Conditions | Yield |
---|---|
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃; | 100% |
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃; under 760 Torr; Rate constant; | 100% |
With hydrogen; palladium-containing anion exchanger AB-17-8-Pd In ethanol at 20 - 40℃; under 750.06 Torr; Kinetics; Product distribution; Further Variations:; Catalysts; | 100% |
Conditions | Yield |
---|---|
With ammonium bromide; ethylenediamine at 70℃; for 2h; Microwave irradiation; | 99% |
In 1,2-dichloro-ethane at 95 - 105℃; under 0 - 1125.11 Torr; Alkaline conditions; Large scale; | 96.5% |
With sodium hydroxide In water at 100℃; for 16h; | 72% |
Alkaline hydrolysis; |
Conditions | Yield |
---|---|
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 120℃; for 16h; Sealed tube; | 99% |
With ammonium hydroxide In water at 20℃; for 9h; Green chemistry; | 96% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In neat (no solvent) at 30℃; for 0.3h; Green chemistry; | 90% |
With water; oxygen; sodium sulfite at 50℃; for 2h; Green chemistry; | 72% |
2-((trimethylsilyl)oxy)aniline
2-amino-phenol
Conditions | Yield |
---|---|
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0833333h; Green chemistry; | 98% |
With rice husk ash supported on anatase-phase titania nanoparticles nanocomposite In methanol at 20℃; for 0.05h; | 94% |
With nano magnetic sulfated zirconia (Fe3O4 at ZrO2/SO42-) In neat (no solvent) at 20℃; for 0.333333h; Green chemistry; | 90% |
Conditions | Yield |
---|---|
With ammonium hydroxide In water at 20℃; for 9h; Green chemistry; | 93% |
With ammonium hydroxide; L-2-O-methyl-chiro-inositol; copper(II) acetate monohydrate; potassium iodide In 1-methyl-pyrrolidin-2-one at 150℃; for 12h; | 70% |
With ammonium hydroxide; copper at 80℃; for 7h; Inert atmosphere; | 65.5% |
Conditions | Yield |
---|---|
Stage #1: phenol With copper(ll) sulfate pentahydrate; copper In water at 30℃; for 2h; Inert atmosphere; Sealed tube; Stage #2: With ammonium hydroxide; sodium hydroxide In water at 20℃; for 1h; pH=~ 9; Inert atmosphere; Sealed tube; | |
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / water / 2 h / 50 - 55 °C 2: iron; acetic acid / water / 0.75 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / 1.08 h / 15 - 25 °C / 9000.9 Torr 2: hydrogenchloride; zinc / water / 1.5 h / 70 °C / 9750.98 Torr / Sealed tube View Scheme | |
Multi-step reaction with 2 steps 1.1: acetic acid 1.2: 12 h / 0 - 25 °C 2.1: ammonium hydroxide; copper / 7 h / 80 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
With aminomethyl polysterene resin formic acid salt; zinc In methanol at 20℃; for 0.3h; | 96% |
With polystyrene-CH2-NH3(+)HCO2(-); magnesium In methanol at 20℃; for 0.266667h; | 96% |
With aminomethylpolystyrene-supported formate; palladium on activated charcoal In methanol at 20℃; for 3.5h; | 95% |
Conditions | Yield |
---|---|
With trifluoroacetic acid In isopropyl alcohol at 70℃; for 18h; | 67% |
With bis(triphenylphosphine)copper(I) cyanide; caesium carbonate; triphenylphosphine Reagent/catalyst; | 62% |
With ethylene glycol; zinc(II) chloride In neat (no solvent) at 120℃; for 6h; Green chemistry; | 62% |
Conditions | Yield |
---|---|
With 3-azapentane-1,5-diamine at 130℃; for 2h; Sealed tube; | 98% |
With ammonium bromide; ethylenediamine at 80℃; for 5h; Microwave irradiation; | 91% |
2-azidophenol
2-amino-phenol
Conditions | Yield |
---|---|
With hydrazinium monoformate; zinc In methanol at 20℃; for 0.166667h; | 96% |
With zinc In methanol at 20℃; for 4h; | 96% |
With aluminium(III) iodide In benzene for 0.25h; Reduction; Heating; | 95% |
With ammonium formate; zinc In methanol at 20℃; for 0.3h; | 85% |
Conditions | Yield |
---|---|
