Conditions | Yield |
---|---|
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 |
---|---|
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 |
---|---|
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; |
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 12h; | A 95% B 3% |
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water for 5h; Kinetics; Product distribution; Further Variations:; pH-values; Heating; | 94% |
1-chloro-2,4-dinitro-benzene
A
2,4-Dinitrophenol
B
5-chloro-2,4-dinitrophenol
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; potassium tert-butylate; ammonia In tetrahydrofuran for 0.25h; | A n/a B 93% |
With potassium tert-butylperoxide In ammonia at -33℃; Mechanism; competition between hydrogen and halogen substitution; other reagent t-butyl hydroperoxide, cumene hydroperoxide, NaOH, t-BuOK; | A 20% B 50% |
With tert.-butylhydroperoxide; potassium tert-butylate; ammonia In tetrahydrofuran for 0.25h; | A 50% B n/a |
Conditions | Yield |
---|---|
With thiophene; sodium hydrogen sulfate; silica gel for 9h; Heating; | 93% |
N-(2,4-dinitro-phenyl)-L-alanine
A
2,4-Dinitrophenol
B
2-methyl-5-nitro-1H-benzimidazole 3-oxide
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water for 2h; Heating; | A n/a B 88% |
2,4-Dinitrophenol
Conditions | Yield |
---|---|
With hydrazine hydrate; caesium carbonate at 20℃; for 15h; | 86% |
Conditions | Yield |
---|---|
With sodium hydroxide for 1h; Heating; | 85% |
With potassium carbonate In dimethyl sulfoxide for 3h; Heating; | 79% |
With Cumene hydroperoxide; potassium tert-butylate In ammonia at -33℃; | 63% |
Conditions | Yield |
---|---|
With Zn(NO3)2*2N2O4 In ethyl acetate at 20℃; for 4h; | A 85% B 8% |
Conditions | Yield |
---|---|
With ferric nitrate; 1,3-di-n-butyl-imidazolium tetrafluoroborate at 60℃; for 2h; | 82% |
With Zn(NO3)2*2N2O4 In dichloromethane for 4h; Heating; | 82% |
With N-Bromosuccinimide; silver nitrate In acetonitrile for 7.5h; Reflux; | 75% |
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% |
2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine
benzylamine
A
1-N-benzyl-2',3',5'-tri-O-acetyladenosine
B
2,4-Dinitrophenol
Conditions | Yield |
---|---|
Stage #1: 2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine; benzylamine In acetonitrile at -30℃; Stage #2: With water In acetonitrile Heating; | A 81% B n/a |
(p-hydroxyphenyl)boronic acid
2,4-Dinitrophenol
Conditions | Yield |
---|---|
With bismuth (III) nitrate pentahydrate In toluene at 70 - 80℃; for 2h; Inert atmosphere; | 77% |
2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine
isopropylamine
B
2,4-Dinitrophenol
Conditions | Yield |
---|---|
Stage #1: 2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine; isopropylamine In acetonitrile at -30℃; Stage #2: With water In acetonitrile Heating; | A 76% B n/a |
meta-dinitrobenzene
aniline
A
2,4-Dinitrophenol
B
N-phenyl-2,4-dinitroaniline
Conditions | Yield |
---|---|
With potassium permanganate; tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 1h; | A 22% B 75% |
A
2,4-Dinitrophenol
B
2-hydroxy-5-nitroaniline
C
2-Phenyl-5,6,7,8-tetrahydro-imidazo<1,2-a>pyridin
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 25℃; for 5h; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation; | A 33% B 22% C 75% |
methanol
2,4-Dinitrofluorobenzene
A
2,4-Dinitrophenol
B
2,4-dinitroanisole
Conditions | Yield |
---|---|
With sodium hydroxide; cetyltrimethylammonim bromide In water at 26℃; Product distribution; other alcohols, var. concentrations alcohols; | A 26% B 74% |
Conditions | Yield |
---|---|
With perchloric acid; montmorillonite K10 supported ammonium nitrate at 50℃; for 1.5h; | A 73% B 23% |
durch Nitrieren; Trennung durch fraktionierte Faellung des Gemisches der Kaliumsalze mit BaCl2; | |
With tetrachloromethane; nitrosylsulfuric acid at 30℃; | |
With nitric acid |
Conditions | Yield |
---|---|
With samarium; copper(l) iodide; potassium iodide In tetrahydrofuran at 20℃; Molecular sieve; diastereoselective reaction; | A n/a B 73% |
Conditions | Yield |
---|---|
With thionyl chloride; bismuth subnitrate In dichloromethane at 20℃; for 2h; | A 72% B 14% |
2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine
ethylamine
B
2,4-Dinitrophenol
Conditions | Yield |
---|---|
