519-44-8

Basic information

• Product Name: 2，4-Dinitro-1，3-benzene diol
• Synonyms: 2，4-Dinitro-1，3-benzene diol;2，4-Dinitroresorcinol;2,4-Dinitrobenzene-1,3-diol
• CAS NO: 519-44-8
• Molecular Formula: C₆H₄N₂O₆
• Molecular Weight: 200
• EINECS: 208-270-3
• Mol File: 519-44-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: 147.5°C
• Boiling Point: 337.8°C (rough estimate)
• Flash Point: 125.3 ºC
• Appearance: /
• Density: 1.7942 (rough estimate)
• Vapor Pressure: 0.00216mmHg at 25°C
• Refractive Index: 1.4738 (estimate)
• PKA: 4.25±0.24(Predicted)
• Water Solubility: 6.261g/L(57.70 oC)
• CAS DataBase Reference: 2，4-Dinitro-1，3-benzene diol(CAS DataBase Reference)
• NIST Chemistry Reference: 2，4-Dinitro-1，3-benzene diol(519-44-8)
• EPA Substance Registry System: 2，4-Dinitro-1，3-benzene diol(519-44-8)

Safety Data

• RIDADR: 0078
• HazardClass: 1.1D
• PackingGroup: II
• Hazardous Substances Data: 519-44-8(Hazardous Substances Data)

Usage

Purification Methods

Crystallise the resorcinol from aqueous EtOH. Its solubility at 25o is 0.25% in EtOH and 0.08g/L in H2O. EXPLOSIVE. [Beilstein 6 II 824, 6 III 4352, 6 IV 5696.]

InChI:InChI=1/C6H4N2O6/c9-4-2-1-3(7(11)12)6(10)5(4)8(13)14/h1-2,9-10H

Synthetic route

2,4-dinitrosoresorcinol (118-02-5) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
With diethyl ether; mixture of gaseous nitrogen oxides
With nitric acid

1-chloro-2,4-dinitrochlorobenzene (10199-85-6) → 2,4-dinitroresorcinol (519-44-8) + 2,4-dichloro-1,3,5-trinitrobenzene (1630-09-7)

Conditions	Yield
With sulfuric acid; nitric acid

4-nitroso-1,3-benzenediol (698-31-7) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
With diethyl ether; mixture of gaseous nitrogen oxides

2-nitroresorcinol (601-89-8) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
With nitric acid at 0℃;

2,4-dinitro-1,3-phenylenediamine (10199-87-8) + furan-2,3,5(4H)-trione pyridine (1:1) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
beim Kochen;

3-amino-2,6-dinitro-phenol (30226-37-0) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
With potassium hydroxide

1,3-diethoxy-2,4-dinitro-benzene (860767-58-4) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
With hydrogenchloride im geschlossenen Rohr;

2,4-dihydroxy-3,5-dinitro-benzoic acid (22604-84-8) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
With water

3-fluoro-2,4-dinitrophenol (361-47-7) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
With sodium hydroxide

3-bromo-2,4-dinitro-phenol (116632-21-4) + furan-2,3,5(4H)-trione pyridine (1:1) → 2,4-dinitroresorcinol (519-44-8)

3-bromo-2,4-dinitro-phenol (116632-21-4) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
With sodium hydroxide

3-fluoro-2,6-dinitro-phenol (361-48-8) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
With sodium hydroxide

1,3-dibromo-2,4-dinitro-benzene (861601-98-1) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
With potassium hydroxide

3-bromo-2,6-dinitro-phenol (116632-22-5) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
With sodium hydroxide

3-dimethylamino-2,6-dinitro-phenol (872282-08-1) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
With potassium hydroxide

2.4-dinitro-phenylene-diamine-(1.3) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
With sodium hydroxide

2-nitroresorcinol (601-89-8) + nitric acid (7697-37-2) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
at 0℃;

1-chloro-2,4-dinitrochlorobenzene (10199-85-6) + HNO3+H2SO4 → 2,4-dinitroresorcinol (519-44-8) + 2,4-dichloro-1,3,5-trinitrobenzene (1630-09-7)

cyclohex-5-ene-1,2,3,4-tetraone-1,3-dioxime (83444-06-8) + nitric acid (7697-37-2) → 2,4-dinitroresorcinol (519-44-8)

diethyl ether (60-29-7) + cyclohex-5-ene-1,2,3,4-tetraone-1,3-dioxime (83444-06-8) + mixture of gaseous nitrogen oxides → 2,4-dinitroresorcinol (519-44-8)

3-amino-2,6-dinitro-phenol (30226-37-0) + aqueous alkaline solution → 2,4-dinitroresorcinol (519-44-8) + ammonia (7664-41-7)

hydrogenchloride (7647-01-0) + 1,3-diethoxy-2,4-dinitro-benzene (860767-58-4) → 2,4-dinitroresorcinol (519-44-8)

hydrogenchloride (7647-01-0) + 3-ethoxy-2,4-dinitro-phenol → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
at 180 - 200℃; im Rohr;

