609-99-4

Basic information

• Product Name: 3,5-Dinitrosalicylic acid
• Synonyms: 2-hydroxy-3,5-dinitro-benzoicaci;3,5-dinitrosalicylic;3,5-dinitro-salicylicaci;Benzoic acid, 2-hydroxy-3,5-dinitro-;Salicylic acid, 3,5-dinitro-;LABOTEST-BB LT00060163;3,5-DINITROSALICYLIC ACID;3,5-DINITROSALICYLIC ACID HYDRATE
• CAS NO: 609-99-4
• Molecular Formula: C₇H₄N₂O₇
• Molecular Weight: 228.12
• EINECS: 210-204-3
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;Aromatics;Miscellaneous Reagents
• Mol File: 609-99-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 170 °C
• Boiling Point: 369.91°C (rough estimate)
• Flash Point: 173.8 °C
• Appearance: Yellow/Powder
• Density: 1.7914 (rough estimate)
• Vapor Pressure: 1.09E-06mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Refrigerator
• Solubility: H2O: soluble50mg/mL
• PKA: 1.57±0.10(Predicted)
• Water Solubility: soluble
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases, strong acids.
• BRN: 2220661
• CAS DataBase Reference: 3,5-Dinitrosalicylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dinitrosalicylic acid(609-99-4)
• EPA Substance Registry System: 3,5-Dinitrosalicylic acid(609-99-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-36/37/38
• Safety Statements: 22-24/25-36-26
• RIDADR: 2811
• WGK Germany: 3
• RTECS: VO2965000
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 609-99-4(Hazardous Substances Data)

Usage

Chemical Properties

solid

Uses

Different sources of media describe the Uses of 609-99-4 differently. You can refer to the following data:
1. 3,5-Dinitrosalicylic acid is a salicylic acid derivative used in colorimeteric determination of reducing sugars.
2. 3,5-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.
3. 3,5-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.

Definition

ChEBI: 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 (C2O) in reducing sugars.

Biochem/physiol Actions

3,5-Dinitrosalicylic acid (DNS) is used in colorimetric determination of reducing sugars and to analyze glycosidase (glycoside hydrolase) activity by quantitation of enzymatically released reducing sugar. The dinitrosalicylic acid method has been compared to the Nelson-Somogi colorimetric method.

Purification Methods

Crystallise the acid from H2O. [Beilstein 10 IV 270.]

InChI: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)/p-2

Synthetic route

Meisenheimer complex A (102976-80-7) → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
With sodium hydroxide for 1.5h; Ambient temperature;	95%
Multi-step reaction with 3 steps 1: 84 percent / potassium thiphenoxide / methanol / 0.5 h / Ambient temperature 2: 90 percent / 20percent HCl / 1 h / Ambient temperature 3: 77 percent / NaOH / H2O / 0.5 h / 80 °C View Scheme

Potassium; 2,4-dinitro-6-(2-thiocyanato-ethoxycarbonyl)-phenolate (102976-79-4) → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
With potassium hydroxide In water at 80℃; for 0.25h;	94%

2-chloro-3,5-dinitrobenzoic acid (2497-91-8) → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
With pyridine; copper; potassium carbonate In water for 2h; Heating;	93%
With sodium hydroxide In water at 60℃;	86%
With sodium hydroxide In water at 25℃; Rate constant; in the presence of cetyltrimethylammonium chloride; other surfactants; var. conc. of NaOH;

salicylic acid (69-72-7) → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
With sulfuric acid; nitric acid In sulfuric acid at 20℃; for 0.5h;	93%
With Zn(NO3)2*2N2O4 In dichloromethane for 0.333333h; Heating;	88%
In conc. nitric acid; sulfuric acid; water	84%

2-Hydroxy-3,5-dinitro-benzoic acid 2-thiocyanato-ethyl ester (102941-66-2) → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
With sulfuric acid for 3h; Heating;	88%

3,5-dinitro-2-(2-hydroxyethoxy)benzoic acid, methyl ester (102941-62-8) → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
With sodium hydroxide In water at 80℃; for 0.5h;	77%
Multi-step reaction with 3 steps 1: 97 percent / methanol / 4 h / Ambient temperature 2: 0.10 g / methanol / 1 h / Ambient temperature 3: 95 percent / aq. NaOH / 1.5 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 94 percent / methanol / 0.5 h / Ambient temperature 2: 95 percent / aq. NaOH / 1.5 h / Ambient temperature View Scheme

