6358-07-2

Basic information

• Product Name: 2-Amino-4-chloro-5-nitrophenol
• Synonyms: TIMTEC-BB SBB000270;2-amino-4-chloro-5-nitro-pheno;2-amino-5-nitro-4-chlorophenol;5-NITRO-2-AMINO-4-CHLORO PHENOL;AMINO(2-)-4-CHLORO-5-NITROPHENOL;5-CHLORO-2-HYDROXY-4-NITROANILINE;4-Chloro-(5-sulfophenyl)-3-methyl-5-pyrazolone;2-Amino-4-chloro-5-nitrophenol
• CAS NO: 6358-07-2
• Molecular Formula: C₆H₅ClN₂O₃
• Molecular Weight: 188.57
• EINECS: 228-760-0
• Product Categories: Intermediates of Dyes and Pigments;Aromatic Phenols;Phenol&Thiophenol&Mercaptan;Phenoles and thiophenoles;Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 6358-07-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 225 °C(lit.)
• Boiling Point: 402.4 °C at 760 mmHg
• Flash Point: 197.2 °C
• Appearance: orange powder
• Density: 1.655 g/cm³
• Vapor Pressure: 4.72E-07mmHg at 25°C
• Refractive Index: 1.695
• PKA: 7.45±0.24(Predicted)
• Water Solubility: <0.01 g/100 mL at 22℃
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases.
• CAS DataBase Reference: 2-Amino-4-chloro-5-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-chloro-5-nitrophenol(6358-07-2)
• EPA Substance Registry System: 2-Amino-4-chloro-5-nitrophenol(6358-07-2)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: SJ5736000
• Hazardous Substances Data: 6358-07-2(Hazardous Substances Data)

Usage

Chemical Properties

orange powder

General Description

Orange powder that turns dark at 392°F.

Reactivity Profile

2-Amino-4-chloro-5-nitrophenol may react with strong oxidizing agents.

Fire Hazard

Flash point data for 2-Amino-4-chloro-5-nitrophenol are not available. 2-Amino-4-chloro-5-nitrophenol is probably combustible.

InChI:InChI=1/C6H5ClN2O3/c7-3-1-4(8)6(10)2-5(3)9(11)12/h1-2,10H,8H2

Synthetic route

5-chloro-2-methyl-6-nitrobenzoxazole (13452-16-9) → 2-amino-4-chloro-5-nitrophenol (6358-07-2)

Conditions	Yield
With mineral acids
With water; sodium hydroxide

5-chloro-2-benzoxazolinone (95-25-0) → 2-amino-4-chloro-5-nitrophenol (6358-07-2)

Conditions	Yield
beim Nitrieren und nachfolgenden Verseifen mit Calciumhydroxyd oder Soda;

phosgene (75-44-5) + 2-hydroxy-5-chloro-aniline (95-85-2) → 2-amino-4-chloro-5-nitrophenol (6358-07-2)

Conditions	Yield
bei dem Nitrieren des entstehenden 5-Chlor-benzoxazolon-(2) und nachfolgende Verseifung mit Calciumhydroxyd oder Soda;

2-hydroxy-5-chloro-aniline (95-85-2) → 4-chloro-6-nitro-2-aminophenol (6358-08-3) + 2-amino-4-chloro-5-nitrophenol (6358-07-2)

Conditions	Yield
beim Nitrieren;

5-chloro-2-methyl-6-nitrobenzoxazole (13452-16-9) + diluted mineral acid → 2-amino-4-chloro-5-nitrophenol (6358-07-2)

2-amino-4-chloro-5-nitrophenol (6358-07-2) + 3-methoxy-2-hydroxybenzaldehyde (148-53-8) → C14H11ClN2O5

Conditions	Yield
Microwave irradiation;	95%

2-amino-4-chloro-5-nitrophenol (6358-07-2) + ortho-chlorobenzoic acid (118-91-2) → 2-(5-chloro-2-hydroxy-4-nitrophenylamino)benzoic acid (1381802-14-7)

Conditions	Yield
With copper; potassium carbonate In ethyl methyl ether at 25 - 30℃; for 2h; Ullmann reaction; Inert atmosphere; Sonication;	92%

2-amino-4-chloro-5-nitrophenol (6358-07-2) + allyl bromide (106-95-6) → 2-(allyloxy)-5-chloro-4-nitroaniline (865715-91-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	90%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	90%

2-amino-4-chloro-5-nitrophenol (6358-07-2) + 5-benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (443667-38-7) → 6-(5-chloro-2-hydroxy-4-nitrophenyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (1314872-89-3)

Conditions	Yield
In ethanol for 5h; Reflux;	89%

(E)-3-(3-methoxy-4-hydroxyphenyl)-2-(3,4,5-trimethoxyphenyl)acrylic acid + 2-amino-4-chloro-5-nitrophenol (6358-07-2) → (E)-4-[2-(5-chloro-6-nitrobenzo[d]oxazol-2-yl)-2-(3,4,5-trimethoxyphenyl)vinyl]-2-methoxyphenol

Conditions	Yield
With polyphosphoric acid at 170℃; for 6h;	88%

5-bromo-3-methoxysalicylaldehyde (5034-74-2) + 2-amino-4-chloro-5-nitrophenol (6358-07-2) → C14H10BrClN2O5

Conditions	Yield
Microwave irradiation;	85%

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (771-03-9) + 2-amino-4-chloro-5-nitrophenol (6358-07-2) → (E)-3-(1-(5-chloro-2-hydroxy-4-nitrophenylamino)ethylidene)-6-methyl-2H-pyran-2,4-dione (1119628-99-7)

