82-71-3

Basic information

• Product Name: 2,4,6-TRINITRORESORCINOL
• Synonyms: 1,3-Benzenediol, 2,4,6-trinitro-;1,3-benzenediol,2,4,6-trinitro-;1,3-Dihydroxy-2,4,6-trinitrobenzene;2,4,6-Trinitro-1,3-benzendiol;2,4,6-Trinitro-1,3-benzenediol;2,4,6-trinitro-3-benzenediol;2,4-Dihydroxy-1,3,5-trinitrobenzene;3-Hydroxy-2,4,6-trinitrophenol
• CAS NO: 82-71-3
• Molecular Formula: C₆H₃N₃O₈
• Molecular Weight: 245.1
• EINECS: 201-436-6
• Mol File: 82-71-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 175.5°; mp 179-180°
• Boiling Point: 388.06°C (rough estimate)
• Flash Point: 126.8°C
• Appearance: /
• Density: 2.012g/cm³
• Vapor Pressure: 0.00104mmHg at 25°C
• Refractive Index: 1.6910 (estimate)
• PKA: 1.20±0.10(Predicted)
• Water Solubility: 5.4g/L(25 oC)
• CAS DataBase Reference: 2,4,6-TRINITRORESORCINOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRINITRORESORCINOL(82-71-3)
• EPA Substance Registry System: 2,4,6-TRINITRORESORCINOL(82-71-3)

Safety Data

• Hazard Codes: E,Xn
• Statements: 2-4-20/21/22
• Safety Statements: 35
• RIDADR: 0219
• HazardClass: 1.1D
• Hazardous Substances Data: 82-71-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow crystals; astringent taste. An initiating explosive. Forms addition compounds with many hydrocarbons; soluble in alcohol and ether; slightly soluble in water.

Uses

2,4,6-Trinitroresorcinol has been used in the manufacture of explosives.

General Description

A yellowish, crystalline solid. May explode under exposure to heat or fire. Primary hazard is blast of an instantaneous explosion, not flying projectiles or fragments. Used as a priming agent. Very sensitive to heat. Water is added to lessen the explosion hazard.

Reactivity Profile

Aromatic nitro compounds, such as TRINITRORESORCINOL, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups.

Hazard

Severe explosion risk when heated.

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.

Safety Profile

Very explosive. Upon decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS and EXPLOSIVES, HIGH.

Purification Methods

Crystallise the phenol from ethyl acetate or water containing HCl [EXPLODES violently on rapid heating.] Its solubility in H 2O is 0.7% at 20o and 3% at 100o. It forms addition compounds with aromatic hydrocarbons, e.g. naphthalene (m 168o), anthracene (m 180o), phenanthrene (m 142o), fluorene (m 134o) and retene (m 141o). [Beilstein 6 H 830, 6 III 4354, 6 IV 5699.]

InChI:InChI=1/C6H3N3O8/c10-5-2(7(12)13)1-3(8(14)15)6(11)4(5)9(16)17/h1,10-11H

Synthetic route

Resorcinol diacetate (108-58-7) → 4,6-dinitroresorcinol (616-74-0) + styphnic acid (82-71-3)

Conditions	Yield
With sulfuric acid; nitric acid; urea at -10 - 0℃; for 1.5h;	A 60% B n/a
With nitric acid man giesst auf Eis, zieht den gebildeten Niederschlag mit Alkohol aus und kocht mit Salzsaeure;

Resorcinol diacetate (108-58-7) → 4,6-dinitroresorcinol (616-74-0) + styphnic acid (82-71-3) + 4-nitroresorcinol (3163-07-3)

Conditions	Yield
With nitric acid; urea at -10 - 5℃; for 2h;	A 44% B n/a C n/a

Resorcinol diacetate (108-58-7) → styphnic acid (82-71-3)

Conditions	Yield
durch Nitrierung und Verseifung des Diacetats mit Natronlauge;