Stage #1: 2-iodophenylamine With copper(l) iodide; 8-Hydroxyquinoline-N-oxide In dimethyl sulfoxide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With cesiumhydroxide monohydrate In water; dimethyl sulfoxide at 100℃; for 36h; Inert atmosphere; | 84% |
With copper(l) iodide; lithium pipecolinate; tetrabutyl ammonium fluoride; sodium hydroxide In water at 130℃; for 24h; | 74% |
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 190℃; for 0.5h; | 80% |
With 1-methyl-pyrrolidin-2-one; potassium carbonate; thiophenol for 0.5h; Heating; | 80% |
With water; hydrogen bromide; Aliquat 336 at 105℃; for 6.5h; Catalytic behavior; | 72% |
With aluminium trichloride In various solvent(s) for 0.5h; Heating; | |
With aluminium trichloride |
Conditions | Yield |
---|---|
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h; | A 4% B 94% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; acetic acid; triphenylphosphine; copper(ll) bromide In water at 40℃; for 6h; | A 15% B n/a |
Conditions | Yield |
---|---|
With ammonium hydroxide; potassium phosphate; Cu0.18Bi0.88O0.88I1.06 In ethanol; water at 80℃; for 20h; Inert atmosphere; Green chemistry; | 76 %Chromat. |
2-hydroxynitrobenzene
benzyl alcohol
A
2-amino-phenol
B
benzoic acid
Conditions | Yield |
---|---|
With potassium hydroxide In 1,3,5-trimethyl-benzene at 160℃; for 24h; Inert atmosphere; Overall yield = 85 percent; |
2-amino-phenol
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; ethanethiol In dichloromethane at 20℃; for 2h; | 90% |
2,6-Dichloro-3,5-difluoro-4-nitro-phenol
B
2-amino-phenol
Conditions | Yield |
---|---|
With hydrogen In methanol; aluminum nickel | |
With hydrogen In methanol; aluminum nickel | |
With hydrogen In methanol; aluminum nickel |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium acetate; hemin; rac-cysteine In water; acetone at 40℃; for 2h; Mechanism; pH=3; pH and reaction time dependency, various catalysts and inhibitors; | |
With dihydrogen peroxide; FePp In ethanol at 38℃; for 0.166667h; Product distribution; borate buffer, pH 9; further educts; | |
With oxygen; titanium(IV) oxide In water at 26.84℃; for 1.5h; pH=6.5; Irradiation; Title compound not separated from byproducts.; | |
With dihydrogen peroxide; bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate salt In ethanol; water at 20℃; for 0.666667h; Overall yield = 80 %; Overall yield = 0.087 g; |
2-((tert-butyldimethylsilyl)oxy)aniline
2-amino-phenol
Conditions | Yield |
---|---|
With tin(ll) chloride In ethanol at 20℃; for 5h; | 88% |
(E)-2-(phenyldiazenyl)phenyl benzoate
A
N-phenyl benzoyl amide
B
2-amino-phenol
Conditions | Yield |
---|---|
With ammonium chloride; zinc In methanol at 80℃; for 6h; Inert atmosphere; | A 71% B 64% |
Conditions | Yield |
---|---|
With 1,3-dimethyl-2-imidazolidinone; sodium trimethylsilanethiolate at 185℃; for 24h; | 96% |
2-chloro-3,5,6-trifluoro-4-nitrophenol
B
2-amino-phenol
Conditions | Yield |
---|---|
aluminum nickel In methanol |
Conditions | Yield |
---|---|
With hydrogenchloride; paraformaldehyde In water |
2-oxo-propionic acid
2-hydroxynitrobenzene
A
3-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one
B
2-amino-phenol
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In water; isopropyl alcohol at 30℃; under 7500.75 Torr; for 10h; Autoclave; | A 28% B n/a |
2-hydroxyphenyl boronic acid
2-amino-phenol
Conditions | Yield |
---|---|
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h; | 80% |
A
3-(2-thienyl)-2-propenoic acid
B
2-amino-phenol
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 1h; Reflux; |
2-amino-phenol
Conditions | Yield |
---|---|
With hydrogenchloride In water at 150℃; for 3h; Microwave irradiation; Sealed tube; | 71% |
Conditions | Yield |
---|---|
