| Identification | More | [Name]
PICRIC ACID | [CAS]
88-89-1 | [Synonyms]
2,4,6-TRINITROPHENOL
2,4,6-trinitrophenol(Dry or wetted with less,by mass)
2-HYDROXY-1,3,5-TRINITROBENZENE
CI 10305
CI NO 10305
PHENOL TRINITRATE
PICRIC ACID
PICRIC ACID, SATURATED
PICRINIC ACID
PICRONITRIC ACID
TRINITROPHENOL
1,3,5-Trinitrophenol
2,4,6-Trinitrofenol
2,4,6-Trinitrofenolo
2,4,6-trinitro-pheno
2,4,6-Trinitrophenyl
Acide picrique
acidepicrique
acidepicrique(french)
Acido picrico | [EINECS(EC#)]
201-865-9 | [Molecular Formula]
C6H3N3O7 | [MDL Number]
MFCD00007102 | [Molecular Weight]
229.1 | [MOL File]
88-89-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Picric acid is a pale yellow, odorless solid. Usually found in solution with 10%20% water. Must be kept wetted; the crystalline form is highly unstable. The dry crystal form is explosive upon rapid heating or mechanical shock. | [Melting point ]
122-123 °C (dried material, Lit. Merck Index 12th Ed.)(lit.)
| [Boiling point ]
300℃ | [density ]
1.00 g/mL at 20 °C
| [vapor density ]
7.9 (vs air)
| [vapor pressure ]
1 mm Hg ( 195 °C)
| [refractive index ]
1.7630 (estimate) | [Fp ]
150℃ | [storage temp. ]
Store at RT. | [solubility ]
alcohol: soluble1 (g/12 mL)(lit.) | [Colour Index ]
10305 | [form ]
solution (saturated aqueous)
| [pka]
0.38(at 25℃) | [color ]
yellow solution | [Specific Gravity]
1.005 | [PH Range]
0.2(colourless)-1(yellow) | [Stability:]
Stability Unstable; may 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 | [explosive limit]
0.01% | [Water Solubility ]
(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) | [λmax]
354nm | [Merck ]
13,7492 | [BRN ]
423400 | [Exposure limits]
TLV-TWA skin 0.1 mg/m3 (ACGIH, OSHA, and MSHA). | [Major Application]
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 | [Contact allergens]
Contact dermatitis occurred primarily in the explosives
industry. | [InChIKey]
OXNIZHLAWKMVMX-UHFFFAOYSA-N | [CAS DataBase Reference]
88-89-1(CAS DataBase Reference) | [EPA Substance Registry System]
Picric acid (88-89-1) |
| Hazard Information | Back Directory | [Chemical Properties]
Also known as picronitric acid, trinitrophenol, nitroxanthic acid, carbazotic acid or phenoltrinitrate, C6H2(N02)3OH is yellow crystals that are soluble in water, alcohol, chloroform, benzene, and ether with a very bitter taste. It is derived by the nitration of phenolsulfonic acid, obtained by heating phenol with concentrated sulfuric acid, and is used for explosives, matches, electric batteries, and etching copper.
| [Chemical Properties]
Picric acid is a highly flammable, white to yellowish crystalline substance. It used in the
manufacture of fi reworks, matches, electric batteries, colored glass, explosives, and disinfectants.