Stage #1: 2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine; ethylamine In acetonitrile at -30℃; Stage #2: With water In acetonitrile Heating; | A 72% B n/a |
Conditions | Yield |
---|---|
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 9.5h; Heating; | 100% |
With N-benzyl-N,N-dimethyl anilinium peroxodisulfate; potassium bromide In acetonitrile for 9.5h; Reflux; regioselective reaction; | 91% |
With poly(4-vinylpyridinium bromochromate) In acetonitrile at 20℃; for 2h; regioselective reaction; | 82% |
2,4-Dinitrophenol
dabsyl chloride
4-(4-Dimethylamino-phenylazo)-benzenesulfonic acid 2,4-dinitro-phenyl ester
Conditions | Yield |
---|---|
With carbonate-bicarbonate buffer In acetone; acetonitrile 1.) 15 min, 2.) reflux; | 100% |
With carbonate-bicarbonate buffer In acetone for 0.5h; Heating; |
2,4-Dinitrophenol
1-ethoxy-2-(trimethylsilyl)vinyl acetate
2,4-dinitrophenyl acetate
Conditions | Yield |
---|---|
In dichloromethane at 40℃; for 22h; | 100% |
Conditions | Yield |
---|---|
Stage #1: 4BF4(1-)*C86H162N6O2(4+) With cobalt(II) acetate In ethanol at 20℃; for 3h; Stage #2: 2,4-Dinitrophenol With oxygen In dichloromethane for 3h; Stage #3: sodium 2,4-dinitrophenoxide With oxygen In dichloromethane Product distribution / selectivity; | 100% |
2,4-Dinitrophenol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2.5h; | 100% |
2,4-Dinitrophenol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2.5h; | 100% |
2,4-Dinitrophenol
Conditions | Yield |
---|---|
In acetonitrile at 40℃; Inert atmosphere; | 100% |
2,4-Dinitrophenol
cobalt(II) acetate
sodium 2,4-dinitrophenoxide
Conditions | Yield |
---|---|
Stage #1: C36H58N4O2(2+)*2BF4(1-); cobalt(II) acetate In ethanol at 20℃; for 2h; Glovebox; Inert atmosphere; Schlenk technique; Stage #2: 2,4-Dinitrophenol With oxygen In dichloromethane for 2h; Stage #3: sodium 2,4-dinitrophenoxide In dichloromethane at 20℃; | 100% |
2,4-Dinitrophenol
cobalt(II) acetate
sodium 2,4-dinitrophenoxide
Conditions | Yield |
---|---|
Stage #1: C36H52N4O2(2+)*2BF4(1-); cobalt(II) acetate In ethanol at 20℃; for 2h; Glovebox; Inert atmosphere; Schlenk technique; Stage #2: 2,4-Dinitrophenol With oxygen In dichloromethane for 2h; Stage #3: sodium 2,4-dinitrophenoxide In dichloromethane at 20℃; | 100% |
Conditions | Yield |
---|---|
With iodine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.333333h; | 99% |
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 12h; | 90% |
Conditions | Yield |
---|---|
With N-butyl-4-methylpyridinium bromide at 170℃; for 0.5h; Inert atmosphere; Ionic liquid; Green chemistry; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
With hydrazine hydrate at 90℃; for 18h; | 98% |
With hydrazine hydrate In water at 110℃; Sealed tube; Green chemistry; | 95% |
With hydrazine hydrate In isopropyl alcohol at 110℃; for 0.25h; Catalytic behavior; Sealed tube; chemoselective reaction; | 94% |
tert.-butylhydroperoxide
2,4-Dinitrophenol
tri(p-tolyl)antimony
toluene
Conditions | Yield |
---|---|
Stage #1: tert.-butylhydroperoxide; 2,4-Dinitrophenol; tri(p-tolyl)antimony In diethyl ether at 20℃; for 24h; Stage #2: toluene In octane | 98% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; pyrographite In tetrahydrofuran; water at 50 - 60℃; for 5h; | 97% |
With sodium tetrahydroborate In ethanol; water at 45℃; for 0.0833333h; | 96% |
Stage #1: 2,4-Dinitrophenol With palladium on activated charcoal In methanol at 20℃; for 0.0833333h; Autoclave; Inert atmosphere; Stage #2: With hydrogen In methanol at 65℃; under 3600.36 - 6375.64 Torr; for 1.5h; Pressure; Temperature; Autoclave; | 96.16% |
2,4-Dinitrophenol
N-phenyl-benzimidoyl chloride
2,4-dinitrophenyl N-phenylbenzimidate
Conditions | Yield |
---|---|
diethylamine In diethyl ether | 96% |
triethylamine In 1,4-dioxane |
Conditions | Yield |
---|---|
With sodium ethanolate at 18 - 20℃; for 0.5h; | 96% |
2,4-Dinitrophenol
tert-butylsulfinyl chloride
2-Methyl-propane-2-sulfinic acid 2,4-dinitro-phenyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 16h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
With sodium hydroxide In neat (no solvent) at 90℃; for 6h; Green chemistry; | 95% |
Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran at 70℃; for 0.5h; | 94% |
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. |
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