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); formic acid; bis(trifluoromethanesulfonyl)amide; triethylamine; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In dibutyl ether at 130℃; for 24h; | A 83% B n/a |
Conditions | Yield |
---|---|
With Au NCs/TiO2 In toluene at 130℃; Inert atmosphere; | 100% |
With ISO-PECH polyamine catalyst In methanol at 20℃; for 0.0666667h; Green chemistry; | 99% |
With Co-doped NiFe2O4 nanoparticle In neat (no solvent) at 70℃; for 2h; | 97% |
2-amino-phenol
dimethyl acetylenedicarboxylate
(2Z)-[2-oxo-2H-1,4-benzoxazine-3(4H)-ylidene]acetic acid methyl ester
Conditions | Yield |
---|---|
at 20℃; for 0.0666667h; Michael addition; | 100% |
In neat (no solvent) at 20℃; for 0.166667h; regioselective reaction; | 98% |
In ethanol at 0℃; for 3h; | 94% |
Conditions | Yield |
---|---|
With magnesium sulfate In tetrahydrofuran at 0 - 20℃; for 8h; | 100% |
In ethanol at 25℃; for 24h; | 91% |
In ethanol for 2h; Reflux; | 85% |
3,4-dimethoxy-benzaldehyde
2-amino-phenol
2-(3,4-dimethoxyphenylmethyleneimino)phenol
Conditions | Yield |
---|---|
In toluene Heating; | 100% |
In ethanol for 3h; Reflux; | 75% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 27℃; for 24h; Inert atmosphere; Glovebox; | 100% |
With triethylamine In dichloromethane at 20℃; for 18h; | 80.5% |
76% |
2-chloro-3-quinoline carboxaldehyde
2-amino-phenol
2-((2-chloroquinolin-3-yl)methyleneamino)phenol
Conditions | Yield |
---|---|
In tetrahydrofuran for 2h; Ambient temperature; | 100% |
In ethanol at 20℃; for 0.333333h; Sonication; | 78% |
With acetic acid In ethanol at 20℃; |
dimethylmonochlorosilane
2-amino-phenol
2,2-dimethyl-2,3-dihydro-benzo[1,3,2]oxazasilole
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 6h; Heating; | 100% |
trimethylsilyl isocyanate
2-amino-phenol
(2-Trimethylsilanyloxy-phenyl)-urea
Conditions | Yield |
---|---|
In tetrahydrofuran at 60 - 65℃; for 5h; | 100% |
2-amino-phenol
1,1,1,3,3,3-hexamethyl-disilazane
2-((trimethylsilyl)oxy)aniline
Conditions | Yield |
---|---|
With 1,3-disulfonic acid imidazolium hydrogen sulfate In neat (no solvent) at 20℃; for 0.0166667h; Green chemistry; | 100% |
With poly(4-vinylpyridine) In acetonitrile at 20℃; for 0.5h; chemoselective reaction; | 98% |
With 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0833333h; Neat (no solvent); chemoselective reaction; | 95% |
Conditions | Yield |
---|---|
In tetrahydrofuran at -20℃; for 0.25h; | 100% |
2-amino-phenol
1,1-dichloro-5-aza-2,8-dioxa-1-phosphaV-dibenzo<9,9',11,11'-tetra-tert-butyl>-bicyclo<3.3.0>octadiene
Conditions | Yield |
---|---|
In benzene for 24h; Ambient temperature; | 100% |
triisopropylsilyl chloride
2-amino-phenol
2-((triisopropylsilyl)oxy)aniline
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 14h; Inert atmosphere; | 100% |
With 1H-imidazole In dichloromethane at 20℃; for 20h; | 99% |
With 1H-imidazole In dichloromethane for 33h; Ambient temperature; | 84% |
With 1H-imidazole; triethylamine In dichloromethane at 20℃; Inert atmosphere; |
di-tert-butyl dicarbonate
2-amino-phenol
tert-butyl (2-hydroxyphenyl)carbamate
Conditions | Yield |
---|---|
copper(II) bis(tetrafluoroborate) at 30 - 33℃; for 1h; | 100% |
In dichloromethane at 23℃; for 22h; Inert atmosphere; | 100% |
With Amberlyst-15 In ethanol at 20℃; | 100% |
N-tert-butyloxycarbonylpiperidin-4-one
2-amino-phenol
1-(tert-butoxycarbonyl)-4-[(2-hydroxyphenyl)amino]piperidine
Conditions | Yield |
---|---|
100% | |
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one; 2-amino-phenol With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 120℃; for 0.0833333h; Microwave irradiation; Stage #2: With water; sodium hydrogencarbonate | 75% |
With sodium tris(acetoxy)borohydride |
