N-(tert-butoxycarbonyl)-4-(dihydroxyboryl)-1-phenylalanine
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride In water; acetone at 55℃; for 1.5h; | 93.2% |
With hydrogenchloride In water; acetone for 4h; Heating; | 70.18% |
With sulfuric acid In 1,4-dioxane at 20℃; for 1h; Hydrolysis; | 67% |
4-borono-N,N-dibenzyl-L-phenylalanine benzyl ester
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride; 5%-palladium/activated carbon; hydrogen In ethanol; water at 60℃; under 3750.38 - 9000.9 Torr; Reagent/catalyst; Temperature; Autoclave; | 91% |
With hydrogenchloride; hydrogen; palladium dihydroxide In ethanol at 20℃; for 19h; Hydrogenolysis; | 44% |
water
(4S)-3-t-butyloxycarbonyl-4-[4-(2,3-dimethyl-2,3-butanediolatoboryl)benzyl]-5-oxazolidinone
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
With sodium hydroxide; sodium periodate; sulfuric acid In 1,4-dioxane; water; acetone 1) NaIO4, NH4OAc, acetone/water, room temp., 48 h; 2) aq. NaOH, 1 h; 3)aq. H2SO4, 1,4-dioxane, room temp., 1 h; removal of solvent, neutralization with aq. NaOH; | 67% |
N-benzyloxycarbonyl-4-borono-L-phenylalanine
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; palladium dihydroxide In ethanol at 20℃; for 19h; Hydrogenolysis; | 63% |
hydrogen
N-benzyloxycarbonyl-4-borono-L-phenylalanine
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol Pd(OH)2/C, room temp., 19 h; filtration, neutralization to pH 7.0 (aq. NaOH), filtration of solid, washing with water; | 63% |
hydrogen
4-borono-N,N-dibenzyl-L-phenylalanine benzyl ester
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol Pd(OH)2/C, room temp., 19 h; filtration, neutralization to pH 7.0 (aq. NaOH), filtration of solid, washing with water; | 44% |
benzyl N-carbobenzyloxy-L-tyrosine
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 99.8 percent / triethylamine / CH2Cl2 / 28 h / 0 - 20 °C 2: 58 percent / Et3N / [PdCl2(PPh3)2] / dioxane / Heating 3: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 4: 207 mg / aq. NaOH / 1 h 5: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme |
4-iodo-L-phenylalanine
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 57 percent / NaCO3 / H2O / 24 h / 130 °C 2: 84 percent / Et3N / [PdCl2(dppf)] / dioxane / 36 h / 80 °C 3: 81 percent / NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 4: 44 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydroxide / 1,4-dioxane; water / 19 °C 1.2: 8 h / 0 - 30 °C 2.1: 1,5-bis(methylamino)-3-oxapentane; tert-butylmagnesium chloride; sodium hydride / mineral oil; tetrahydrofuran / 22.5 h / 0 - 30 °C / Inert atmosphere 3.1: hydrogenchloride / water; acetone / 4 h / Heating View Scheme |
N-<(Benzyloxy)carbonyl>-4-iodo-L-phenylalanine
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 97 percent / p-TsOH*H2O / toluene / 3 h / Heating 2: 72 percent / Et3N / [PdCl2(dppf)] / dioxane / 27 h / 80 °C 3: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 4: 1.30 g / aq. NaOH / 1 h 5: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: 96 percent / Cs2CO3 / methanol; dimethylformamide / 2 h / 20 °C 2: 82 percent / Et3N / [PdCl2(dppf)] / dioxane / 100 °C 3: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 4: 207 mg / aq. NaOH / 1 h 5: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme |
L-Nα-Cbz-4-(O-trifluoromethanesulfonate)tyrosine benzyl ester
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 5 percent / Et3N / [PdCl2(dppf)] / dioxane / 80 °C 2: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 3: 207 mg / aq. NaOH / 1 h 4: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme |
(4S)-3-benzyloxycarbonyl-4-(4-iodobenzyl)-5-oxazolidinone
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 72 percent / Et3N / [PdCl2(dppf)] / dioxane / 27 h / 80 °C 2: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 3: 1.30 g / aq. NaOH / 1 h 4: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme |
