2,4,6-Trinitrophenol
2,4,6-TRINITROPHENOL · TRINITROPHENOL · picric · Carbazotic Acid · Acide picrique · Pikrinsaeure · 2,4,6-Trinitrofenol · PICRIC ACID SOLUTION
Identifikatoren & physikalische Daten
| CAS No. | 88-89-1 |
|---|---|
| Summenformel | C6H3N3O7 |
| Durchschnittliche Molmasse | 229,1 g/mol |
| Monoisotopische Masse | 228,99709944 g/mol |
| SMILES | O=[N+]([O-])c1cc([N+](=O)[O-])c(O)c([N+](=O)[O-])c1 |
| InChIKey | OXNIZHLAWKMVMX-UHFFFAOYSA-N |
| PubChem CID | 6954 |
| ChEMBL | CHEMBL108541 |
| ChEBI | CHEBI:46149 |
| EC No. | 201-865-9 |
| DTXSID | DTXSID4025909 |
| Lokaler Name | 2,4,6-Trinitrophenol |
Chemische & physikalische Eigenschaften
| XLogP | 0,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 158 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 7 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 292 |
| Stoffklassen | Other Uses -> ExplosivesFlammable agents - 4th degree |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | log Kow = 1.442.031.64 |
| Geruch | Odorless |
| Geschmack | Intensely bitter |
| Dichte | 1.76 (NIOSH, 2024) - Denser than waterwill sink1.763 (NTP, 1992) - Denser than water1.763 g/cu cm1.8 g/cm³1.763 no temp1.00 g/mL at 20 °C |
| Color/Form | Pale yellow crystalsYellow solid [Note: Usually used as an aqueous solution]Yellow leaves from waterprisms from diethyl etherplates from ethanolColorless crystals from ligroin or concentrated hydrochloric acidyellow leaflets from water |
| Löslichkeit | 1 % (NIOSH, 2024)1 to 10 mg/mL at 75 °F (NTP, 1992)In water, 1.27X10+4 mg/L at 25 °CSlightly soluble in water1 g in 12 mL alcohol, 10 mL benzene, 35 mL chloroform, and 65 mL etherSoluble in ethanol, ether, benzene, chloroformvery soluble in acetonealcohol: soluble1 (g/12 mL)(lit.)(mg/L):66,670 at 100 °C (quoted, Windholz et al., 1983) 14,000 at 20 °C, 68,000 at 100 °C (quoted, Verschueren, 1983) |
| Corrosivity | Attacks common metals, except for aluminum and tin |
| Flammpunkt | 302 °F (NIOSH, 2024)302 °F (NTP, 1992)150 °C (302 °F) - closed cup150 °C c.c.150℃ |
| Siedepunkt | Explodes above 572 °F (NIOSH, 2024)greater than 572 °F at 760 mmHg (Sublimes/explodes) (NTP, 1992)Explodes above 572 °FBP: Explodes300℃ |
| Schmelzpunkt | 122-123 °C (dried material, Lit. Merck Index 12th Ed.)(lit.) |
| Dampfdichte | 7.9 (vs air) |
| Dampfdruck | 1 mm Hg ( 195 °C) |
| Brechungsindex | 1.7630 (estimate) |
| Lagerbedingungen | Store at RT. |
| pKa (Säurekonstante) | 0.38(at 25℃) |
| Aggregatzustand | solution (saturated aqueous) |
| Wichte | 1.005 |
| Farbe | yellow solution |
| Explosionsgrenze | 0.01% |
| Spezifische Wärmekapazität | Cp(crystal): 1.05 J/(g·K), at 25℃ |
| Merck | 13,7492 |
| BRN | 423400 |
| Henry-Konstante | 3.0×105 mol/(m3Pa) at 25℃, Ebert et al. (2023) |
| Stabilität | Stability Unstablemay detonate if struck, heated or ground. Highly flammable if dry. May explode if dry - keep wet at all times. Keep water content above 20%. Flammable. Incompatible with strong oxidizing agents, bases, most common metals, ammonia, strong reducing agents. Avoid shock, friction, heat. Compounds formed by reaction with |
| Hauptanwendungen | Explosives, power circuits, energetic materials, liquefied gas fuels, thin films, power generation, batteries, fuel cells, steel, gold films, nanopowder, antifreeze fluid for automobiles, polymerization inhibitors, tattoo removal from skin, antiinfiammatroy agent, treatment of neoplasm |
| InChIKey | OXNIZHLAWKMVMX-UHFFFAOYSA-N |
| CAS Datenbank | 88-89-1(CAS DataBase Reference) |
