gemcitabine
gemcitabine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water; isopropyl alcohol at 20 - 70℃; | 93.4% |
With hydrogenchloride In water; acetone at 20℃; for 2h; Product distribution / selectivity; | 91.5% |
With hydrogenchloride In isopropyl alcohol at 0 - 5℃; for 2h; pH=2; | 90% |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water; acetone at 20℃; for 2h; Product distribution / selectivity; | 91.9% |
With hydrogenchloride In water; acetone at 20℃; for 2h; Product distribution / selectivity; | 91.9% |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water; acetone at 20℃; for 2h; Product distribution / selectivity; | 91.5% |
With hydrogenchloride In water; acetone at 20℃; for 2h; Product distribution / selectivity; | 91.5% |
(2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Stage #1: (2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate With ammonia In methanol at 20℃; for 6h; Inert atmosphere; Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20℃; pH=2; Heating; | 90% |
With sodium methylate In methanol at 20℃; for 4h; Reagent/catalyst; | 90% |
Stage #1: (2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate With ammonium hydroxide In methanol at 20℃; for 16h; Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20℃; | 78% |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water; acetone at 0 - 5℃; Green chemistry; Industrial scale; | 88% |
3′,5′-O-bis(tert-butoxycarbonyl)-gemcitabine
A
gemcitabine hydrochloride
Conditions | Yield |
---|---|
With sodium carbonate In methanol at 24℃; for 4h; Hydrolysis; | A 10% B 85% |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 3',5'-di-O-benzoyl-β-2'-deoxy-2',2'-difluorocytidine With ammonium hydroxide; water In methanol for 6h; Reflux; Stage #2: With hydrogenchloride In methanol; water at 20℃; for 12h; pH=3; | 85% |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Stage #1: N-1-acetyl-2-deoxy-2,2-difluorocytidine 3,5-dicinnamonate With ammonia In methanol Stage #2: With hydrogenchloride In water | 80% |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Stage #1: C30H21Cl2F2N3O7 With ammonium hydroxide In methanol at 20℃; for 16h; Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20℃; | 79% |
(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate
4-(N-trimethylsilylacetamido)-2-trimethylsiloxypyrimidine
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Stage #1: (2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate With triethylamine In tetrahydrofuran at 0 - 5℃; Stage #2: 4-(N-trimethylsilylacetamido)-2-trimethylsiloxypyrimidine With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0 - 5℃; Stage #3: In methanol at 40℃; | 50.5% |
α/β-1-(2-oxo-4-amino-1H-pyrimidin-1-yl)-2-desoxy-2,2'-difluororibose hydrochloride
gemcitabine hydrochloride
Conditions | Yield |
---|---|
In water; isopropyl alcohol at 25℃; for 2h; Purification / work up; Resolution of anomeric mixture; |
2’-deoxy-2’,2’-difluoro-cytidine
A
2'-deoxy-2',2'-difluorocytidine hydrochloride
B
gemcitabine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water; isopropyl alcohol at -4 - 60℃; for 6.5h; |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Stage #1: C26H24F2N4O8 With ammonia; water In methanol at 20℃; for 24h; Stage #2: With hydrogenchloride In water at 0 - 5℃; for 4h; Product distribution / selectivity; | n/a |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Stage #1: C26H24F2N4O8 With ammonia; water In methanol at 20℃; for 24h; Stage #2: With hydrogenchloride In water at 0 - 5℃; for 4h; Product distribution / selectivity; | n/a |
2’-deoxy-2’,2’-difluoro-cytidine
gemcitabine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; water at 10 - 68℃; for 1.5h; Product distribution / selectivity; | |
With hydrogenchloride In 1,2-dimethoxyethane; water at 10 - 68℃; for 1.5h; Product distribution / selectivity; |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 3',5'-dicinnamoyl-2'-deoxy-2',2'-difluorocytidine With methanol; ammonia at 20℃; for 4 - 6h; Stage #2: With hydrogenchloride In dichloromethane; water Product distribution / selectivity; |
