2,2-dimethyl-5-(phenyl-λ3-iodaneylidene)-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
iodobenzene
C
acetone
Conditions | Yield |
---|---|
With dirhodium tetraacetate In dichloromethane at 20℃; Product distribution; | A 33% B 100% C 5% |
A
cycl-isopropylidene malonate
B
1,1-bis(4-t-butylphenyl)methane
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 99% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 98% |
5-(bis(4-methoxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
4,4'-dianisylmethane
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 96% |
A
cycl-isopropylidene malonate
B
1-benzyl-4-tert-butylbenzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 96% |
A
cycl-isopropylidene malonate
B
m-benzylanisole
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 95% |
6,6-dimethyl-4,8-dioxo-5,7-dioxa-1,2-diazaspiro<2.5>oct-1-ene
cycl-isopropylidene malonate
Conditions | Yield |
---|---|
With benzophenone In methanol Irradiation; | 93% |
A
cycl-isopropylidene malonate
B
bis(3-methoxyphenyl)methane
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 93% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 65℃; under 760.051 Torr; for 96h; Sealed tube; | A n/a B 91% |
2,2-dimethyl-5-(2-(4-(octyloxy)phenyl)hexan-2-yl)-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
1-(hexan-2-yl)-4-(octyloxy)benzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 90% |
2,2-dimethyl-5-(2-(2-(octyloxy)phenyl)propan-2-yl)-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
1-isopropyl-2-(octyloxy)benzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 48h; | A n/a B 90% |
A
cycl-isopropylidene malonate
B
1-butyl-4-(1-methylethyl)benzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 90% |
2,2-dimethyl-5-(2-(4-(octyloxy)phenyl)butan-2-yl)-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
1-(sec-butyl)-4-octyloxybenzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 86% |
5-[1-(2-ethylphenyl)-1-methylethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
1-ethyl-2-isopropylbenzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 83% |
2,2-dimethyl-5(1-(4-(octyloxy)phenyl)cyclohexyl)-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
1-cyclohexyl-4-(octyloxy)benzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 82% |
A
cycl-isopropylidene malonate
B
1-isopropoxy-4-isopropylbenzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 82% |
5-((4-fluorophenyl)(4-methoxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
1-(4-fluorobenzyl)-4-methoxybenzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 81% |
5-((4-fluorophenyl)(phenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
4-fluorodiphenylmethane
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 81% |
A
cycl-isopropylidene malonate
B
1-isopropyl-4-neopentylbenzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 81% |
2,2-dimethyl-5-(1-methyl-1-phenylethyl)-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
Isopropylbenzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A 80% B n/a |
5-(2-([1,1'-biphenyl]-4-yl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
4-isopropylbiphenyl
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 80% |
5-(2-(3-(tert-butyl)phenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
1-tert-butyl-3-isopropylbenzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 65℃; under 760.051 Torr; for 24h; Sealed tube; | A n/a B 80% |
Conditions | Yield |
---|---|
With sulfuric acid; acetic anhydride at 60℃; | 78% |
Stage #1: malonic acid With sulfuric acid; acetic anhydride at 0℃; for 1h; Stage #2: acetone In acetic anhydride at 0℃; for 30h; | 77% |
With sulfuric acid; acetic anhydride at -5 - 0℃; for 3h; | 70.9% |