| EPA chemische Informationen | Picric acid (88-89-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH201: (Deleted) Explosivemass explosion hazard [Danger Explosives]P210, P230, P240, P250, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P370+P380, P372, P373, P401, P403+P233, P405, and P501 (click each P-code to see the statement)H201 (98.5%): (Deleted) ExplosiveP203, P210, P230, P240, P250, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P321, P330, P333+P317, P337+P317, P361+P364, P362+P364, P370+P380, P372, P373, P391, P401, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Phenol, 2,4,6-trinitro-Status: Cease Manufacture Update: 03-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23472Phenol, 2,4,6-trinitro- (wetted with >30% water): HSNO Approval: HSR001448 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Phenol, 2,4,6-trinitro-: Human health tier I assessment |
| DOT-Kennzeichnung | Explosive 1.1DFlammable Solid |
| Brandgefahren | Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:· Flammable/combustible material. |
| Brandpotenzial | Flammable solid.Flammable solid when exposed to heat or flame ... .It will burn once ignited by a flame and will continue to burn quietly if the quantity is small or the material is thinly spread over a large area. /Trinitrophenol, dry/ |
| Gesundheitsgefahren | Excerpt from NIOSH Pocket Guide for Picric acid:Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:· Some are toxic and may be fatal if inhaled, ingested or absorbed through skin. Specifically, Dinitrophenol, wetted (UN1320) |
Anwendungen & Verwendung
Beschreibung
Pikrinsäure bildet hellgelbe bis gelbe geruchlose, bitter schmeckende Blättchen. Der Schmelzpunkt reiner Pikrinsäure liegt bei 122.5 ℃, wobei die Säure bereits zu sublimieren beginnt. Sie verpufft beim Erhitzen auf über 225 ℃. Pikrinsäure ist mäßig löslich in Ethanol, Diethylether und Chloroform, leicht löslich in Benzol und Aceton. In heißem Wasser ist sie gut löslich (7.24 g in 100 g 100 ℃ heißem Wasser), in kaltem dagegen kaum (0.81 g in 100 g 10 ℃ kaltem Wasser). Pikrinsäure fand als Sprengstoff im militärischen Bereich breite Verwendung, wird aber nicht mehr verwendet, da sie stark färbt und dazu neigt, mit Metallen stoßempfindliche Pikrate zu bilden. An Sprengkraft übertrifft sie das Trinitrotoluol sowohl hinsichtlich der freiwerdenden Energie als auch der Detonationgeschwindigkeit. Angezündet schmilzt sie und brennt mit rauchender Flamme. Erst unter Einschluss, bei Kontakt mit Metallen (Pikratbildung) oder bei einer großen Anhäufung explodiert brennende Pikrinsäure. Trotz ihrer Gefährlichkeit ist sie heute noch in vielen Laboratorien zu finden. Aus Sicherheitsgründen wird sie mit 10% Wasseranteil gelagert.
Beschreibung
Picric acid is a white to yellowish crystalline substance, soluble in most organic solvents and highly flammable. Picric acid is a derivative of phenol. It reacts with metals to form metal picrates, which like picric acid itself are highly sensitive. It is often used for tissue fixative (Bouin solution) for histology specimens, as a booster to detonate another, less sensitive explosive, such as trinitotoluene (TNT). It is used in the manufacture of fireworks, matches, electric batteries, coloured glass, dyes, antiseptics, explosives, disinfectants, leather industries, pharmaceutical, and textile. Picric acid is also used as a yellow dye, as an antiseptic, and in the synthesis of chloropicrin, or nitro-trichloromethane. Picric acids are highly sensitive to heat, shock, or friction and because of the explosive nature it is among the most hazardous substances found in the laboratory.
Verwenden
Picric acid and its metal salts are used as explosives. It is also used in making matches; electric batteries, colored glass; in etching copper; and for dyeing textiles.