Conditions | Yield |
---|---|
With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In 1,2-dimethoxyethane; water at 95℃; for 20h; Catalytic behavior; Solvent; Schlenk technique; Inert atmosphere; Sealed tube; | 99% |
With copper; potassium carbonate In N,N-dimethyl acetamide at 180℃; for 40h; Schlenk technique; Inert atmosphere; | 99% |
With copper; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 42h; Inert atmosphere; | 96% |
[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate
4-bromo-aniline
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With copper diacetate; sodium carbonate In ethylene glycol; isopropyl alcohol at 90℃; for 16h; | 98.46% |
With copper diacetate; sodium carbonate; ethylene glycol In isopropyl alcohol at 85℃; for 16h; Ullmann Condensation; Inert atmosphere; | 65% |
With copper diacetate; sodium carbonate In ethylene glycol; isopropyl alcohol for 16h; Inert atmosphere; Reflux; Green chemistry; |
Conditions | Yield |
---|---|
With palladium diacetate; cesium fluoride In acetonitrile at 60℃; for 12h; Schlenk technique; | 96% |
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 150℃; for 24h; | 95% |
With potassium phosphate In N,N-dimethyl-formamide at 190℃; for 1h; Microwave irradiation; | 91% |
With caesium carbonate In dimethyl sulfoxide at 160℃; for 48h; Inert atmosphere; | 80% |
With potassium fluoride; 18-crown-6 ether In dimethyl sulfoxide for 24h; Reflux; | 68.3% |
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 66% |
N,N-diphenylaminobenzene
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With N-Bromosuccinimide In chloroform at 20℃; for 24h; | 91% |
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 16 h / 0 °C / Inert atmosphere 2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tetrakis(acetonitrile)copper(I)tetrafluoroborate; 2.9-dimethyl-1,10-phenanthroline; iodine; methyloxirane / tetrahydrofuran / 21 h / 21 °C / Flow reactor; Irradiation View Scheme |
Conditions | Yield |
---|---|
With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide at 140℃; Ullmann reaction; Inert atmosphere; | 85% |
With copper; potassium carbonate; nitrobenzene at 120 - 160℃; Inert atmosphere; | 85% |
With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In toluene at 110℃; for 24h; Inert atmosphere; sealed tube; | 83% |
1,4-bromoiodobenzene
9H-carbazole
A
N-(4-bromophenyl)carbazole
B
9-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazole
Conditions | Yield |
---|---|
With copper; potassium carbonate In Triethylene glycol dimethyl ether at 180 - 200℃; for 24h; Ullmann condensation; | A 71% B 28% |
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 111℃; for 26h; Schlenk technique; Inert atmosphere; chemoselective reaction; | A 49% B 13% |
1-azido-4-bromobenzene
2-Biphenylboronic acid
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; sodium carbonate In 1,4-dioxane at 80℃; for 12h; Schlenk technique; | 70% |
Conditions | Yield |
---|---|
With copper diacetate; palladium diacetate; caesium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 120℃; for 12h; Sealed tube; | 48% |
1.4-dibromobenzene
copper(I) iodide
9H-carbazole
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With potassium carbonate; 18-crown-6 ether | 35% |
1,3,4-trimethylimidazolidin-2-one
1.4-dibromobenzene
9H-carbazole
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With potassium carbonate; 18-crown-6 ether; copper(I) iodide | 35% |
Conditions | Yield |
---|---|
With potassium carbonate; copper(II) sulfate at 210℃; Inert atmosphere; | 31% |
4-N,N-diphenylamino-1-bromobenzene
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; 2.9-dimethyl-1,10-phenanthroline; iodine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; methyloxirane In tetrahydrofuran at 21℃; for 21h; Reagent/catalyst; Flow reactor; Irradiation; | 19% |
1,4-bromoiodobenzene
9H-carbazole
A
N-(4-bromophenyl)carbazole
B
9-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazole
C
9-(4-iodophenyl)carbazole
Conditions | Yield |
---|---|
With copper(l) iodide; 18-crown-6 ether; potassium carbonate at 175℃; for 24h; Schlenk technique; Inert atmosphere; | A 20 %Spectr. B 9% C 33 %Spectr. |
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
1.4-dibromobenzene
copper(I) iodide
9H-carbazole
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With potassium carbonate; 18-crown-6 ether |
phenylboronic acid
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / ethanol / 6 h / Reflux; Inert atmosphere 2.1: hydrazine hydrate / methanol / 2 h / 20 °C 3.1: hydrogenchloride; sodium nitrite / tetrahydrofuran; water / 0.33 h / Cooling with ice 3.2: 20 °C / Cooling with ice 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C 5.1: copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / ethanol / 6 h / Reflux 2.1: sodium nitrite; hydrogenchloride / water; tetrahydrofuran / 0 °C 2.2: Sandmeyer Reaction / 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4.1: sodium carbonate; copper diacetate / isopropyl alcohol; ethylene glycol / 16 h / Inert atmosphere; Reflux; Green chemistry View Scheme |
o-nitroiodobenzene