4-N-Acetylcytosine
3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose
A
2'-deoxy-2',2'-difluorocytidine hydrochloride
B
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 4-N-Acetylcytosine With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In 1,2-dichloro-ethane for 3h; Heating / reflux; Stage #2: 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20 - 75℃; for 14 - 16h; Heating / reflux; Stage #3: With hydrogenchloride In water; 1,2-dichloro-ethane |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water; ethyl acetate at 20℃; Product distribution / selectivity; |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / methanol / 3 h / 20 °C / pH Ca. 7 / Reflux 2.1: ammonium hydroxide; water / methanol / 6 h / Reflux 2.2: 12 h / 20 °C / pH 3 View Scheme |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride / toluene; water / 3 h / 20 - 70 °C 2.1: triethylamine / methanol / 3 h / 20 °C / pH Ca. 7 / Reflux 3.1: ammonium hydroxide; water / methanol / 6 h / Reflux 3.2: 12 h / 20 °C / pH 3 View Scheme |
(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 2 h / 5 - 20 °C 2: 3 h / 120 °C / Heating 3: sodium t-butanolate / methanol / 2 h / 20 °C 4: hydrogenchloride / isopropyl alcohol; water / 20 - 70 °C View Scheme |
2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 3 h / 120 °C / Heating 2: sodium t-butanolate / methanol / 2 h / 20 °C 3: hydrogenchloride / isopropyl alcohol; water / 20 - 70 °C View Scheme |
3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: ethanol / 50 - 60 °C 2: 3 h / 120 °C / Heating 3: sodium t-butanolate / methanol / 2 h / 20 °C 4: hydrogenchloride / isopropyl alcohol; water / 20 - 70 °C View Scheme |
(erytro) ethyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxy propionate
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1H-imidazole / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Industrial scale 2: diisobutylaluminium hydride / toluene; methanol / -50 - -20 °C / Inert atmosphere; Industrial scale 3: binaphthol phosphonate / N,N-dimethyl-formamide / 10 h / 20 °C / Industrial scale 4: hydrogenchloride / water; acetone; ethanol / 0 - 5 °C / Green chemistry; Industrial scale View Scheme |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: diisobutylaluminium hydride / toluene; methanol / -50 - -20 °C / Inert atmosphere; Industrial scale 2: binaphthol phosphonate / N,N-dimethyl-formamide / 10 h / 20 °C / Industrial scale 3: hydrogenchloride / water; acetone; ethanol / 0 - 5 °C / Green chemistry; Industrial scale View Scheme |
gemcitabine hydrochloride
Allyl chloroformate
4-allyloxycarbonylamino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
Conditions | Yield |
---|---|
Stage #1: gemcitabine hydrochloride With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In 1,4-dioxane for 2h; Heating; Stage #2: Allyl chloroformate With 1-methyl-1H-imidazole In dichloromethane at 20℃; for 4h; Stage #3: With triethylamine In methanol at 20℃; Further stages.; | 99% |
Stage #1: gemcitabine hydrochloride With pyridine; chloro-trimethyl-silane at 0℃; for 2h; Stage #2: Allyl chloroformate at 0 - 45℃; | 70% |
tert-butyldimethylsilyl chloride
gemcitabine hydrochloride
4-amino-1-((2R,4R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3,3-difluoro-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
Conditions | Yield |
---|---|
at 20℃; | 98.5% |
With 1H-imidazole; triethylamine In N,N-dimethyl-formamide at 25℃; for 24h; | 95% |
With 1H-imidazole; triethylamine at 20℃; for 24h; Inert atmosphere; | 91% |
With 1-methyl-1H-imidazole; iodine In tetrahydrofuran; pyridine at 20℃; | 64% |
With 1H-imidazole In dichloromethane at 20℃; |
tert-butyldimethylsilyl chloride
gemcitabine hydrochloride
4-amino-1-((2R,4R,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3,3-difluoro-4-hydroxytetrahydrofuran-2-yl)pyrimidin-2(1H)-one
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; for 15h; | 98% |
With 1H-imidazole In N,N-dimethyl-formamide at 20 - 25℃; for 2h; | 93% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 12h; | 92% |
