(imidazole-1-yl)-2,4,6-trinitrobenzene
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
With water | 100% |
2,4,6-trinitrochlorobenzene
sodium methylate
acetylacetone
A
2,4,6-Trinitrophenol
B
1-methoxy-2,4,6-trinitrobenzene
C
3-(2,4,6-trinitrophenyl)-2,4-pentanedione
Conditions | Yield |
---|---|
In methanol; dimethyl sulfoxide at 25℃; Rate constant; Mechanism; | A 1% B 1% C 96% |
S,S'-bis(2,4,6-trinitrophenyl) dithiooxalate
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
With nitric acid | 95% |
With nitric acid for 1h; Product distribution; | |
Multi-step reaction with 2 steps 1: conc. HNO3 / 25 - 30 °C 2: 91 percent / H2O, H2SO4 / 4 h / 50 °C View Scheme |
2,4,6-trinitrochlorobenzene
sodium methylate
acetoacetic acid methyl ester
A
2,4,6-Trinitrophenol
B
methyl 2-(2,4,6-trinitrophenyl)-3-oxobutanoate
Conditions | Yield |
---|---|
In methanol at 25℃; Rate constant; Mechanism; | A n/a B 94% |
Conditions | Yield |
---|---|
With NO+*18-crown-6*H(NO3)2- In various solvent(s) for 2h; Nitration; Heating; | A 94% B 5% |
With Zn(NO3)2*2N2O4 In ethyl acetate at 20℃; for 0.25h; | A 86% B 8% |
1,2,3,5-tetranitrobenzene
A
4,6-dinitrobenzofuroxan
B
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In methanol at 45 - 50℃; for 1h; | A 93% B n/a |
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.5h; | A n/a B 92% |
2,4,6-trinitronitrosobenzene
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
With sulfuric acid; water at 50℃; for 4h; | 91% |
Conditions | Yield |
---|---|
With Zn(NO3)2*2N2O4 In dichloromethane for 0.583333h; Heating; | 90% |
With nitric acid |
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.5h; | A n/a B 88% |
Conditions | Yield |
---|---|
With nitric acid In dimethyl sulfoxide at 100℃; for 4h; | 87% |
With copper(II) nitrate trihydrate In acetonitrile at 70℃; for 20h; Inert atmosphere; Irradiation; | 75% |
technische Herstellung durch Sulfonierung und anschl. Nitrierung; |
Conditions | Yield |
---|---|
With Zn(NO3)2*2N2O4 In dichloromethane for 1.5h; Heating; | 86% |
With nitric acid |
phenol
A
2,4-Dinitrophenol
B
2,4,6-Trinitrophenol
C
p-benzoquinone
Conditions | Yield |
---|---|
With NO+*18-crown-6*H(NO3)2- In ethyl acetate for 0.166667h; Nitration; Heating; | A 82% B 8% C 3% |
With silica-acetate; dinitrogen tetraoxide In ethyl acetate for 0.166667h; Heating; | A 74% B 8% C 10% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; copper(II) nitrate trihydrate In acetonitrile at 70℃; for 20h; Reagent/catalyst; Solvent; Temperature; Time; Inert atmosphere; Irradiation; Green chemistry; | 78% |
9-acetoxy-10-(4'-acetoxyphenyl)-anthracene
A
9,10-phenanthrenequinone
B
2,4,6-Trinitrophenol
C
10-hydroxy-10-(3',5'-dinitro-4'-hydroxyphenyl)anthrone-9
Conditions | Yield |
---|---|
With nitric acid In acetic acid at 105 - 110℃; for 0.25h; | A 75% B 75% C 10% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; copper(II) nitrate trihydrate In acetonitrile at 70℃; for 20h; Inert atmosphere; Irradiation; Green chemistry; | 70% |
Conditions | Yield |
---|---|
With nitric acid at 170℃; for 0.333333h; | A 66% B 21% |
With nitric acid at 170℃; for 0.25h; Product distribution; variation of temperature, reaction time, concentration of nitric acid, proportion of nitric acid; | A 63% B 18% |
With nitric acid at 170℃; for 0.333333h; | A 55% B 25% |
With nitric acid at 180 - 185℃; under 11400 Torr; |
