Conditions | Yield |
---|---|
With sodium hydroxide; hexachloroethane; tetrabutylammomium bromide In dichloromethane at 55℃; | 71% |
With phosphorus pentachloride |
tetrachlo-5-iodoropyridine
A
2,3,4,6-Tetrachloropyridine
B
2,3,4,5,6-pentachloropyridine
Conditions | Yield |
---|---|
With copper In N,N-dimethyl-formamide at 150℃; | A 3% B n/a C 71% |
4-Bromo-2,3,5,6-tetrachloropyridine
A
2,3,5,6-tetrachloropyridine
B
2,3,4,6-Tetrachloropyridine
C
2,3,4,5,6-pentachloropyridine
D
octachloro-4,4'-bipyridyl
Conditions | Yield |
---|---|
With Isopropylbenzene; copper In N,N-dimethyl-formamide at 150℃; for 1h; Further byproducts given; | A 63% B 15% C 16% D 17% |
tetrachloro-4-iodopyridine
A
2,3,5,6-tetrachloropyridine
B
2,3,4,5,6-pentachloropyridine
C
octachloro-4,4'-bipyridyl
Conditions | Yield |
---|---|
With copper In N,N-dimethyl-formamide at 150℃; | A 22% B 4% C 52% |
bis(2,3,5,6-tetrachloropyridin-4-yl)sulfane
A
2,3,4,5,6-pentachloropyridine
B
hexachlorodipyrido<5,4-b;3,4-d>thiophen
Conditions | Yield |
---|---|
In tetrachloromethane for 24h; Irradiation; | A 6.5% B 44% |
4-Bromo-2,3,5,6-tetrachloropyridine
A
2,3,5,6-tetrachloropyridine
B
2,3,4,6-Tetrachloropyridine
C
2,3,4,5,6-pentachloropyridine
E
octachloro-4,4'-bipyridyl
Conditions | Yield |
---|---|
With para-xylene; copper In N,N-dimethyl-formamide at 150℃; for 1h; Product distribution; Mechanism; the similar reaction without p-xylene; in presence cumene, benzoyl chloride instead p-xylene; other reagent (CuCl); other polychloroiodoarenes; tetrahalohenopyridylcopper intermediate; evidence against free radical or pyridyne intermediates; | A 42% B 5% C 15% D 4% E 18% |
4-Bromo-2,3,5,6-tetrachloropyridine
A
2,3,5,6-tetrachloropyridine
B
2,3,4,5,6-pentachloropyridine
D
octachloro-4,4'-bipyridyl
Conditions | Yield |
---|---|
With para-xylene; copper In N,N-dimethyl-formamide at 150℃; for 1h; Further byproducts given; | A 42% B 15% C 4% D 18% |
With copper In N,N-dimethyl-formamide at 150℃; for 0.5h; | A 17% B 21% C 8% D 14% |
With copper In N,N-dimethyl-formamide at 150℃; for 0.5h; Further byproducts given; | A 10% B 10% C 9% D 8% |
tetrachloro-4-(2-pyridylthio)pyridine
A
2,3,4,5,6-pentachloropyridine
B
1,3,4-trichlorodipyrido<2,3-b;3,4-d>thiophen
Conditions | Yield |
---|---|
In tetrahydrofuran; ethanol for 6h; Irradiation; | A 39% B 13% |
tetrachloromethane
2,3,5,6-tetrachloropyridine
A
2,3,4,5,6-pentachloropyridine
B
4-dichloromethyl-2,3,5,6-tetrachloropyridine
Conditions | Yield |
---|---|
With tetrachloromethane; tetrabutylammomium bromide In sodium hydroxide at 50℃; for 4h; | A n/a B 30% C n/a |
tetrachloro-4-pyridylcopper
benzoyl chloride
A
2,3,5,6-tetrachloropyridine
B
4-benzoyltetrachloropyridine
C
2,3,4,5,6-pentachloropyridine
D
octachloro-4,4'-bipyridyl
Conditions | Yield |
---|---|
With para-xylene In N,N-dimethyl-formamide for 23h; Product distribution; Mechanism; Heating; the similar reaction without p-xylene; other reaction times; similar range of products to those obtained from 4-bromotetrachloropyridine; | A 12% B 13% C 1% D 2.5% |
tetrachloro-4-pyridylcopper
A
2,3,5,6-tetrachloropyridine
B
4-benzoyltetrachloropyridine
C
2,3,4,5,6-pentachloropyridine
D
octachloro-4,4'-bipyridyl
Conditions | Yield |
---|---|
With para-xylene; benzoyl chloride In N,N-dimethyl-formamide for 23h; Heating; | A 12% B 13% C 1% D 2.5% |
1-pyrrolidino-1-cycloheptene
2,3,4,5,6-pentachloropyridine N-oxide
A
1-(tetrachloro-2-pyridyl)cyclohexene
B
2,3,4,5,6-pentachloropyridine
C