Pharmaceutical, textile, and leather industries also make use of picric acid. | [Uses]
Preparation of organic derivatives for identification. | [Uses]
Explosives, matches; in leather industry; electric batteries; etching copper; manufacture of colored glass; textile mordant; also as reagent. | [General Description]
A paste or slurry consisting of the yellow crystalline solid mixed with water. The dry compound is a sensitive high explosive. The mixture with water is considered safe for storage, handling and shipping. Can be detonated with a number 8 electric blasting cap. The primary hazard is blast where the entire load explodes instantaneously and not from flying projectiles fragments. Can explode under prolonged exposure to heat. | [Reactivity Profile]
PICRIC ACID, WET, WITH NOT LESS THAN 10% WATER(88-89-1) undergoes vigorous reactions with both oxidizing or reducing agents. Burns if ignited by a flame and continues to burns quietly if the quantity is small or, if large, is thinly spread over an area. The dry compound can explode if shocked or exposed to heat. Wetting significantly reduces the tendency to explode. Readily forms salts on contact with many metals (including copper, lead, mercury, zinc, nickel, iron) . The salts are sensitive explosives when subjected to heat, friction, or impact. Contact with concrete floors may form the friction-sensitive explosive calcium picrate [Urbanski, 1964, vol. 1, p. 518]. Contact with metallic zinc or lead can cause detonation. Salts with ammonia, amines and complexes with hydrocarbons are less sensitive [Kirk-Othmer, 1965, vol. 8, p. 617]. | [Air & Water Reactions]
Water soluble. | [Health Hazard]
Exposures to picric acid cause different adverse effects on the skin of animals and humans,
such as allergies, dermatitis, irritation, and sensitization. Absorption of picric acid by the
system causes headache, fever, nausea, diarrhea, and coma. In high concentrations, picric
acid is known to cause damage to the erythrocytes, kidneys, and liver. | [Health Hazard]
Some are toxic and may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may cause pollution. | [Potential Exposure]
Picric acid is used in the synthesis of dye intermediates and in manufacturing picrates; in the manufacture of explosives, rocket fuels; fireworks, colored glass; matches, electric batteries; and disinfectants. It is also used in the pharmaceutical and leather industries; in copper and steel etching; forensic chemistry; histology, textile printing; and photographic emulsions. | [First aid]
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. | [Shipping]
UN0154 Picric acid, dry or wetted with ＜30% water, by mass, Hazard Class: 1D; Labels:1D-Explosive (with a mass explosion hazard); D-Substances or articles which may mass detonate (with blast and/or fragment hazard) when exposed to fire. UN1344 Picric acid, wetted with not less than 30% water, Hazard Class: 4.1; Labels: 4.1-Flammable solid. | [Incompatibilities]
Explosive when dry. Violent reaction with oxidizers and reducing materials. Air or oxygen is not required for decomposition. Shock sensitive compounds can be formed on contact with plaster, concrete. An explosive mixture results when the aqueous solution crystallizes. May explosively decompose from heat, shock, friction, or concussion. Copper, lead, zinc and other metals, or their salts can form other salts that are initiators and much more sensitive to shock than this chemical. Corrodes metals. | [Waste Disposal]
Controlled incineration in a rotary kiln incinerator equipped with particulate abatement and wet scrubber devices. | [Physical properties]
White to yellow crystals. Usually present in moist forms because dry picric acid is shock sensitive. | [Definition]
A yellow crystalline
solid made by nitrating phenolsulfonic
acid. It is used as a dye and as an explosive.
With aromatic hydrocarbons picric acid
forms characteristic charge-transfer complexes
(misleadingly called picrates), used
in analysis for identifying the hydrocarbon. | [Production Methods]
Picric acid is used in making explosives; as a burster in
projectiles; in rocket fuels, fireworks, colored glass, batteries,
and disinfectants; in the pharmaceutical and leather industries;
as a fast dye for wool and silk; in metal etching and
photographic chemicals; and as a laboratory reagent. | [Fire Hazard]
Picric acid is a high explosive. It is as stable as TNT and about as sensitive to explosive decomposition as TNT. It reacts with many metals and bases, readily forming metal picrates, which are highly sensitive explosive compounds. Metal picrates of iron(III), copper(II), and lead in the dry state are as sensitive as PETN. Its sensitivity is reduced by wetting with water. It explodes when heated above 300°C (572°F). | [Carcinogenicity]
Picric acid was mutagenic in the Ames
Salmonella assay in the presence of metabolic
activation. | [Environmental Fate]
Chemical/Physical. Picric acid explodes when heated >300 °C (Weast, 1986). Shock sensitive!
(quoted, Keith and Walters, 1992). | [Purification Methods]
Crystallise the acid first from acetic acid, then acetone, toluene, CHCl3, aqueous 30% EtOH, 95% EtOH, MeOH or H2O. Dry it in a vacuum for 2hours. Alternatively, dry it over Mg(ClO4)2 or fuse (CARE) and allow it to solidify under a vacuum three times. Because it is EXPLOSIVE, picric acid should be stored moistened with H2O, and only small portions should be dried at any one time. The dry acid should NOT be heated. [Beilstein 6 IV 1388.] | [Toxicity evaluation]
Metabolic and respiratory acidosis is thought to be the main
consequence of picric acid exposure, and is typically the cause of
death when reported. An uncoupler of mitochondrial metabolism,
picric acid can destroy erythrocytes, cause gastroenteritis,
hemorrhagic nephritis, and acute hepatitis. Reduction to the
N-acetyl derivative may also play a role in its inherent toxicity. |
| Safety Data | Back Directory | [Hazard Codes ]
F,T,E,Xn | [Risk Statements ]
R1:Explosive when dry.