1-methyl-4-nitrosobenzene (623-11-0) + 2-amino-3,5-dinitro-benzoic acid (609-97-2) → 3,5-dinitrosalicylic acid (609-99-4)

2-chloro-3,5-dinitrobenzoic acid (2497-91-8) + furan-2,3,5(4H)-trione pyridine (1:1) → 3,5-dinitrosalicylic acid (609-99-4)

2-hydroxy-3,5-dinitro-benzoic acid-(4-nitro-phenyl ester) (52803-54-0) + furan-2,3,5(4H)-trione pyridine (1:1) → 4-nitro-phenol (100-02-7) + 3,5-dinitrosalicylic acid (609-99-4)

3-nitrosalicylic acid (85-38-1) → 2,6-dinitrophenol (573-56-8) + 3,5-dinitrosalicylic acid (609-99-4)

5-nitrosalicylic acid (96-97-9) → 3,5-dinitrosalicylic acid (609-99-4) + 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With nitric acid

2-hydroxy-3,5-dinitro-benzonitrile (25844-84-2) → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
bei der Verseifung;

2-iodo-3,5-dinitro-benzoic acid (22049-25-8) → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
With sodium hydroxide

2-hydroxy-3,5-dinitro-benzoic acid phenyl ester (52040-46-7) + furan-2,3,5(4H)-trione pyridine (1:1) → 3,5-dinitrosalicylic acid (609-99-4) + phenol (108-95-2)

2-hydroxy-5-formylbenzoic acid (616-76-2) → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
With nitric acid at 0 - 5℃;

2-amino-3,5-dinitro-benzoic acid (609-97-2) → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
With alkaline solution
Multi-step reaction with 2 steps 1: sodium nitrite; aqueous sulfuric acid / Eintragen des Reaktionsgemisches in kaltes Wasser und Behandeln der erhaltenen Diazoniumsalz-Loesung mit wss. Kaliumjodid-Loesung 2: aq. NaOH solution View Scheme

2-fluoro-3,5-dinitrobenzoic acid (445-65-8) → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
With sodium hydroxide
With water

2-amino-3,5-dinitro-benzoic acid methyl ester (22603-10-7) + furan-2,3,5(4H)-trione pyridine (1:1) → 3,5-dinitrosalicylic acid (609-99-4)

2,3,5-trinitro-benzoic acid (102312-37-8) → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
With water

2-hydroxy-3,5-dinitro-benzoic acid-(2-nitro-phenyl ester) + furan-2,3,5(4H)-trione pyridine (1:1) → 3,5-dinitrosalicylic acid (609-99-4) + 2-hydroxynitrobenzene (88-75-5)

methyl salicylate (119-36-8) → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
With sulfuric acid; nitric acid durch Verseifen mit konz. Kalilauge;

Dimethylarsinic acid (75-60-5) + 3,5-dinitrosalicylic acid anion (52040-82-1) → 3,5-dinitrosalicylic acid (609-99-4) + cacodylic acid anion (15132-04-4)

Conditions	Yield
at 25℃; Rate constant;

3.5-Dinitro-aspirin, (O-Acetyl-3.5-dinitro-salicylsaeure) (19073-90-6) → 3,5-dinitrosalicylic acid (609-99-4) + acetic acid (64-19-7)

Conditions	Yield
With water In acetonitrile at 25℃; Rate constant;

2-(2-Carboxy-benzenesulfinyl)-3,5-dinitro-benzoic acid → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
With water In 1,4-dioxane

piperidine (110-89-4) + 2-chloro-3,5-dinitrobenzoic acid (2497-91-8) + copper-powder → 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
in Gegenwart von saeurebindenden Mitteln;

2-methyl-5,7-dinitro-benzofuran (16238-02-1) + acetone (67-64-1) + potassium permanganate → 3,5-dinitrosalicylic acid (609-99-4)

nitric acid (7697-37-2) + acetic acid (64-19-7) + salicylic acid (69-72-7) → 3-nitrosalicylic acid (85-38-1) + 2,3-dinitrophenol (66-56-8) + 5-nitrosalicylic acid (96-97-9) + 3,5-dinitrosalicylic acid (609-99-4)

3,5-dinitrosalicylaldehyde (2460-59-5) + alkaline permanganate → 3,5-dinitrosalicylic acid (609-99-4)

2-chloro-3,5-dinitrobenzoic acid (2497-91-8) + water (7732-18-5) → 2,4-Dinitrophenol (51-28-5) + carbon dioxide (124-38-9) + 3,5-dinitrosalicylic acid (609-99-4)