Conditions	Yield
With triethylamine In 1,4-dioxane for 16h; Reflux;	83%

2-amino-4-chloro-5-nitrophenol (6358-07-2) + 5-nitro-o-vanilline (17028-61-4) → C14H10ClN3O7

Conditions	Yield
Heating;	80%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4) + 2-amino-4-chloro-5-nitrophenol (6358-07-2) → C16H20ClN3O6

Conditions	Yield
Stage #1: 1-(tert-butoxycarbonyl)-L-proline With triethylamine; methyl chloroformate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 2-amino-4-chloro-5-nitrophenol In tetrahydrofuran at 0 - 20℃; Further stages.;	78%

2-amino-4-chloro-5-nitrophenol (6358-07-2) + 5-chlorosalicyclaldehyde (635-93-8) → (E)-4-chloro-2-{[(5-chloro-2-hydroxy-4-nitrophenyl)imino]methyl}phenol

Conditions	Yield
In ethanol for 3h; Reflux;	78%

2-amino-4-chloro-5-nitrophenol (6358-07-2) + 3-methoxy-2-hydroxybenzaldehyde (148-53-8) → C14H11ClN2O5

Conditions	Yield
In methanol for 1h; Reflux;	76%

2-(4-fluoro-3-(trifluoromethyl)phenoxy)butanoic chloride (113614-10-1, 113614-29-2) + 2-amino-4-chloro-5-nitrophenol (6358-07-2) → N-(5-chloro-2-hydroxy-4-nitrophenyl)-2-(4-fluoro-3-(trifluoromethyl)phenoxy)butanoic amide

Conditions	Yield
In acetic acid for 3h; Heating / reflux;	74%

bis(trichloromethyl) carbonate (32315-10-9) + 2-amino-4-chloro-5-nitrophenol (6358-07-2) → 5-chloro-6-nitrobenzo[d]oxazol-2(3H)-one (27087-06-5)

Conditions	Yield
With pyridine In tetrahydrofuran at 5 - 20℃; for 3.5h;	74%

3,3-bis(3,4,5-trimethoxyphenyl)acrylaldehyde + 2-amino-4-chloro-5-nitrophenol (6358-07-2) → 2-(2,2-bis(3,4,5-trimethoxyphenyl)vinyl)-5-chloro-6-nitrobenzoxazole

Conditions	Yield
Stage #1: 3,3-bis(3,4,5-trimethoxyphenyl)acrylaldehyde; 2-amino-4-chloro-5-nitrophenol In ethanol for 3h; Reflux; Stage #2: With lead(IV) tetraacetate; acetic acid at 20℃; for 1h;	73%

2-amino-4-chloro-5-nitrophenol (6358-07-2) + Ethyl 2-bromopropionate (535-11-5, 41978-69-2) → 6-chloro-3,4-dihydro-2-methyl-7-nitro-3-oxo-2H-1,4-benzoxazine

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; 1,8-diazabicyclo[5.4.0]undec-7-ene at 180℃; for 0.05h; microwave irradiation;	72%
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 5℃; for 4h;	72%

Upstream product

• 95-25-0 5-chloro-2-benzoxazolinone 
• 13452-16-9 5-chloro-2-methyl-6-nitrobenzoxazole 
• 95-85-2 2-hydroxy-5-chloro-aniline 
• 75-44-5 phosgene 

Downstream Products

• 118534-36-4 2-benzyloxy-5-chloro-4-nitroaniline 
• 865715-91-9 2-(allyloxy)-5-chloro-4-nitroaniline 
• 102405-48-1 (2-amino-4-chloro-5-nitrophenol)pivalate 
• 1119628-99-7 (E)-3-(1-(5-chloro-2-hydroxy-4-nitrophenylamino)ethylidene)-6-methyl-2H-pyran-2,4-dione 
• 1325228-37-2 6-nitro-5-chloro-2-(2-hydroxyphenyl)benzoxazole 
• 1325228-42-9 6-nitro-5-chloro-2-(5-bromo-2-hydroxyphenyl)benzoxazole 
• 1428335-97-0 2-morpholino-6-nitro-5-phenylbenzo[d]oxazole 
• 1428336-00-8 6’-((4-methoxybenzyl)amino)-N-(2-morpholino-5-phenylbenzo[d]oxazol-6-yl)-[2,3'-bipyridine]-6-carboxamide 
• 1428335-98-1 C₁₇H₁₇N₃O₂ 
• 1428335-99-2 6-bromo-N-(2-morpholino-5-phenylbenzo[d]oxazol-6-yl)picolinamide 
• 1428335-41-4 C₂₈H₂₄N₆O₄ 
• 1428336-18-8 2-(2-morpholino-6-nitrobenzo[d]oxazol-5-yl) phenol 
• 1428336-19-9 C₁₇H₁₇N₃O₃ 
• 1428336-20-2 C₂₃H₁₉BrN₄O₄ 

Relevant articles and documents

Method for synthesizing 2-amino-4-chloro-5-nitrophenol in micro-channel reactor

The invention discloses a method for synthesizing 2-amino-4-chloro-5-nitrophenol. The 2-amino-4-chloro-5-nitrophenol is prepared from 5-chloro-2-methylbenzoxazole through a series reaction using a micro-channel reactor and a batch reactor. The 2-amino-4-c