5427-30-5

Usage

Uses

Used in Chemical Synthesis:
(3-Aminophenyl)phosphonic acid is used as an intermediate in the production of various chemicals. Its versatile structure allows it to be a key component in organic reactions, making it valuable in the synthesis of a wide range of compounds.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, (3-Aminophenyl)phosphonic acid is used as an intermediate for the synthesis of various drugs. Its unique chemical properties enable it to be incorporated into the development of new medications, potentially leading to advancements in healthcare and treatment options.

InChI:InChI=1/C6H8NO3P/c7-5-2-1-3-6(4-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)

Synthetic route

(3-aminophenyl)phosphonate de diethyle (89277-85-0) → m-aminophenylphosphonic acid (5427-30-5)

Conditions	Yield
With hydrogenchloride In water for 12h; Heating;	99%

(m-nitrophenyl)phosphonic acid (5337-19-9) → m-aminophenylphosphonic acid (5427-30-5)

Conditions	Yield
aluminum nickel; palladium(II) chloride In water	85%
With hydrazine hydrate; nickel In ethanol; isopropyl alcohol for 4h; Heating;	73%
With hydrogen; palladium on activated charcoal In methanol for 6h;	56%

phenylphosphonate (1571-33-1) → m-aminophenylphosphonic acid (5427-30-5)

Conditions	Yield
(i) NO2/HNO3, (ii) aq. NaOH, Na2S; Multistep reaction;
Multi-step reaction with 2 steps 1: 42 percent / HNO3; H2SO4 / 2 h / 0 °C 2: 56 percent / H2 / Pd/C / methanol / 6 h View Scheme
Multi-step reaction with 2 steps 1: nitric acid / 0 °C 2: ammonium sulfide View Scheme

(m-nitrophenyl)phosphonic acid (5337-19-9) + ammonium sulfide → m-aminophenylphosphonic acid (5427-30-5)

(m-nitrophenyl)phosphonic acid (5337-19-9) + sodium amalgam → m-aminophenylphosphonic acid (5427-30-5)

hydrogenchloride (7647-01-0) + (m-nitrophenyl)phosphonic acid (5337-19-9) + tin → m-aminophenylphosphonic acid (5427-30-5)

3-Iodoaniline (626-01-7) → m-aminophenylphosphonic acid (5427-30-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / NaH / tetrahydrofuran; acetonitrile / 2.5 h / 25 °C / Irradiation 2: 99 percent / 8M HCl / H2O / 12 h / Heating View Scheme

phenyltetrachlorophosphorane (4895-65-2) → m-aminophenylphosphonic acid (5427-30-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: water 2: nitric acid / 0 °C 3: ammonium sulfide View Scheme

Dichlorophenylphosphine (644-97-3) → m-aminophenylphosphonic acid (5427-30-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: chlorine 2: water 3: nitric acid / 0 °C 4: ammonium sulfide View Scheme

benzene (71-43-2) → m-aminophenylphosphonic acid (5427-30-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: phosphorus trichloride 2: chlorine 3: water 4: nitric acid / 0 °C 5: ammonium sulfide View Scheme

monomethyl (3-nitrophenyl)phosphonate (1220125-40-5) → m-aminophenylphosphonic acid (5427-30-5)

Conditions	Yield
Stage #1: monomethyl (3-nitrophenyl)phosphonate With trimethylsilyl bromide In N,N-dimethyl-formamide at 60℃; for 2h; Stage #2: With hydrogen; palladium on carbon In methanol; water
Multi-step reaction with 2 steps 1: trimethylsilyl bromide / N,N-dimethyl-formamide / 2 h / 60 °C 2: hydrogen; palladium on activated charcoal / water; methanol View Scheme

m-iodonitrobenzene (645-00-1) → m-aminophenylphosphonic acid (5427-30-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / tetrakis(triphenylphosphine) palladium(0) / acetonitrile / 70 °C 2: trimethylsilyl bromide / N,N-dimethyl-formamide / 2 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine; tetrakis(triphenylphosphine) palladium(0) / acetonitrile / 70 °C 2: trimethylsilyl bromide / N,N-dimethyl-formamide / 2 h / 60 °C 3: hydrogen; palladium on activated charcoal / water; methanol View Scheme

m-iodonitrobenzene (645-00-1) + Dimethyl phosphite (868-85-9) → m-aminophenylphosphonic acid (5427-30-5)

Conditions	Yield
Stage #1: m-iodonitrobenzene; Dimethyl phosphite With tetrakis(triphenylphosphine) palladium(0); triethylamine In acetone at 70℃; Stage #2: With trimethylsilyl bromide In N,N-dimethyl-formamide at 60℃; for 2h; Stage #3: With palladium on activated charcoal; hydrogen In methanol; water

1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid (116-81-4) + m-aminophenylphosphonic acid (5427-30-5) → 1-amino-2-sulfo-4-(m-phosphonoanilino)anthraquinone

