16196-03-5

Upstream product

• 286-20-4 cyclohexane-1,2-epoxide 
• 868-85-9 Dimethyl phosphite 
• 1421958-59-9 C₁₃H₂₈NOP 
• 931-50-0 cyclohexylmagnesium bromide 
• 108-85-0 1-bromocyclohexane 
• 882185-82-2 3,4-dibromo-1-cyclohexyl-3-methyl-2,3,4,5-tetrahydro-1H-phosphole 1-oxide 
• 872514-93-7 3-methyl-1-cyclohexyl-2,5-dihydro-1H-phosphole oxide 
• 67-56-1 methanol 
• 110-83-8 cyclohexene 
• 149-73-5 trimethyl orthoformate 
• 13822-56-5 3-(trimethoxysilyl)propan-1-amine 
• 14684-31-2 methyl hypophosphite 

Downstream Products

• 17915-23-0 Cyclohexylphosphinsaeure-<3-hydroxy-propylester>-diaethylamid 
• 17915-28-5 Cyclohexylphosphinsaeure-(3-hydroxy-propylester) 

Relevant academic research and scientific papers

Synthesis of 2-pyridylphosphinate and thiophosphinate derivatives by nucleophilic aromatic substitution of N-methoxypyridinium tosylates

We developed a straightforward and cost-effective method for the synthesis of 2-pyridylphosphinate derivatives based on a nucleophilic aromatic substitution of N-methoxypyridinium salts. The method proved to be useful for synthesizing various 2-pyridylphosphinates and thiophosphinates, including an optically active compound, from H-phosphinate precursors.

New 7-phosphanorbornenes derived from 2-methyl-1-phenyl- And 1-cyclohexyl-3-methyl-2,5-dihydro-1H-phosphole 1-oxides

Novel 7-phosphanorbornene derivatives, such as 4, 5, 10, and 11 were synthesized utilizing 1-phenyl-2-methyl-2,5-dihydro-1H-phosphole oxide (1) and 1-cyclohexyl-3-methyl-2,5-dihydro-1H-phosphole oxide (7) as the starting materials. Products 4 and 10 were

Synthesis of H-phosphinates by the UV light - Mediated fragmentation- related phosphorylation using simple P-heterocycles

Photolysis of aryl-substituted 2,5-dihydrophosphole oxides (5a-e and 8) in the presence of methanol afforded methyl aryl-H-phosphinates (2a-e) in good yields. In the case of 1-ethyl-, cyclohexyl-, or ethoxy-2,5-dihydrophosphole oxides, the reaction was mu

Recent advances in phosphorus-carbon bond formation: Synthesis of H-phosphinic acid derivatives from hypophosphorous compounds

This account summarizes the research conducted in our laboratory over the past five years. New methodologies were devised for the formation of P-C bonds with a focus on the reactions of hypophosphorous acid derivatives. Three types of reactions have been developed: palladium-catalyzed cross-coupling, room-temperature radical addition, and palladium-catalyzed addition. Our results are summarized in each of these areas and include some of our most recent data. (1) Our palladium-catalyzed cross-coupling has been extended to the direct coupling of alkyl phosphinates with a variety of aryl, heteroaryl, and even alkenyl electrophiles. (2) The addition of sodium hypophosphite under radical conditions is extended from alkenes to alkynes. (3) The catalytic addition of hypophosphorous compounds using palladium catalysts (hydrophosphinylation) is also discussed.

A novel and convenient preparation of hypophosphite esters

Only a few methods have been described for the preparation of hypophosphite esters (alkyl phosphinates, ROP(O)H2). As a result, comparatively few applications have been reported, and these intermediates have not been widely exploited in organop

Microwave catalyzed reactions of H-dimethylphosphonate with oxiranes

Microwave catalyzed reactions of H-dimethylphosphonate with 1,2-epoxydecane, 5,6-epoxy-1-hexene, 1,2-epoxybutane and cyclohexene oxide have been found to cause oxirane ring opening, deoxygenation and hydrophosphorylation. 1,2-Epoxydecane gave three pairs

Triethylborane-initiated room temperature radical addition of hypophosphites to olefins: Synthesis of monosubstituted phosphinic acids and esters

A novel and practical approach to monosubstituted phosphinic acid (alkylphosphonous acid) derivatives from hypophosphite salts or esters is described. Phosphorus-centered radical formation is initiated with Et3B/O2, and the reaction is conveniently conducted at room temperature in an open flask. In contrast to previously reported conditions for the radical reaction of hypophosphorous acid and sodium hypophosphite (peroxide initiators, acid catalysis, heat), the method proceeds under neutral conditions and therefore tolerates a wide range of functional groups. Previously inaccessible phosphinic acids can be prepared in a single step from cheap starting materials. Excellent selectivity is observed for monoaddition, and symmetrical dialkyl phosphinates do not form in significant amounts. Monosubstituted phosphinic acids are usually obtained in better than 90% purity by a simple extractive workup; however, isolated yields are diminished if the substituent is polar. Because radicals derived from hypophosphites are electrophilic, the reaction is limited to the use of electron-rich olefins. The reaction conditions can also be employed in the room temperature radical reduction of alkyl halides and provide an exceptionally mild and environmentally friendly alternative to the use of tributyltin hydride. The remarkable mild nature of the reaction conditions allows for the radical reaction of sensitive alkyl hypophosphites to occur, in which case, a catalytic amount of Et3B suffices to deliver alkyl phosphinate esters in reasonable yield.