610-81-1

Basic information

• Product Name: 4-Amino-3-nitrophenol
• Synonyms: JAROCOL 4A3NP;4-AMINO-3-NITROPHENOL;4-HYDROXY-2-NITROANILINE;3-NITRO-4-AMINOPHENOL;2-amino-5-hydroxynitrobenzene;4-amino-3-nitro-pheno;4-Amino-3-nitrophenol;2-Amino-5-hydroxynitrobenzene; 4-Hydroxy-2-nitroaniline ;4-Amino-3-Nitrophenol98%
• CAS NO: 610-81-1
• Molecular Formula: C₆H₆N₂O₃
• Molecular Weight: 154.12
• EINECS: 210-236-8
• Product Categories: Aromatic Phenols;Phenol&Thiophenol&Mercaptan;Phenoles and thiophenoles;Amines;Aromatics;Intermediates & Fine Chemicals;Mutagenesis Research Chemicals;Pharmaceuticals
• Mol File: 610-81-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 150-154 °C(lit.)
• Boiling Point: 322.46°C (rough estimate)
• Flash Point: 180.3 °C
• Appearance: deep violet/Crystalline Powder
• Density: 1.3617 (estimate)
• Vapor Pressure: 3.87E-06mmHg at 25°C
• Refractive Index: 1.6890 (rough estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.21±0.10(Predicted)
• Water Solubility: soluble
• Stability: Hygroscopic
• BRN: 2210196
• CAS DataBase Reference: 4-Amino-3-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-3-nitrophenol(610-81-1)
• EPA Substance Registry System: 4-Amino-3-nitrophenol(610-81-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• RIDADR: 2811
• WGK Germany: 3
• PackingGroup: III
• Hazardous Substances Data: 610-81-1(Hazardous Substances Data)

Usage

Chemical Properties

Dark red powder

Uses

Different sources of media describe the Uses of 610-81-1 differently. You can refer to the following data:
1. 4-Amino-3-nitrophenol is an aminonitrophenol isomer used in hair dyes, potent human skin sensitizers and other cosmetic products with very low levels of mutagenic activity.
2. 4-Amino-3-nitrophenol was used in the synthesis of benzimidazole based Factor Xa (trypsin-like serine protease) inhibitors and 4-(4-amino-3-nitrophenoxy)phthalonitrile. It was also employed as matrix during visible matrix-assisted laser desorption/ionization mass spectrometry.

Contact allergens

This hair dye used for semipermanent colors seems to be a rare sensitizer.

InChI:InChI=1/C6H6N2O3/c7-5-2-1-4(9)3-6(5)8(10)11/h1-3,9H,7H2

Synthetic route

4-amino-phenol (123-30-8) → 4-amino-2-nitrophenol (119-34-6) + 4-hydroxy-2-nitroaniline (610-81-1)

Conditions	Yield
With bromine; silver nitrate; triphenylphosphine In acetonitrile at 20℃; for 0.0833333h;	A 40% B 50%

1-benzoylamino-4-benzoyloxy-2-nitro-benzene → 4-hydroxy-2-nitroaniline (610-81-1)

Conditions	Yield
With sulfuric acid

N-(4-hydroxy-2-nitrophenyl)-acetamide (7403-75-0) → 4-hydroxy-2-nitroaniline (610-81-1)

Conditions	Yield
With hydrogenchloride
Stage #1: N-(4-hydroxy-2-nitrophenyl)-acetamide With thionyl chloride In methanol at 70℃; for 0.5h; Stage #2: With potassium carbonate In methanol at 20℃; for 0.5h;

4-acetamido-3-nitrophenyl acetate (2243-69-8) + furan-2,3,5(4H)-trione pyridine (1:1) → 4-hydroxy-2-nitroaniline (610-81-1)

4-acetamido-3-nitrophenyl acetate (2243-69-8) → 4-hydroxy-2-nitroaniline (610-81-1)