4,6-dinitroresorcinol (616-74-0) → styphnic acid (82-71-3)

Conditions	Yield
With sulfuric acid; nitric acid

3-fluorophenol (372-20-3) → styphnic acid (82-71-3)

Conditions	Yield
With sulfuric acid; nitric acid

meta-nitrophenol (554-84-7) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid
Multi-step reaction with 2 steps 1: durch Nitrieren 2: nitric acid View Scheme
Multi-step reaction with 2 steps 1: HNO3+H2SO4 2: water View Scheme

ortho-nitrobenzoic acid (552-16-9) → styphnic acid (82-71-3)

Conditions	Yield
With sulfuric acid; nitric acid

2,5-dinitrophenol (329-71-5) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid

2,5-dinitrophenol (329-71-5) → styphnic acid (82-71-3) + 2,4,5-trinitrophenol (610-26-4) + 2,3,6-trinitrophenol (603-10-1)

Conditions	Yield
beim Nitrieren;

4-hydroxysalicylic acid (89-86-1) → styphnic acid (82-71-3) + 2,4-dihydroxy-5-nitrobenzoic acid (13722-96-8)

Conditions	Yield
With nitric acid

2,4-dinitrosoresorcinol (118-02-5) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid
With nitric acid

3,4-dinitophenol (577-71-9) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid

3,4-dinitophenol (577-71-9) → styphnic acid (82-71-3) + 2,4,5-trinitrophenol (610-26-4)

Conditions	Yield
beim Nitrieren;
beim Nitrieren;

3-chloro-2,4,6-trinitro-phenol (1706-82-7) → styphnic acid (82-71-3)

Conditions	Yield
With sodium carbonate

4-nitroso-1,3-benzenediol (698-31-7) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid

2-nitroresorcinol (601-89-8) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid

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

Conditions	Yield
With nitric acid

4,6-dihydroxyisophthalic acid (19829-74-4) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid

2,3,4,6-Tetranitro-phenol (641-16-7) → styphnic acid (82-71-3)

Conditions	Yield
With water

2,4,6-triiodoresorcinol (19403-92-0) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid

2,3-dinitrophenol (66-56-8) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid

2,3-dinitrophenol (66-56-8) → styphnic acid (82-71-3) + 2,3,6-trinitrophenol (603-10-1)

Conditions	Yield
beim Nitrieren;
beim Nitrieren;

2-hydroxy-4-nitrobenzoic acid (619-19-2) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid

1,3,5-trinitrobenzenediamine (1630-08-6) → styphnic acid (82-71-3)

Conditions	Yield
With alkaline solution

2,4,5-trinitrophenol (610-26-4) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid

N,N'-dimethyl-2,4,6-trinitro-m-phenylenediamine (24388-40-7) → styphnic acid (82-71-3)

Conditions	Yield
With potassium hydroxide

5-bromo-4-hydroxysalicylic acid (7355-22-8) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid

resorcinol-4,6-sulfonic acid (17724-11-7) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid
With nitrogen oxides

2,3,6-trinitrophenol (603-10-1) → styphnic acid (82-71-3)

Conditions	Yield
With nitric acid

N-methyl-2,3,4,6,N-pentanitro-aniline (134282-37-4) → styphnic acid (82-71-3)

Conditions	Yield
With sodium carbonate

thallium(I) nitrate + styphnic acid (82-71-3) → (half acid) thallous styphnate (157760-75-3)

Conditions	Yield
In water; acetone byproducts: HNO3; aq. soln. of TlNO3 added to ice-cold acetone soln. of styphnic acid; stirred for 10 min; evapd., recrystd. (hot water), filtered off, dried (air, warm oven, vacuum desiccator over silica gel); elem. anal.;	98%

copper carbonate hydroxide + styphnic acid (82-71-3) + di(tetrazol-1-yl)methane → C6HN3O8(2-)*C3H4N8*Cu(2+)*H2O

