Conditions | Yield |
---|---|
In water at 46 - 100℃; Acidic ion exchange resin; | A 98.2% B 0.6% |
Katapak-catalyst In water at 46 - 100℃; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With sulfuric acid for 5h; Reagent/catalyst; Reflux; | 96% |
ion exchange resin with sulphonic acid groups In water at 70℃; for 0.2h; Industry scale; | 95.9% |
ion-exchange resines In water Product distribution; continuous apparatus (rectification of the formed methylal); |
1-(methoxymethyl)-2-pyrrolidinone
chloromethyl methyl ether
A
1-(chloromethyl)pyrrolidin-2-one
B
Dimethoxymethane
Conditions | Yield |
---|---|
Heating; | A 96% B n/a |
dimethyldimethoxysilan
2,2-dimethyl-[1,3,2]dioxasilinane
A
Dimethoxymethane
B
2,2,4,4,6-Pentamethyl-1,3-dioxa-2-silacyclohexane
Conditions | Yield |
---|---|
With tin(IV) chloride at 65℃; Product distribution; other reaction conditions; also with 1,3-dioxane and 4,4-dimethyl-1,3-dioxane; | A n/a B 94% |
methanol
phenylacetylene
A
benzoic acid methyl ester
B
Dimethoxymethane
Conditions | Yield |
---|---|
With bis-[(trifluoroacetoxy)iodo]benzene at 60℃; for 15h; Time; Reagent/catalyst; Concentration; Temperature; Sealed tube; | A 82% B n/a |
Dimethyl ether
A
methanol
B
formaldehyd
C
Dimethoxymethane
D
Methyl formate
Conditions | Yield |
---|---|
With nitrogen; oxygen at 239.84℃; Conversion of starting material; | A 19.4% B 79% C 0.1% D 1.6% |
With nitrogen; oxygen at 199.84 - 259.84℃; Rate constant; | A 17.3% B 69.2% C 0% D 1.6% |
With nitrogen; oxygen at 239.84℃; Conversion of starting material; | A 22.4% B 60.1% C 0% D 5% |
methanol
dichloromethane
carbon monoxide
A
Dimethoxymethane
B
acetic acid methyl ester
C
methyl methoxyacetate
D
malonic acid dimethyl ester
Conditions | Yield |
---|---|
With Methyl formate; sodium methylate; Co2(CO)6{P(C4H9-n)3}2 at 80℃; under 11250.9 Torr; for 15h; electrolysis; | A 8% B n/a C 3% D 74.5% |
With Methyl formate; sodium methylate; Co2(CO)6{P(C4H9-n)3}2 at 80℃; under 11250.9 Torr; for 15h; Product distribution; Mechanism; electrolysis, var. of catalyst, its reduction method, ratio; | A 8% B n/a C 3% D 74.5% |
With sodium hydroxide; carbon-doped cobalt at 80℃; under 23560 Torr; for 1h; | A 1.2 % Chromat. B 7.5 % Chromat. C 1.9 % Chromat. D 28.8 % Chromat. |
methanethiosulfonic acid S-methyl ester
A
formic acid
B
methanesulfonic acid
C
Dimethoxymethane
D
Methyl formate
Conditions | Yield |
---|---|
With oxygen In methanol Irradiation; | A n/a B 72% C n/a D n/a |
Conditions | Yield |
---|---|
With methanol; sulfuric acid Heating; | A n/a B 70% |
Conditions | Yield |
---|---|
With 4-vinylpyridine at 125℃; under 6000.6 Torr; for 2h; | 58% |
Conditions | Yield |
---|---|
With oxygen at 139.84℃; under 760.051 Torr; Reagent/catalyst; Temperature; Time; Inert atmosphere; | 50% |
With V(V) complex at 140℃; under 760.051 Torr; for 4h; Catalytic behavior; Temperature; Sealed tube; chemoselective reaction; | 9% |
With oxygen; Mo12V3W1.2Cu1.2Sb0.5Ox at 200 - 350℃; Product distribution / selectivity; Gas phase; | 1.6% |
Conditions | Yield |
---|---|
With cobalt(II) tetrafluoroborate hexahydrate; hydrogen; bis(trifluoromethanesulfonyl)amide; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 80℃; under 60006 Torr; for 22h; Catalytic behavior; Reagent/catalyst; Schlenk technique; Autoclave; | 41% |
methanol
chloroprene
A
Dimethoxymethane
B
2-chloro-3,3-dimethoxyprop-1-ene
C
methoxymethanol
D
acrylic acid methyl ester
Conditions | Yield |
---|---|
With ozone at -78℃; Further byproducts given; | A 24 % Spectr. B 40% C 75 % Spectr. D n/a |
trans-4-tert-butylcyclohexanol
chloromethyl methyl ether
A
Dimethoxymethane
C
