3,5-Dinitrosalicylic acid
Basic information
- CAS
609-99-4- Standard SMILES
O=C(O)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1O- InChIKey
LWFUFLREGJMOIZ-UHFFFAOYSA-N- Molecular formula
- C7H4N2O7
- Average molar mass
- 228.12 g/mol
- Monoisotopic mass
- 228.00185047
Overview
3,5-dinitrosalicylic acid is a monohydroxybenzoic acid consisting of 2-hydroxybenzoic acid having nitro substituents at the 3- and 5-positions. It is used in colorimetric testing for the presence of free carbonyl groups (C=O) in reducing sugars. It has a role as a hapten. It is a monohydroxybenzoic acid and a C-nitro compound. It is functionally related to a salicylic acid.
Names & identifiers
- Preferred name
- 3,5-Dinitrosalicylic acid
- IUPAC
- 2-hydroxy-3,5-dinitrobenzoic acid
- English name
- 3,5-Dinitrosalicylic acid
- Molecular formula
- C7H4N2O7
- Molecular weight
- 228.12
Names & synonyms
3,5-DINITROSALICYLIC ACID609-99-42-Hydroxy-3,5-dinitrobenzoic acid3,5-Dinitro-2-hydroxybenzoic acidBenzoic acid, 2-hydroxy-3,5-dinitro-3,5-Dinitrosalicylate2ACT5NW8HUCHEBI:53648NSC-181DTXSID9060576RefChem:91630DTXCID0042909
Show more names
3,5-dinitrosalicylicNSC 181RARECHEM AL BE 01713,5-Dinitro salicyliDinitro salicylic acLABOTEST-BB LT000601635-Dinitrosalicylic acid3,5-Dinitrosalicyls?ure
210-204-3Salicylic acid, 3,5-dinitro-3,5-Dinitro salicylic acido-DNCPo-dinitrocarboxylphenolMFCD000071043,5-dinitro-2-salicylic acidA1BNY
Database identifiers
- CAS
609-99-4- PubChem CID
- 11873
- DTXSID
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 149 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 1
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 320
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Nitrobenzoic Acids
SpringerMaterials PropertiesDiffusion
LogP1.71
Vapor Pressure0.00000002 [mmHg]
Physical DescriptionLight yellow solid; [Sigma-Aldrich MSDS]
Ionization Efficiency
Negative
1.22
10.5
Agilent XCT
Electrospray ionization
ammonia (10nM)
Physicochemical properties
- Melting point
- 168 · 168-172 °C (lit.)
- Boiling point
- 369.91 °C · 369.91°C (rough estimate)
- Density
- 1.7914 · 1.7914 (rough estimate)
- bulk density
- 400 kg/m3 · 400kg/m3
- refractive index
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 10.6% (7 of 66) of reports.
Danger
H302 (81.8%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 66 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzoic acid, 2-hydroxy-3,5-dinitro-
REACH registered substance: 3,5-dinitrosalicylic acid (EC: 210-204-3)
2-Hydroxy-3,5-dinitrobenzoic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes somnolence and muscle contraction or spasticity in oral lethal-dose studies of mice and rats; Causes liver changes and weight loss in 30-day intermittent oral studies of rats; [RTECS] An irritant; Harmful by ingestion; [Sigma-Aldrich MSDS] See Salicylic acid.
DOT Hazard Classification
3,5-Dinitrosalicylic acid (lead salt) (dry)
Forbidden explosives/materials (49 eCFR § 173.54/§ 173.21)
Hazard Classes and CategoriesAcute Tox. 4 (81.8%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationBenzoic acid, 2-hydroxy-3,5-dinitro-: ACTIVE
Applications
Uses3,5-Dinitrosalicylic acid is a salicylic acid derivative used in colorimeteric determination of reducing sugars.
Uses3,5-Dinitrosalicylic acid is used in the quantification of reducing sugars by colorimetry. It is utilized for the analysis of glycosidase (glycoside hydrolase) activity by quantitation of enzymatically released reducing sugar. It is also used to detect reducing substances in urine and for quantifying carbohydrate level in blood. It acts as an important raw material and an intermediate in the production of organic chemicals such as agrochemicals, organic synthesis, pharmaceuticals and dyes.
Uses3,5-Dinitrosalicylic acid was used as a reagent for the preparation of oxazolines from amino alcohols and for the spectrophotometric determination of ampicillin. It was also used to measure the effects of silver nanoparticles on the membrane leakage of the reducing sugars.
Preparation methods
Preparation3,5-Dinitrosalicylic acid is prepared by the nitration of salicylic acid. Salicylic acid is added to a mixed acid solution and nitrated at 15–25°C. The reaction mixture is then slowly poured into ice water, yielding a yellow solid precipitate. After filtration and washing with water, the pure product is obtained.
Upstream & downstream products
Upstream raw materials
Related reactions
8 records
Compound notes
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