2-Amino-6-nitro-benzoic acid

HCID 95795

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Basic information

CAS: 50573-74-5
Standard SMILES: Nc1cccc([N+](=O)[O-])c1C(=O)O
InChIKey: GGKYLHNARFFORH-UHFFFAOYSA-N
Molecular formula: C7H6N2O4
Average molar mass: 182.13 g/mol
Monoisotopic mass: 182.03275667

Names & identifiers

Preferred name: 2-Amino-6-nitro-benzoic acid
IUPAC: 2-amino-6-nitrobenzoic acid
English name: 2-Amino-6-nitrobenzoic acid
Molecular formula: C7H6N2O4
Molecular weight: 182.13

Names & synonyms

2-amino-6-nitro-benzoic acidRefChem:464806610-543-02-Amino-6-nitrobenzoic acid50573-74-56-Nitroanthranilic AcidBenzoic acid, 2-amino-6-nitro-MFCD000347852-Amino-6-nitrobenzoicacidNSC 369536-Nitro-2-Aminobenzoesaure2-nitro-6-amino benzoic acid

Show more names

RSYY(Apremilast)-16-Nitroanthanilic acid2-Amino-6-nitrobenzoicaci6-NitroanthranilicAcid>2-Amino-6-nitrobenzoic acidBenzoic acid,2-amino-6-nitro-Anthranilicacid, 6-nitro- (6CI,7CI)6-Nitroanthranilic Acid , 97.0%(LC&T2-Amino-6-nitrobenzoic acid USP/EP/BP

DTXSID20198594NSC-36953CS-W002163AC-2863SY003157EN300-93139AE-848/01467029Z1255442308

Database identifiers

CAS: 50573-74-5
PubChem CID: 95795
DTXSID: DTXSID20198594
EC Number: 610-543-0
Nikkaji: J89.563F

Properties

Computed structural properties

XLogP: 0.8
Topological polar surface area: 109 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 5
Rotatable bonds: 1
Heavy atoms: 13
Formal charge: 0
Complexity: 225

Physicochemical properties

Melting point: 189 °C · 189 °C (decomp)
Boiling point: 412.3 · 412.3±35.0 °C(Predicted)
Density: 1.568 · 1.568±0.06 g/cm3(Predicted)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: soluble in Methanol
pka: 2.11 · 2.11±0.30(Predicted)
form: Solid
color: Light yellow to Brown
InChI: InChI=1S/C7H6N2O4/c8-4-2-1-3-5(9(12)13)6(4)7(10)11/h1-3H,8H2,(H,10,11)
InChIKey: GGKYLHNARFFORH-UHFFFAOYSA-N
SMILES: C(O)(=O)C1=C([N+]([O-])=O)C=CC=C1N
UNSPSC Code: 12352106 · 12352106
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Hazard Codes: Xn
Risk Statements: 22 · 22
WGK Germany: 3 · WGK 3
HS Code: 2921490090 · 2921490090
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H318 (90.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)

Aggregated GHS information provided per 31 reports by companies from 3 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesEye Dam. 1 (90.3%)

Safety data

wgk: WGK 3
hs_code: 2921490090
risk_code: 22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Precautionary statements: P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Applications

Uses2-Amino-6-nitrobenzoic Acid is the secondary metabolite of dinitrobenzyl glucuronide related to the formation of genotoxic compound of dinitrotoluene in rats.

Preparation methods · 1 item

Preparation20.3 g of 2-chloro-6-nitrobenzoic acid, 1.2 g of cuprous oxide, 40 g of cesium carbonate, 50 g of DMF, and 85 g of 30% self-prepared ammonia solution were added to a 500 mL autoclave. The temperature was raised to 90 °C, and ammonia gas was introduced during the reaction to maintain the pressure inside the autoclave at 0.7~0.8 MPa. The reaction was carried out for 12 h. Samples were taken for control. The phases were separated, and the upper layer was collected. Hydrochloric acid was added to acidify to pH 1~2. The mixture was filtered, and the filtrate was collected. The mixture was extracted three times with diethyl ether, and the upper ether phase was collected. The solvent was removed by distillation to obtain 18.7 g of crude 2-amino-6-nitrobenzoic acid (HPLC purity: 88%), yield: 90%. Recrystallization with ethyl acetate yielded 15.5 g of 2-amino-6-nitrobenzoic acid product (HPLC purity > 97%), overall yield: 85%.