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CAS No.: | 51-28-5 |
---|---|
Name: | 2,4-Dinitrophenol |
Article Data: | 482 |
Molecular Structure: | |
Formula: | C6H4N2O5 |
Molecular Weight: | 184.108 |
Synonyms: | 2,4-Dinitro Phenol,51-28-5;2,4-Dinitro Phenol;Solfo Black BB;Osmotox-Plus;Nitrophene (VAN);Tertrosulphur PBR;1alpha-2,4-Dinitrophenol;Camello mosquito coils;.alpha.-Dinitrophenol;Dinitrofenolo [Italian];Chemox PE;2,4-Dinitrophenol/2,4-Dinitrophenol,2,4-Dinitrophenol,DNP;alpha-Dinitrophenol;Phenol, .alpha.-dinitro-;Nitrophen (VAN);Solfo Black G;Tertrosulphur Black PB;Solfo Black 2B Supra;Dinofan;Solfo Black B;Nitro kleenup;Osmoplastic-R;2, 4-Dinitrofenol;Shirakiku brand mosquito coils;Phenol, 2,4-dinitro-;X 32;1-Hydroxy-2,4-dinitrobenzene;Maroxol-50;Fenoxyl carbon N;Phenol, alpha-dinitro-;Dinitrofenolo;Cobra salts (Impregna salts); |
EINECS: | 200-087-7 |
Density: | 1.651 g/cm3 |
Melting Point: | 108-112 °C(lit.) |
Boiling Point: | 312.1 °C at 760 mmHg |
Flash Point: | 142.8 °C |
Solubility: | 0.6 g/100 mL (18 ºC) |
Appearance: | light yellow crystal powder |
Hazard Symbols: | T,N,Xi,F |
Risk Codes: | 23/24/25-33-50-39/23/24/25-11-52/53 |
Safety: | 28-37-45-61-28A-36/37-16-7 |
Transport Information: | UN 1320 4.1/PG 1 |
PSA: | 111.87000 |
LogP: | 2.25500 |
Conditions | Yield |
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With water; sodium hydroxide at 100℃; for 1.5h; | 100% |
With potassium carbonate In ethanol | 97.5% |
Stage #1: 1-chloro-2,4-dinitro-benzene With sodium hydroxide In water; acetonitrile for 1h; Reflux; Stage #2: With hydrogenchloride In water; acetonitrile Kinetics; Thermodynamic data; Solvent; Temperature; | 97% |
Conditions | Yield |
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With ammonium hydroxide; sodium sulfite In methanol at 70℃; for 48h; | 100% |
triethylamine N-oxide
1-chloro-2,4-dinitro-benzene
A
2,4-Dinitrophenol
B
triethylamine hydrochloride
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 24h; | A 98% B 98.5% |
In N,N-dimethyl-formamide for 24h; Ambient temperature; | A 98% B 98.5% |
Conditions | Yield |
---|---|
With trichloroisocyanuric acid; silica gel; sodium nitrite at 20℃; for 0.25h; | 98% |
With dinitrogen tetraoxide; ferric nitrate In ethyl acetate for 0.166667h; Heating; | 96% |
With chromium(III) nitrate; dinitrogen tetraoxide In ethyl acetate for 0.25h; Nitration; reflux; | 95% |
Conditions | Yield |
---|---|
With water; sodium hydroxide at 100℃; for 1.5h; | 98% |
With potassium hydroxide |
trimethylamine-N-oxide
N,N-dimethyl-formamide
1-chloro-2,4-dinitro-benzene
A
2,4-Dinitrophenol
B
trimethylamine hydrochloride
Conditions | Yield |
---|---|
for 24h; Ambient temperature; | A 97% B 98% |
trimethylamine-N-oxide
1-chloro-2,4-dinitro-benzene
A
2,4-Dinitrophenol
B
trimethylamine hydrochloride
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 24h; Ambient temperature; | A 97% B 98% |
Conditions | Yield |
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With dimethylbromosulphonium bromide; tetrabutylammonium nitrite In acetonitrile at 20℃; for 24h; regioselective reaction; | 97% |
With perchloric acid; montmorillonite K10 supported ammonium nitrate at 50℃; for 1.5h; | 95% |
With Zn(NO3)2*2N2O4 In dichloromethane at 20℃; for 5h; | 95% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; potassium tert-butylate; ammonia In tetrahydrofuran for 0.25h; | 96% |
With Cumene hydroperoxide; potassium tert-butylate In N,N,N,N,N,N-hexamethylphosphoric triamide at 15 - 20℃; for 1.5h; | 92% |
With potassium hydroxide; Cumene hydroperoxide In ammonia at -33℃; | 90% |
Conditions | Yield |
---|---|
With triethylamine In water; acetonitrile at 25℃; for 7h; Kinetics; Reagent/catalyst; | A n/a B 96% |
With triethylamine hydrochloride; triethylamine In water; acetonitrile at 25℃; Rate constant; different Et3N concentrations; | |
With sodium ethanolate In ethanol at 25℃; Kinetics; Further Variations:; Reagents; Elimination; |
The IUPAC name of this chemical is 2,4-Dinitrophenol. With the CAS registry number 51-28-5 and EINECS registry number 200-087-7, it is also named as Phenol,2,4-dinitro-. In addition, the molecular formula is C6H4N2O5 and the molecular weight is 184.11. It is a kind of yellow crystalline solid that has a sweet, musty odor and belongs to the classes of Intermediates of Dyes and Pigments; Aromatic Phenols; Organics; Phenoles and thiophenoles; Analytical Chemistry; Indicator (pH); pH Indicators; Dye Intermediate; Alpha Sort; D; DAlphabetic; DID - DINPesticides; Metabolites; Others; Pesticides; Volatiles/ Semivolatiles. What's more, it sublimes when carefully heated and is volatile with steam. It should be sealed in a cool place and should avoid the light.