Conditions	Yield
With sodium hydroxide
With hydrogen bromide
Multi-step reaction with 2 steps 1: bromine; acetic acid 2: concentrated aqueous hydrochloric acid View Scheme

1-acetylamino-2-nitro-4-(3-nitro-benzoyloxy)-benzene → 4-hydroxy-2-nitroaniline (610-81-1)

Conditions	Yield
With sulfuric acid

o-azidonitrobenzene (1516-58-1) → 4-hydroxy-2-nitroaniline (610-81-1)

Conditions	Yield
With sulfuric acid

sulfuric acid (7664-93-9) + o-azidonitrobenzene (1516-58-1) → 4-hydroxy-2-nitroaniline (610-81-1)

o-nitro-diazobenzeneimide → 4-hydroxy-2-nitroaniline (610-81-1)

Conditions	Yield
With sulfuric acid

4-acetamido-3-nitrophenyl acetate (2243-69-8) + boiling fuming hydrochloric acid → 4-hydroxy-2-nitroaniline (610-81-1)

sulfuric acid (7664-93-9) + 1-benzoylamino-4-benzoyloxy-2-nitro-benzene → 4-hydroxy-2-nitroaniline (610-81-1) + benzoic acid (65-85-0)

sulfuric acid (7664-93-9) + 2-nitro-toluene-4-sulfonic acid-(4-ethoxy-2-nitro-anilide) (861560-26-1) → 4-hydroxy-2-nitroaniline (610-81-1)

Conditions	Yield
at 80 - 90℃;

sulfuric acid (7664-93-9) + 1-acetylamino-2-nitro-4-(2-nitro-toluene-4-sulfonyloxy)-benzene → 4-methyl-3-nitro-benzenesulfonic acid (97-06-3) + 4-hydroxy-2-nitroaniline (610-81-1)

1-acetoxy-4-(toluene-4-sulfonylamino)-benzene (450365-10-3) + acetic anhydride (108-24-7) + HNO3+H2SO4 → 4-hydroxy-2-nitroaniline (610-81-1) + 4-amino-3,5-dinitrophenol (32654-60-7)

sulfuric acid (7664-93-9) + 1-acetylamino-2-nitro-4-(3-nitro-benzoyloxy)-benzene → 4-hydroxy-2-nitroaniline (610-81-1) + 3-nitrobenzoic acid (121-92-6)

4'-(benzyloxy)benzanilide (80824-77-7) → 4-hydroxy-2-nitroaniline (610-81-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / 0 - 10 °C 2: sulfuric acid View Scheme

4-acetaminophenol (103-90-2) → 4-hydroxy-2-nitroaniline (610-81-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: natrium carbonate 2: concentrated sulfuric acid; nitric acid / <17 3: concentrated sulfuric acid View Scheme

4-acetamidophenyl benzoate (537-52-0) → 4-hydroxy-2-nitroaniline (610-81-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated sulfuric acid; nitric acid / <17 2: concentrated sulfuric acid View Scheme

4-acetoxyacetanilide (2623-33-8) → 4-hydroxy-2-nitroaniline (610-81-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid 2: NaOH-solution View Scheme

2-nitro-aniline (88-74-4) → 4-hydroxy-2-nitroaniline (610-81-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) (diazotization), (ii) aq. NaN3 2: aq. H2SO4 View Scheme

Acetanilid (103-84-4) → 4-hydroxy-2-nitroaniline (610-81-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: nitric acid; boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene; acetic acid / water / 2.5 h / 60 °C 2.1: thionyl chloride / methanol / 0.5 h / 70 °C 2.2: 0.5 h / 20 °C View Scheme

4-hydroxy-2-nitroaniline (610-81-1) → 3,4-diaminophenol (615-72-5)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In ethanol for 3.5h;	100%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 3.5h;	100%
With hydrazine hydrate; nickel In ethanol at 20℃; for 0.5h;	96%

