3-NITRO-4-(TRIFLUOROMETHYL)BENZOIC ACID Chemical Properties

Melting point:

169°C

Boiling point:

330.0±42.0 °C(Predicted)

Density 

1.596

storage temp. 

2-8°C

solubility 

Acetone (Slightly), Methanol (Slightly)

form 

Solid

pka

3.03±0.10(Predicted)

color 

Yellow

InChI

InChI=1S/C8H4F3NO4/c9-8(10,11)5-2-1-4(7(13)14)3-6(5)12(15)16/h1-3H,(H,13,14)

InChIKey

NIWGMOJIGTUDFT-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

116965-16-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HazardClass 

IRRITANT, IRRITANT-HARMFUL

HS Code 

2916399090

3-NITRO-4-(TRIFLUOROMETHYL)BENZOIC ACID Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

3-Nitro-4-trifluoromethylbenzoic Acid is useful intermediate for the preparation of trifluoromethylated (benzoxazolyl)actinocins.

Synthesis

Step B Synthesis of 3-nitro-4-(trifluoromethyl)benzoic acid: To a rapidly stirred mixture containing 1.00 g (4.88 mmol) of 2-nitro-4-methylbenzotrifluoride (from Step A), 236 mg (0.732 mmol) of tetra-n-butylammonium bromide, 51 mg (0.244 mmol) of ruthenium trichloride hydrate, and 2 mL of 1,2-dichloroethane to which 5.8 mL (~22 mmol) of 13% aqueous sodium hypochlorite solution (~3.8 M) was added in five additions. At each addition of sodium hypochlorite solution, the pH of the reaction mixture was adjusted by the addition of 5N NaOH solution and maintained between 8.5 and 10.5. The next portion of sodium hypochlorite solution was added only after the pH had stabilized for about 5 minutes. The entire addition process took about 2 h. The final pH was 10.3. The reaction mixture was stirred overnight at 45 °C and then cooled to room temperature for two-phase separation. The aqueous phase was acidified to pH 3 with 20% sulfuric acid and subsequently extracted three times with ethyl acetate. The combined organic extracts were washed sequentially with water (3 times) and brine and then dried with anhydrous Na2SO4. The residue obtained by concentrating the organic phase was dissolved in 5% NaHCO3 aqueous solution and adjusted with 5% NaOH to pH 9. The aqueous phase was washed sequentially with dichloromethane (2 times) and ether. Subsequently, the aqueous phase was acidified to pH 3 with 20% sulfuric acid and extracted with ethyl acetate to afford 563 mg (49% yield) of the title compound as an off-white solid with a melting point of 156-158° C. TLC analytical conditions: 1:1 hexanes-EtOAc; Mass Spectrometry (EI) m/e 235 (M+); 200 MHz 1H NMR (CD3OD) δ 7.87 (d, J= 8Hz, 1H), 8.31 (d, J=8Hz, 1H), 8.45 (s, 1H).

References

[1] Patent: US5262412, 1993, A

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