R4:Forms very sensitive explosive metallic compounds.
R11:Highly Flammable.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R2:Risk of explosion by shock, friction, fire or other sources of ignition.
R36:Irritating to the eyes.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S35:This material and its container must be disposed of in a safe way .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S37:Wear suitable gloves .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37:Wear suitable protective clothing and gloves .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 1344 4.1/PG 1
| [WGK Germany ]
2
| [RTECS ]
TJ7875000
| [HazardClass ]
4.1 | [PackingGroup ]
I | [Precautions]
Workers should use protective clothing, avoid skin contact, and use goggles and face
masks to avoid dust. | [Safety Profile]
Poison by ingestion and
subcutaneous routes. Mutation data
reported. An irritant and an allergen. Shin
contact can cause local and systemic allergic
reactions. Flammable solid when exposed to
heat or flame; can react vigorously with
oxidzing materials. Very unstable. A severe
explosion hazard when shocked or exposed
to heat. It forms salts easily, and many of its
salts, known as picrates, are more sensitive
explosives than picric acid. It forms unstable
salts with concrete, NH3, bases, and metals
(e.g., copper, lead, mercury, and zinc). Many
of these are heat-, friction-, or impact-
sensitive. Mixtures with uranium perchlorate
are extremely powerful explosives. mxtures
with aluminum and water igmte after a delay
period. Can react vigorously with reducing
materials. Used in synthesis of dyes, as a
drug, to manufacture explosives and
matches, to etch copper, and to make
colored glass. See also NITRO
COMPOUNDS OF AROMATIC
HYDROCARBONS and EXPLOSIVES,
HIGH. | [Hazardous Substances Data]
88-89-1(Hazardous Substances Data) | [Toxicity]
LC50 (48-h) for red killifish 513 mg/L (Yoshioka et al., 1986). | [IDLA]
75 mg/m3 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Sulfuric acid-->Nitric acid-->Phenol-->2,4-Dinitrochlorobenzene | [Preparation Products]
L-Proline-->L-Lysine-->1H-Imidazole-4-carbaldehyde-->2,2-diphenyl-1-picrylhydrazyl-->4-Imidazolemethanol hydrochloride-->Urocanic acid-->N-OMEGA-ACETYLHISTAMINE-->4-IMIDAZOLEACETIC ACID HYDROCHLORIDE-->4(5)-CYANOMETHYLIMIDAZOLE-->trans-2,5-Dimethylpiperazine-->2,3,4,5-Tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one-->5,6-DIHYDRO-4-(2-METHYL-2-PHENYLHYDRAZINO)-2-1H-PYRIDINONE-->2,4-Piperadinedione-->4-AMINO-5-IMIDAZOLECARBOXAMIDE-->3-AMINO-PROPIONIC ACID ETHYL ESTER-->Mordant Brown 49-->2-Methyl-1-butanethiol-->5-methylquinolin-8-ol-->2,4,6-TRINITROANILINE-->Trichloronitromethane-->Leuco sulfur black 2 (C.I. 53195)-->Sulphur Black 2 |
| Questions and Answers (Q&A) | Back Directory | [Description]
It is an organic compound (chemical formula: (O2N)2C6H2OH) with a better taste. It is also one of most acidic phenols with many applications such as being an explosive, used in medicine, and dyes. One of its biggest applications is used in munitions and explosives such as TATB. It is also used in organic chemistry for the manufacture of some crystalline salts. In metallurgy, it can be used in optical metallography for revealing the prior austenite grain boundary in the ferritic steels. It is also used as a component in the bouin solution for histology specimens. In clinical chemistry, it can be used in the Jaffe reaction to test the creatinine. It is manufactured through the reaction between phenols and sulfuric acid to generate p-hydroxyphenylsufonic acid, followed by nitration with concentrated nitric acid to obtain the final product.
| [References]
https://en.wikipedia.org/wiki/Picric_acid
https://pubchem.ncbi.nlm.nih.gov/compound/picric_acid#section=InChI
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