4-hydroxy-2-nitroaniline (610-81-1) + tert-butyldimethylsilyl chloride (18162-48-6) → 4-{[tert-butyl(dimethyl)silyl]oxy}-2-nitroaniline (215656-99-8)

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; Cooling with ice;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	100%

4-hydroxy-2-nitroaniline (610-81-1) + tert-butyldimethylsilyl chloride (18162-48-6) → 3-tert-butyldimethylsiloxy-2-amino-1-nitrobenzene (639084-14-3)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18h;	100%

1-pyrrolidineethanol (2955-88-6) + 4-hydroxy-2-nitroaniline (610-81-1) → 2-nitro-4-(2-(pyrrolidin-1-yl)ethoxy)aniline

Conditions	Yield
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	100%

4-hydroxy-2-nitroaniline (610-81-1) → 4-{[tert-butyl(dimethyl)silyl]oxy}-2-nitroaniline (215656-99-8)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	100%

triisopropylsilyl chloride (13154-24-0) + 4-hydroxy-2-nitroaniline (610-81-1) → 2-nitro-4-((triisopropylsilyl)oxy)aniline (1262887-34-2)

Conditions	Yield
With 1H-imidazole In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	99%

4-hydroxy-2-nitroaniline (610-81-1) + p-chlorphenylisocyanate (104-12-1) → 1-(4-chlorophenyl)-3-(4-hydroxy-2-nitro-phenyl)urea (862014-82-2)

Conditions	Yield
In tetrahydrofuran; dichloromethane at 20℃; for 20h;	98%

4-hydroxy-2-nitroaniline (610-81-1) + 2-haloacetonitrile → 2-(4-amino-3-nitrophenoxy)acetonitrile (1414615-74-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; chemoselective reaction;	98%

4-hydroxy-2-nitroaniline (610-81-1) + ethyl bromoacetate (105-36-2) → ethyl 2-(4-amino-3-nitrophenoxy)acetate (59820-64-3)

Conditions	Yield
With potassium carbonate In acetone at 25℃; for 8h;	98%
With potassium carbonate In N,N-dimethyl-formamide for 2.5h;	94%
With potassium carbonate In acetone at 20℃;	75.2%
With potassium carbonate In acetone at 20℃; Inert atmosphere;	75.2%

4-hydroxy-2-nitroaniline (610-81-1) + 1-octyl p-toluenesulfonate (3386-35-4) → 2-nitro-4-octyloxyaniline (1018902-72-1)

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;	98%

CYANAMID (420-04-2) + 4-hydroxy-2-nitroaniline (610-81-1) → 3-amino-7-hydroxybenzo[e][1,2,4]triazine 1-oxide (157284-07-6)

Conditions	Yield
Stage #1: CYANAMID; 4-hydroxy-2-nitroaniline at 100℃; for 0.166667h; Stage #2: With hydrogenchloride In water at 20 - 100℃; for 1.5h; Stage #3: With sodium hydroxide In water at 20 - 100℃; for 1h;	97%
Stage #1: CYANAMID; 4-hydroxy-2-nitroaniline In water; acetic acid for 48h; Heating / reflux; Stage #2: With sodium hydroxide In water; acetic acid Heating / reflux;	51.7%

1H-imidazole (288-32-4) + 4-hydroxy-2-nitroaniline (610-81-1) + tert-butyldimethylsilyl chloride (18162-48-6) → 4-{[tert-butyl(dimethyl)silyl]oxy}-2-nitroaniline (215656-99-8)

Conditions	Yield
In ethyl acetate; N,N-dimethyl-formamide	97%
In ethyl acetate; N,N-dimethyl-formamide	97%
In ethyl acetate; N,N-dimethyl-formamide	97%
In N,N-dimethyl-formamide	26.5 g (76%)

4-hydroxy-2-nitroaniline (610-81-1) → 3-amino-7-hydroxybenzo[e][1,2,4]triazine 1-oxide (157284-07-6)

