1623-06-9

Basic information

• Product Name: propyl dihydrogen phosphate
• Synonyms: propyl dihydrogen phosphate;Phosphoric acid dihydrogen propyl ester;Propyl phosphate, (Pro)(ho)2po
• CAS NO: 1623-06-9
• Molecular Formula: C₃H₉O₄P
• Molecular Weight: 140.074921
• EINECS: 216-601-8
• Mol File: 1623-06-9.mol

Chemical Properties

• Boiling Point: 260.9°Cat760mmHg
• Flash Point: 111.6°C
• Appearance: /
• Density: 1.352g/cm³
• Vapor Pressure: 0.00355mmHg at 25°C
• Refractive Index: 1.446
• CAS DataBase Reference: propyl dihydrogen phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: propyl dihydrogen phosphate(1623-06-9)
• EPA Substance Registry System: propyl dihydrogen phosphate(1623-06-9)

Safety Data

• Hazardous Substances Data: 1623-06-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 13, p. 411, 1972 DOI: 10.1016/S0040-4039(01)84338-0

InChI:InChI=1/C3H9O4P/c1-2-3-7-8(4,5)6/h2-3H2,1H3,(H2,4,5,6)

Upstream product

• 71-23-8 propan-1-ol 
• 75-77-4 chloro-trimethyl-silane 
• 513-08-6 phosphoric acid tripropyl ester 
• 107-08-4 1-iodo-propane 

Relevant articles and documents

Method for synthesis of n-propyl phosphoric acid

The invention provides a preparation method for n-propyl phosphate. The preparation method comprises the following steps: (1) reacting tri-n-propyl phosphite with bromopropane under the catalysis of potassium iodide to obtain n-propyl di-n-propyl phosphate, wherein the reaction temperature is 50-70 DEG C; (2) reacting n-propyl di-n-propyl phosphate with trimethylsilyl chloride at the circumfluence temperature in an aprotic solvent under the catalysis of potassium bromide or potassium iodide to obtain n-propyl phosphate. The preparation method is easy to get the adopted raw materials, low in toxicity, less in by-products, easy to purify, low in cost and suitable for industrialized production. The reaction route of the preparation method is as follows: (as is shown in the Specification).

Human P2Y14 receptor agonists: Truncation of the hexose moiety of uridine-5′-diphosphoglucose and its replacement with alkyl and aryl groups

Uridine-5′-diphosphoglucose (UDPG) activates the P2Y14 receptor, a neuroimmune system GPCR. P2Y14 receptor tolerates glucose substitution with small alkyl or aryl groups or its truncation to uridine 5′-diphosphate (UDP), a full agonist at the human P2Y14 receptor expressed in HEK-293 cells. 2-Thiouracil derivatives displayed selectivity for activation of the human P2Y14 vs the P2Y6 receptor, such as 2-thio-UDP 4 (EC50=1.92 nMat P2Y14, 224-fold selectivity vs P2Y6) and its β-propyloxy ester 18. EC50 values of the β-methyl ester of UDP and its 2-thio analogue were 2730 and 56 nM, respectively. β-tert-Butyl ester of 4 was 11-fold more potent than UDPG, but β-aryloxy or larger, branched β-alkyl esters, such as cyclohexyl, were less potent. Ribose replacement of UDP with a rigid North or South methanocarba (bicyclo[3.1.0]hexane) group abolished P2Y14 receptor agonist activity. α,β-Methylene and difluoromethylene groups were well tolerated at the P2Y14 receptor and are expected to provide enhanced stability in biological systems. α,β-Methylene-2-thio-UDP 11 (EC50 = 0.92 nM) was 2160-fold selective versus P2Y6. Thus, these nucleotides and their congeners may serve as important pharmacological probes for the detection and characterization of the P2Y14 receptor.

Regioselective phosphorylation of carbohydrates and various alcohols by bacterial acid phosphatases; probing the substrate specificity of the enzyme from Shigella flexneri

Bacterial non-specific acid phosphatases normally catalyze the dephosphorylation of a variety of substrates. As shown previously the enzymes from Shigella flexneri and Salmonella enterica are also able to catalyze the phosphorylation of inosine to inosine monophosphate and D-glucose to D-glucose 6-phosphate (D-G6P) using cheap pyrophosphate as the phosphate donor. After optimization high yields (95%) are achieved in the latter reaction and we show here that it is possible to use these enzymes in a preparative manner. This prompted us to investigate by using 31P NMR and HPLC also the phosphorylation of a broad range of carbohydrates and alcohols. Many cyclic carbohydrates are phosphorylated in a regioselective manner. Non-cyclic carbohydrates are phosphorylated as well. Phosphorylation of linear alcohols, cyclic and aromatic alcohols is also possible. In all cases the acid phosphatase from Shigella prefers a primary alcohol function above a secondary one. We conclude that these enzymes are an attractive alternative to existing chemical and enzymatic methods in the phosphorylation of a broad range of compounds.

Synthesis of Trialkyl Phosphates from White Phosphorus

A new method was proposed for preparing trialkyl phosphates directly from white phosphorus by its electrolysis in a mixture of acetonitrile, alcohol, and water with tetraethylammonium iodide as supporting electrolyte. To increase the amount of the product synthesized in the unit volume of the electrolyte solution and the productivity of the process, phosphorus and water are added to the electrolyte in portions, which allows synthesis of up to 1 mol of trialkyl phosphate in 1 1 of the electrolyte solution.

Poly-perfluoroalkyl-substituted alcohols and acids, and derivatives thereof

Di-, tri- and poly-perfluoroalkyl-substituted alcohols and acids and derivatives thereof are described which are prepared from perfluoroalkyl iodides and di-, tri- or polyallyl alcohols or acids. These compounds contain two or more perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkenyl groups and one or two alcohol or acid groups or derivatized alcohol or acid functions. They can be reacted with isocyanates, epoxy compounds, anhydrides, acids or acid derivatives to prepare a great variety of oil- and water-repellent compositions which are useful for oil- and water-repellent treatment of textiles, glass, paper, leather and other substrates.

CONVENIENT SYNTHETIC ROUTE TO MONO- OR DIAKLYL PHOSPHATE FROM INORGANIC PHOSPHORUS ACIDS

Mono- or dialkyl phosphate was synthesized in a favorable yield by oxidation of phosphonic or phosphinic acid in alcohol with oxygen at the presence of a catalytic amount of copper(II)chloride.The reaction may proceed via the formation of corresponding phosphorochloridate or phosphorochloridite.

Phosphorylation with Pyrophosphoric Acid

Dihydrogenphosphates of primary and secondary aliphatic alcohols as well as phenol were prepared by a very simple procedure with pyrophosphoric acid. t-Butyl and benzyl dihydrogenphosphates could be obtained by a slight modification of the reaction conditions.For the purpose of phosphorylation pyrophosphoric acid was more reactive than orthophosphoric acid.