Conditions	Yield
With sodium hydrogencarbonate; sodium carbonate; copper(l) chloride In water at 70℃; for 20h;	56.5%

m-aminophenylphosphonic acid (5427-30-5) → (3-hydroxy-phenyl)-phosphonic acid (33733-31-2)

Conditions	Yield
With hydrogenchloride; ethyl nitrite

m-aminophenylphosphonic acid (5427-30-5) → 3-chloro-phenyl phosphonic acid (5431-34-5)

Conditions	Yield
Diazotization.Behandeln der Diazonium-Salz-Loesung mit Kupfer(I)-chlorid und wss.Salzsaeure;
(i) NaNO2, aq. HCl, (ii) CuCl, aq. HCl; Multistep reaction;

m-aminophenylphosphonic acid (5427-30-5) → 3-bromophenylphosphonic Acid (6959-02-0)

Conditions	Yield
Diazotization.Behandeln der Diazoniumsalz-Loesung mit Natriumbromid,Kupfer(II)-sulfat und wss.Bromwasserstoffsaeure unter Zusatz von Kupfer;

m-aminophenylphosphonic acid (5427-30-5) → (3-amino-2,4,6-tribromo-phenyl)-phosphonic acid

Conditions	Yield
With hydrogenchloride; bromine

m-aminophenylphosphonic acid (5427-30-5) → (3-iodo-phenyl)-phosphonic acid (99969-18-3)

Conditions	Yield
Diazotization.Behandeln der Diazoniumsalz-Loesung mit Kaliumjodid;

m-aminophenylphosphonic acid (5427-30-5) + chloroformic acid ethyl ester (541-41-3) → (3-ethoxycarbonylamino-phenyl)-phosphonic acid (861378-75-8)

Conditions	Yield
With alkali at 0℃;

m-aminophenylphosphonic acid (5427-30-5) + C20H12Cl2N6O6S2(2-)*2Na(1+) → C26H19ClN7O9PS2(2-)*2Na(1+)

Conditions	Yield
In water at 50℃; pH = 6.0-6.5;

m-aminophenylphosphonic acid (5427-30-5) + MG 40-1 → C29H19ClN7O11PS2(2-)*2Na(1+)

Conditions	Yield
In water at 50℃; pH = 6.0-6.5;

m-aminophenylphosphonic acid (5427-30-5) + RB 4 (13324-20-4) → C29H19ClN7O11PS2(2-)*2Na(1+)

Conditions	Yield
In water at 50℃; pH = 6.0-6.5;

m-aminophenylphosphonic acid (5427-30-5) + C19H9Cl2N6O10S3(3-)*3Na(1+) → C25H16ClN7O13PS3(3-)*3Na(1+)

Conditions	Yield
In water at 50℃; pH = 6.0-6.5;

m-aminophenylphosphonic acid (5427-30-5) + C19H10Cl4N8O7S2(2-)*2Na(1+) → C25H17Cl3N9O10PS2(2-)*2Na(1+)

Conditions	Yield
In water at 50℃; pH = 6.0-6.5;

m-aminophenylphosphonic acid (5427-30-5) + C26H19ClN7O9PS2(2-)*2Na(1+) → C32H26N8O12P2S2(2-)*2Na(1+)

Conditions	Yield
In water at 100 - 102℃; for 4h;

m-aminophenylphosphonic acid (5427-30-5) + C29H19ClN7O11PS2(2-)*2Na(1+) → C35H26N8O14P2S2(2-)*2Na(1+)

Conditions	Yield
In water at 100 - 102℃; for 4h;

m-aminophenylphosphonic acid (5427-30-5) + C29H19ClN7O11PS2(2-)*2Na(1+) → C35H26N8O14P2S2(2-)*2Na(1+)

Conditions	Yield
In water at 100 - 102℃; for 4h;

m-aminophenylphosphonic acid (5427-30-5) + C25H16ClN7O13PS3(3-)*3Na(1+) → C31H23N8O16P2S3(3-)*3Na(1+)

Conditions	Yield
In water at 100 - 102℃; for 4h;

m-aminophenylphosphonic acid (5427-30-5) + C25H17Cl3N9O10PS2(2-)*2Na(1+) → C31H24Cl2N10O13P2S2(2-)*2Na(1+)

Conditions	Yield
In water at 100 - 102℃; for 4h;

m-aminophenylphosphonic acid (5427-30-5) + soda lime → phosphoric acid (86119-84-8, 7664-38-2) + aniline (62-53-3)

m-aminophenylphosphonic acid (5427-30-5) + aniline (62-53-3) → 3-(4'-aminophenylazo)benzenephosphonic acid

m-aminophenylphosphonic acid (5427-30-5) + phenol (108-95-2) → 3-(4'-hydroxyphenylazo)benzenephosphonic acid

m-aminophenylphosphonic acid (5427-30-5) → C35H26N8O14P2S2(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O / 50 °C / pH = 6.0-6.5 2: H2O / 4 h / 100 - 102 °C View Scheme

m-aminophenylphosphonic acid (5427-30-5) → C35H26N8O14P2S2(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O / 50 °C / pH = 6.0-6.5 2: H2O / 4 h / 100 - 102 °C View Scheme