Physical properties about this chemical are: (1)ACD/LogP: 1.72; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.251; (4)ACD/LogD (pH 7.4): ; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 7.011; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 7; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 111.87 Å2; (13)Index of Refraction: 1.661; (14)Molar Refractivity: 41.225 cm3; (15)Molar Volume: 111.547 cm3; (16)Polarizability: 16.343 ×10-24cm3; (17)Surface Tension: 79.667 dyne/cm; (18)Density: 1.651 g/cm3; (19)Flash Point: 142.78 °C; (20)Enthalpy of Vaporization: 57.512 kJ/mol; (21)Boiling Point: 312.097 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
Preparation of 2,4-Dinitrophenol: it can be prepared by 2,4-dinitrochlorobenzene. At first, add water into the pot, stir and heat it to 60 °C, then add the melting 2,4-dinitrochlorobenzene and continue to heat up to 90 °C. When add in sodium hydroxide solution, you should control the temperature no more than 102-104 °C and insulation for 30 minutes. Then go through the operation of cooling and filtering to get the products.
Uses of 2,4-Dinitrophenol: it is mainly used to produce heterogeneous and sulfide dyestuff, such as vulcanization black BN; BRN, etc. Also it can be used as acid base indicator and used to test potassium, ammonium and magnesium, etc. In addition, it can be used to get 2-bromo-4,6-dinitro-phenol. This reaction will need reagents Br2 and conc.H2SO4. The reaction time is 3.5 hours at reaction temperature of 100 °C. The yield is about 78%.
When you are using this chemical, please be cautious about it as the following:
This chemical is very toxic to aquatic organisms and toxic by inhalation, in contact with skin and if swallowed. And it has danger of very serious irreversible and cumulative effects. In addition, it is highly flammable and harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. During using it, wear suitable protective clothing and gloves and avoid release to the environment. If contact it with skin, wash immediately with plenty of soap-suds. Keep container tightly closed and keep away from sources of ignition. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). What's more, it is refer to special instructions/safety data sheets.
You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(c(cc1[N+](=O)[O-])[N+](=O)[O-])O
(2)InChI: InChI=1/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H
(3)InChIKey: UFBJCMHMOXMLKC-UHFFFAOYAV
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
bird - wild | LD50 | oral | 13mg/kg (13mg/kg) | Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972. | |
cat | LD50 | oral | 75mg/kg (75mg/kg) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 62, 1982. | |
dog | LCLo | inhalation | 300mg/m3/30M (300mg/m3) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 62, 1982. | |
dog | LDLo | intravenous | 15mg/kg (15mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 187, 1933. | |
dog | LDLo | oral | 30mg/kg (30mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 187, 1933. | |
dog | LDLo | subcutaneous | 20mg/kg (20mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 187, 1933. | |
guinea pig | LD50 | intraperitoneal | 28mg/kg (28mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 381, 1958. | |
guinea pig | LD50 | oral | 81mg/kg (81mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: TETANY BEHAVIORAL: ATAXIA | Farmakologiya i Toksikologiya Vol. 28, Pg. 493, 1965. |
guinea pig | LDLo | skin | 700mg/kg (700mg/kg) | Journal of Industrial Hygiene and Toxicology. Vol. 30, Pg. 10, 1948. | |
guinea pig | LDLo | subcutaneous | 25mg/kg (25mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 192, Pg. 331, 1939. | |
human | LDLo | oral | 36mg/kg (36mg/kg) | BEHAVIORAL: COMA CARDIAC: CHANGE IN RATE | JAMA, Journal of the American Medical Association. Vol. 101, Pg. 1333, 1933. |
mammal (species unspecified) | LD50 | unreported | 40mg/kg (40mg/kg) | "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 97, 1971. | |
mouse | LD50 | intraperitoneal | 26mg/kg (26mg/kg) | Biochemical Pharmacology. Vol. 18, Pg. 1389, 1969. | |
mouse | LD50 | intravenous | 56mg/kg (56mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Toxicology and Applied Pharmacology. Vol. 6, Pg. 232, 1964. |
mouse | LD50 | oral | 45mg/kg (45mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: ATAXIA BEHAVIORAL: TETANY | Farmakologiya i Toksikologiya Vol. 28, Pg. 493, 1965. |
mouse | LD50 | subcutaneous | 58mg/kg (58mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Toxicology and Applied Pharmacology. Vol. 6, Pg. 232, 1964. |
pigeon | LD50 | intramuscular | 6500ug/kg (6.5mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 53, Pg. 58, 1935. | |
rabbit | LD50 | oral | 30mg/kg (30mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: TETANY BEHAVIORAL: ATAXIA | Farmakologiya i Toksikologiya Vol. 28, Pg. 493, 1965. |
rabbit | LDLo | subcutaneous | 20mg/kg (20mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 187, 1933. | |
rat | LD50 | intraperitoneal | 20mg/kg (20mg/kg) | Journal of Pharmacy and Pharmacology. Vol. 17, Pg. 814, 1965. | |
rat | LD50 | intravenous | 72mg/kg (72mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Toxicology and Applied Pharmacology. Vol. 6, Pg. 232, 1964. |
rat | LD50 | oral | 30mg/kg (30mg/kg) | Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972. | |
rat | LD50 | subcutaneous | 25mg/kg (25mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 187, 1933. |