4682-03-5

Basic information

• Product Name: Diazodinitrophenol
• Synonyms: 6-Diazo-2,4-dinitro-2,4-cyclohexadien-1-one;6-Diazo-2,4-dinitro-2,4-cyclohexadiene-1-one;DDNP;6-Diazo-2,4-dinitrophenole
• CAS NO: 4682-03-5
• Molecular Formula: C₆H₂N₄O₅
• Molecular Weight: 210.1039
• EINECS: 225-134-9
• Mol File: 4682-03-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 349.61°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.8297 (rough estimate)
• Refractive Index: 1.6900 (estimate)
• CAS DataBase Reference: Diazodinitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: Diazodinitrophenol(4682-03-5)
• EPA Substance Registry System: Diazodinitrophenol(4682-03-5)

Safety Data

• RIDADR: 0074
• HazardClass: 1.1A
• Hazardous Substances Data: 4682-03-5(Hazardous Substances Data)

Usage

General Description

A yellow crystalline solid that darkens on exposure to sunlight. Must be shipped wet with at least 40% water or water and denatured alcohol mixture. May explode due to shock, heat, flame, or friction if dry. May explode under prolonged exposure to heat or fire. Primary hazard is blast of an instantaneous explosion, not flying projectiles or fragments.

Air & Water Reactions

Dust may form an explosive mixture in air.

Reactivity Profile

Diazodinitrophenol is a diazo compound. Azo, diazo, azido compounds can detonate. The nitro groups would facilitate rapid decomposition. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.

Health Hazard

Fire may produce irritating, corrosive and/or toxic gases.

Fire Hazard

MAY EXPLODE AND THROW FRAGMENTS 1600 meters (1 MILE) OR MORE IF FIRE REACHES CARGO.

InChI:InChI=1/C6H4N4O5/c7-8-4-1-3(9(12)13)2-5(6(4)11)10(14)15/h1-2,4,6H

Synthetic route

2-chloro-3,5-dinitroaniline (88140-44-7) → 2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5)

Conditions	Yield
With nitric acid In various solvent(s) Ambient temperature;	36%

picramic acid (96-91-3) → 2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5)

Conditions	Yield
With ethanol; cis-nitrous acid
With hydrogenchloride; sodium nitrite Diazotization;
With sulfuric acid; sodium nitrite Diazotization;

N,2,3,5-tetranitroaniline (57204-57-6) → 2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5)

Conditions	Yield
In ethyl acetate at 60℃;

sodium picramate (831-52-7) → 2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5)

Conditions	Yield
With hydrogenchloride; sodium nitrite for 1h;

sulfuric acid (7664-93-9) + picramic acid (96-91-3) + NaNO2 → 2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5)

Conditions	Yield
unter Kuehlung;

ethanol (64-17-5) + picramic acid (96-91-3) + nitros gases → 2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5)

Conditions	Yield

2-chloro-3,5-dinitrobenzoic acid (2497-91-8) → 2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 20percent oleum, sodium azide / 1,2-dichloro-ethane / 3 h / Heating 2: 36 percent / 100percent nitric acid / various solvent(s) / Ambient temperature View Scheme

3, 5-dinitroaniline (618-87-1) → 2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70percent nitric acid / H2SO4 / 0 °C 2: ethyl acetate / 60 °C View Scheme

ortho-chlorobenzoic acid (118-91-2) → 2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 100percent nitric acid / H2SO4 / 125 °C 2: 20percent oleum, sodium azide / 1,2-dichloro-ethane / 3 h / Heating 3: 36 percent / 100percent nitric acid / various solvent(s) / Ambient temperature View Scheme

diazoacetone (2684-62-0) + 2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5) → 1-(5,7-dinitro-1H-benz[e][1,3,4]oxadiazin-3-yl)-ethanone (112656-44-7)

Conditions	Yield

chloroform (67-66-3) + 2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5) + triphenylphosphine (603-35-0) → 3,5-dinitro-[1,2]benzoquinone-1-(triphenylphosphoranylidene-hydrazone) (47739-00-4)

Conditions	Yield

2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5) + triphenylphosphine (603-35-0) → 3,5-dinitro-[1,2]benzoquinone-1-(triphenylphosphoranylidene-hydrazone) (47739-00-4)

Conditions	Yield
With chloroform

diazomethane (186581-53-3, 908094-01-9) + 2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5) → 5,7-dinitro-3H-benzo[1,3,4]oxadiazine (25649-49-4)

Conditions	Yield
In tetrahydrofuran; diethyl ether

2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5) + ethyl aminocrotonate (626-34-6, 7318-00-5, 41867-20-3) → 2-(2-Hydroxy-3,5-dinitro-phenyl-hydrazono)-3-imino-buttersaeureaethylester

Conditions	Yield
With acetic acid In ethanol; chloroform

2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5) + ethyl 3-methylaminocrotonate (870-85-9) → 2-(2-Hydroxy-3,5-dinitro-phenyl-hydrazono)-3-methylimino-buttersaeureaethylester (5507-07-3)

Conditions	Yield
With acetic acid In ethanol

2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5) + tris(morpholino)phosphine (5815-61-2) → (2-hydroxy-3,5-dinitro-phenyldiazenyl)-tri-morpholin-4-yl-phosphonium betaine (3028-36-2)

Conditions	Yield
In water; N,N-dimethyl-formamide

2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5) → sodium 6-azido-2,4-dinitrophenolate

Conditions	Yield
With sodium azide In acetone for 0.5h;

1,4-dioxane (123-91-1) + diazoacetone (2684-62-0) + 2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5) → 2-acetyl-6,8-dinitro-4H-benzo<1,3,4>oxadiazine

Conditions	Yield

ethanol (64-17-5) + 2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5) + potassium carbonate → 2,4-Dinitrophenol (51-28-5)

Conditions	Yield

2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5) + potassium sulfite → potassium salt of/the/ 4.6-dinitro-1-oxy-benzene-diazosulfonic acid-(2)

Conditions	Yield

2-hydroxy-3,5-dinitro-benzenediazonium betaine (4682-03-5) → 2-(2-Hydroxy-3,5-dinitrophenyl-hydrazono)-3-oxo-buttersaeureaethylester (5294-38-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: AcOH / ethanol; CHCl3 2: aq. HCl / methanol View Scheme

Upstream product

• 118-91-2 ortho-chlorobenzoic acid 
• 618-87-1 3, 5-dinitroaniline 
• 2497-91-8 2-chloro-3,5-dinitrobenzoic acid 
• 64-17-5 ethanol 
• 96-91-3 picramic acid 
• 7664-93-9 sulfuric acid 
• 831-52-7 sodium picramate 
• 88140-44-7 2-chloro-3,5-dinitroaniline 
• 57204-57-6 N,2,3,5-tetranitroaniline 

Downstream Products

• 5294-38-2 2-(2-Hydroxy-3,5-dinitrophenyl-hydrazono)-3-oxo-buttersaeureaethylester 
• 51-28-5 2,4-Dinitrophenol 
• 47739-00-4 3,5-dinitro-[1,2]benzoquinone-1-(triphenylphosphoranylidene-hydrazone) 

Relevant articles and documents

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Synthesis of Polynitrodiazophenols

The formation of diazophenols by nitration of suitably substituted anilines and rearrangement of the nitroaromatic nitramines so formed is presented.The scope of the reaction is discussed, and a mechanism for the nitramine/diazophenol rearrangement is proposed which is consistent with 15N-labeling experiments.