2,2-dimethyl-5-(2-(4-(octyloxy)phenyl)propan-2-yl)-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
1-isopropyl-4-(octyloxy)benzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 78% |
5-(2-(4-(tert-butyl)phenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
p-tert.-Butyl-cumol
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 65℃; under 760.051 Torr; for 48h; Sealed tube; | A n/a B 76% |
A
cycl-isopropylidene malonate
B
1-isobutyl-4-isopropylbenzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 72% |
2,2-dimethyl-5-(3-methyl-2-(4-(octyloxy)phenyl)butan-2-yl)-1,3-dioxane-4,6-dione
A
cycl-isopropylidene malonate
B
1-(3-methylbutan-2-yl)-4-(octyloxy)benzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; | A n/a B 70% |
A
cycl-isopropylidene malonate
B
1-tert-butoxy-4-isopropylbenzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 48h; | A n/a B 70% |
methanol
5-diazo-2,2-dimethyl-1,3-dioxane-4,6-dion
A
6,6-dimethyl-4,8-dioxo-5,7-dioxa-1,2-diazaspiro<2.5>oct-1-ene
B
cycl-isopropylidene malonate
C
methyl 2,2-dimethyl-5-oxo-1,3-dioxolane-4-carboxylate
D
2,2-dimethyl-4,6-dioxo-5-methoxy-1,3-dioxane
Conditions | Yield |
---|---|
for 1.16667h; Product distribution; Irradiation; | A 4.5% B 3% C 64% D 2.5% |
In tetrahydrofuran at 18 - 20℃; for 9h; UV-irradiation; | A 23% B 8% C 25% D n/a |
pyrrolidine
cycl-isopropylidene malonate
2-Methylbutyraldehyde
Conditions | Yield |
---|---|
In diethyl ether for 0.166667h; | 100% |
pyrrolidine
cycl-isopropylidene malonate
d,l-2-ethylhexanal
5-(2-Ethyl-1-pyrrolidin-1-yl-hexyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione
Conditions | Yield |
---|---|
In diethyl ether for 0.166667h; | 100% |
pyrrolidine
cycl-isopropylidene malonate
benzaldehyde
2,2-Dimethyl-5-(phenyl-pyrrolidin-1-yl-methyl)-[1,3]dioxane-4,6-dione
Conditions | Yield |
---|---|
In diethyl ether for 0.166667h; | 100% |
pyrrolidine
cycl-isopropylidene malonate
propionaldehyde
2,2-Dimethyl-5-(1-pyrrolidin-1-yl-propyl)-[1,3]dioxane-4,6-dione
Conditions | Yield |
---|---|
In diethyl ether for 0.166667h; | 100% |
pyrrolidine
cycl-isopropylidene malonate
butyraldehyde
2,2-Dimethyl-5-(1-pyrrolidin-1-yl-butyl)-[1,3]dioxane-4,6-dione
Conditions | Yield |
---|---|
In diethyl ether for 0.166667h; | 100% |
pyrrolidine
cycl-isopropylidene malonate
isobutyraldehyde
2,2-Dimethyl-5-(2-methyl-1-pyrrolidin-1-yl-propyl)-[1,3]dioxane-4,6-dione
Conditions | Yield |
---|---|
In diethyl ether for 0.166667h; | 100% |
4-methyleneoxetan-2-one
cycl-isopropylidene malonate
2,2-dimethyl-5-(1-hydroxy-3-oxobutylidene)-1,3-dioxane-4,6-dione
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 2h; | 100% |
Stage #1: 4-methyleneoxetan-2-one; cycl-isopropylidene malonate With triethylamine In dichloromethane at 0 - 20℃; for 2h; Stage #2: With hydrogenchloride In dichloromethane; water | 100% |
With triethylamine In dichloromethane at 20℃; | 100% |
cycl-isopropylidene malonate
1,1-bis(phenylsulfonyl)ethylene
5-(2,2-Bis-benzenesulfonyl-ethyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione
Conditions | Yield |
---|---|
N-benzyl-trimethylammonium hydroxide In 1,4-dioxane | 100% |
cycl-isopropylidene malonate
(+/-)-3-Methyl-4,4,4-trichlorobutanoyl Chloride
2,2-Dimethyl-5-(4,4,4-trichloro-3-methyl-butyryl)-[1,3]dioxane-4,6-dione
Conditions | Yield |
---|---|
With pyridine In dichloromethane 1. 1 h/-5 deg C 2. 30 min/room temperature; | 100% |
cycl-isopropylidene malonate
Rhodinoic acid chloride
5-(3,7-Dimethyl-oct-7-enoyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0℃; | 100% |
cycl-isopropylidene malonate
C18H14N4O2
2-<(4,4-dimethyl-2,6-dioxo-3,5-dioxanylidene)methyl>-3-methylindole
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 0.333333h; Ambient temperature; | 100% |