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / ethanol / 6 h / Reflux; Inert atmosphere 2.1: hydrazine hydrate / methanol / 2 h / 20 °C 3.1: hydrogenchloride; sodium nitrite / tetrahydrofuran; water / 0.33 h / Cooling with ice 3.2: 20 °C / Cooling with ice 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C 5.1: copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / Inert atmosphere View Scheme |
2-nitrobiphenyl
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: hydrazine hydrate / methanol / 2 h / 20 °C 2.1: hydrogenchloride; sodium nitrite / tetrahydrofuran; water / 0.33 h / Cooling with ice 2.2: 20 °C / Cooling with ice 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C 4.1: copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / Inert atmosphere View Scheme |
2-phenylaniline
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride; sodium nitrite / tetrahydrofuran; water / 0.33 h / Cooling with ice 1.2: 20 °C / Cooling with ice 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C 3.1: copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium nitrite; hydrogenchloride / water; tetrahydrofuran / 0 °C 1.2: Sandmeyer Reaction / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 3.1: sodium carbonate; copper diacetate / isopropyl alcohol; ethylene glycol / 16 h / Inert atmosphere; Reflux; Green chemistry View Scheme |
2-iodobiphenyl
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C 2: copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 2: sodium carbonate; copper diacetate / isopropyl alcohol; ethylene glycol / 16 h / Inert atmosphere; Reflux; Green chemistry View Scheme |
2-iodophenylamine
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / ethanol / 6 h / Reflux 2.1: sodium nitrite; hydrogenchloride / water; tetrahydrofuran / 0 °C 2.2: Sandmeyer Reaction / 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4.1: sodium carbonate; copper diacetate / isopropyl alcohol; ethylene glycol / 16 h / Inert atmosphere; Reflux; Green chemistry View Scheme |
2-Bromobiphenyl
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Schlenk technique 1.2: 10 h / -78 - 20 °C / Schlenk technique 1.3: 1 h / 20 °C / pH 6 - 7 / Schlenk technique 2.1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; sodium carbonate / 1,4-dioxane / 12 h / 80 °C / Schlenk technique View Scheme |
N-(4-bromophenyl)carbazole
3-bromo-9-(4-bromophenyl)-9H-carbazole
Conditions | Yield |
---|---|
With N-Bromosuccinimide at 20℃; for 12h; Inert atmosphere; | 100% |
With N-Bromosuccinimide at 20℃; | 98% |
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 12.5h; | 92% |
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
Stage #1: N-(4-bromophenyl)carbazole With methanesulfonic acid In dichloromethane at 0℃; Inert atmosphere; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 0.0166667h; Reagent/catalyst; Inert atmosphere; regioselective reaction; | 99% |
With iron(III) chloride In chloroform at 20℃; for 40h; Inert atmosphere; |
N-(4-bromophenyl)carbazole
9‐(4‐bromophenyl)‐3,6‐diiodocarbazole
Conditions | Yield |
---|---|
With potassium iodate; potassium iodide In acetic acid at 80℃; for 4h; | 98% |
With potassium iodate; acetic acid; potassium iodide for 4h; Reflux; Inert atmosphere; | 85% |
With potassium iodate; acetic acid; potassium iodide at 135℃; for 18h; | 82.22% |
N-(4-bromophenyl)carbazole
3,6-dibromo-9-(4-bromophenyl)-9H-carbazole
Conditions | Yield |
---|---|
With N-Bromosuccinimide In dichloromethane at 0℃; for 16h; Schlenk technique; Darkness; Inert atmosphere; | 98% |
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 3h; | 88% |
With N-Bromosuccinimide at 0℃; for 8h; Darkness; | 87% |
5-(phenylthio)quinolin-8-amine
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With potassium carbonate; nickel dichloride In tetrahydrofuran at 100℃; for 24h; Inert atmosphere; | 97% |
N-(4-bromophenyl)carbazole
bis(pinacol)diborane
9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium diacetate In dimethyl sulfoxide at 80℃; for 8h; Inert atmosphere; | 96.8% |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 85℃; for 48h; | 87% |
Stage #1: N-(4-bromophenyl)carbazole; bis(pinacol)diborane With potassium acetate In dimethyl sulfoxide at 60℃; for 0.25h; Stage #2: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dichloromethane; dimethyl sulfoxide at 80℃; for 6h; | 86% |
Conditions | Yield |
---|---|
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; tetrabutylammomium bromide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; zinc In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; | 96% |
8-amino quinoline
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With sodium hydroxide; nickel dichloride In N,N-dimethyl-formamide at 150℃; for 16h; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique; | 96% |
With potassium carbonate; nickel dibromide In tetrahydrofuran at 100℃; for 24h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; | 95% |
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With 1,1'-bis(diisopropylphosphino)ferrocene; Pd(dippf)maleimide; sodium t-butanolate In toluene at 120℃; for 24h; Inert atmosphere; | 95% |
