2-Amino-4-nitrobenzoic acid Chemical Properties

Melting point:

257 °C (dec.)(lit.)

Boiling point:

315.51°C (rough estimate)

Density 

1.5181 (rough estimate)

refractive index 

1.5880 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Powder

pka

3.92±0.13(Predicted)

color 

Orange

Water Solubility 

<0.01 g/100 mL at 22 ºC

InChI

InChI=1S/C7H6N2O4/c8-6-3-4(9(12)13)1-2-5(6)7(10)11/h1-3H,8H2,(H,10,11)

InChIKey

UEALKTCRMBVTFN-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C([N+]([O-])=O)C=C1N

CAS DataBase Reference

619-17-0(CAS DataBase Reference)

EPA Substance Registry System

4-Nitroanthranilic acid (619-17-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

CB3675000

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29224999

Hazardous Substances Data

619-17-0(Hazardous Substances Data)

MSDS

• Language:English Provider:4-Nitro-2-aminobenzoic acid
• Language:English Provider:SigmaAldrich

2-Amino-4-nitrobenzoic acid Usage And Synthesis

Chemical Properties

Orange crystalline powder

Physical properties

2-Amino-4-nitrobenzoic acid has three crystal structures^[1], respectively: monoclinic-1B, monoclinic-1C, and triclinic-1. Compound monoclinic-1B crystallises in the A ˚ space group P21/c with a = 4.039(4), b = 27.23(2), c = 7.284(7) Å, b = 112.783(15); compound monoclinic-1C crystallises in the space group P21/c with a = 3.71050(10), b = 25.3092(8), c = 24.3555 (17) A ˚ , b = 93.459(7) , and triclinic-1 crystallises in the space group P-1 with a = 3.7522(3), b = 8.5536(6), c = 24.4118(17), a = 88.738(9), b = 86.625(9), c = 87.769(9).
[1] SOLANGE M. S. V. WARDELL; James L W. Three New Polymorphs of 2-Amino-4-nitrobenzoic Acid[J]. Journal of Chemical Crystallography, 2015, 46 1: 34-43. DOI:10.1007/s10870-015-0625-8.

Uses

2-Amino-4-nitrobenzoic acid (also known as 4-Nitroanthranilic acid) is primarily used as an intermediate in the synthesis of dyes and pharmaceuticals. It is also used in crystal or eutectic molecular structure research.

Uses

peptide synthesis

Definition

ChEBI: 4-nitroanthranilic acid is an aminobenzoic acid that is anthranilic acid with a nitro substituent at position 4. It has a role as a mutagen. It is an aminobenzoic acid and a nitrobenzoic acid. It is functionally related to an anthranilic acid.

General Description

Orange prisms or orange powder. Sweet taste.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4-Nitroanthranilic acid is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents.

Fire Hazard

Flash point data for 4-Nitroanthranilic acid are not available; however, 4-Nitroanthranilic acid is probably combustible.

reaction suitability

reaction type: solution phase peptide synthesis

Purification Methods

Crystallise the acid from water, EtOH (m 271o) or aqueous EtOH (m 269o). The acetyl derivative has m 217o (from EtOH), m 222o (from aqueous EtOH). [Chapman & Stephen J Chem Soc 1796 1925, Beilstein 14 II 234, 14 III 975, 14 IV 1087.]

2-Amino-4-nitrobenzoic acid (619-17-0)Related Product Information

• 4-Aminobenzoic acid
• 4-Nitrobenzoic acid
• Methyl anthranilate
• POLYURETHANE
• Benzocaine
• Glycine
• 6-Aminocaproic acid
• 4-Dimethylaminobenzoic acid
• Urethane
• 2-Amino-4-methylbenzoic acid
• 2-Amino-4-nitrophenol
• NITROGEN DIOXIDE
• Anthranilic acid
• 3-NITROANTHRANILIC ACID,3-NITROANTHRANILIC ACID, 2-AMINO-3-NITROBENZOIC ACID
• 5-NITROANTHRANILIC ACID,5-NITROANTHRANILIC ACID, TECH., 90%,2-AMINO-5-NITROBENZOIC ACID / 5-NITROANTHRANILIC ACID
• 2,4,6-TRINITROBENZOIC ACID
• 5-CHLORO-2,4-DINITROBENZOIC ACID
• 2,4-DINITROBENZOIC ACID