4-Nitrophthalic acid Chemical Properties

Melting point:

159-161 °C (lit.)

Boiling point:

350.79°C (rough estimate)

Density 

1.6342 (rough estimate)

refractive index 

1.5282 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

880g/l

form 

Crystalline Powder

pka

pK1:2.11 (25°C)

color 

Yellow to beige

PH

1 (10g/l, H2O, 20℃)

Odor

Odorless

PH Range

1

Water Solubility 

880 g/l at 20 °C

BRN 

1882262

InChIKey

SLBQXWXKPNIVSQ-UHFFFAOYSA-N

CAS DataBase Reference

610-27-5(CAS DataBase Reference)

EPA Substance Registry System

1,2-Benzenedicarboxylic acid, 4-nitro- (610-27-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

TSCA 

Yes

HS Code 

29173980

MSDS

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4-Nitrophthalic acid Usage And Synthesis

Chemical Properties

Light-Beige Solid

Uses

4-Nitrophthalic Acid is an impurity of Apremilast.

General Description

The tissue-specific activity of 4-nitrophthalic acid was studied.

Synthesis

The general procedure for the synthesis of 4-nitrophthalic acid from 4-nitrophthalonitrile was as follows: 4-nitrophthalonitrile (2 mmol) was dissolved in 5 ml of [bmim]HSO4 ionic liquid and the reaction mixture was heated at 60-65°C for 1-3 hours. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was poured into water containing crushed ice to induce precipitation of the product. Subsequently, the precipitate is collected by filtration and dried. The product yield of this method was generally higher than 90% and the purity of the product met the requirements without further purification. The filtrate was concentrated under vacuum, washed twice with diethyl ether and concentrated again under high vacuum. After drying, about 95% of the ionic liquid was recovered, and its authenticity was verified by comparison with the original ionic liquid. The recovered ionic liquid showed comparable efficiency to the original ionic liquid in the reaction of converting nitrile to acid and could be reused 5-6 times without significant reduction in activity.

Purification Methods

Crystallise 4-nitrophthalic acid from Et2O, EtOAc or *C6H6 (m 166o). The amide has m 200o (from EtOH). [Beilstein 9 H 828, 9 IV 4234.]

References

[1] Tetrahedron Letters, 2014, vol. 55, # 28, p. 3802 - 3804

4-Nitrophthalic acid(610-27-5)Related Product Information

• Potassium hydrogen phthalate
• Diethyl phthalate
• Bis(2-ethylhexyl) phthalate
• Dimethyl phthalate
• 4-Nitrophthalonitrile
• 2-Nitrocinnamic acid
• 4-Nitrobenzoic acid
• 3-NITROPHTHALIC ACID,m-Nitrophthalic acid,3-Nitrophthalic acid 96%,3-NITROPHTHALIC ACID pure,o-Nitrophthalic acid
• Dibutyl phthalate
• Phthalic acid
• 2-Nitrobenzoic acid
• 3-Nitrophthalic Acid Anhydride
• 4-Nitrophthalic acid anhydride
• 4-Nitro-o-phenylenediamine
• 4-Nitrophthalimide
• (R)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethylaMine
• Apremilast Impurity 34
• (S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethylaMine N-acetyl-L-leucine salt