4-Chloro-3-nitroanisole Chemical Properties

Melting point:

41-43 °C (lit.)

Boiling point:

293°C

Density 

1.366

refractive index 

1.6000 (estimate)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Amber

BRN 

640872

InChI

InChI=1S/C7H6ClNO3/c1-12-5-2-3-6(8)7(4-5)9(10)11/h2-4H,1H3

InChIKey

HISHUMDTGXICEZ-UHFFFAOYSA-N

SMILES

C1(Cl)=CC=C(OC)C=C1[N+]([O-])=O

CAS DataBase Reference

10298-80-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

BZ8580000

Hazard Note 

Irritant

HS Code 

29093090

MSDS

• Language:English Provider:1-Chloro-4-methoxy-2-nitrobenzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Chloro-3-nitroanisole Usage And Synthesis

Chemical Properties

beige to ochre powder

Uses

4-Chloro-3-nitroanisole can be used as disperse azo dyes.

Uses

4-chloro-3-nitroanisole is used to synthesize a group of derivatives of 7-methanesulfonylamino-6-phenoxychromone at the pyrone and phenoxy rings.

Synthesis

In a reaction vessel, a concentrated phosphoric acid solution with a mass fraction of 80% and 100 mL of water were added, followed by 4-amino-3-nitroanisole (2) 0.25 mol. The stirring speed was controlled to 230 rpm and the temperature of the solution was lowered to 9 °C. A solution configured from potassium nitrite 0.25 mol dissolved in 100 mL of water was added slowly. A further 200 mL of potassium bisulfite solution with a mass fraction of 55% was added to the reaction vessel, the reaction temperature was maintained at 8 °C, and the reaction lasted for 50 min. 0.30 mol of stannous bromide was dissolved in 130 mL of concentrated potassium chloride solution, and the diazonium salt solution was rapidly added to the stannous bromide solution at 19 °C and allowed to stand for 5 hours. Subsequently, the temperature of the solution was gradually raised to 70 °C until no gas escaped. The distillate was collected by steam distillation and extracted with acetone. The extracts were combined and washed sequentially with sodium bicarbonate solution and potassium chloride solution and finally dehydrated by activated alumina. After recovery of acetone, 43.71 g of yellow solid 4-chloro-3-nitroanisole was obtained in 93% yield.

References

[1] Chemistry - A European Journal, 2017, vol. 23, # 42, p. 9996 - 10000
[2] Patent: CN104292107, 2016, B. Location in patent: Paragraph 0030; 0031
[3] Patent: CN105439868, 2016, A. Location in patent: Paragraph 0014; 0015
[4] Tetrahedron Letters, 2010, vol. 51, # 51, p. 6769 - 6771
[5] Organic Process Research and Development, 2017, vol. 21, # 1, p. 44 - 51

4-Chloro-3-nitroanisole(10298-80-3)Related Product Information

• Azoic Diazo Component 1
• 4-Methyl-3-nitroanisole
• 1-Chloro-3-nitrobenzene
• 4-Bromo-3-nitroanisole
• 2-Chloro-3-nitrobenzoic acid
• 4-CHLORO-3-METHYLANISOLE
• 2-Methyl-3-nitroanisole
• 4-Chloro-3-nitrobenzoic acid
• 4-Nitrobenzoic acid
• 4-Chloro-3-nitrobenzonitrile
• N-(5-Methoxy-2-phenoxyphenyl)methanesulfonamide
• Iguratimod Impurity 10
• Iguratimod
• N-(4-(2-aminoacetyl)-5-methoxy-2-phenoxyphenyl)methanesulfonamide hydrochloride
• MethanesulfonaMide, N-[4-[2-(forMylaMino)acetyl]-5-hydroxy-2-phenoxyphenyl]-
• Iguratimod Impurity 11
• Phenol
• Iguratimod Impurity 2