Conditions	Yield
In water at 50℃;	96%

styphnic acid (82-71-3) → disodium styphnate (56402-05-2, 57765-57-8)

Conditions	Yield
With sodium hydroxide In ethanol at 20℃;	94%

N,N-dimethylaminomethylferrocene (1271-86-9) + styphnic acid (82-71-3) → ferrocenylmethyldimethylammonium 2,4,6-trinitroresorcinolate

Conditions	Yield
In acetone at 20℃; for 3h;	92.3%

1,5-diaminotetrazole (2165-21-1) + styphnic acid (82-71-3) + cobalt(II) carbonate (759403-02-6) → [Co(1,5-diaminotetrazole)2(H2O)4](2,4,6-trinitroresorcinol(-1H))2)2*2H2O

Conditions	Yield
In water CoCO3 added to resorcinol deriv. soln. in H2O at 50°C; stirred; to aq. soln. of tetrazole deriv. warmed to 60°C added above soln. dropwise under strong stirring; allowed to stir at 60°C for 30 min; ppt. collected by filtration, washed with water, dried in vac.; elem. anal.;	91%

styphnic acid (82-71-3) + 5,6,7,8-tetrahydrotetrazolo<1,5-b><1,2,4>triazine (117039-70-0) → C6H3N3O8*C3H6N6

Conditions	Yield
In methanol at 60℃; for 0.5h;	91%

1-amino-1,2,3-triazole (584-14-5) + copper(II) carbonate + styphnic acid (82-71-3) → Cu(2+)*C6HN3O8(2-)*2C2H4N4

Conditions	Yield
In water at 70℃;	91%

N-(ferrocenylmethyltrimethyl)imidazole (207352-36-1) + styphnic acid (82-71-3) + water (7732-18-5) + zinc(II) sulfate (7733-02-0) → [Zn(ferrocenylmethylimidazole)4(H2O)2](2,4,6-trinitroresorcinolate)

Conditions	Yield
In ethanol for 1h; Reflux;	90%

cobalt(II) sulfate + 1-(ferrocenylmethyltrimethyl)triazole (713108-31-7) + styphnic acid (82-71-3) + water (7732-18-5) → [Co(ferrocenylmethyl-1,2,4-triazole)4(H2O)2](2,4,6-trinitroresorcinolate)*2H2O

Conditions	Yield
In ethanol for 1h; Reflux;	90%

chromium(III) nitrate + N-(ferrocenylmethyltrimethyl)imidazole (207352-36-1) + styphnic acid (82-71-3) + water (7732-18-5) → [Cr(ferrocenylmethylimidazole)4(H2O)2]2(2,4,6-trinitroresorcinolate)3

Conditions	Yield
In ethanol for 1h; Reflux;	89%

1-(ferrocenylmethyltrimethyl)triazole (713108-31-7) + styphnic acid (82-71-3) + water (7732-18-5) + cadmium(II) nitrate → [Cd(ferrocenylmethyl-1,2,4-triazole)4(H2O)2](2,4,6-trinitroresorcinolate)

Conditions	Yield
In ethanol for 1h; Reflux;	89%

bismuth(III) nitrate + N-(ferrocenylmethyltrimethyl)imidazole (207352-36-1) + styphnic acid (82-71-3) + water (7732-18-5) → [Br(ferrocenylmethylimidazole)4(H2O)2]2(2,4,6-trinitroresorcinolate)3

Conditions	Yield
In ethanol for 1h; Reflux;	88%

styphnic acid (82-71-3) + silver nitrate → silver styphnate

Conditions	Yield
With sodium carbonate; acetic acid In water glacial acetic acid added to boiling soln. of styphnic acid and anhyd. Na2CO3; boiling soln. of AgNO3 added under stirring; ppt. filtered off; washed (water, methanol, petroleum spirit); air-dried; elem. anal.;	87%

cobalt(II) sulfate + N-(ferrocenylmethyltrimethyl)imidazole (207352-36-1) + styphnic acid (82-71-3) + water (7732-18-5) → [Co(ferrocenylmethylimidazole)4(H2O)2](2,4,6-trinitroresorcinolate)