Conditions	Yield
	97%
	93%

4-hydroxy-2-nitroaniline (610-81-1) + 1-(halomethyl)-4-bromo-2-fluorobenzene → C13H10BrFN2O3 (1414615-68-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; chemoselective reaction;	97%

formic acid (64-18-6) + 4-hydroxy-2-nitroaniline (610-81-1) → 5-hydroxy-1H-benzimidazole (41292-65-3)

Conditions	Yield
With tin(ll) chloride at 130℃; for 0.0833333h; microwave;	95%
With iron; ammonium chloride In isopropyl alcohol at 80℃; for 1h;	87%

4-hydroxy-2-nitroaniline (610-81-1) + 6-bromoacetyl-2-dimethylaminonaphthalene (210832-86-3) → C20H19N3O4 (1552301-13-9)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 4h; Inert atmosphere;	95%

di-tert-butyl dicarbonate (24424-99-5) + 4-hydroxy-2-nitroaniline (610-81-1) → tert-butyl N-(4-hydroxy-2-nitrophenyl)carbamate (201811-20-3)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 25℃; for 2h;	95%

4-Nitrophthalonitrile (31643-49-9) + 4-hydroxy-2-nitroaniline (610-81-1) → 4-(4-amino-3-nitrophenoxy)phthalonitrile

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 20℃; for 26h;	94%

2,5-dimethyl-2,3-dihydrofuran-3-one (14400-67-0) + 4-hydroxy-2-nitroaniline (610-81-1) → 2,5-dimethyl-2-(4-hydroxy-2-nitrophenylazo)-3-oxo-2,3-dihydrofuran

Conditions	Yield
Stage #1: 4-hydroxy-2-nitroaniline With hydrogenchloride; sodium nitrite at 0℃; for 1h; Stage #2: 2,5-dimethyl-2,3-dihydrofuran-3-one In water at 20℃; for 1h;	93%

2-(morpholin-4-yl)ethanol (622-40-2) + 4-hydroxy-2-nitroaniline (610-81-1) → 4-(2-morpholin-4-yl-ethoxy)-2-nitro-phenylamine

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In ethyl acetate	92%
With diisopropyl (E)-azodicarboxylate; triphenylphosphine In tetrahydrofuran
With diisopropyl (E)-azodicarboxylate; triphenylphosphine In tetrahydrofuran

4-hydroxy-2-nitroaniline (610-81-1) + tert-butyl (5-iodo-pentyl)-carbamate → tert-butyl 5-(4-amino-3-nitrophenoxy)pentylcarbamate (1261238-07-6)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h; Inert atmosphere;	92%

4-hydroxy-2-nitroaniline (610-81-1) + methyl iodide (74-88-4) → 4-methoxy-2-nitroaniline (96-96-8)

Conditions	Yield
Stage #1: 4-hydroxy-2-nitroaniline With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 24h; Inert atmosphere;	90%
Stage #1: 4-hydroxy-2-nitroaniline With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.5h; Cooling with ice; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 12h;	89%
With potassium carbonate In acetone

4-hydroxy-2-nitroaniline (610-81-1) + 4-(halomethyl)chlorobenzene → 1-amino-4-(4-chloro-phenylmethoxy)-2-nitro-benzene (74388-24-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; chemoselective reaction;	90%

4-hydroxy-2-nitroaniline (610-81-1) + tert-butyl-3-iodoazetidine-1-carboxylate (254454-54-1) → tert-butyl 3-(4-amino-3-nitro-phenoxy)azetidine-1-carboxylate

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 16h; Inert atmosphere;	90%

4-hydroxy-2-nitroaniline (610-81-1) + 1,2-bis-tosyloxyethane (6315-52-2) → 4,4'-(ethane-1,2-diylbis(oxy))bis(2-nitroaniline) (67499-48-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h;	89.2%
With potassium carbonate In acetonitrile at 80℃; for 24h;	69%

4-hydroxy-2-nitroaniline (610-81-1) → 4-iodo-3-nitrophenol (113305-56-9)

