2-Chloro-5-nitrophenol Chemical Properties

Melting point:

118-121°C

Boiling point:

276.1±25.0 °C(Predicted)

Density 

1.554±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

6.72±0.19(Predicted)

color 

Brown

InChIKey

BUMGQSCPTLELLS-UHFFFAOYSA-N

CAS DataBase Reference

619-10-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Harmful/Irritant

HS Code 

2908990000

2-Chloro-5-nitrophenol Usage And Synthesis

Chemical Properties

Light Brown Crystalline Solid

Uses

2-Chloro-5-nitrophenol (cas# 619-10-3) is a compound useful in organic synthesis.

Synthesis

General procedure for the synthesis of 2-chloro-5-nitrophenol from 2-amino-5-nitrophenol: In Preparation Example 14, 1-amino-5-nitrophenol (2 g, 12.97 mmol) and sodium nitrite (0.9 g, 12.97 mmol) were firstly dissolved in 10 ml of water and stirred well. Subsequently, 30 ml of 48% fluoboric acid (HBF4) was slowly added at room temperature with continuous stirring for 30 minutes. Next, copper (I) chloride (642 mg, 6.48 mmol) was added and the reaction mixture was heated to 80°C and maintained for 3 hours. After completion of the reaction, the mixture was poured into ice-cold water at 0°C and extracted with 200 ml of saturated sodium bicarbonate solution and 200 ml of ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated in vacuum. Purification by column chromatography (hexane/ethyl acetate, 15/1) gave 2-chloro-5-nitrophenol (0.46 g, 23% yield). Referring to the exemplary method of synthesis 9, the target compound (0.167 g, 94% yield) was further reacted with 2-chloro-5-nitrophenol (0.36 g, 2.29 mmol).

References

[1] Patent: US2011/9390, 2011, A1. Location in patent: Page/Page column 16
[2] Patent: WO2009/130481, 2009, A1. Location in patent: Page/Page column 128-129
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 3, p. 668 - 671
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 23, p. 7398 - 7405
[5] Tetrahedron Letters, 2005, vol. 46, # 23, p. 4023 - 4026

2-Chloro-5-nitrophenol(619-10-3)Related Product Information

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• 4-Chlorophenol
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• 2-Chloro-5-nitrobenzoic acid
• 2,4-Dichloro-5-nitrophenol
• 1,4-DIBUTOXY-2-CHLORO-5-NITROBENZENE
• 1-Chloro-2,5-dimethoxy-4-nitrobenzene
• o-Anisaldehyde
• 2-CHLORO-5-NITROANISOLE
• 2-Chloro-4-fluoro-5-nitrophenol
• 1-CHLORO-2,5-DIETHOXY-4-NITROBENZENE
• 2-Nitrophenol
• 2,5-DINITROPHENOL
• Nitrophenol
• 3-Nitrophenol
• PICRIC ACID
• 4-Chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline
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