2-(Triphenylphosphoranylidene)propionaldehyde

Base Information

• Chemical Name: 2-(Triphenylphosphoranylidene)propionaldehyde
• CAS No.: 24720-64-7
• Molecular Formula: C21H19 O P
• Molecular Weight: 318.355
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID70401520
• Nikkaji Number: J1.629.311C,J789.947E
• Wikidata: Q82204674
• Mol file: 24720-64-7.mol

Synonyms:24720-64-7;2-(Triphenylphosphoranylidene)propionaldehyde;2-(Triphenylphosphoranylidene)propanal;Propanal, 2-(triphenylphosphoranylidene)-;2-(triphenyl-lambda5-phosphanylidene)propanal;2-(Triphenyl-l5-phosphanylidene)propanal;MFCD00075596;2-(triphenylphosphoranylidene)-propionaldehyde;SCHEMBL1376790;DTXSID70401520;VHUQEFAWBCDBSC-UHFFFAOYSA-N;ZAA72064;AKOS015912942;1-formylethylidene(triphenyl)phosphorane;alpha-formylethylidenetriphenylphosphorane;AC-28346;AS-10113;SY066786;(1-formylethylidene)-triphenyl-phosphorane;2-(triphenylphosphanylidene)-propionaldehyde;2-(triphenyl-phosphanylidene)-propionaldehyde;AM20120718;CS-0113100;FT-0765452;2-(triphenyl-phosphoranylidene)-propionaldehyde;2-(Triphenylphosphoranylidene)propionaldehyde, 98%;A877812;J-015644

Chemical Property of 2-(Triphenylphosphoranylidene)propionaldehyde

Chemical Property:

• Vapor Pressure: 7.42E-09mmHg at 25°C
• Melting Point: 219-221ºC(lit.)
• Boiling Point: 478.5°C at 760 mmHg
• Flash Point: 243.2°C
• PSA: 26.88000
• Density: 1.14g/cm³
• LogP: 3.37170
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 318.117352223
• Heavy Atom Count: 23
• Complexity: 383

Purity/Quality:

99% ^*data from raw suppliers

2-(Triphenylphosphoranylidene)propionaldehyde ^*data from reagent suppliers

Safty Information:

• Statements: 22-36/37/38
• Safety Statements: 26-37/39

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
• Uses: Reactant for:? ;Preparation of acitretin analogs with antitumor activity1? ;Stereoselective synthesis of essential building blocks of phorboxazole A via hetero Diels-Alder and stereoselective hetero-Michael addition/equilibration2? ;Preparation of C1-C14 fragment of sarcoglaucol-16-one via Z-selective ando-type Horner-Wadsworth-Emmons olefination3? ;Wittig reactions4? ;Synthesis of ring-expanded and epothilone-hybridized macrosphelide analogs as apoptosis-inducing agents5? ;Preparation of phosphonic acid-containing analogs of mycophenolic acid as inhibitors 2-(Triphenylphosphoranylidene)propionaldehyde is a reagent used in the asymmetric synthesis of hispidanin A via oxidative alkoxylation and stereoselective Diels-Alder reaction. Also acts as a reagent in the stereoselective synthesis of 10-epi-tirandamycin E. Reactant for:Preparation of acitretin analogs with antitumor activityStereoselective synthesis of essential building blocks of phorboxazole A via hetero Diels-Alder and stereoselective hetero-Michael addition/equilibrationPreparation of C1-C14 fragment of sarcoglaucol-16-one via Z-selective ando-type Horner-Wadsworth-Emmons olefinationWittig reactionsSynthesis of ring-expanded and epothilone-hybridized macrosphelide analogs as apoptosis-inducing agentsPreparation of phosphonic acid-containing analogs of mycophenolic acid as inhibitors of IMPDH

Technology Process of 2-(Triphenylphosphoranylidene)propionaldehyde

There total 8 articles about 2-(Triphenylphosphoranylidene)propionaldehyde 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: 83.0%

(palladium(II)(p-methoxyphenylisocyanido)(η3-2-(Me)allyl)((acetylmethylene)triphenylphosphorane))BF4 + p-methoxyphenylisonitrile (10349-38-9) → (palladium(II)bis(p-methoxyphenylisocyanido)(η3-2-(Me)allyl))BF4 + 2-(triphenylphosphoranylidene)propionaldehyde (24720-64-7)

Guidance literature:

In 1,2-dichloro-ethane; Under N2 a soln. of Pd(CNC6H4OCH3)(Ch3C3H4)(Ph3PC(H)COCH3) in 1,2-dichloroethane is treated with CNC6H4OCH3, mixt. is stirred for 30 min at room temp.; Taken to dryness under reduced pressure, residue extd. with C6H6, insoluble compound is filtered off, washed with Et2O, elem. anal.;

DOI:10.1016/0022-328X(89)87191-8

Reference yield: 78.0%

ethyltriphenylphosphonium iodide (4736-60-1) + formic acid ethyl ester (109-94-4) → 2-(triphenylphosphoranylidene)propionaldehyde (24720-64-7)

Guidance literature:

ethyltriphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; toluene; at 22 ℃; for 1h;

formic acid ethyl ester; With potassium tert-butylate; In tetrahydrofuran; toluene; at 0 ℃; for 0.25h;

DOI:10.1021/jo990342r

Reference yield:

<2-(Dimethylamino)vinyliden>triphenylphosphoran (82248-14-4) → 2-(triphenylphosphoranylidene)propionaldehyde (24720-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / benzene

2: 1) 2 N H₂SO₄, 2) 0.5 N NaOH / 1) H₂O, 30 min, 2) H₂O

With sodium hydroxide; sulfuric acid; In benzene;

upstream raw materials:

<2-(Dimethylamino)-1-methylvinyl>triphenylphosphonium-chlorid

ethyltriphenylphosphonium bromide

formic acid ethyl ester

ethyltriphenylphosphonium iodide

Downstream raw materials:

Triphenyl-1-ethoxy-propen-⁽¹⁾-yl-⁽²⁾-phosphoniumbromid

(E)-4-acetoxy-2-methylcrotonaldehyde

(Z)-4-Acetoxy-2-methyl-2-butenal

menthofuran

Refernces

• 1、 Facchin, Giacomo,Bertani, Roberta,Zanotto, Livio,Calligaris, Mario,Nardin, Giorgio. "Preparation and characterization of PdII-ylide complexes of type 3-2-XC3H4)>BF4 (X=H, Me; R=p-C6H4OMe, C(Me)3, Me, C6H11, p-c6H4NO2). Crystal structure of (η3-2-MeC3H4)>BF4". . p. 409 - 420. Retrieved 1989.
• 2、 Ruder, Suzanne M.,Norwood, Bradley K.. "Reaction of Oxygen Nucleophiles With β-Alkoxyvinylphosphonium Salts. Isolation of Phosphine Oxides.". . p. 861 - 864. Retrieved 2007/10/02.