3,5-Dinitrosalicylic acid

3,5-Dinitrosalicylic acid[1]
Names
Preferred IUPAC name
2-Hydroxy-3,5-dinitrobenzoic acid
Other names
3,5-Dinitrosalicylic acid
Identifiers
3D model (JSmol)
2220661
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.278
EC Number
  • 210-204-3
5309
KEGG
UNII
  • InChI=1S/C7H4N2O7/c10-6-4(7(11)12)1-3(8(13)14)2-5(6)9(15)16/h1-2,10H,(H,11,12) checkY
    Key: LWFUFLREGJMOIZ-UHFFFAOYSA-N checkY
  • InChI=1/C7H4N2O7/c10-6-4(7(11)12)1-3(8(13)14)2-5(6)9(15)16/h1-2,10H,(H,11,12)
    Key: LWFUFLREGJMOIZ-UHFFFAOYAQ
  • c1c(cc(c(c1C(=O)O)O)[N+](=O)[O-])[N+](=O)[O-]
Properties[1]
C7H4N2O7
Molar mass 228.116 g·mol−1
Appearance Yellow needles or plates
Density 1.70 g/cm3
Melting point 182 °C (360 °F; 455 K)[1] (decomposes at 275 °C (527 °F; 548 K))[2]
2 g/100mL (20 °C (68 °F; 293 K))
Solubility in organic solvents Soluble in ethanol, diethyl ether, benzene
log P 1.71[2]
Hazards
GHS labelling:[3]
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H318
P264, P270, P280, P301+P312+P330, P305+P351+P338+P310, P501
NFPA 704 (fire diamond)
[2]
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Lethal dose or concentration (LD, LC):
860 mg/kg (Oral, rat)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)
Infobox references

3,5-Dinitrosalicylic acid (DNS or DNSA, IUPAC name 2-hydroxy-3,5-dinitrobenzoic acid) is an aromatic compound that reacts with reducing sugars and other reducing molecules to form 3-amino-5-nitrosalicylic acid, which strongly absorbs light at 540 nm.

Synthesis

3,5-Dinitrosalicylic acid can be prepared by the nitration of salicylic acid:[4]

Uses

DNS method measurements.

It was first introduced as a method to detect reducing substances in urine by James B. Sumner.[5] It has since been widely used (for example) for quantifying carbohydrate levels in blood.[6] It is mainly used in assay of alpha-amylase, however enzymatic methods are usually preferred due to DNS's lack of specificity.[7]

Safety

Although specific sensitivity information is not given, Sigma-Aldrich lists the storage class of the free acid as "other explosive materials".[3]

Various metal salts of DNS are explosives of varying sensitivity. The copper salt explodes on rapid heating, while the lead salt is a primary explosive as impact sensitive as mercury fulminate.[8] The barium salt is friction sensitive and both it and the dipotassium salts are impact sensitive (though not extremely so).[9]

References

  1. 1 2 3 Lide, David R., ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). Boca Raton, Florida: CRC Press. pp. 3–318, 3–319. ISBN 0-8493-0487-3.
  2. 1 2 3 "SDS - 3,5-dinitrosalicylic acid". www.fishersci.com. ThermoFisher Scientific. 19 December 2025. p. 3. Retrieved 22 March 2026.
  3. 1 2 3 Sigma-Aldrich Co., 3,5-dinitrosalicylic acid. Retrieved on 21 March 2026.
  4. ↑ Thiel, W.; Mayer, R.; Jauer, E.-A.; Modrow, H.; Dost, H. (1986). "Synthesis and Spectral Characterization of Blue Dyes of the Benzene Series". J. Prakt. Chem. 328 (4). Leipzig, Germany: 497–514. doi:10.1002/prac.19863280406.
  5. ↑ Sumner, James B.; Graham, V.A. (June 1921). "Dinitrosalicylic Acid: A Reagent for the Estimation of Sugar in Normal and Diabetic Urine" (pdf). Journal of Biological Chemistry. 47 (1): 5–9. doi:10.1016/S0021-9258(18)86093-8. S2CID 34820005.
  6. ↑ Wang, Nam Sun. "Glucose Assay By Dinitrosalicylic Colorimetric Method". College Park, MD: Department of Chemical & Biomolecular Engineering, University of Maryland. Retrieved 21 March 2026.
  7. ↑ Miller, Gail Lorenz (1959). "Use of dinitrosalicylic acid reagent for determination of reducing sugar". Anal. Chem. 31 (3): 426–428. doi:10.1021/ac60147a030.
  8. ↑ Fedoroff, Basil T.; Sheffield, Oliver E.; Kaye, Seymour M. (1 January 1975). "Hydroxybenzoic acid and derivatives". Encyclopedia of Explosives and Related Items (PDF) (Technical report). Vol. 7, H2 to Lysol. Dover, NJ: Picatinny Arsenal. pp. H-237. LCCN 61-61759. ADA019502, PATR 2700.
  9. ↑ Kaye, Seymour M. (1 January 1978). Encyclopedia of Explosives and Related Items (PDF) (Technical report). Vol. 9, QDX through Type Explosives. Dover, NJ: Army Armament Research And Development Center - Large Caliber Weapon Systems Lab. pp. S-32, S-33. LCCN 61-61759. ADA097595, PATR 2700.
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