103680-47-3

Basic information

• Product Name: 3-aminopropylphosphinic acid
• Synonyms: 3-aminopropylphosphinic acid;CGP-27492;3-APPA;3-APPA (CGP 27492)
• CAS NO: 103680-47-3
• Molecular Formula: C₃H₁₀NO₂P
• Molecular Weight: 123.09
• Product Categories: GABA
• Mol File: 103680-47-3.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• CAS DataBase Reference: 3-aminopropylphosphinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-aminopropylphosphinic acid(103680-47-3)
• EPA Substance Registry System: 3-aminopropylphosphinic acid(103680-47-3)

Safety Data

• Hazardous Substances Data: 103680-47-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C3H10NO2P/c4-2-1-3-7(5)6/h7H,1-4H2,(H,5,6)

Upstream product

• 103680-62-2 3-aminopropyl(diethoxymethyl)-phosphinic acid ethyl ester 
• 107-11-9 1-amino-2-propene 

Relevant articles and documents

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.

UV-mediated hydrophosphinylation of unactivated alkenes with phosphinates under batch and flow conditions

A UV-mediated hydrophosphinylation of unactivated alkenes with H-phosphinates and hypophosphorous acid under radical free conditions is presented. The reaction affords selectively a large number of structurally diverse organophosphorous compounds in moderate to good yields under mild reaction conditions in the presence of an organic sensitizer as catalyst irradiated by UV-A LEDs. Furthermore, the high yielding hydrophosphinylation in continuous flow is disclosed.

Convenient syntheses of phosphinic analogues of γ-aminobutyric- and glutamic acids

Three-steps, one-pot synthesis of 2-amino-4-(hydroxyphosphinyl)butyric acid from dibutyl ester of vinylphosphinic acid was carried out with an overall yield of 66%. 3-Aminopropylphosphinic acid was prepared from allylamine in three steps with an overall y

Synthesis of P,N-heterocycles from ω-amino-H-phosphinates: Conformationally restricted α-amino acid analogs

(Chemical Equation Presented) P,N-Heterocycles (3-hydroxy-1,3- azaphospholane and 3-hydroxy-1,3-azaphosphorinane-3-oxide) are synthesized in moderate yield from readily available ω-amino-H-phosphinates and aldehydes or ketones via an intramolecular Kabachnik-Fields reaction. The products are conformationally restricted phosphinic analogs of α-amino acids. The multigram-scale syntheses of the H2N(CH2) nPO2H2 phosphinic precursors (n = 1, 2, 3) and some derivatives are also described.

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.

DIETHOXYMETHYLPHOSPHONITES AND PHOSPHINATES. INTERMEDIATES FOR THE SYNTHESIS OF α,β- AND γ-AMINOALKYLPHOSPHONOUS ACIDS

New building blocks for the synthesis of functional alkyl phosphonous acids are described.Diethoxymethylphosphonites and phosphinates are readily prepared and undergo reactions typical of phosphites and phosphonates.The products are stable to chemical transformations, readily handled and purified, and easily transformed to the phosphonous acids.

SYNTHESIS OF γ-AMINOPROPYLPHOSPHONOUS ACIDS USING HYPOPHOSPHOROUS ACID SYNTHONS

γ-Aminopropylphosphonous acids have heen synthesised using hypophosphorous acid synthons.