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Picric acid

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Picric acid

EINECS 201-865-9
CAS No. 88-89-1 Density 1.856 g/cm3
Solubility Melting Point 122-123 °C
Formula C6H3N3O7 Boiling Point 303.6 °C at 760 mmHg
Molecular Weight 229.12 Flash Point 133.9 °C
Transport Information UN 1344 4.1/PG 1 Appearance Yellow solid
Safety 35-45-37-28-36/37-36-26-16-25 Risk Codes 1-4-11-23/24/25-2-36-20/21/22
Molecular Structure Molecular Structure of 88-89-1 (Picric acid) Hazard Symbols FlammableF, ToxicT, ExplosiveE, HarmfulXn
Synonyms

Picric acid(6CI,8CI);1-Hydroxy-2,4,6-trinitrobenzene;2,4,6-Trinitrophenol;C.I. 10305;Carbazotic acid;Melinite;NSC 36947;NSC 56147;Nitroxanthic acid;Picral;Picronitric acid;Trinitrophenol;

 

Picric acid Chemical Properties

Molecular Structure of Picric acid (CAS NO.88-89-1):

IUPAC Name: 2,4,6-trinitrophenol
Molecular formula: C6H3N3O7
Molar mass: 229.1
EINECS: 201-865-9
H bond acceptors: 10
H bond donors: 1
Freely Rotating Bonds: 4
Polar Surface Area: 146.69 Å2
Index of Refraction: 1.701
Molar Refractivity: 47.77 cm3
Molar Volume: 123.3 cm3
Surface Tension: 98.5 dyne/cm
Density: 1.856 g/cm3
Flash Point: 133.9 °C
Enthalpy of Vaporization: 56.56 kJ/mol
Boiling Point: 303.6 °C at 760 mmHg
Vapour Pressure: 0.000514 mmHg at 25°C
Melting point: 122-123 °C
Storage temp: Store at RT
Appearance: Colorless to yellow solid
EINECS: 201-865-9
Merck: 13,7492
InChI
InChI=1/C6H3N3O7/c10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16/h1-2,10H
Smiles
c1(c(c(cc(c1)[N+](=O)[O-])[N+](=O)[O-])O)[N+](=O)[O-]
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
Product Categories: Intermediates of Dyes and Pigments; Organics

Picric acid History

  Picric acid (CAS NO.88-89-1) was probably first mentioned in the alchemical writings of Johann Rudolf Glauber in 1742. Its synthesis from phenol, and the correct determination of its formula, were successfully accomplished in 1841. Not until 1830 did chemists think to use picric acid as an explosive. Before then, chemists assumed that only the salts of picric acid were explosive, not the acid itself. In 1873 Hermann Sprengel proved it could be detonated and by 1894 the Russian workers had worked out a method of manufacture for artillery shells. In 1887 the French government adopted it under the name melinite, with addition of gun cotton. Since 1888, Britain started manufacturing a very similar mixture in Lydd, Kent, under the name lyddite.

Picric acid Production

Picric acid (88-89-1) is manufactured by the nitration of mixed phenolsulfonates with mixed acid. Mixed acid increases the yield of desired products.

Picric acid Toxicity Data With Reference

1.    

mma-sat 5 µmol/plate

    MUREAV    Mutation Research. 90 (1981),91.
2.    

sln-dmg-par 1500 ppm

    ENMUDM    Environmental Mutagenesis. 7 (1985),677.
3.    

orl-rat LD50:200 mg/kg

    JTEHD6    Journal of Toxicology and Environmental Health. 37 (1992),313.
4.    

scu-dog LDLo:60 mg/kg

    HBAMAK    “Abdernalden’s Handbuch der Biologischen Arbeitsmethoden.“ 4 (1935),1289.
5.    

orl-cat LDLo:250 mg/kg

    HBAMAK    “Abdernalden’s Handbuch der Biologischen Arbeitsmethoden.“ 4 (1935),1289.
6.    

unr-dog LDLo:60 mg/kg

    XPHBAO    U.S. Public Health Service, Public Health Bulletin. 271 (1941),151.
7.    

orl-rbt LDLo:120 mg/kg

    XPHBAO    U.S. Public Health Service, Public Health Bulletin. 271 (1941),151.
8.    

orl-gpg LDLo:100 mg/kg

    HBAMAK    “Abdernalden’s Handbuch der Biologischen Arbeitsmethoden.“ 4 (1935),1289.
9.    

scu-pgn LDLo:200 mg/kg

    HBAMAK    “Abdernalden’s Handbuch der Biologischen Arbeitsmethoden.“ 4 (1935),1289.

Picric acid Consensus Reports

PICRIC ACID(88-89-1) is  reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Picric acid Safety Profile

Hazard Codes: F,T,E,Xn
Risk Statements: 1-4-11-23/24/25-2-36-20/21/22
1: Explosive when dry 
4:  Forms very sensitive explosive metallic compounds
11:  Highly Flammable 
23/24/25:  Toxic by inhalation, in contact with skin and if swallowed 
2: Risk of explosion by shock, friction, fire or other sources of ignition
36:  Irritating to the eyes 
20/21/22:  Harmful by inhalation, in contact with skin and if swallowed 
Safety Statements: 35-45-37-28-36/37-36-26-16
35:  This material and its container must be disposed of in a safe way 
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
37:  Wear suitable gloves 
36/37:  Wear suitable protective clothing and gloves 
36:  Wear suitable protective clothing 
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
16:  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
Modern safety precautions recommend storing picric acid wet. Dry picric acid is relatively sensitive to shock and friction, so laboratories that use it store it in bottles under a layer of water, rendering it safe. Glass or plastic bottles are required, as picric acid can easily form metal picrate salts that are even more sensitive and hazardous than the acid itself.

Picric acid Standards and Recommendations

OSHA PEL: TWA 0.1 mg/m3 (skin)
ACGIH TLV: TWA 0.1 mg/m3
DFG MAK: 0.1 mg/m3
DOT Classification:  4.1; Label: Flammable Solid (NA 1344, UN 1344)

Picric acid Specification

  Picric acid , with CAS number of 88-89-1, can be called Carbazotic Acid; phenol trinitrate; picronitric acid; trinitrophenol; 2,4,6-trinitro-1-phenol; 2-hydroxy-1,3,5-trinitrobenzene; TNP; 2,4,6-trinitrophenol . The heavy metal salts of picric acid are dangerously sensitive, and its major use is for the manufacture of ammonium picrate (Explosive D). Picric acid (CAS NO.88-89-1) has found some use in organic chemistry for the preparation of crystalline salts of organic bases (picrates) for the purpose of identification and characterization. Workplace drug testing utilizes picric acid for the Jaffe Reaction to test for creatinine. It forms a colored complex that can be measured using spectroscopy. Much less commonly, wet picric acid has been used as a skin dye or temporary branding agent. In the early 20th century, picric acid was stocked in pharmacies as an antiseptic and as a treatment for burns, malaria, herpes, and smallpox.

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