C18H18BNO6
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.30 g / aq. NaOH / 1 h 2: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme |
N-benzyloxycarbonyl-4-iodo-L-phenylalanine benzyl ester
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 82 percent / Et3N / [PdCl2(dppf)] / dioxane / 100 °C 2: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 3: 207 mg / aq. NaOH / 1 h 4: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme |
(4S)-3-benzyloxycarbonyl-4-[4-(2,3-dimethyl-2,3-butanediolatoboryl)benzyl]-5-oxazolidinone
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 2: 1.30 g / aq. NaOH / 1 h 3: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme |
4-iodo-N,N-dibenzyl-L-phenylalanine benzyl ester
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 84 percent / Et3N / [PdCl2(dppf)] / dioxane / 36 h / 80 °C 2: 81 percent / NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 3: 44 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: Bis<2-(N,N-dimethylamino)aethyl>aether; isopropylmagnesium chloride / tetrahydrofuran / 0 - 5 °C 1.2: 4 h / -20 °C 2.1: hydrogenchloride 3.1: hydrogenchloride; 5%-palladium/activated carbon; hydrogen / ethanol; water / 60 °C / 3750.38 - 9000.9 Torr / Autoclave View Scheme |
benzyl (S)-2-[(benzyloxycarbonyl)amino]-3-[4-(borono)phenyl]propionate
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 207 mg / aq. NaOH / 1 h 2: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme |
N-benzyloxycarbonyl-4-(2,3-dimethyl-2,3-butanediolatoboryl)-L-phenylalanine benzyl ester
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 2: 207 mg / aq. NaOH / 1 h 3: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme |
N,N-dibenzyl-4-(2,3-dimethyl-2,3-butanediolatoboryl)-L-phenylalanine benzyl ester
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 81 percent / NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 2: 44 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme |
Cbz-Tyr(Nf)-OBzl
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 58 percent / Et3N / [PdCl2(PPh3)2] / dioxane / Heating 2: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 3: 207 mg / aq. NaOH / 1 h 4: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme |
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / 20 - 25 °C / pH 3 - 4 2: hydrogenchloride / acetone; water / 1.5 h / 55 °C View Scheme |
N-Boc-4-I-Phe-OH
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: n-butyllithium / 2-methyltetrahydrofuran; hexane / 2.5 h / -85 - -76 °C 2: hydrogenchloride / 20 - 25 °C / pH 3 - 4 3: hydrogenchloride / acetone; water / 1.5 h / 55 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1,5-bis(methylamino)-3-oxapentane; tert-butylmagnesium chloride; sodium hydride / mineral oil; tetrahydrofuran / 22.5 h / 0 - 30 °C / Inert atmosphere 2: hydrogenchloride / water; acetone / 4 h / Heating View Scheme |
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride 2: hydrogenchloride; 5%-palladium/activated carbon; hydrogen / ethanol; water / 60 °C / 3750.38 - 9000.9 Torr / Autoclave View Scheme |
4-chloro-6-(2,2,2-trifluoro-1-(3'-fluoro-[1,1'-biphenyl]-4-yl)ethoxy)pyrimidin-2-amine
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Stage #1: 4-chloro-6-(2,2,2-trifluoro-1-(3'-fluoro-[1,1'-biphenyl]-4-yl)ethoxy)pyrimidin-2-amine; p-borono-L-phenylalanine With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 150℃; for 0.116667h; Suzuki Coupling; Microwave irradiation; Stage #2: With sodium hydroxide In water Stage #3: With hydrogenchloride In diethyl ether; water at 0℃; for 0.5h; pH=6.5; | 99% |
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 150℃; for 0.116667h; Suzuki coupling; Microwave irradiation; |
Conditions | Yield |
---|---|