N-(4-bromophenyl)carbazole
N-(4-hydroxyphenyl)carbazole
Conditions | Yield |
---|---|
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 36h; Glovebox; Irradiation; Inert atmosphere; | 95% |
With oxygen; triethylamine; sodium iodide In acetonitrile at 32℃; for 24h; Schlenk technique; UV-irradiation; | 40% |
4-phenyl-8-aminoquinoline
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With nickel dichloride; sodium t-butanolate In water; N,N-dimethyl-formamide at 150℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique; | 95% |
With nickel(II) sulphate; caesium carbonate In acetonitrile at 100℃; for 24h; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene at 120℃; for 12h; Inert atmosphere; | 94% |
N-(4-bromophenyl)carbazole
4,4'-bis(9H-carbazol-9-yl)biphenyl
Conditions | Yield |
---|---|
Stage #1: N-(4-bromophenyl)carbazole With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Inert atmosphere; Stage #2: With copper(l) cyanide In tetrahydrofuran; pentane at -78 - 25℃; Inert atmosphere; Stage #3: In tetrahydrofuran; pentane at 25℃; for 3h; Inert atmosphere; | 93% |
Allylchlorodimethylsilane
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
Stage #1: N-(4-bromophenyl)carbazole With n-butyllithium In tetrahydrofuran; acetone at -78℃; for 3h; Inert atmosphere; Stage #2: Allylchlorodimethylsilane In tetrahydrofuran at 20℃; | 93% |
6-methoxyquinolin-8-amine
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With nickel(II) fluoride; potassium carbonate In tetrahydrofuran at 100℃; for 24h; Inert atmosphere; | 93% |
With nickel dichloride; sodium t-butanolate In water; N,N-dimethyl-formamide at 150℃; for 16h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique; | 83% |
5-phenylquinoline-8-amine
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With nickel dichloride; sodium t-butanolate In water; N,N-dimethyl-formamide at 150℃; for 16h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique; | 93% |
With nickel(II) fluoride; potassium carbonate In tetrahydrofuran at 100℃; for 24h; Inert atmosphere; | 91% |
2,3-dimethyl-2,3-butane diol
Triisopropyl borate
N-(4-bromophenyl)carbazole
9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole
Conditions | Yield |
---|---|
Stage #1: N-(4-bromophenyl)carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran; hexane at 20℃; for 69h; Schlenk technique; Inert atmosphere; | 93% |
Stage #1: N-(4-bromophenyl)carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Schlenk technique; Sealed tube; Stage #2: Triisopropyl borate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Sealed tube; Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran at 20℃; for 69h; Inert atmosphere; Schlenk technique; | 67% |
N-(4-bromophenyl)carbazole
C22H17N3
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 24h; Buchwald-Hartwig Coupling; Inert atmosphere; Reflux; | 92% |
9,9″-diphenyl-9H,9′H,9″H-3,3':6′,3″-tercarbazole
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 10h; Inert atmosphere; Reflux; | 92% |
N-(4-bromophenyl)carbazole
p-toluidine
9-[4-(4-methylphenylamino)phenyl]-9H-carbazole
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene at 108℃; for 2h; Inert atmosphere; | 92% |
N-(4-bromophenyl)carbazole
Conditions | Yield |
---|---|
With nickel dichloride; sodium t-butanolate In water; N,N-dimethyl-formamide at 150℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique; | 92% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere; | 92% |
N-phenyl-N-[4-(9-phenylcarbazole-3-yl)phenyl]amine
N-(4-bromophenyl)carbazole
4-(9H-carbazol-9-yl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In hexane; toluene at 80℃; for 5h; Inert atmosphere; | 91% |
N-(4-bromophenyl)carbazole
2-phenylaniline
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 6h; Inert atmosphere; Reflux; | 91% |
N-(4-bromophenyl)carbazole
4-fluorobenzoyl chloride
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 12h; Friedel-Crafts Acylation; | 91% |
The 9-(4-Bromophenyl)carbazole, with the CAS registry number 57102-42-8, is also known as N-(4-bromophenyl)carbazole. This chemical's molecular formula is C18H12BrN and formula weight is 322.20. What's more, both its IUPAC name and systematic name are the same which is called 9-(4-Bromophenyl)carbazole.
Physical properties about this chemical are: (1)ACD/LogP: 6.97; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.97; (4)ACD/LogD (pH 7.4): 6.97; (5)ACD/BCF (pH 5.5): 116447.37; (6)ACD/BCF (pH 7.4): 116447.37; (7)ACD/KOC (pH 5.5): 147202.06; (8)ACD/KOC (pH 7.4): 147202.06; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.672; (13)Molar Refractivity: 86.81 cm3; (14)Molar Volume: 231.6 cm3; (15)Surface Tension: 47.3 dyne/cm; (16)Density: 1.39 g/cm3; (17)Flash Point: 227.6 °C; (18)Enthalpy of Vaporization: 71.19 kJ/mol; (19)Boiling Point: 452.7 °C at 760 mmHg; (20)Vapour Pressure: 2.2E-08 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3N2C4=CC=C(C=C4)Br
(2)InChI: InChI=1S/C18H12BrN/c19-13-9-11-14(12-10-13)20-17-7-3-1-5-15(17)16-6-2-4-8-18(16)20/h1-12H
(3)InChIKey: XSDKKRKTDZMKCH-UHFFFAOYSA-N
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