With triethylamine In tetrahydrofuran for 0.5h; Ambient temperature; Yield given; |
cycl-isopropylidene malonate
Hexanoyl chloride
2,2-dimethyl-5-(1-oxohexyl)-1,3-dioxane-4,6-dione
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 16h; Inert atmosphere; | 100% |
With pyridine In dichloromethane | 62% |
With pyridine In dichloromethane Ambient temperature; |
cycl-isopropylidene malonate
orthoformic acid triethyl ester
5-(ethoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione
Conditions | Yield |
---|---|
at 80℃; for 3h; | 100% |
With zinc diacetate at 90℃; for 1h; Condensation; | 85% |
at 105℃; for 2h; | 80% |
cycl-isopropylidene malonate
phenylacetyl chloride
5-(1-hydroxy-2-phenylethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; Acylation; | 100% |
With dmap Inert atmosphere; | 75% |
Stage #1: cycl-isopropylidene malonate With pyridine In dichloromethane at 0℃; Stage #2: phenylacetyl chloride In dichloromethane at 0 - 20℃; Stage #3: With hydrogenchloride In dichloromethane; water Cooling with ice; | 71% |
cycl-isopropylidene malonate
tert-butyl alcohol
mono-tert-butyl malonate
Conditions | Yield |
---|---|
for 6h; Reflux; | 100% |
Reflux; | 97% |
Stage #1: cycl-isopropylidene malonate; tert-butyl alcohol for 5h; Reflux; Stage #2: With ammonia; water In ethanol at 5℃; for 0.0833333h; Stage #3: With hydrogenchloride In water | 62% |
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; 4-toluenesulfonyl azide; triethylamine for 3h; Ambient temperature; | 100% |
With 2-azido-1,3-dimethylimidazolinium chloride; triethylamine In tetrahydrofuran at 0℃; for 0.166667h; | 95% |
With 2-azido-1,3-dimethylimidazolinium chloride; triethylamine In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; | 95% |
cycl-isopropylidene malonate
N-tert-butoxycarbonyl-L-phenylalanine
(S)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h; | 100% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 12h; Inert atmosphere; | 95% |
Stage #1: cycl-isopropylidene malonate; N-tert-butoxycarbonyl-L-phenylalanine With dmap In dichloromethane for 0.166667h; Cooling with ice; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane for 10h; Cooling with ice; | 77% |
cycl-isopropylidene malonate
cyclopropanecarboxylic acid chloride
5-(cyclopropyl(hydroxy)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; Acylation; | 100% |
Stage #1: cycl-isopropylidene malonate With pyridine In dichloromethane at 0℃; for 0.25h; Stage #2: cyclopropanecarboxylic acid chloride In dichloromethane at 0 - 20℃; for 3h; | 60% |
With pyridine In dichloromethane at 0 - 20℃; for 3h; Acylation; |
cycl-isopropylidene malonate
4-hydroxy-benzaldehyde
5-(4-hydroxy-benzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione
Conditions | Yield |
---|---|
at 50℃; for 1h; Knoevenagel condensation; | 100% |
In water; toluene at 23 - 33℃; for 4.66667h; Knoevenagel condensation; Large scale reaction; | 99% |
With cobalt(III) oxide In water for 0.0833333h; Knoevenagel Condensation; Reflux; | 99% |
cycl-isopropylidene malonate
4-dimethylamino-benzaldehyde
5-(4-N,N-dimethylaminobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
Conditions | Yield |
---|---|
at 50℃; for 1h; Knoevenagel condensation; | 100% |
With ethylammonium nitrate at 20℃; for 0.5h; Knoevenagel condensation; | 97% |
In various solvent(s) at 20℃; for 0.5h; Knoevenagel condensation; | 97% |
cycl-isopropylidene malonate
isopropyl alcohol
i-propyl malonic half ester
Conditions | Yield |
---|---|
In acetonitrile for 22h; Heating; | 100% |
Reflux; | 76% |
In toluene for 5h; Heating; |
cycl-isopropylidene malonate
N-tert-butoxycarbonyl-L-phenylalanine
