Methyl 4-chloro-3-nitrobenzoate Chemical Properties

Melting point:

80 °C

Boiling point:

313.2±22.0 °C(Predicted)

Density 

1.5220

refractive index 

1.6000 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Light yellow to Green

Water Solubility 

Soluble in water.

BRN 

1643729

InChI

InChI=1S/C8H6ClNO4/c1-14-8(11)5-2-3-6(9)7(4-5)10(12)13/h2-4H,1H3

InChIKey

XRTKWPWDSUNLHS-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

14719-83-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-37

Hazard Note 

Irritant

HS Code 

29163990

MSDS

• Language:English Provider:ALFA

Methyl 4-chloro-3-nitrobenzoate Usage And Synthesis

Uses

Methyl 4-chloro-3-nitrobenzoate, is used as starting material for the preparation of the methyl benzoates

Synthesis

Procedure for the synthesis of methyl 4-chloro-3-nitrobenzoate (1): 4-chloro-3-nitrobenzoic acid (5.0 g, 24.8 mmol) was dissolved in 200 mL of methanol and 4.15 mL (29.8 mmol) of triethylamine was added. The reaction mixture was cooled in an ice-salt bath and 3.19 mL (44.7 mmol) of acetyl chloride was added slowly and dropwise. The reaction mixture was stirred under reflux conditions for 6 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in 100 mL of water and then extracted twice with ethyl acetate (100 mL). The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was recrystallized with ether (10 mL) to give white crystals of methyl 4-chloro-3-nitrobenzoate (4.81 g, 92% yield). Thin Layer Chromatography (TLC) Rf = 0.55 (unfolding agent: ethyl acetate/cyclohexane = 7/3); melting point 79-80 °C. Infrared spectroscopy (IR) showed the carbonyl absorption peak located at 1716 cm-1; 1H NMR spectrum (300 MHz, DMSO-d6) δ 3.90 (single peak, 3H, OCH3), 7.90 (double peak, 1H, H5, J5-6 = 8.1 Hz), 8.15 (double-double peak, 1H, H6, J6-5 = 8.1 Hz, J5-2 = 1.5 Hz ), 8.49 (double peaks, 1H, H2, J2-6 = 1.5Hz). Molecular formula: C8H6ClNO4.

References

[1] Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 3927 - 3936
[2] Heterocyclic Communications, 2001, vol. 7, # 5, p. 455 - 460
[3] Chemical Research in Toxicology, 1997, vol. 10, # 4, p. 439 - 449
[4] Synthetic Communications, 2002, vol. 32, # 11, p. 1703 - 1707
[5] Journal of Organic Chemistry, 2003, vol. 68, # 14, p. 5525 - 5533

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