With N-chloro-succinimide; sodium hydrogencarbonate In water at 20℃; for 0.5h; Reagent/catalyst; | 95% |
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
With N-Bromosuccinimide; [123I] sodium iodide; sodium hydrogencarbonate; sodium hydroxide In water at 20℃; for 0.5h; | 93% |
p-borono-L-phenylalanine
6-chloropurine
Conditions | Yield |
---|---|
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; acetonitrile at 150℃; for 0.0833333h; Suzuki-Miyaura cross-coupling; microwave irradiation; | 90% |
p-borono-L-phenylalanine
7-deaza-2'-deoxy-7-iodoadenosine
Conditions | Yield |
---|---|
With sodium carbonate; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 100℃; for 1h; Suzuki-Miyaura cross-coupling reaction; | 89% |
p-borono-L-phenylalanine
L-tyrosine
Conditions | Yield |
---|---|
With sodium L-ascorbate; fluorescein free acid In aq. phosphate buffer for 0.5h; pH=7.4; Irradiation; | 85% |
6-Chloropurine riboside
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; acetonitrile at 150℃; for 0.0166667h; Suzuki-Miyaura cross-coupling; microwave irradiation; | 84% |
p-borono-L-phenylalanine
8-bromoadenine
Conditions | Yield |
---|---|
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; acetonitrile at 150℃; for 0.0833333h; Suzuki-Miyaura cross-coupling; microwave irradiation; | 84% |
1-Fluoro-2-iodobenzene
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 150℃; Suzuki coupling; Irradiation; | 81% |
Conditions | Yield |
---|---|
hydrogenchloride | 80% |
5-Iodo-2'-deoxyuridine
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
With sodium carbonate; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 100℃; for 1.5h; Suzuki-Miyaura cross-coupling reaction; | 78% |
p-borono-L-phenylalanine
8-bromoadenosine
Conditions | Yield |
---|---|
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; acetonitrile at 150℃; for 0.0833333h; Suzuki-Miyaura cross-coupling; microwave irradiation; | 76% |
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In acetonitrile at 90℃; for 2h; Suzuki coupling; | 71% |
p-borono-L-phenylalanine
8-bromo-2'-deoxyadenosine
Conditions | Yield |
---|---|
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In acetonitrile at 90℃; Suzuki coupling; | 75% |
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; acetonitrile at 90℃; for 2h; Suzuki-Miyaura cross-coupling; | 75% |
With sodium carbonate; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 90℃; for 2h; Suzuki-Miyaura cross-coupling reaction; | 75% |
4-chloro-6-[R-2,2,2-trifluoro-1-(5-fluoro-2-(3-methylpyrazol-1-yl)phenyl)ethoxy]pyrimidin-2-ylamine
p-borono-L-phenylalanine
(S)-2-amino-3-[4-(2-amino-6-{(R)-2,2,2-trifluoro-1-[5-fluoro-2-(3-methyl-pyrazol-1-yl)-phenyl]-ethoxy}-pyrimidin-4-yl)-phenyl]-propionic acid
Conditions | Yield |
---|---|
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 160℃; for 0.166667h; Microwave irradiation; | 75% |
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 160℃; for 0.166667h; Microwave irradiation; Sealed tube; | 1.163 g |
p-borono-L-phenylalanine
2-chloro-1-methyl-benzimidazole
Conditions | Yield |
---|---|
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 150℃; for 0.0833333h; Suzuki coupling; Irradiation; | 73% |
di-tert-butyl dicarbonate
p-borono-L-phenylalanine
N-(tert-butoxycarbonyl)-4-(dihydroxyboryl)-1-phenylalanine
Conditions | Yield |
---|---|
With sodium carbonate In water; acetone at 20℃; for 24h; | 72% |
With potassium carbonate In ethanol; water at 20℃; for 0.5h; Product distribution / selectivity; | |
Stage #1: di-tert-butyl dicarbonate; p-borono-L-phenylalanine With potassium hydrogencarbonate In ethanol; water at 20℃; Stage #2: With potassium carbonate In ethanol; water at 20℃; for 2.5h; |
p-borono-L-phenylalanine
2,6-Dichlorobenzoyl chloride
(S)-2-(2,6-dichloro-benzoylamino)-3-(4-boronophenyl)-propionic acid
