5427-30-5

Basic information

• Product Name: (3-Aminophenyl)phosphonic acid
• Synonyms: (3-aminophenyl)phosphonic acid;(3-azanylphenyl)phosphonic acid
• CAS NO: 5427-30-5
• Molecular Formula: C₆H₈NO₃P
• Molecular Weight: 173.11
• EINECS: 226-577-0
• Mol File: 5427-30-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 463.2 °C at 760 mmHg
• Flash Point: 233.9 °C
• Appearance: /
• Density: 1.51 g/cm³
• Vapor Pressure: 2.23E-09mmHg at 25°C
• Refractive Index: 1.618
• PKA: pK3: 7.16 (25°C)
• CAS DataBase Reference: (3-Aminophenyl)phosphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3-Aminophenyl)phosphonic acid(5427-30-5)
• EPA Substance Registry System: (3-Aminophenyl)phosphonic acid(5427-30-5)

Safety Data

• Hazardous Substances Data: 5427-30-5(Hazardous Substances Data)

Usage

General Description

"(3-Aminophenyl)phosphonic acid" is a chemical compound usually used as an intermediate for producing various kinds of chemicals, including organic reactions and pharmaceutical synthesis. (3-Aminophenyl)phosphonic acid has the molecular formula C6H8NO3P, and it is characterized by an amine group attached to a phenyl ring and a phosphonic acid group. It's a slightly hazardous compound, which, if not handled properly, can cause skin or eye irritation. It is typically stored in a cool, dry place to maintain its stability and maximize its shelf-life. Conducting research in well-ventilated environments is recommended due to this compound's potential for producing an irritant vapor.

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

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

Downstream Products

• 33733-31-2 (3-hydroxy-phenyl)-phosphonic acid 
• 5431-34-5 3-chloro-phenyl phosphonic acid 
• 6959-02-0 3-bromophenylphosphonic Acid 
• 99969-18-3 (3-iodo-phenyl)-phosphonic acid 
• 70911-39-6 3-(4'-aminophenylazo)benzenephosphonic acid 
• 1220125-15-4 N⁵-(3-phosphonophenyl)-L-glutamine 
• 108-21-4 Isopropyl acetate 
• 86119-84-8 phosphoric acid 
• 62-53-3 aniline 

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