 1482 - 1486. Retrieved 2018.
• 7、 Menger, Martina,Christmann, Mathias. "Formal synthesis of actinoranone using a one-pot semipinacol rearrangement/Wittig reaction". . p. 10 - 16. Retrieved 2019.
• 8、 Liu, Yong-Liang,Wang, Xiao-Ping,Wei, Jie,Li, Ya. "PPh3-catalyzed β-selective addition of α-fluoro β-dicarbonyl compounds to allenoates". supporting information. . Retrieved 2021/12/02.
• 9、 Liu, Xin,Werner, Thomas. "Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides". supporting information. p. 1096 - 1104. Retrieved 2020/12/31.