71140-70-0

Basic information

• Product Name: 4-CARBOXYBUTYLDIPHENYLPHOSPHINE OXIDE
• Synonyms: 5-(Diphenylphosphinyl)pentanoic Acid;4-CARBOXYBUTYLDIPHENYLPHOSPHINE OXIDE
• CAS NO: 71140-70-0
• Molecular Formula: C₁₇H₁₉O₃P
• Molecular Weight: 302.3047
• Product Categories: Aromatics, Miscellaneous Reagents
• Mol File: 71140-70-0.mol

Chemical Properties

• Boiling Point: 462.7 °C at 760 mmHg
• Flash Point: 233.7 °C
• Appearance: /
• Density: 1.19 g/cm³
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 4-CARBOXYBUTYLDIPHENYLPHOSPHINE OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CARBOXYBUTYLDIPHENYLPHOSPHINE OXIDE(71140-70-0)
• EPA Substance Registry System: 4-CARBOXYBUTYLDIPHENYLPHOSPHINE OXIDE(71140-70-0)

Safety Data

• Hazardous Substances Data: 71140-70-0(Hazardous Substances Data)

Usage

Uses

Used in Coordination Polymers:
4-Carboxybutyldiphenylphosphine oxide is used as a ligand in the preparation of praseodymium coordination polymers. The diphenylphosphorylvalerate ligand in these polymers allows for the creation of stable and well-defined structures with potential applications in various areas, such as catalysis, materials science, and medicine.
Used in Prostaglandin Analogs:
4-Carboxybutyldiphenylphosphine oxide is also a by-product in the preparation of prostaglandin analogs. Prostaglandins are bioactive compounds that play important roles in various physiological processes, such as inflammation, pain, and blood clotting. The development of prostaglandin analogs has significant implications in the pharmaceutical industry for the treatment of various diseases and conditions.
Used as a Standard in Analytical Chemistry:
Due to its common production in the Wittig reaction, 4-Carboxybutyldiphenylphosphine oxide can be used as a standard for analyzing products of synthetic routes that utilize this reaction. This allows for accurate determination of the efficiency and selectivity of the reaction, as well as the purity of the synthesized olefins.

Upstream product

• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 41264-12-4 (4-Carbohydroxybutyl)-triphenylphosphonium 
• 626-19-7 Isophthalaldehyde 
• 16045-88-8 boron trifluoride methanol complex 
• 90560-22-8 5-methoxy-benzene-1,3-dicarbaldehyde 
• 2067-33-6 5-bromopentanoic acid 
• 603-35-0 triphenylphosphine 

Downstream Products

• 146964-27-4 Methyl 5-diphenylphosphinoylpentanoate 
• 146964-29-6 (5-hydroxypentyl)diphenylphosphine oxide 

Relevant articles and documents

Double Wittig reactions with 4-carboxybutylidene triphenylphosphorane as the key step in the synthesis of benzene derivatives metadisubstituted with ωω'-difunctionalized six-carbon chains

Using a double Wittig reaction from diformylbenzene derivatives, a direct synthetic way to 1,3-di(5-carboxypent-1-yl)benzene compounds is discussed.

Stereochemically controlled Synthesis of Unsaturated Alcohols by the Horner-Wittig Reaction

Single isomers (E or Z) of unsaturated alcohols with two to five carbon atoms between the double bond and the OH group may be made by the phosphine oxide version of the Horner-Wittig reaction.Hydroxyalkyldiphenylphosphine oxides react with aldehydes either directly or as silyl ethers to give a moderately Z-selective synthesis, while rearrangement of esters of the same alcohols by acyl transfer or acylation of alkyldiphenylphosphine oxides with lactones gives hydroxy ketones whose reduction and elimination leads to an E-selective synthesis.In most cases, separation of the diastereoisomers of the Horner-Wittig intermediates leads to the preparation of pure E- or Z-alkenols.

Biotin biosynthesis: Preparation of the postulated intermediate thiol

Previous work in our group led us to postulate thiol 3 as the first intermediate in the biotransformation of dethiobiotin 1 into biotin 2.A new synthesis of this thiol is described here starting from the lactone 4, an intermediate in the Hofmann La Roche industrial synthesis of biotin.After the failure of the Wittig approach, the side-chain was successfully introduced through a Grignard addition to the lactone followed by reduction of the ketone.Deoxygenation of the xanthate afforded the protected alcohol 29.To obtain the deprotected hydroxy acid 34a it was necessary to oxidize the double bond before the debenzylation of the imidazolidinone ring.The acid 34a was readily transformed into 3.Keywords: biotin / biosynthesis / alcohol deoxygenation / debenzylation

13-AZA-14-OXO-15-OXAPROSTAGLANDINS

13-Aza-14-oxo-15-oxaprostaglandins in optically active form have been synthesized, starting from Corey's bicyclic lactone.