(2'S)-5-<(1-hydroxy-3-phenyl-2-t-butoxycarbonylamino)-propylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; | 100% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; | |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; for 14h; Inert atmosphere; | |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; |
cycl-isopropylidene malonate
Boc-D-Phe-OH
5-[(2R)-2-(tert-Butoxycarbonylamino)-1-hydroxy-3-phenylpropylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; | 100% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 2h; |
cycl-isopropylidene malonate
2-methyl-benzyl alcohol
2-oxo-2H-chromene-3-carboxylic acid
Conditions | Yield |
---|---|
With piperdinium acetate In ethanol for 2h; Heating; | 100% |
With piperidine; acetic acid In benzene Knoevenagel condensation; Heating; | 92% |
With lithium perchlorate for 0.0138889h; Irradiation; | 89% |
cycl-isopropylidene malonate
3-methoxy-2-hydroxybenzaldehyde
8-methoxy-2-oxo-2H-chromene-3-carboxylic acid
Conditions | Yield |
---|---|
With piperdinium acetate In ethanol for 2h; Heating; | 100% |
In water for 1h; Reflux; | 99% |
With β‐cyclodextrin In water at 70℃; for 0.25h; Green chemistry; | 97% |
Conditions | Yield |
---|---|
In toluene at 100℃; Inert atmosphere; | 100% |
In toluene Heating; | 85% |
cycl-isopropylidene malonate
[3-(3,5-bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-benzyloxy)-5-hydroxymethyl-phenyl]-methanol
Conditions | Yield |
---|---|
at 120℃; for 4h; | 100% |
cycl-isopropylidene malonate
{3-[3,5-bis-(3,5-bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-benzyloxy)-benzyloxy]-5-hydroxymethyl-phenyl}-methanol
Conditions | Yield |
---|---|
at 120℃; for 4h; | 100% |
Conditions | Yield |
---|---|
at 120℃; for 4h; | 100% |
Reported in EPA TSCA Inventory.
ASSAY: 98.0% min
LOSS ON DRYING: 0.5% max
Meldrum's acid , its cas register number is 2033-24-1. It also can be called 2,2-Dimethyl-1,3-dioxane-4,6-dione; 2,2-Dimethyl-4,6-dioxo-m-dioxane; 2,2-Dimethyl-m-dioxane-4,6-dione; Isopropylidene malonate; m-Dioxane-4,6-dione, 2,2-dimethyl-; 1,3-Dioxane-4,6-dione, 2,2-dimethyl- ; Malonic acid, cyclic isopropylidene ester (8CI). It is a brown white solid. Meldrum's acid is an intermediate for different organic syntheses. It is an important intermediate in syntheses of vitamins B1 and B6, barbiturate, non-steroidal anti-inflammatory agent, other numerous pharmaceutical, agrochemical and flavor & fragrance compound. As an alternative to its original preparation, Meldrum's acid can be synthesized from malonic acid, isopropenyl acetate, and catalytic sulfuric acid.
Physical properties about Meldrum's acid are: (1)ACD/LogP: -1.579; (2)ACD/LogD (pH 5.5): -1.58; (3)ACD/LogD (pH 7.4): -1.58; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 3.30; (7)ACD/KOC (pH 7.4): 3.30; (8)#H bond acceptors: 4; (9)Index of Refraction: 1.434; (10)Molar Refractivity: 31.24 cm3; (11)Molar Volume: 119.95 cm3; (12)Polarizability: 12.384 10-24cm3; (13)Surface Tension: 33.2239990234375 dyne/cm; (14)Density: 1.202 g/cm3; (15)Flash Point: 195.118 °C; (16)Enthalpy of Vaporization: 60.204 kJ/mol; (17)Boiling Point: 356.749 °C at 760 mmHg
When you are using Meldrum's acid, please be cautious about it as the following:
1. Wear suitable gloves and eye/face protection;
2. Avoid contact with skin and eyes;
3. Avoid exposure - obtain special instruction before use;
4. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
5. Wear suitable protective clothing;
6. 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/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3;
(2)InChIKey=GXHFUVWIGNLZSC-UHFFFAOYSA-N;
(3)SmilesC1(OC(CC(O1)=O)=O)(C)C;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 180mg/kg (180mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04102, |
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