Conditions | Yield |
---|---|
With nitric acid at 160 - 170℃; for 0.0833333h; | A 65% B 25% |
Conditions | Yield |
---|---|
With nitric acid | 60% |
With sulfuric acid; nitric acid anfangs bei Raumtemperatur, zuletzt bei 65grad; | |
With nitric acid |
picryl bromide
A
1,3,5-trinitrobenzene
B
m-Anisidine
C
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
With copper In nitrobenzene for 9h; Product distribution; Irradiation; other solvent, var. time; | A 51% B 27% C n/a |
Conditions | Yield |
---|---|
With Cumene hydroperoxide; potassium tert-butylate In N,N,N,N,N,N-hexamethylphosphoric triamide at -5 - 5℃; for 0.25h; | 50% |
With sodium carbonate; potassium hexacyanoferrate(III) |
Conditions | Yield |
---|---|
With nitric acid | A 50% B n/a |
With nitric acid | A >99 B n/a |
N-butyl-2,4,6-trinitroaniline
A
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water for 18h; Heating; | A 10.4% B 46.3% |
9-acetoxy-10-(4'-acetoxyphenyl)-anthracene
A
10-hydroxy-10-(4'-hydroxyphenyl)anthrone-9
B
9,10-phenanthrenequinone
C
2,4,6-Trinitrophenol
D
10-hydroxy-10-(3',5'-dinitro-4'-hydroxyphenyl)anthrone-9
Conditions | Yield |
---|---|
With nitric acid In acetic acid at 90 - 95℃; for 0.0833333h; Mechanism; Product distribution; other 9-acetoxyanthracene derivatives, other temperatures; | A 10% B 30% C 30% D 20% |
With nitric acid In acetic acid at 90 - 95℃; for 0.0833333h; | A 10% B 30% C 30% D 20% |
N-(2,4,6-trinitrophenyl)acetamide
A
picramide
B
2,4,6-Trinitrophenol
C
1,2,3,5-tetranitrobenzene
Conditions | Yield |
---|---|
With sulfuric acid; ozone for 72h; Ambient temperature; | A 5% B n/a C 29% |
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
With 2,2'-[1,1'-(ethylenedioxydinitrilo)diethylidyne]diphenol In acetone for 1461h; | 25.9% |
2-thiazolylamine
1-methoxy-2,4,6-trinitrobenzene
A
2-N-(2,4,6-trinitrophenyl)thiazoleamine
B
[3-Methyl-3H-thiazol-(2Z)-ylidene]-(2,4,6-trinitro-phenyl)-amine
C
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
With sodium acetate In methanol | A n/a B 20% C 20% |
4-methylthiazol-2-ylamine
1-methoxy-2,4,6-trinitrobenzene
A
2-N-(2,4,6-trinitrophenyl)-4-methylthiazoleamine
B
[3,4-Dimethyl-3H-thiazol-(2Z)-ylidene]-(2,4,6-trinitro-phenyl)-amine
C
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
With sodium acetate In methanol | A n/a B 20% C 20% |
Conditions | Yield |
---|---|
With nitric acid In acetic acid at 100℃; for 0.5h; | 20% |
morpholine-4-carboxylic acid amide
2,4,6-Trinitrophenol
Picric acid; compound with morpholine-4-carboxylic acid amide
Conditions | Yield |
---|---|
In hexane; isopropyl alcohol Heating; | 100% |
78% |
Te,Te-di(p-methoxyphenyl)-N-(p-tolylsulfonyl)tellurimide
2,4,6-Trinitrophenol
bis oxide
Conditions | Yield |
---|---|
In diethyl ether; dichloromethane for 0.5h; | 100% |
N-(p-tolylsulfonyl)diphenyltellurimide
2,4,6-Trinitrophenol
A
toluene-4-sulfonamide
B
bis oxide
Conditions | Yield |
---|---|
In diethyl ether; dichloromethane for 0.5h; | A 78% B 100% |
2,4,6-Trinitrophenol
N-(trifluoroacetyl)-di(p-methoxyphenyl)tellurimide
bis oxide
Conditions | Yield |
---|---|
In diethyl ether; dichloromethane for 0.5h; | 100% |
2,4,6-Trinitrophenol
(Z)-3-(pyrrolidin-1-ylmethylene)-3H-indole
3-(1-pyrrolidinylmethylene)-3H-indolium picrate
Conditions | Yield |
---|---|
In ethanol Ambient temperature; | 100% |
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
In water | 100% |