Upstream product

• 1220125-40-5 monomethyl (3-nitrophenyl)phosphonate 
• 645-00-1 m-iodonitrobenzene 
• 868-85-9 Dimethyl phosphite 
• 71-43-2 benzene 
• 644-97-3 Dichlorophenylphosphine 
• 4895-65-2 phenyltetrachlorophosphorane 
• 626-01-7 3-Iodoaniline 
• 89277-85-0 (3-aminophenyl)phosphonate de diethyle 
• 5337-19-9 (m-nitrophenyl)phosphonic acid 
• 7647-01-0 hydrogenchloride 
• 1571-33-1 phenylphosphonate 

Downstream Products

• 86119-84-8 phosphoric acid 
• 62-53-3 aniline 
• 1220125-15-4 N⁵-(3-phosphonophenyl)-L-glutamine 
• 108-21-4 Isopropyl acetate 
• 861378-75-8 (3-ethoxycarbonylamino-phenyl)-phosphonic acid 
• 99969-18-3 (3-iodo-phenyl)-phosphonic acid 
• 6959-02-0 3-bromophenylphosphonic Acid 
• 5431-34-5 3-chloro-phenyl phosphonic acid 
• 33733-31-2 (3-hydroxy-phenyl)-phosphonic acid 

Relevant academic research and scientific papers

PROPHYLACTIC AGENT OR THERAPEUTIC AGENT FOR DIABETES OR OBESITY

A medicament having an excellent CaSR agonist action which enables the prevention or treatment of diabetes or obesity is provided by a composition comprising the compound represented by general formula (I) as defined, or a salt thereof.

GLUTAMATE DERIVATIVES OR SALTS THEREOF

Compounds having an excellent CaSR agonist activity are in demand. The invention provides glutamate derivatives or salts thereof, pharmaceutical compositions comprising the glutamate derivatives, preventive or therapeutic agents for diarrhea, hyperparathyroidism or peptic ulcer.

CASR AGONIST

By searching various kinds of compounds having CaSR agonistic activity, the present invention provides CaSR agonistic agents, pharmaceutical compositions, preventive or therapeutic agents for diarrhea and kokumi-imparting agents each of which comprise the compound. More specifically, the present invention provides CaSR agonistic agents, pharmaceutical compositions, preventive or therapeutic agents for diarrhea and kokumi-imparting agents each of which comprise a glutamic acid derivative having CaSR agonistic activity or pharmaceutically acceptable salts thereof.

The assembly of rotaxane-like dye/cyclodextrin/surface complexes on aluminium trihydroxide or goethite

Simple azo-dyes carrying phosphonic acid and arsonic acid substituents such as 4-(4′-hydroxyphenyl azo)phenylphosphonic acid (5) and 4-(4′-hydroxyphenylazo)phenylarsonic acid (6) bind more strongly to high surface area oxides such as aluminium trihydroxide and goethite than their carboxylic and sulfonic acid analogues and the phosphonate-functionalized dyes have been shown to have greater humidity fastness when printed onto commercial alumina-coated papers. Adsorption isotherm measurements provide evidence for the formation of ternary dye/cyclodextrin/surface complexes. Dyes which form such ternary complexes show higher light fastness when printed onto alumina coated papers in an ink formulation containing α-cyclodextrin. The Royal Society of Chemistry 2006.

PREPARATION D'AMINOPHENYL-, NITROPHENYL-, PYRIDYL-, ET QUINOLYLPHOSPHONATES SOUS PHOTOSTIMULATION OU ASSISTANCE METALLIQUE; ACCES AUX ACIDES AMINOPHOSPHONIQUES CORRESPONDANTS

Our aim was to study the aromatic nucleophilic substitution between the sodium anion of diethylphosphite and several halogenated substrates like: iodo-anilines, iodo-nitrobenzenes, bromo- and iodopyridines, bromoquinoline.Two coupling processes have been evaluted.The first one is the photostimulated nucleophilic substitution (SRN1), the second the promoted arylation by transition metals.We obtain good results with the first method which is efficient and simple; by contrast the second one has given only few positive results.We describe five aromatic aminophosphonic acids.

Process for preparing m-aminobenzenephosphonic acid

M-Aminobenzenephosphonic acid is prepared from the relatively inexpensive starting material benzenephosphonous acid by nitrating the acid starting material under controlled conditions followed by oxidation and reduction procedures to produce the desired product in high yields.