gemcitabine hydrochloride
p-toluenesulfonyl chloride
N-(1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
Stage #1: gemcitabine hydrochloride With pyridine; chloro-trimethyl-silane at 20℃; for 2h; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride at 20 - 60℃; for 20h; Inert atmosphere; | 96% |
Stage #1: gemcitabine hydrochloride With pyridine; chloro-trimethyl-silane Stage #2: p-toluenesulfonyl chloride Stage #3: With ammonia In methanol |
di-tert-butyl dicarbonate
gemcitabine hydrochloride
(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl tert-butyl carbonate
Conditions | Yield |
---|---|
With sodium carbonate In 1,4-dioxane; water at 20℃; for 50h; | 95% |
With sodium carbonate In 1,4-dioxane; water at 20℃; for 48h; | 87% |
With sodium carbonate In 1,4-dioxane; water at 20℃; for 48h; | 87% |
gemcitabine hydrochloride
Deoxydifluorouridine
Conditions | Yield |
---|---|
With acetic acid; sodium nitrite In water at 20℃; for 48h; | 95% |
Multi-step reaction with 3 steps 1: pyridine / 15 h / 25 °C 2: acetic acid / water / 14 h / Reflux 3: ammonia / methanol / 15 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: pyridine / 15 h / 25 °C 2: acetic acid / water / 14 h / Reflux 3: ammonia / methanol / 15 h / 20 °C View Scheme |
benzoyl chloride
gemcitabine hydrochloride
(2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; for 12h; Temperature; Inert atmosphere; | 93.5% |
With pyridine at 0 - 20℃; Inert atmosphere; | 93.5% |
With pyridine at 0 - 20℃; Inert atmosphere; | 93.5% |
Conditions | Yield |
---|---|
With pyridine In water at 30℃; for 22h; Inert atmosphere; | 91.2% |
di-tert-butyl dicarbonate
gemcitabine hydrochloride
3′,5′-O-bis(tert-butoxycarbonyl)-gemcitabine
Conditions | Yield |
---|---|
With potassium hydroxide In 1,4-dioxane at 24℃; Substitution; | 90% |
With potassium hydroxide In 1,4-dioxane at 22℃; for 2h; Inert atmosphere; | 71% |
With potassium hydroxide In 1,4-dioxane; water at 4 - 22℃; for 1h; Inert atmosphere; | 71% |
benzoyl chloride
gemcitabine hydrochloride
N4-benzoyl-2'-deoxy-2',2'-difluorocytidine
Conditions | Yield |
---|---|
Stage #1: gemcitabine hydrochloride With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 2.5h; Reflux; Stage #2: benzoyl chloride With 1-methyl-1H-imidazole In dichloromethane at 20℃; for 3h; Stage #3: With triethylamine In methanol; dichloromethane at 20℃; for 1.5h; | 83% |
Stage #1: gemcitabine hydrochloride With pyridine; chloro-trimethyl-silane at 0 - 20℃; for 0.5h; Stage #2: benzoyl chloride at 0 - 20℃; | 76% |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
With pyridine at 50℃; for 20h; Inert atmosphere; | 80.1% |
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Stage #1: gemcitabine hydrochloride With water; bromine at 0 - 5℃; for 1h; Stage #2: With tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine In hexane at 0 - 60℃; for 1h; Reagent/catalyst; Temperature; | 70.8% |
gemcitabine hydrochloride
11-azidoundecanoic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 65℃; Inert atmosphere; | 70% |
Conditions | Yield |
---|---|
With pyridine In dimethyl sulfoxide at 20℃; for 24h; | 68.6% |
(N-(methacryloyl)glycylphenylalanylleucylglycyl)thiazolidine-2-thione
gemcitabine hydrochloride
N-methacyloylglycylphenylalanylleucylglycyl-gemcitabine
Conditions | Yield |
---|---|
With pyridine at 50℃; for 12h; Inert atmosphere; | 66.1% |
With pyridine at 50℃; for 12h; Inert atmosphere; | 66.1% |
10-undecenoic acid
gemcitabine hydrochloride
4-N-(10-undecenoyl)-2'-deoxy-2',2'-difluorocytidine
Conditions | Yield |
---|---|
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide; N,N-dimethyl-formamide at 20 - 65℃; Inert atmosphere; | 66% |
gemcitabine hydrochloride
N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid
Conditions | Yield |
---|---|
Stage #1: N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 0.5h; Cooling with ice; Stage #2: gemcitabine hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; | 65% |