2-chloro-7-(tetrachloro-2-pyridyl)cycloheptanone
Conditions | Yield |
---|---|
In toluene for 14h; Heating; Yields of byproduct given; | A 11% B n/a C n/a |
In toluene for 14h; Heating; Yields of byproduct given; | A n/a B n/a C 5% |
1-(N-morpholino)cyclopent-1-ene
2,3,4,5,6-pentachloropyridine N-oxide
A
2-(tetrachloro-N-oxido-2-pyridyl)cyclopentanone
B
2,3,4,5,6-pentachloropyridine
Conditions | Yield |
---|---|
In toluene for 14h; Heating; | A 6% B 1% |
Conditions | Yield |
---|---|
With phosphorus pentachloride | |
With chlorine |
Conditions | Yield |
---|---|
With chlorine at 130 - 150℃; |
Conditions | Yield |
---|---|
With chlorine at 115 - 120℃; |
Conditions | Yield |
---|---|
With phosphorus pentachloride |
2-Cyanopyridine
A
2,3,4,5,6-pentachloropyridine
B
6-chloro-pyridine-2-carbonitrile
C
3,4,5,6-tetrachloropicolinonitrile
D
3,4,5-trichloro-2-picolinonitrile
Conditions | Yield |
---|---|
With chlorine In tetrachloromethane at 630℃; for 0.00138889h; Product distribution; var. contact times, temperatures, and solvent systems; | A 6.1 % Chromat. B 2.0 % Chromat. C 75.4 % Chromat. D 7.7 % Chromat. |
2,3,4,5-tetrachloro-6-(trichloromethyl)-pyridine
A
tetrachloromethane
B
2,3,4,5,6-pentachloropyridine
Conditions | Yield |
---|---|
With chlorine at 200℃; Rate constant; |
2,3,5,6-tetrachloropyridine
phosphorus pentachloride
2,3,4,5,6-pentachloropyridine
Conditions | Yield |
---|---|
at 300℃; im Rohr; |
pyridine N-oxide
hydrogenchloride
sulfuryl dichloride
A
2-chloropyridine
B
4-Chloropyridine
C
2,3,4,5,6-pentachloropyridine
Conditions | Yield |
---|---|
at 120℃; |
pyridine
chlorine
A
3-Chloropyridine
B
3,4,5-trichloropyridine
C
2,3,4,5,6-pentachloropyridine
D
3,5-dichloropyridine
Conditions | Yield |
---|---|
at 170℃; beim Behandeln des Pyridin-hydrochlorids; |
3,4,5-trichloro-2-trichloromethyl pyridine
A
tetrachloromethane
B
2,3,4,5-tetrachloro-pyridine
C
2,3,4,5,6-pentachloropyridine
D
2,3,4,5-tetrachloro-6-(trichloromethyl)-pyridine
Conditions | Yield |
---|---|
With chlorine at 200℃; for 18h; Title compound not separated from byproducts; | A n/a B 9.7 % Chromat. C 3.2 % Chromat. D 11.8 % Chromat. E n/a |
With chlorine at 200℃; for 18h; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With chlorine at 245℃; Thermodynamic data; Kinetics; Rate constant; other temperature, irrradiation, activation energies; | |
With chlorine at 200℃; for 18h; Product distribution; other time; | A n/a B 9.7 % Chromat. C 3.2 % Chromat. D 11.8 % Chromat. E n/a |
A
2,3,4,5,6-pentachloropyridine
B
hexachloroethane
C
hexachlorobenzene
D
octachlorostyrene
Conditions | Yield |
---|---|
With aluminium trichloride at 300℃; for 24h; Chlorination; cyclization; Further byproducts given. Title compound not separated from byproducts; |
A
2,3,4,5,6-pentachloropyridine
B
Hexachlorobutadiene
C
hexachlorobenzene
D
octachlorostyrene
Conditions | Yield |
---|---|
With melt electrolyte at 700℃; Formation of xenobiotics; electrolysis; Further byproducts given. Title compound not separated from byproducts; |
2,3,4,5,6-pentachloropyridine
Conditions | Yield |
---|---|
With oxygen; urea; copper dichloride at 300℃; Formation of xenobiotics; |
2,3,5-trichloropyridine
2,3,4,5,6-pentachloropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: C2Cl6; nBu4NBr; aq. NaOH / 4 h / 50 °C 2: 71 percent / C2Cl6; nBu4NBr; aq. NaOH / CH2Cl2 / 55 °C View Scheme |
4-Bromo-2,3,5,6-tetrachloropyridine
2,3,4,5,6-pentachloropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 39 percent / potassium carbonate / acetone / 2 h / Heating 2: 39 percent / tetrahydrofuran; ethanol / 6 h / Irradiation View Scheme |