3-bromo-2,6-dinitro-phenol (116632-22-5) + aqueous NaOH-solution → 2,4-dinitroresorcinol (519-44-8)

3-fluoro-2,4-dinitrophenol (361-47-7) + diluted NaOH-solution → 2,4-dinitroresorcinol (519-44-8)

3-fluoro-2,6-dinitro-phenol (361-48-8) + diluted NaOH-solution → 2,4-dinitroresorcinol (519-44-8)

2,4-dihydroxy-3,5-dinitro-benzoic acid (22604-84-8) + water (7732-18-5) → 2,4-dinitroresorcinol (519-44-8) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5)

3-dimethylamino-2,6-dinitro-phenol (872282-08-1) + aqueous KOH → 2,4-dinitroresorcinol (519-44-8) + dimethyl amine (124-40-3)

2,6-dichloronitrobenzene (601-88-7) → 2,4-dinitroresorcinol (519-44-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid 2: sulfuric acid; nitric acid View Scheme

naphthalene (91-20-3) + 2,4-dinitroresorcinol (519-44-8) → 2,4-dinitro-resorcinol; compound with naphthalene

2,4-dinitroresorcinol (519-44-8) + diazotiertes 4-(4-Nitro-benzolsulfonyl)-anilin → 4-[4-(4-nitro-benzenesulfonyl)-phenylazo]-2,6-dinitroso-resorcinol

Conditions	Yield
With methanol

2,4-dinitroresorcinol (519-44-8) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid

2,4-dinitroresorcinol (519-44-8) → 2,4-dinitro-1,3-phenylenediamine (10199-87-8)

Conditions	Yield
With ammonia at 115℃;

2,4-dinitroresorcinol (519-44-8) → 4-bromo-2,6-dinitro-resorcinol + 2,4,5,6-tetrabromo-resorcinol (151291-59-7)

Conditions	Yield
With bromine; acetic acid

2,4-dinitroresorcinol (519-44-8) → 2-amino-4-nitro-resorcinol (871894-52-9)

Conditions	Yield
With ammonium hydroxide; ethanol; hydrogen sulfide at 70℃;
Multi-step reaction with 2 steps 1: glacial acetic acid; tin (II)-chloride; concentrated hydrochloric acid / 40 - 70 °C / und Behandeln des Reaktionsgemisches mit Natriumacetat und Acetanhydrid 2: concentrated hydrochloric acid View Scheme

2,4-dinitroresorcinol (519-44-8) → acetic acid-(2,6-dihydroxy-3-nitro-anilide) (872283-74-4)

Conditions	Yield
With hydrogenchloride; acetic acid; tin(ll) chloride at 40 - 70℃; und Behandeln des Reaktionsgemisches mit Natriumacetat und Acetanhydrid;

2,4-dinitroresorcinol (519-44-8) → 1-chloro-2,4-dinitrochlorobenzene (10199-85-6)

Conditions	Yield
With N,N-dimethyl-formamide; trichlorophosphate

pyridine (110-86-1) + 2,4-dinitroresorcinol (519-44-8) + p-toluenesulfonyl chloride (98-59-9) → N-<2.4-dinitro-3-oxy-phenyl>-pyridinium-p-toluenesulfonate + <2.4-dinitro-3-oxy-phenyl>-pyridinium betaine

2,4-dinitroresorcinol (519-44-8) + nitric acid (7697-37-2) → styphnic acid (82-71-3)

Upstream product

• 10199-85-6 1-chloro-2,4-dinitrochlorobenzene 
• 601-89-8 2-nitroresorcinol 
• 30226-37-0 3-amino-2,6-dinitro-phenol 
• 22604-84-8 2,4-dihydroxy-3,5-dinitro-benzoic acid 
• 860767-58-4 1,3-diethoxy-2,4-dinitro-benzene 
• 10199-87-8 2,4-dinitro-1,3-phenylenediamine 
• 698-31-7 4-nitroso-1,3-benzenediol 
• 118-02-5 2,4-dinitrosoresorcinol 
• 860209-26-3 2,3,4-trinitro-phenetole 
• 1777-85-1 acetic acid-(4-ethoxy-2,3-dinitro-anilide) 
• 3914-05-4 4-ethoxy-2,3-dinitro-aniline 
• 4280-24-4 (2,3-dinitrophenyl)ethylether 
• 27684-84-0 5-bromo-2-nitrophenol 
• 1670-17-3 N,N-dimethyl-2,4-dinitroaniline 

Downstream Products

• 872283-74-4 acetic acid-(2,6-dihydroxy-3-nitro-anilide) 
• 151291-59-7 2,4,5,6-tetrabromo-resorcinol 
• 871894-52-9 2-amino-4-nitro-resorcinol 
• 82-71-3 styphnic acid 
• 10199-85-6 1-chloro-2,4-dinitrochlorobenzene 
• 10199-87-8 2,4-dinitro-1,3-phenylenediamine