Conditions	Yield
In ethanol for 1h; Reflux;	87%

styphnic acid (82-71-3) + ethylenediamine (107-15-3) → C2H8N2*C6H3N3O8

Conditions	Yield
In methanol at 45℃; for 1h;	86%

nickel(II) carbonate (719261-06-0) + 1-methyl-1,2,3,4-tetrazole (16681-77-9) + styphnic acid (82-71-3) + water (7732-18-5) → C4H16N8NiO4(2+)*2C6H2N3O8(1-)*2H2O

Conditions	Yield
at 70℃; for 0.0833333h;	86%

lead(II) nitrate + 1-(ferrocenylmethyltrimethyl)triazole (713108-31-7) + styphnic acid (82-71-3) + water (7732-18-5) → [Pb(ferrocenylmethyl-1,2,4-triazole)4(H2O)2](2,4,6-trinitroresorcinolate)·3H2O

Conditions	Yield
In ethanol for 1h; Reflux;	86%

chromium(III) nitrate + 1-(ferrocenylmethyltrimethyl)triazole (713108-31-7) + styphnic acid (82-71-3) + water (7732-18-5) → [Cr(ferrocenylmethyl-1,2,4-triazole)4(H2O)2]2(2,4,6-trinitroresorcinolate)3*4H2O

Conditions	Yield
In ethanol for 1h; Reflux;	86%

bismuth(III) nitrate + 1-(ferrocenylmethyltrimethyl)triazole (713108-31-7) + styphnic acid (82-71-3) + water (7732-18-5) → [Bi(ferrocenylmethyl-1,2,4-triazole)4(H2O)2]2(2,4,6-trinitroresorcinolate)3*4H2O

Conditions	Yield
In ethanol for 1h; Reflux;	86%

1-(ferrocenylmethyltrimethyl)triazole (713108-31-7) + styphnic acid (82-71-3) + water (7732-18-5) + copper(II) sulfate (7758-99-8) → [Cu(ferrocenylmethyl-1,2,4-triazole)4(H2O)2](2,4,6-trinitroresorcinolate)

Conditions	Yield
In ethanol for 1h; Reflux;	86%

N-(ferrocenylmethyltrimethyl)imidazole (207352-36-1) + styphnic acid (82-71-3) + water (7732-18-5) + cadmium(II) nitrate → [Cd(ferrocenylmethylimidazole)4(H2O)2](2,4,6-trinitroresorcinolate)

Conditions	Yield
In ethanol for 1h; Reflux;	85%

copper(II) carbonate + 1-methyl-1,2,3,4-tetrazole (16681-77-9) + styphnic acid (82-71-3) → C16H12CuN14O16

Conditions	Yield
In water at 70℃; for 0.0833333h;	84%

manganese (II) sulfate monohydrate + N-(ferrocenylmethyltrimethyl)imidazole (207352-36-1) + styphnic acid (82-71-3) + water (7732-18-5) → [Mn(ferrocenylmethylimidazole)4(H2O)2](2,4,6-trinitroresorcinolate)

Conditions	Yield
In ethanol for 1h; Reflux;	83%

diaminoglyoxime (2580-79-2) + styphnic acid (82-71-3) → C2H6N4O2*C6H3N3O8

Conditions	Yield
In methanol Solvent;	82%

manganese(II)carbonate + 1-methyl-1,2,3,4-tetrazole (16681-77-9) + styphnic acid (82-71-3) → C20H20MnN22O16