Conditions | Yield |
---|---|
In 1,2-dichloro-benzene at 80℃; for 3h; | 100% |
In 1,2-dichloro-benzene at 60℃; | 87% |
In 1,2-dichloro-benzene at 80 - 90℃; |
Conditions | Yield |
---|---|
In 1,2-dichloro-benzene at 120℃; for 3h; | 100% |
In 1,2-dichloro-benzene Heating; | |
Heating; |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 120℃; for 1h; | 100% |
Heating; |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 120℃; for 2h; | 100% |
Conditions | Yield |
---|---|
Stage #1: 2,3,4,5,6-pentachloropyridine With manganese; ammonium acetate In ethanol; water at 40℃; for 6h; Stage #2: With ammonia In ethanol; water at 65℃; for 1h; pH=8 - 9; Concentration; Temperature; | 99.5% |
With ammonium chloride; zinc In acetonitrile at 80℃; for 3h; Reagent/catalyst; Solvent; Temperature; Green chemistry; | 88.4% |
With ammonium chloride; dimethyl methane phosphonate; zinc In water for 0.5h; Yield given; |
Conditions | Yield |
---|---|
With nickel dichloride at 150℃; for 0.5h; | 99% |
2,3,4,5,6-pentachloropyridine
phenylboronic acid
2,3,4,5,6-pentaphenylpyridine
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); potassium phosphate; 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl In toluene at 100℃; for 20h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Sealed tube; | 99% |
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II) | 99% |
2,3,4,5,6-pentachloropyridine
4-methylphenylboronic acid
2,3,4,5,6-pentakis(4-tolyl)pyridine
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); potassium phosphate; 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl In toluene at 100℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Sealed tube; | 99% |
2,3,4,5,6-pentachloropyridine
4-methoxyphenylboronic acid
2,3,4,5,6-pentakis(4-methoxyphenyl)pyridine
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); potassium phosphate; 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl In toluene at 100℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Sealed tube; | 99% |
2,3,4,5,6-pentachloropyridine
2,3,5,6-tetrachloro-4-azidopyridine
Conditions | Yield |
---|---|
With sodium azide In acetone at 20℃; | 98% |
2,3,4,5,6-pentachloropyridine
A
2,3,6-trichloropyridine
B
2,3,5-trichloropyridine
C
2,3,5,6-tetrachloropyridine
Conditions | Yield |
---|---|
With ammonium chloride; dimethyl methane phosphonate; zinc In water at 85 - 90℃; Product distribution; other ammonium salts; other methylphosphonates/phosphates; | A 0.9% B 1% C 97.6% |
2,3,4,5,6-pentachloropyridine
sodium thiomethoxide
2,3,5,6-tetrachloro-4-methylmercaptopyridine
Conditions | Yield |
---|---|
With sodium iodide In methanol; water at 20℃; for 4h; Solvent; Reagent/catalyst; Cooling with ice; | 96% |
In tetrahydrofuran; water at 20℃; for 1h; Temperature; Large scale; |
Conditions | Yield |
---|---|
With potassium fluoride at 90℃; for 1.5h; Temperature; Reagent/catalyst; Concentration; | 95.42% |
With hydrogen fluoride; tetramethylammonium fluoride In water; isopropyl alcohol at -10 - 135℃; Temperature; Flow reactor; Green chemistry; | 94.7% |
With potassium fluoride In sulfolane at 190℃; for 72h; | 93% |
Conditions | Yield |
---|---|
In 1,2-dichloro-benzene at 20℃; for 24h; | 95% |
2,3,4,5,6-pentachloropyridine
3,5-dichloro-2,4,6-triazido-pyridine
Conditions | Yield |
---|---|
With sodium azide In water; acetone at 70℃; for 72h; azidation; | 94% |
With sodium azide In acetone at 70℃; for 72h; | 84% |
