4-Chloro-3,5-dinitrobenzoic acid

CAS NO.：118-97-8
Empirical Formula: C7H3ClN2O6
Molecular Weight: 246.56
MDL number: MFCD00007080
EINECS: 204-290-1
SAFETY DATA SHEET (SDS)
Update Date: 2024-10-29 11:48:30

What is 4-Chloro-3,5-dinitrobenzoic acid?

Chemical properties

yellow crystals

The Uses of 4-Chloro-3,5-dinitrobenzoic acid

4-Chloro-3,5-dinitrobenzoic-15N2 Acid is an intermediate in synthesizing Lodoxamide-15N2,d2 (L469367), a labelled form of Lodoxamide. It is an antiallergic drug that acts as a mast cell stabilizer. It is effective in the treatment of allergic conjunctivitis and in decreasing vascular permeability.

Hazard

irritant

Synthesis

The synthesis of 4-Chloro-3,5-dinitrobenzoic acid is as follows:
4-chloro-benzoic acid (20 g, 0.128 mol) was dissolved in H₂SO₄ (d = 1.835 g/mL, 300 mL) at80 C, and KNO₃ (66 g, 0.65 mol) was added. The reaction mixture was heated to 125 C using ahigh-pressure flask and kept for 2 h, after which the reaction was cooled to rt and poured onto ice.The yield of 4-Chloro-3,5-dinitrobenzoic acid was 28 g (89%) .
synthesis of 4-Chloro-3,5-dinitrobenzoic acid.png

Purification Methods

Crystallise the acid from EtOH/ H2O, EtOH or *C6H6. The 1:1 naphthalene complex (by fusing various ratios of ingredients and recrystallising from EtOH) has m 122o. [Beilstein 9 H 416, 9 III 1953, 9 IV 1360.]

Properties of 4-Chloro-3,5-dinitrobenzoic acid

Melting point:	159-162 °C (lit.)
Boiling point:	315°C
Density	1.9543 (rough estimate)
refractive index	1.6500 (estimate)
Flash point:	186°C
storage temp.	Sealed in dry,2-8°C
solubility	soluble in Methanol
form	powder to crystal
pka	2?+-.0.10(Predicted)
color	Light orange to Yellow to Green
BRN	668253
InChI	InChI=1S/C7H3ClN2O6/c8-6-4(9(13)14)1-3(7(11)12)2-5(6)10(15)16/h1-2H,(H,11,12)
CAS DataBase Reference	118-97-8(CAS DataBase Reference)
EPA Substance Registry System	Benzoic acid, 4-chloro-3,5-dinitro- (118-97-8)

Safety information for 4-Chloro-3,5-dinitrobenzoic acid

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation
Precautionary Statement Codes	P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P332+P313:IF SKIN irritation occurs: Get medical advice/attention. P337+P313:IF eye irritation persists: Get medical advice/attention.