3-Hydroxy-2-nitrobenzoic acid Chemical Properties

Melting point:

179-181°C

Boiling point:

363°C

Density 

1.631

Flash point:

167°C

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

2.07±0.10(Predicted)

form 

Solid

color 

Light Beige to Light Brown

BRN 

2372248

InChI

InChI=1S/C7H5NO5/c9-5-3-1-2-4(7(10)11)6(5)8(12)13/h1-3,9H,(H,10,11)

InChIKey

KPDBKQKRDJPBRM-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

602-00-6(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37

HS Code 

29163990

MSDS

• Language:English Provider:ALFA

3-Hydroxy-2-nitrobenzoic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

3-Hydroxy-2-nitrobenzoic Acid (cas# 602-00-6) is a compound useful in organic synthesis.

Synthesis

Step 1: 3-Chloro-2-nitrobenzoic acid (30 g, 0.148 mol) was dissolved in aqueous potassium hydroxide solution (240 g, 4.277 mol in 300 mL H2O) and stirred at room temperature until completely dissolved. Subsequently, the reaction mixture was heated to 110°C and kept for 12 hours for the reaction. Upon completion of the reaction, the mixture was cooled to room temperature, diluted with water and acidified with concentrated hydrochloric acid to pH 2. The acidified mixture was cooled at 0°C and subsequently extracted with ethyl acetate (2 x 500 mL). The organic layers were combined, washed with brine solution, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure to give 3-hydroxy-2-nitrobenzoic acid (27 g, 99% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 13.8 (brs, 1H), 11.21 (s, 1H), 7.47 (t, J = 8.0 Hz, 1H), 7.39 (dd, J' = 8.0 Hz, J'' = 1.6 Hz, 1H), 7.30 (dd, J'' = 7.6 Hz, J'' = 0.8 Hz. 1H); ESI-MS: calculated mass: 183.02; observed mass: 182.10 [M-H]-.

References

[1] Patent: WO2007/125405, 2007, A2. Location in patent: Page/Page column 24; 72
[2] Patent: WO2014/169167, 2014, A1. Location in patent: Page/Page column 61
[3] Dalton Transactions, 2012, vol. 41, # 31, p. 9272 - 9275
[4] Patent: US2014/87992, 2014, A1. Location in patent: Paragraph 0312-0313
[5] Patent: US2009/197863, 2009, A1. Location in patent: Page/Page column 55

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