2,3,4,5,6-pentachloropyridine
phenylacetylene
2,3,4,5,6-pentakis(phenylethynyl)pyridine
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; diisopropylamine; XPhos In 1,4-dioxane at 80℃; for 10h; Sonogashira coupling; Inert atmosphere; Sealed tube; | 92% |
2,3,4,5,6-pentachloropyridine
A
2,3,5,6-tetrachloro-4-pyridinol
B
3,4,5,6-tetrachloro-2-pyridinol
Conditions | Yield |
---|---|
With potassium hydroxide In tert-butyl alcohol for 10h; Heating; | A n/a B 90% |
2,3,4,5,6-pentachloropyridine
N-(4-chlorophenyl)formamide
2,3,5,6-tetrachloro-N-(4-chlorophenyl)pyridin-4-amine
Conditions | Yield |
---|---|
Stage #1: N-(4-chlorophenyl)formamide With potassium carbonate In acetonitrile for 0.5h; Reflux; Stage #2: 2,3,4,5,6-pentachloropyridine In acetonitrile at 85℃; for 12h; Solvent; Temperature; | 90% |
2,3,4,5,6-pentachloropyridine
1,3,4-trichloro-9-(4-methylbenzylidene)-6-(p-tolyl)-6,7,8,9-tetrahydrocyclopenta[D]pyrido[4′,3′:4,5]thiazolo[3,2-a]pyrimidine
Conditions | Yield |
---|---|
Stage #1: 1,3,4-trichloro-9-(4-methylbenzylidene)-6-(p-tolyl)-6,7,8,9-tetrahydrocyclopenta[D]pyrido[4′,3′:4,5]thiazolo[3,2-a]pyrimidine With potassium carbonate In acetonitrile at 100 - 110℃; for 0.5h; Stage #2: 2,3,4,5,6-pentachloropyridine In acetonitrile for 24h; Solvent; Reflux; | 90% |
Conditions | Yield |
---|---|
In acetone for 5h; Heating; | 89% |
In acetone | 89% |
2,3,4,5,6-pentachloropyridine
4-tert-Butylphenylacetylene
2,3,4,5,6-pentakis(4-tert-butylphenylethynyl)pyridine
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; diisopropylamine; XPhos In 1,4-dioxane at 80℃; for 10h; Sonogashira coupling; Inert atmosphere; Sealed tube; | 89% |
2,3,4,5,6-pentachloropyridine
4-tert-butylphenylboronic acid
2,3,4,5,6-pentakis(4-tert-butylphenyl)pyridine
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); potassium phosphate; 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl In toluene at 100℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Sealed tube; | 89% |
2,3,4,5,6-pentachloropyridine
4-trifluoromethoxyphenylboronic acid
2,3,4,5,6-pentakis[4-(trifluoromethoxy)phenyl]pyridine
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); potassium phosphate; 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl In toluene at 100℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Sealed tube; | 89% |
2,3,4,5,6-pentachloropyridine
8-(4-methylbenzylidene)-3,4,5,6,7,8-hexahydro-4-(4-methylphenyl)quinazoline-2(1H)-thione
Conditions | Yield |
---|---|
Stage #1: 8-(4-methylbenzylidene)-3,4,5,6,7,8-hexahydro-4-(4-methylphenyl)quinazoline-2(1H)-thione With potassium carbonate In acetonitrile at 100 - 110℃; for 0.5h; Stage #2: 2,3,4,5,6-pentachloropyridine In acetonitrile for 22h; Reflux; | 89% |
Conditions | Yield |
---|---|
Stage #1: C24H26N2O4S With potassium carbonate In acetonitrile at 100 - 110℃; for 0.5h; Stage #2: 2,3,4,5,6-pentachloropyridine In acetonitrile for 25h; Reflux; | 89% |
1-ethynyl-4-fluorobenzene
2,3,4,5,6-pentachloropyridine
2,3,4,5,6-pentakis(4-fluorophenylethynyl)pyridine
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; diisopropylamine; XPhos In 1,4-dioxane at 80℃; for 8h; Sonogashira coupling; Inert atmosphere; Sealed tube; | 88% |
2,3,4,5,6-pentachloropyridine
7-(4-methoxybenzylidene)-4-(4-methoxyphenyl)-3, 4, 6,7-tetrahydro-1H cyclopenta[d]pyrimidin-2(5H)-thione
Conditions | Yield |
---|---|