3-(tert-butyloxycarbonylamino)propionic acid
gemcitabine hydrochloride
Conditions | Yield |
---|---|
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide; N,N-dimethyl-formamide Inert atmosphere; Heating; | 65% |
12-hydroxydodecanoic acid
4-Nitrophenyl chloroformate
gemcitabine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 12-hydroxydodecanoic acid; 4-Nitrophenyl chloroformate With pyridine; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 5h; Stage #2: gemcitabine hydrochloride With triethylamine In N,N-dimethyl-formamide for 24h; | 64.3% |
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 25℃; for 18h; Inert atmosphere; | 63% |
Stage #1: 3-(tritylthio) propanoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: gemcitabine hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 0.408333h; | 45% |
Conditions | Yield |
---|---|
Stage #1: gemcitabine hydrochloride With pyridine; chloro-trimethyl-silane In acetonitrile at 0 - 20℃; for 4h; Stage #2: hex-5-ynoic acid With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile at 60℃; for 18h; Stage #3: With ethanol at 45℃; for 4h; | 63% |
The Gemcitabine hydrochloride, with the CAS registry number 122111-03-9, is also known as 4-Amino-1-[3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-pyrimidin-2-one hydrochloride. It belongs to the product categories of Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals.This chemical's molecular formula is C20H24O2 and molecular weight is 296.40. What's more,Its systematic name is Cytidine,2'-deoxy-2',2'-difluor-,monohydrochloride. Ii is a White crystalline granular, odorless. Gemcitabine hydrochloride is approved by the Food and Drug Administration (FDA) to be used by itself to treat pancreatic cancer that is advanced or has metastasized (spread to other parts of the body). It is used in patients who cannot be treated with surgery and have already been treated with other chemotherapy.[National Cancer Institute].
Physical properties about Gemcitabine hydrochloride are:
(1)#H bond acceptors: 7; (2)#H bond donors: 4 ; (3)#Freely Rotating Bonds: 4; (4)Polar Surface Area: 108.38 Å2; (5)Flash Point: 255.1 °C; (6)Enthalpy of Vaporization: 88.26 kJ/mol ; (7)Boiling Point: 498.2 °C at 760 mmHg; (8)Vapour Pressure: 5.15E-12 mmHg at 25°C.(9)Melting Point: >250°C dec; (10)Appearance: White crystalline granular, odorless.
Safety Information of Gemcitabine hydrochloride:
The Gemcitabine hydrochloride is harmful in contact with skin,may cause heritable genetic damage,possible risk of impaired fertility, and possible risk of harm to the unborn child.It is irritating to eyes and skin.Avoid contact with eyes.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.When you use it wear suitable protective clothing and gloves.Avoid exposure - obtain special instruction before use.
Uses of Gemcitabine hydrochloride:
Gemcitabine hydrochloride can be used as an antineoplastic. It is a chemotherapy drug that is given as a treatment for some types of cancer. Gemcitabine hydrochloride is most commonly used to treat non small cell lung cancer, pancreatic,bladder cancer and breast cancer.
You can still convert the following datas into molecular structure:
(1)SMILES:Cl.N/C1=N/C(=O)N(/C=C1)C2O[C@H](CO)[C@@H](O)C2(F)F;
(2)Std. InChI:InChI=1S/C9H11F2N3O4.ClH/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17;/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17);1H/t4-,6-,7?;/m1./s1;
(3)Std. InChIKey:OKKDEIYWILRZIA-UNPZIQMISA-N.
The toxicity data of Gemcitabine hydrochloride as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 500mg/kg (500mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 391, 2000. | |
rat | LD50 | intravenous | 236mg/kg (236mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 391, 2000. | |
women | TDLo | parenteral | 300mg/kg/12W- (300mg/kg) | LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)" LUNGS, THORAX, OR RESPIRATION: CONSOLIDATION LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Cancer Vol. 80, Pg. 286, 1997. |
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