Conditions	Yield
In water at 70℃; for 0.0833333h;	82%

N-(ferrocenylmethyltrimethyl)imidazole (207352-36-1) + styphnic acid (82-71-3) + water (7732-18-5) + iron(II) sulfate → [Fe(ferrocenylmethylimidazole)4(H2O)2](2,4,6-trinitroresorcinolate)

Conditions	Yield
In ethanol for 1h; Reflux;	82%

lead(II) nitrate + N-(ferrocenylmethyltrimethyl)imidazole (207352-36-1) + styphnic acid (82-71-3) + water (7732-18-5) → [Pb(ferrocenylmethylimidazole)4(H2O)2](2,4,6-trinitroresorcinolate)

Conditions	Yield
In ethanol for 1h; Reflux;	81%

nickel(II) sulphate + N-(ferrocenylmethyltrimethyl)imidazole (207352-36-1) + styphnic acid (82-71-3) + water (7732-18-5) → [Ni(ferrocenylmethylimidazole)4(H2O)2](2,4,6-trinitroresorcinolate)

Conditions	Yield
In ethanol for 1h; Reflux;	81%

4-(1H-1,2,4-triazol-3-yl)-4H-1,2,4-triazole (68984-29-2) + aqueous cadmium chloride + styphnic acid (82-71-3) → C8H16CdN12O4(2+)*2C6H2N3O8(1-)

Conditions	Yield
Stage #1: 4-(1H-1,2,4-triazol-3-yl)-4H-1,2,4-triazole; styphnic acid In water at 80℃; for 0.5h; Stage #2: aqueous cadmium chloride In water at 80℃;	80%

manganese (II) sulfate monohydrate + 1-(ferrocenylmethyltrimethyl)triazole (713108-31-7) + styphnic acid (82-71-3) + water (7732-18-5) → [Mn(ferrocenylmethyl-1,2,4-triazole)4(H2O)2](2,4,6-trinitroresorcinolate)·6H2O

Conditions	Yield
In ethanol for 1h; Reflux;	80%

Upstream product

• 554-84-7 meta-nitrophenol 
• 66-56-8 2,3-dinitrophenol 
• 619-19-2 2-hydroxy-4-nitrobenzoic acid 
• 3564-63-4 3-hydroxy-2-isopropyl-furo[3,2-g]chromen-7-one 
• 7697-37-2 nitric acid 
• 133-26-6 peucedanin 
• 209404-44-4 (+/-)-homopterocarpin 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 65-85-0 benzoic acid 
• 372-20-3 3-fluorophenol 
• 99-09-2 3-nitro-aniline 
• 89-86-1 4-hydroxysalicylic acid 
• 329-71-5 2,5-dinitrophenol 

Downstream Products

• 23872-88-0 1-(3-hydroxy-2,4,6-trinitro-phenyl)-pyridinium betaine 
• 66778-13-0 lead styphnate monohydrate 
• 13066-97-2 2,4,6-triamino-resorcinol 
• 3566-59-4 2-amino-4,6-dinitro-resorcinol 
• 15245-44-0 lead styphnate 
• 157760-75-3 (half acid) thallous styphnate 
• 464-10-8 bromopicrin 
• 76-06-2 chloropicrin 
• 1630-09-7 2,4-dichloro-1,3,5-trinitrobenzene 

Relevant articles and documents

Measurement, correlation of solubility and thermodynamic properties analysis of 2,4,6-trinitroresorcinol hydrate in pure and binary solvents