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
In water | 100% |
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
In water | 100% |
tetraethylammonium chloride
2,4,6-Trinitrophenol
tetraethylammonium picrate
Conditions | Yield |
---|---|
With 2-chloropyridine In acetonitrile Product distribution; without reagent; | 100% |
2,4,6-Trinitrophenol
4-(2-Benzyl-aziridin-1-yl)-5-methoxy-[1,2]benzoquinone
Conditions | Yield |
---|---|
In acetonitrile at 50℃; for 0.0833333h; | 100% |
Conditions | Yield |
---|---|
In methanol; water | 100% |
Conditions | Yield |
---|---|
In chloroform-d1 Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In chloroform | 100% |
Conditions | Yield |
---|---|
In chloroform | 100% |
Conditions | Yield |
---|---|
In chloroform | 100% |
Conditions | Yield |
---|---|
In ethanol for 2h; Ambient temperature; | 99% |
pentaphenylantimony
2,4,6-Trinitrophenol
(2,4,6-trinitrophenoxy)tetraphenylantimony
Conditions | Yield |
---|---|
In toluene room temperature; | 99% |
1,2,3-trimethylimidazolium hydrogen carbonate
2,4,6-Trinitrophenol
1,2,3-trimethylimidazolium picrate
Conditions | Yield |
---|---|
In ethanol; water at 20℃; for 24h; | 98% |
N,N-dimethylpyrrolidinium hydrogen carbonate
2,4,6-Trinitrophenol
N,N-dimethylpyrrolidinium picrate
Conditions | Yield |
---|---|
In ethanol; water at 20℃; for 24h; | 98% |
1-methyl-1H-imidazole
2,4,6-Trinitrophenol
1-methylimidazolium picrate
Conditions | Yield |
---|---|
In ethanol; water at 40℃; for 10h; | 98% |
1,2-dimethyl-1H-imidazole
2,4,6-Trinitrophenol
1,2-dimethylimidazole*2,4,6-trinitrophenol
Conditions | Yield |
---|---|
In ethanol; water at 40℃; for 10h; | 98% |
Conditions | Yield |
---|---|
In ethanol; water at 40℃; for 10h; | 98% |
2,4,6-Trinitrophenol
1-butyl-2-methyl-1H-imidazole
1-butyl-2-methylimidazolium picrate
Conditions | Yield |
---|---|
In ethanol; water at 40℃; for 10h; | 98% |
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
In water | 98% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.75h; Equilibrium constant; | 98% |
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
In water aq. soln. of Co complex added to aq. soln. of picric acid, stirred; ppt. filtered, washed with water and EtOH, dried; elem. anal.; | 97.4% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; pyrographite In tetrahydrofuran; water at 50 - 60℃; for 4h; | 97% |
With sodium tetrahydroborate; antimony(III) fluoride In water; acetonitrile at 20℃; for 0.5h; | 90% |
With hydrogenchloride; tin(ll) chloride Electrolysis; |
2,4,6-Trinitrophenol
Conditions | Yield |
---|---|
In ethanol | 97% |
2,4,6-Trinitrophenol
1-tert-butyl-2-dimethoxyphosphoryl-3,3-dimethylaziridinium 2,4,6-trinitrophenoxide
Conditions | Yield |
---|---|
In diethyl ether at 20℃; for 24h; Inert atmosphere; | 97% |
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 (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 (88-89-1) is manufactured by the nitration of mixed phenolsulfonates with mixed acid. Mixed acid increases the yield of desired products.
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(88-89-1) is reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
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.
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 , 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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