4-bromo-benzaldehyde
2-amino-phenol
2-(4-bromo-benzylidenamino)-phenol
Conditions | Yield |
---|---|
In methanol at 20℃; for 1h; | 100% |
In methanol at 20℃; for 1h; | 100% |
In ethanol Heating; | 96% |
2-amino-phenol
Conditions | Yield |
---|---|
With triethylamine In ethanol for 2h; Cyclization; Heating; | 100% |
3-methoxy-4-hydroxybenzoic acid
2-amino-phenol
4-(benzo[d]oxazol-2ʹ-yl)-2-methoxyphenol
Conditions | Yield |
---|---|
With trimethylsilylphosphate at 180℃; for 0.5h; | 100% |
With Trimethylsilyl polyphosphate at 180℃; for 16.75h; Cooling with ice; | 10.63 g |
3-methoxy-4-methylbenzoyl chloride
2-amino-phenol
N-(2-hydroxyphenyl)-3-methoxy-4-methylbenzamide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; | 100% |
3-vinyl-cyclohex-2-enone
2-amino-phenol
3-[2-(2-aminophenylsulfanyl)ethyl]cyclohex-2-enone
Conditions | Yield |
---|---|
With triethylamine In benzene at 0 - 25℃; for 7h; | 100% |
1,2-bis(2,4,5-trimethylthiophene-3-yl)maleic anhydride
2-amino-phenol
N-(2-hydroxyphenyl)-2,3-bis(2,4,5-trimethyl-3-thienyl)maleimide
Conditions | Yield |
---|---|
With triethylamine In toluene for 24h; Heating; | 100% |
Conditions | Yield |
---|---|
acetic acid In ethanol for 12h; | 100% |
With air In methanol at 60℃; for 1h; | 90.9% |
In methanol at 20℃; | 87% |
2-amino-phenol
4-(benzo[d]oxazol-2-yl)-2-nitrobenzeneamine
Conditions | Yield |
---|---|
In ethanol at 95℃; for 5h; | 100% |
ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate
2-amino-phenol
ethyl 2-(2-hydroxyphenylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 100% |
Conditions | Yield |
---|---|
Stage #1: C17H21NO4 With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 20℃; for 18h; Stage #2: 2-amino-phenol In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 3h; | 100% |
Conditions | Yield |
---|---|
Stage #1: 2-amino-phenol With hydrogenchloride; sodium nitrite In water at 5℃; for 0.166667h; Stage #2: 4-Hexylresorcinol With sodium hydroxide In water at 5℃; Cooling with ice; Stage #3: With hydrogenchloride In water | 100% |
2-amino-phenol
acetylenedicarboxylic acid diethyl ester
(2Z)-[2-oxo-2H-1,4-benzoxazine-3(4H)-ylidene]acetic acid ethyl ester
Conditions | Yield |
---|---|
at 20℃; for 0.0833333h; Michael addition; | 100% |
at 20℃; for 0.0833333h; | |
With sodium chloride Milling; | > 95 %Chromat. |
1-Methyl-4-piperidone
p-methoxyphenylisocyanide
2-amino-phenol
2-(4-(benzo[d]oxazol-2-yl)-1-methylpiperidin-4-ylamino)phenol
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In 2,2,2-trifluoroethanol at 55℃; for 24h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; | 100% |
benzaldehyde
nitrobenzene
2-amino-phenol
A
2-phenylbenzo[d]oxazole
B
benzylidene phenylamine
Conditions | Yield |
---|---|
With Au NCs/TiO2 In toluene at 130℃; Inert atmosphere; | A 100% B 28% |
2-(2,4,6-trimethylphenylamino)-2-oxoacetic acid ethyl ester
2-amino-phenol
N-2-hydroxyphenyl-N'-mesityloxalamide
Conditions | Yield |
---|---|
With triethylamine In toluene Reflux; | 100% |
With boric acid for 1h; Heating; | 70% |
2-Aminophenol is an organic compound with the formula C6H4(OH)NH2. Along with its isomer 4-aminophenol, it is an amphoteric molecule and a reducing agent. It is a useful reagent for the synthesis of dyes and heterocyclic compounds. Reflecting its slight hydrophilic character, white powder is moderately soluble in alcohols and can be recrystallised from hot water. O-Aminophenol should avoid the condition like incompatible materials,light. It is incompatibilities with other materials light, acids, acid chlorides, acid anhydrides, chloroformates. Its hazardous decomposition products are nitrogen oxides, carbon monoxide, carbon dioxide. Its hazardous polymerization has not been reported.