The solubility of 2,4,6-trinitroresorcinol hydrate (TNR?2/3H2O) in the pure solvents (methanol, ethanol, isopropanol and water) and the binary mixed solvents (methanol-water, ethanol-water and isopropanol-water) was measured by the laser dynamic method from 298.15 K to 323.15 K under the atmospheric pressure. The TNR?2/3H2O do not change before and after the solubility measurement in the selected solvents. The solubility increases with the increase of the temperature, and methanol is more suitable for the cooling crystallization of TNR?2/3H2O. In the pure solvents, the solubility order at the same temperature is: methanol > ethanol > isopropanol > water, which may be affected by the properties (such as hydrogen bond, polarity, dielectric constant, cohesive energy density etc.) of the alcohol solvents, self-association of water molecules, the hydrophobic wing of the TNR?2/3H2O and so on. In the mixed solvents, the solubility has different sensitivity to the content of organic components (x2) in the solvent. The possible reason is that: the interaction between solvent and solvent plays an important role (the formation of azeotropic mixtures of alcohols and water, the interaction between water and alcohol solvents, the properties of the solvents etc.). The solubility data of TNR?2/3H2O were compared with that of 2,4,6-trinitrophenol (TNP) that have been reported. It can be found that the solubility of TNP is always greater than that of TNR?2/3H2O with the same solvent and temperature, and x2 = 0.63–0.69 (ethanol-water) and x2 ≈ 0.73 (isopropanol-water) are more suitable as the solvents for solution crystallization to separate TNR?2/3H2O from the mixture of TNP and TNR?2/3H2O. The experimental mole fraction solubility data (xexp) of TNR?2/3H2O were correlated by the modified Apelblat, Van't Hoff, CNIBS R-K, and Jouyban-Acree-modified Apelblat model. All of these models give satisfactory results, and the Van't Hoff model has better correlation and helps to expand the solubility data of TNR?2/3H2O. The thermodynamic properties during the dissolution process were analyzed based on the Van't Hoff. And the dissolution of TNR?2/3H2O in the solvents used is considered to be an “endothermic, non-spontaneous and entropy-driven” process and the enthalpy is the main contributor to the Gibbs free energy in the process of dissolution.

Synthesis, Characterization, and Properties of Pentanitrobenzene C6H(NO2)5

The synthesis of the polynitroaromatic compound pentanitrobenzene was re-examined by modern spectroscopic, structural and physicochemical methods. Originally prepared in 1979, this material could exhibit interesting properties as an oxygen-rich energetic building block. The energies of formation were calculated with the GAUSSIAN program package and the detonation parameters were predicted using the EXPLO5 computer code. The performance data were determined and compared to the common oxidizer ammonium perchlorate. The crystal structure of pentanitrobenzene was determined by X-ray crystallography, and those of 2,3,4,6-tetranitroaniline and styphnic acid (trinitroresorcinol) were re-determined.

Systematic evaluation of a new organic material: 1-methyl-1H-imidazol-3-ium-2,4,6-trinitrobenzene-1,3-bis(olate) for optoelectronics through spectral, structural, electrical, optical, quantum chemical and Hirshfeld surface studies

A new organic material, 1-methyl-1H-imidazol-3-ium-2,4,6-trinitrobenzene-1,3-bis(olate) (MITB), was synthesized and crystallized by solution growth-slow evaporation technique at ambient temperature. The characteristic functional groups in MITB were identified from FT-IR spectrum. 1H, 13C and DEPT-135 NMR spectroscopic techniques were used to ascertain types of carbons and protons in MITB. The compound crystallizes in the monoclinic system with a space group of P21/c. The electrostatic attraction between anions and cations stabilizes the crystal lattice and the N-H…O and C-H…O hydrogen bonds linking the cations and anions supplement the stable three dimensional networks. The material was thermally stable up to 178 °C. The molecular structure was optimized by Gaussian 09 program at B3LYP/6–311++G(d,p) level of basis set. Hydrogen bonding interactions are responsible for greater hyperpolarizability value of MITB and the value was found to be 34 times greater than that of reference material, urea. HOMO-LUMO, electrostatic potential surface and Mulliken atomic charges were calculated to explore covalent and non covalent interactions present in MITB. Hirshfeld surface analysis was carried out to estimate prominent covalent and non covalent interactions. Dielectric constant and dielectric loss have been determined to find MITB's suitability for optoelectronic applications.