(Triphenylphosphoranylidene)acetaldehyde

Base Information

• Chemical Name: (Triphenylphosphoranylidene)acetaldehyde
• CAS No.: 2136-75-6
• Molecular Formula: C20H17 O P
• Molecular Weight: 304.328
• Hs Code.: 29319090
• European Community (EC) Number: 218-375-6
• UNII: P7LZM6552K
• DSSTox Substance ID: DTXSID60175622
• Nikkaji Number: J1.188.527F,J298.723F
• Wikidata: Q72514809
• Mol file: 2136-75-6.mol

Synonyms:2136-75-6;(Triphenylphosphoranylidene)acetaldehyde;(Formylmethylene)triphenylphosphorane;2-(Triphenylphosphoranylidene)acetaldehyde;Formylmethylenetriphenylphosphorane;Formylmethylene triphenylphosphorane;Acetaldehyde, (triphenylphosphoranylidene)-;2-(triphenyl-lambda5-phosphanylidene)acetaldehyde;(triphenylphosphoranylidene) acetaldehyde;MFCD00006994;C20H17OP;SCHEMBL181926;P7LZM6552K;DTXSID60175622;formylmethylene-triphenylphosphoran;2-Oxoethylidenetriphenylphosphorane;formylmethylene-triphenylphosphorane;formylmethylenetriphenyl phosphorane;formylmethylidenetriphenylphosphorane;BCP22984;CS-M0489;EINECS 218-375-6;triphenylphosphoranylideneacetaldehyde;(2-Oxoethylidene)triphenylphosphorane;(formylmethylene)-triphenylphosphorane;triphenylphosphoranylidene acetaldehyde;AKOS005259852;2-triphenylphosphoranylideneacetaldehyde;(triphenylphosphoranylidene)-acetaldehyde;(triphenylphosphoranylidene)acetoaldehyde;FORMYLMETHYLENETRIPHENYLPHOSPORANE;SY030499;2-(triphenylphosphoranylidene) acetaldehyde;1-(Triphenylphosphonio)-2-oxoethane-1-ide;AM20060547;FT-0604969;T2001;(Triphenylphosphoranylidene)acetaldehyde, 95%;Acetaldehyde, 2-(triphenylphosphoranylidene)-;EN300-18526;(triphenyl-lambda*5*-phosphanylidene)-acetaldehyde;A815294;A1-00320;J-502071;Z62436289;(Triphenylphosphoranylidene)acetaldehyde, technical, >=95% (NT/PNMR)

Chemical Property of (Triphenylphosphoranylidene)acetaldehyde

Chemical Property:

• Appearance/Colour: pink to brown crystalline powder
• Vapor Pressure: 1.2E-08mmHg at 25°C
• Melting Point: 185-188 °C(lit.)
• Refractive Index: 1.62
• Boiling Point: 472.618 °C at 760 mmHg
• Flash Point: 239.631 °C
• PSA: 26.88000
• Density: 1.162 g/cm³
• LogP: 2.98160
• Storage Temp.: Keep Cold
• Sensitive.: Air Sensitive
• Solubility.: Soluble in Chloroform, Methanol.
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 304.101702159
• Heavy Atom Count: 22
• Complexity: 344

Purity/Quality:

97% ^*data from raw suppliers

(Triphenylphosphoranylidene)acetaldehyde ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(=CC=O)(C2=CC=CC=C2)C3=CC=CC=C3
• Uses: (Formylmethylene)triphenylphosphorane is used as Wittig reagent. It is also used as Pharmaceutical Intermediates. It is employed as raw material in organic Synthesis, Agrochemicals. Wittig reagent for the conversion of aldehydes and ketones to two-carbon homologated, α,β-unsaturated carbonyl compounds.

Technology Process of (Triphenylphosphoranylidene)acetaldehyde

There total 11 articles about (Triphenylphosphoranylidene)acetaldehyde 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: 97.0%

formylmethyltriphenylphosphonium chloride (62942-43-2) → (triphenylphosphoranylidene)acetaldehyde (2136-75-6)

Guidance literature:

With sodium hydroxide; In water; at 20 - 30 ℃; for 0.5h;

Reference yield: 81.0%

Methylenetriphenylphosphorane (19493-09-5) + formic acid ethyl ester (109-94-4) → (triphenylphosphoranylidene)acetaldehyde (2136-75-6)

Guidance literature:

In benzene;

Reference yield: 76.0%

Methyltriphenylphosphonium bromide (1779-49-3) + formic acid ethyl ester (109-94-4) → (triphenylphosphoranylidene)acetaldehyde (2136-75-6)

Guidance literature:

Methyltriphenylphosphonium bromide; With potassium tert-butylate; In diethyl ether; at 20 ℃; for 1.5h;

formic acid ethyl ester; In diethyl ether; at 20 ℃;

DOI:10.1021/ol401015e

upstream raw materials:

triphenylphosphine

Bromoacetaldehyde diethyl acetal

Methyltriphenylphosphonium bromide

formic acid ethyl ester

Downstream raw materials:

trans-3-(3-pyridyl)acrolein

(E)-3-(2,5-Dihydroxy-phenyl)-propenal

(E)-3-[(2R,3R)-3-Pentyl-1-(toluene-4-sulfonyl)-aziridin-2-yl]-propenal

(E)-3-[(2R,3R)-3-(2-Benzyloxy-ethyl)-1-(toluene-4-sulfonyl)-aziridin-2-yl]-propenal

Refernces

Synthesis of leukotriene analogs

10.1002/ardp.19843170714

The research focuses on the synthesis of leukotriene analogs, which are biologically active compounds derived from polyunsaturated fatty acids, particularly relevant to immediate hypersensitivity reactions and inflammation. The purpose of this study was to develop a simple chemical synthesis method for C-15 and C-17 leukotriene analogs, acting as partial agonists/antagonists of slow reacting substance of anaphylaxis (SRS-A). The synthesis began with the epoxide 15 and involved reactions with formylmethylenetriphenylphosphorane and hexyltriphenylphosphorane, among other reagents, to produce the desired leukotriene analogs. The final products, C-17 LTA,methyl ester 3 and C-15 LTA,methyl ester 4, were purified and further reacted with glutathione, cysteinylglycine, and cysteine to yield peptide conjugates.

A SYNTHESIS OF L-lyxo-L-altro-NONITOL, A NEW NONITOL

10.1016/0008-6215(86)84007-1

The study focuses on the synthesis of L-lyxo-L-altro-nonitol, a new nonitol compound. The researchers used catalytic osmylation of (E)-6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-non-7-enopyranose (1.5) to obtain a mixture of 6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-L-lyxo-D-gulacto-nonopyranose (16) and the α-D-xylo-D-gulacto isomer 17. After debenzylation, crystalline 1,2:3,4-di-O-isopropylidene-α-L-lyxo-D-gulacto-nonopyranose (21) was isolated and converted into L-lyxo-L-altro-nonitol (L-lyxo-D-gulacto-nonitol) (23). The study also explored the preparation of the allylic alcohol 15 through Wittig olefination of 6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptodiol-1,5-pyranose (13) with formylmethylenetriphenylphosphorane or (methoxycarbonylmethylene)triphenylphosphorane, followed by appropriate reduction of the enal 14 or conjugate ester 24. The study provides a new route to nonoses and nonitols, which have been traditionally challenging to synthesize.