Physical properties about 2-Aminophenol are: (1)ACD/LogP: 0.497; (2)ACD/LogD (pH 5.5): 0.43; (3)ACD/LogD (pH 7.4): 0.49; (4)ACD/BCF (pH 5.5): 1.21; (5)ACD/BCF (pH 7.4): 1.39; (6)ACD/KOC (pH 5.5): 38.36; (7)ACD/KOC (pH 7.4): 44.05; (8)#H bond acceptors: 2; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.637; (12)Molar Refractivity: 32.371 cm3; (13)Molar Volume: 90.144 cm3; (14)Polarizability: 12.833 10-24cm3; (15)Surface Tension: 57.4010009765625 dyne/cm; (16)Density: 1.211 g/cm3; (17)Flash Point: 95.62 °C; (18)Enthalpy of Vaporization: 49.037 kJ/mol; (19)Boiling Point: 234.496 °C at 760 mmHg; (20)Vapour Pressure: 0.0350000001490116 mmHg at 25°C
Uses of 2-Aminophenol: 2-Aminophenol has a variety of uses. As a reducing agent, it is marketed under the names of Atomal and Ortol to develop black and white photographs. 2-Aminophenol is an intermediate in the synthesis of dyes. It is particularly useful in yielding tridentate ligands for metal-complex dyes when diazotized and coupled to a phenol, naphthol, or other aromatic or resonant dye species. Metal complex dyes using copper or chromium are commonly used for producing dull colors. Tridentate ligand dyes are particularly useful, since they are more stable than their bi- or mono-dentate counterparts.
When you are using this chemical, please be cautious about it as the following:
1. After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer);
2. Wear suitable protective clothing and gloves;
3. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
4. Wear suitable protective clothing, gloves and eye/face protection;
5. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C6H7NO/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2;
(2)InChIKey=CDAWCLOXVUBKRW-UHFFFAOYSA-N;
(3)Smilesc1(c(cccc1)O)N;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | subcutaneous | 37mg/kg (37mg/kg) | LUNGS, THORAX, OR RESPIRATION: CYANOSIS LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: GENERAL ANESTHETIC | Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 72, Pg. 241, 1913. |
guinea pig | LD50 | skin | > 1gm/kg (1000mg/kg) | National Technical Information Service. Vol. OTS0555965, | |
mouse | LD50 | intraperitoneal | 200mg/kg (200mg/kg) | National Technical Information Service. Vol. AD691-490, | |
mouse | LD50 | oral | 800mg/kg (800mg/kg) | LUNGS, THORAX, OR RESPIRATION: CYANOSIS BEHAVIORAL: TREMOR | National Technical Information Service. Vol. OTS0555965, |
mouse | LD50 | unreported | 675mg/kg (675mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 50(3), Pg. 4, 1985. | |
quail | LD50 | oral | 316mg/kg (316mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
rat | LD50 | oral | 951mg/kg (951mg/kg) | BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: CYANOSIS | National Technical Information Service. Vol. OTS0555965, |
rat | LD50 | subcutaneous | 37mg/kg (37mg/kg) | Yakkyoku. Pharmacy. Vol. 32, Pg. 1093, 1981. | |
rat | LD50 | unreported | 1406mg/kg (1406mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 50(3), Pg. 4, 1985. | |
rat | LDLo | intraperitoneal | 300mg/kg (300mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 131, Pg. 151, 1961. |
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