Conditions	Yield
With hydrogenchloride; potassium iodide; sodium nitrite	89%
Stage #1: 4-hydroxy-2-nitroaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With potassium iodide In water at 0℃; for 3.5h; Darkness;	89%
Stage #1: 4-hydroxy-2-nitroaniline With hydrogenchloride; sodium nitrite at 0℃; for 1h; Stage #2: With potassium iodide In water at 20℃; Sandmayer reaction;	83%

3,5-dimethylbenzoic acid (499-06-9) + 4-hydroxy-2-nitroaniline (610-81-1) → 4-amino-3-nitrophenyl 3,5-dimethylbenzoate (197223-18-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 15h; Esterification; Heating;	89%

4,5-dimethyl-2-nitrobenzenamine (6972-71-0) + 4-hydroxy-2-nitroaniline (610-81-1) → 1-(4-hydroxy-2-nitrophenyl)-1H-pyrrole (251649-40-8)

Conditions	Yield
With acetic acid for 1h; Clauson-Kaas reaction; Heating;	89%

4-hydroxy-2-nitroaniline (610-81-1) + 4-methoxy-benzaldehyde (123-11-5) → 2-(4-methoxyphenyl)-1H-benzimidazol-5-ol

Conditions	Yield
With sodium dithionite In ethanol at 80℃; for 12h;	89%

4-hydroxy-2-nitroaniline (610-81-1) + trifluoroacetic acid (76-05-1) → 2-(trifluoromethyl)-1H-benzimidazol-5-ol

Conditions	Yield
With tin(ll) chloride at 130℃; for 0.0833333h; microwave;	89%

Upstream product

• 2243-69-8 4-acetamido-3-nitrophenyl acetate 
• 7664-93-9 sulfuric acid 
• 537-52-0 4-acetamidophenyl benzoate 
• 103-84-4 Acetanilid 
• 88-74-4 2-nitro-aniline 
• 2623-33-8 4-acetoxyacetanilide 
• 103-90-2 4-acetaminophenol 
• 80824-77-7 4'-(benzyloxy)benzanilide 
• 123-30-8 4-amino-phenol 
• 450365-10-3 1-acetoxy-4-(toluene-4-sulfonylamino)-benzene 
• 108-24-7 acetic anhydride 
• 861560-26-1 2-nitro-toluene-4-sulfonic acid-(4-ethoxy-2-nitro-anilide) 
• 1516-58-1 o-azidonitrobenzene 
• 7403-75-0 N-(4-hydroxy-2-nitrophenyl)-acetamide 

Downstream Products

• 173918-36-0 3-nitro-1,4-benzoquinone diazide 
• 96-96-8 4-methoxy-2-nitroaniline 
• 75-50-3 trimethylamine 
• 197223-18-0 4-amino-3-nitrophenyl 3,5-dimethylbenzoate 
• 26697-35-8 4-benzyloxy-2-nitroaniline 
• 554-84-7 meta-nitrophenol 
• 215656-99-8 4-{[tert-butyl(dimethyl)silyl]oxy}-2-nitroaniline 
• 238405-36-2 {5-[7-(3,5-dimethoxy-benzyloxy)-1,1-dioxo-1,3,4,5-tetrahydro-1λ⁶-benzo[f][1,2,5]thiadiazepin-2-yl]-5-hydroxycarbamoyl-pentyl}-carbamic acid tert-butyl ester 
• 238406-32-1 6-tert-butoxycarbonylamino-2-[7-(3,5-dimethoxy-benzyloxy)-1,1-dioxo-1,3,4,5-tetrahydro-1λ⁶-benzo[f][1,2,5]thiadiazepin-2-yl]-hexanoic acid methyl ester 
• 1054620-34-6 2-[7-(3,5-diethoxy-benzyloxy)-1,1-dioxo-1,3,4,5-tetrahydro-1λ⁶-benzo[f][1,2,5]thiadiazepin-2-yl]-pentanedioic acid 1-tert-butyl ester 5-methyl ester 

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