Conditions | Yield |
---|---|
With sodium carbonate In water; acetonitrile at 50℃; for 1h; | 71% |
With sodium carbonate In water; acetonitrile | |
Stage #1: p-borono-L-phenylalanine; 2,6-Dichlorobenzoyl chloride With sodium carbonate In water; acetonitrile at 50℃; for 1h; Stage #2: With hydrogenchloride; water In acetonitrile at 0℃; for 0.5h; pH=2; | |
With sodium carbonate In acetonitrile |
2-bromofuran
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In acetonitrile at 150℃; for 0.5h; Suzuki Coupling; Microwave irradiation; | 70% |
9-(2-deoxy-β-D-erythro-pentofuranosyl)-7-iodo-7-deazapurine 5'-O-triphosphate
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
With caesium carbonate; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 110℃; for 0.5h; Suzuki-Miyaura cross-coupling reaction; | 66% |
5-bromo-furan-2-carboxylic acid
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In acetonitrile at 150℃; for 0.5h; Suzuki Coupling; Microwave irradiation; | 64% |
6-chloropurine-2'-deoxyriboside
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; acetonitrile at 90℃; for 1.5h; Suzuki-Miyaura cross-coupling; | 63% |
(5-bromo-pyrazin-2-yl)-(4'-methyl-biphenyl-2-ylmethyl)-amine
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Stage #1: (5-bromo-pyrazin-2-yl)-(4'-methyl-biphenyl-2-ylmethyl)-amine; p-borono-L-phenylalanine With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 150℃; for 0.0833333h; Suzuki Coupling; Microwave irradiation; Stage #2: Acidic conditions; | 63% |
C18H18ClN5O
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Stage #1: C18H18ClN5O; p-borono-L-phenylalanine With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 150℃; for 0.0833333h; Suzuki Coupling; Microwave irradiation; Stage #2: With trifluoroacetic acid In methanol; water | 63% |
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In acetonitrile at 150℃; for 0.166667h; Suzuki coupling; Microwave irradiation; |
9-benzyl-6-chloro-9H-purine
p-borono-L-phenylalanine
Conditions | Yield |
---|---|
Stage #1: 9-benzyl-6-chloro-9H-purine; p-borono-L-phenylalanine With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 4h; Stage #2: With hydrogenchloride In 1,4-dioxane; water | 61% |
p-borono-L-phenylalanine
2-chloro-1-methyl-1H-indole-3-carbonitrile
Conditions | Yield |
---|---|
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 150℃; for 0.166667h; Suzuki coupling; Irradiation; | 60% |
The L-Phenylalanine,4-borono-, with the CAS registry number 76410-58-7, has the systematic name and IUPAC name of 4-(dihydroxyboranyl)-L-phenylalanine. It is a kind of white to off-white powder, and belongs to the product category of Boronic Acids. And the molecular formula of the chemical is C9H12BNO4. What's more, it should be stored at 2-8°C. Neutron absorbing (10)B-cpd used in thermal neutron capturetherapy of malignant melanoma. It is a white to off-white powder.
The characteristics of 4-Borono-L-phenylalanine are as followings:
(1)ACD/LogP: 0.49; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -2.01; (4)ACD/LogD (pH 7.4): -2.05; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 48 Å2; (13)Index of Refraction: 1.59; (14)Molar Refractivity: 52.42 cm3; (15)Molar Volume: 155.1 cm3; (16)Polarizability: 20.78×10-24cm3; (17)Surface Tension: 64.6 dyne/cm; (18)Density: 1.34 g/cm3; (19)Flash Point: 225.5 °C; (20)Enthalpy of Vaporization: 74.61 kJ/mol; (21)Boiling Point: 449.3 °C at 760 mmHg; (22)Vapour Pressure: 7.39E-09 mmHg at 25°C.
Safety Information of 4-Borono-L-phenylalanine :
You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C(O)[C@@H](N)Cc1ccc(cc1)B(O)O
(2)InChI: InChI=1/C9H12BNO4/c11-8(9(12)13)5-6-1-3-7(4-2-6)10(14)15/h1-4,8,14-15H,5,11H2,(H,12,13)/t8-/m0/s1
(3)InChIKey: NFIVJOSXJDORSP-QMMMGPOBBD
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