Conditions	Yield
at 180 - 190℃;

methanol (67-56-1) + 3,5-dinitrosalicylic acid (609-99-4) → methyl-3,5-dinitrosalicylate (22633-33-6)

Conditions	Yield
With sulfuric acid for 15h; Heating;	94%
With sulfuric acid
With sulfuric acid for 24h; Heating;	2.1 g

Upstream product

• 96-97-9 5-nitrosalicylic acid 
• 25844-84-2 2-hydroxy-3,5-dinitro-benzonitrile 
• 75-60-5 Dimethylarsinic acid 
• 52040-82-1 3,5-dinitrosalicylic acid anion 
• 110-89-4 piperidine 
• 2497-91-8 2-chloro-3,5-dinitrobenzoic acid 
• 16238-02-1 2-methyl-5,7-dinitro-benzofuran 
• 67-64-1 acetone 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 69-72-7 salicylic acid 
• 616-76-2 2-hydroxy-5-formylbenzoic acid 
• 125708-28-3 2-methylamino-3,5-dinitro-benzoic acid 
• 102312-37-8 2,3,5-trinitro-benzoic acid 

Downstream Products

• 51-28-5 2,4-Dinitrophenol 
• 2497-91-8 2-chloro-3,5-dinitrobenzoic acid 
• 15968-55-5 6-iodo-2,4-dinitrophenol 
• 831-51-6 3-amino-5-nitrosalicylic acid 
• 66306-10-3 2-hydroxy-3,5-dinitro-benzoyl chloride 
• 118-75-2 chloranil 
• 68507-68-6 4-(2-hydroxy-3,5-dinitro-benzoyl)-morpholine 
• 92415-50-4 2-Hydroxy-3,5-dinitro-benzoic acid; compound with biphenyl-3,4,3',4'-tetraamine 
• 76519-51-2 2-Hydroxy-3,5-dinitro-benzoic acid; compound with naphthalene 
• 76519-55-6 2-Hydroxy-3,5-dinitro-benzoic acid; compound with 1-methyl-naphthalene 
• 90481-48-4 2-Benzothiazol-2-yl-4,6-dinitro-phenol 
• 124-38-9 carbon dioxide 
• 88-89-1 2,4,6-Trinitrophenol 
• 52040-82-1 3,5-dinitrosalicylic acid anion 

Relevant articles and documents

Intramolecular base catalysed hydrolysis of ortho-hydroxyaryl esters: The anomalous position of methyl 3,5-dinitrosalicylate on the Linear Free Energy Relationship plot

The pKa of the ortho-hydroxy group in methyl 3,5-dinitrosalicylate, HMDNS, is 2.45. Rate constants for the reaction of its conjugate base, MDNS- with hydroxide anion and water are 5.3 × 10-2 mol dm-3 s-1 and 6.6 × 10-6 s-1, respectively at 25°C. The rate constant for the uncatalysed reaction of HMDNS and water is 6.5 × 10-6 s-1 and so there is no evidence for intramolecular general base catalysis of the water reaction with MDNS- by the weakly basic ortho-O-. By means of Bronsted plots the water reaction of MDNS- is compared with that of a group of other salicylate esters (β = 0) and also a structurally different group of esters (β = 0.4), both of which undergo intramolecular base catalysed hydrolysis. Although the title ester structurally belongs to the first set of compounds, its anomalous position on the plot clearly corresponds to the trend of the second set. This is explained in terms of differences in resonance stabilisation and hydrogen bonding in the transition state.

NOVEL WATER SOLUBLE POLYIMIDE RESIN, ITS PREPARATION AND USE

The present invention relates to a novel water soluble polyimide resin, which contains a hydrophilic functional group such as —OH, —COOH to increase the solubility of the polyimide resin in alkali aqueous solution, and is suitable for using as an insulation film in electronic and photoelectric products. The present invention also relates to preparation and use of the above polyimide.

Process for the synthesis of hydroxy aromatic acids

Hydroxy aromatic acids are produced in high yields and high purity (>95%) from halogenated aromatic acids in a reaction mixture containing a copper source and a ligand that coordinates to copper.

Nitration of aromatic compounds by Zn(NO3)2· 2N2O4 and its charcoal-supported system

Zn(NO3)2·N2O4 and its charcoal supported system were found to be efficient nitrating agents. Mononitration of aromatic compounds such as benzene, alkyl benzenes, halobenzenes, nitrobenzene, anisol, and the highly selective mono-, di-, and trinitration of phenol, and dinitraion of substituted phenols were also performed in the presence of these reagents.