Stage #1: 7-(4-methoxybenzylidene)-4-(4-methoxyphenyl)-3, 4, 6,7-tetrahydro-1H cyclopenta[d]pyrimidin-2(5H)-thione With potassium carbonate In acetonitrile at 100 - 110℃; for 0.5h; Stage #2: 2,3,4,5,6-pentachloropyridine In acetonitrile for 26h; Reflux; | 88% |
2,3,4,5,6-pentachloropyridine
Conditions | Yield |
---|---|
With boron trifluoride; fluorine In trifluoroacetic acid at 10℃; for 3h; | 87% |
2,3,4,5,6-pentachloropyridine
potassium S-i-propyltrithiocarbonate
2,3,5,6-tetrachloro-4-(isopropylsulfanyl)pyridine
Conditions | Yield |
---|---|
In ethanol at 20℃; for 6h; Substitution; | 87% |
2,3,4,5,6-pentachloropyridine
8-(4-methoxybenzylidene)-3,4,5,6,7,8-hexahydro-4-(4-methoxyphenyl)quinazoline-2(1H)-thione
Conditions | Yield |
---|---|
Stage #1: 8-(4-methoxybenzylidene)-3,4,5,6,7,8-hexahydro-4-(4-methoxyphenyl)quinazoline-2(1H)-thione With potassium carbonate In acetonitrile at 100 - 110℃; for 0.5h; Stage #2: 2,3,4,5,6-pentachloropyridine In acetonitrile for 23h; Reflux; | 87% |
The Pentachloropyridine is an organic compound with the formula C5Cl5N. The IUPAC name of this chemical is 2,3,4,5,6-pentachloropyridine. With the CAS registry number 2176-62-7, it is also named as pyridine, 2,3,4,5,6-pentachloro-. The product's categories are Chloropyridines; Halopyridines; C5Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Pyridines. Besides, it is white to off-white flake, which should be stored in a closed cool and dry place. It is used as a pesticide and pharmaceutical intermediates, which can be used for production pesticides of chlorpyrifos and dichloro-pyridine acid.
Physical properties about Pentachloropyridine are: (1)ACD/LogP: 3.61; (2)ACD/LogD (pH 5.5): 3.61; (3)ACD/LogD (pH 7.4): 3.61; (4)ACD/BCF (pH 5.5): 323.72; (5)ACD/BCF (pH 7.4): 323.72; (6)ACD/KOC (pH 5.5): 2179.63; (7)ACD/KOC (pH 7.4): 2179.63; (8)#H bond acceptors: 1; (9)Polar Surface Area: 12.89 Å2; (10)Index of Refraction: 1.601; (11)Molar Refractivity: 48.81 cm3; (12)Molar Volume: 142.4 cm3; (13)Polarizability: 19.35×10-24cm3; (14)Surface Tension: 51.1 dyne/cm; (15)Density: 1.764 g/cm3; (16)Flash Point: 151.5 °C; (17)Enthalpy of Vaporization: 50.02 kJ/mol; (18)Boiling Point: 282.3 °C at 760 mmHg; (19)Vapour Pressure: 0.00579 mmHg at 25°C.
Preparation: this chemical can be prepared by octachloro-4,4'-sulfanediyl-bis-pyridine. This reaction will need reagent CCl4. The reaction time is 22 hours. The yield is about 44%.
Uses of Pentachloropyridine: it can be used to produce 3,5-dichloro-2,4,6-trifluoro-pyridine at temperature of 190 °C. It will need reagent KF and solvent tetrahydrothiophene 1,1-dioxide with reaction time of 3 days. The yield is about 93%.
When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed and may cause sensitisation by inhalation and skin contact. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, do not breathe dust and avoid contact with skin and eyes.
You can still convert the following datas into molecular structure:
(1)SMILES: Clc1c(Cl)c(Cl)nc(Cl)c1Cl
(2)InChI: InChI=1/C5Cl5N/c6-1-2(7)4(9)11-5(10)3(1)8
(3)InChIKey: DNDPLEAVNVOOQZ-UHFFFAOYAW
(4)Std. InChI: InChI=1S/C5Cl5N/c6-1-2(7)4(9)11-5(10)3(1)8
(5)Std. InChIKey: DNDPLEAVNVOOQZ-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 235mg/kg (235mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ANTIPSYCHOTIC LIVER: FATTY LIVER DEGERATION | Toxicology and Applied Pharmacology. Vol. 11, Pg. 361, 1967. |
rat | LD50 | oral | 435mg/kg (435mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | National Technical Information Service. Vol. OTS0536503, |
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