Methyl 2-(triphenylphosphoranylidene)propanoate

Base Information

• Chemical Name: Methyl 2-(triphenylphosphoranylidene)propanoate
• CAS No.: 2605-68-7
• Molecular Formula: C22H21 O2 P
• Molecular Weight: 348.381
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID30441907
• Nikkaji Number: J329.165K
• Wikidata: Q72492254
• Mol file: 2605-68-7.mol

Synonyms:2605-68-7;Methyl 2-(triphenylphosphoranylidene)propanoate;carbmethoxy ethylidene triphenyl phosphorane;methyl 2-(triphenyl-lambda5-phosphanylidene)propanoate;Propanoic acid, 2-(triphenylphosphoranylidene)-, methyl ester;MFCD08062441;1-METHOXYCARBONYLETHYLIDENETRIPHENYLPHOSPHORANE;SCHEMBL1827594;DTXSID30441907;WCXPAYJKBTVUBC-UHFFFAOYSA-N;CAA60568;AKOS016005567;1-carbomethoxyethylidene triphenylphosphine;AS-71133;BP-20608;SY119838;CS-0030442;Methyl 2-(triphenylphosphoranediyl)propionate;Methyl2-(triphenylphosphoranylidene)propanoate;C74350;methyl 2-(triphenylphosphoranylidene)propionate;methyl 2-(triphenylphosphoranyli-dene) propionate;[1-(methoxycarbonyl)ethylidene]triphenylphosphorane;A919253;methyl 2-(triphenyl-$l^{5-phosphanylidene)propanoate;Methyl 2-(triphenyl-lambda~5~-phosphanylidene)propanoate;METHYL 2-(TRIPHENYL-??-PHOSPHANYLIDENE)PROPANOATE

Chemical Property of Methyl 2-(triphenylphosphoranylidene)propanoate

Chemical Property:

• Melting Point: 153-156℃ (ethyl acetate )
• Boiling Point: 485.8±28.0 °C(Predicted)
• PSA: 36.11000
• Density: 1.16±0.1 g/cm3 (20 ºC 760 Torr)
• LogP: 3.34580
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 348.12791691
• Heavy Atom Count: 25
• Complexity: 440

Purity/Quality:

99%, ^*data from raw suppliers

Methyl2-(triphenylphosphoranylidene)propanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)OC

Technology Process of Methyl 2-(triphenylphosphoranylidene)propanoate

There total 7 articles about Methyl 2-(triphenylphosphoranylidene)propanoate 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%

(1-methoxy-1-oxopropan-2-yl)triphenylphosphonium iodide (56904-90-6) → methyl 2-(triphenylphosphoranylidene)propionate (2605-68-7)

Guidance literature:

With sodium hydroxide; In dichloromethane; water;

DOI:10.1002/(sici)1099-0690(199911)1999:11<2909::aid-ejoc2909>3.0.co;2-5

Reference yield: 97.0%

Methyl 2-bromopropionate (5445-17-0) + triphenylphosphine (603-35-0) → methyl 2-(triphenylphosphoranylidene)propionate (2605-68-7)

Guidance literature:

Methyl 2-bromopropionate; triphenylphosphine; In water; at 70 - 80 ℃; for 23h;

With sodium hydroxide; In water; for 0.0833333h;

DOI:10.3390/molecules25194527

Reference yield:

triphenylphosphine (603-35-0) → methyl 2-(triphenylphosphoranylidene)propionate (2605-68-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / ethyl acetate / 24 h / Heating

2: Et₃N; molecular sieves 3 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

With 3 A molecular sieve; triethylamine; In dichloromethane; ethyl acetate;

DOI:10.1016/j.tet.2007.07.079

upstream raw materials:

(1-methoxy-1-oxopropan-2-yl)triphenylphosphonium iodide

Methyl 2-bromopropionate

triphenylphosphine

methyl 2-iodopropionate

Downstream raw materials:

methyl (E)-2-methyl-2-butenoate

ethyl (E)-2-methyl-5-phenyl-pent-2-enoate

(E)-2-Methyl-5-((1S,6R)-6-p-tolylsulfanyl-bicyclo[4.1.0]hept-1-yl)-pent-2-enoic acid methyl ester

Methyl-(E)-2-methyl-4-phenyl-2-buteonate

Refernces

• 1、 Boisse, Thomas,Rigo, Beno?t,Millet, Régis,Hénichart, Jean-Pierre. "From dicarbonylallene to 1-aryl-3,6-dimethyl-4-aminoaryl-2-pyridones: a one-pot versatile and uncatalyzed synthesis". . p. 10511 - 10520. Retrieved 2007.
• 2、 Orfanidou, Maria,Petsi, Marina,Zografos, Alexandros L.. "Organocatalytic epoxidation and allylic oxidation of alkenes by molecular oxygen". supporting information. p. 9172 - 9178. Retrieved 2021/11/30.
• 3、 Chen, Weiqiang,Walker, Johannes C. L.,Oestreich, Martin. "Metal-Free Transfer Hydroiodination of C-C Multiple Bonds". . p. 1135 - 1140. Retrieved 2019/01/11.