trans-4-tert-butyl-O-(methoxymethyl)cyclohexanol
Conditions | Yield |
---|---|
Stage #1: chloromethyl methyl ether With 1H-imidazole In d7-N,N-dimethylformamide for 0.166667h; Stage #2: trans-4-tert-butylcyclohexanol for 24h; | A n/a B n/a C 40% |
methanol
2-chloro-3-methylbutadiene
A
Dimethoxymethane
B
acetic acid methyl ester
C
methacrylic acid methyl ester
D
2-Chlor-3,3-dimethoxy-1-buten
Conditions | Yield |
---|---|
With ozone at -78℃; Further byproducts given. Yields of byproduct given; | A n/a B n/a C n/a D 39% |
Conditions | Yield |
---|---|
With PHTHALIMAX S4 vanadia-titania catalyst; oxygen at 139.84℃; under 760.051 Torr; Inert atmosphere; | A 38% B n/a |
at 150℃; for 18h; Product distribution; | A 0.72 mmol B 2.24 mmol |
chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) at 20℃; Product distribution; Further Variations:; Catalysts; Electrolysis; |
Conditions | Yield |
---|---|
With oxygen at 169.84℃; under 760.051 Torr; Inert atmosphere; | A n/a B 30% C n/a |
With titanium(IV) oxide at 275℃; | A 49 %Chromat. B 7 %Chromat. C 44 %Chromat. |
With oxygen at 249.84℃; for 1.16667h; chemoselective reaction; |
Conditions | Yield |
---|---|
With oxygen at 159.84℃; under 760.051 Torr; Temperature; Inert atmosphere; | A n/a B 28% |
With oxygen; iron(II) molybdate at 200 - 250℃; Product distribution / selectivity; Gas phase; | A n/a B 1.4% |
molecular sieve at 230℃; Product distribution; Mechanism; other alcohols; other catalysts; |
Conditions | Yield |
---|---|
With oxygen at 169.84℃; under 760.051 Torr; Reagent/catalyst; Temperature; Inert atmosphere; | A 28% B n/a |
With oxygen; molybdenum(VI) oxide at 215℃; Product distribution; Investigation of methanol conversion in contact with MoO3 in a flow reactor in helium as a carrier gas. Investigation of the effect of the oxygen partial pressure in the reactive gas and reaction time in the absence of oxygen.; | |
With 2,6-di-tert-butyl-pyridine; H5PV2Mo10O40; oxygen; silica gel at 179.85℃; Product distribution; Further Variations:; Reagents; |
Conditions | Yield |
---|---|
With oxygen at 159.84℃; under 760.051 Torr; Reagent/catalyst; Temperature; Inert atmosphere; | A 28% B n/a C n/a |
With PHTHALIMAX S4 vanadia-titania catalyst; oxygen at 159.84℃; under 760.051 Torr; Inert atmosphere; | A 17% B n/a C n/a |
With silicomolybdic acid at 170℃; for 1h; Product distribution; other reagents, other organic oxygen-containing compounds; |
Conditions | Yield |
---|---|
With phosphotungstic acid; platinum In water at 20℃; Product distribution; electrocatalytic oxidation of methanol investigated; | A n/a B 26% C n/a |
With phosphotungstic acid; platinum In water at 20℃; electrocatalytic oxidation; | A n/a B 26% C n/a |
With helium; water; oxygen at 24.9℃; under 757.6 Torr; Product distribution; gas phase fuel cell; variation of pressures; |
1-hexadecene ozonide
A
Dimethoxymethane
B
n-pentadecanal
C
Methyl formate
D
palmitic acid
E
pentadecanoic acid methyl ester
F
1,1-dimethoxy-pentadecane
Conditions | Yield |
---|---|
In methanol at 90℃; for 6h; Mechanism; Product distribution; Kinetics; other solvents; other objects of study: energy data, velocity constant; | A 19.6% B 8.8% C 21.3% D 20.3% E 2.2% F 14.1% |
butyl-[1,2,4]trioxolane
methanol
A
pentanal
B
Dimethoxymethane
C
Methyl formate
D
methyl valerate
E
1,1-dimethoxy-pentane
F
valeric acid
Conditions | Yield |
---|---|
at 90℃; for 6h; Product distribution; Thermodynamic data; Rate constant; other temperature, ΔS (excit.), ΔG (excit.), ΔH (excit.); | A 2.8% B 18.3% C 20.4% D 3.7% E 18.4% F 15.9% |
butyl-[1,2,4]trioxolane
A
formaldehyd
B
pentanal
C
Dimethoxymethane
D
Methyl formate
E
1,1-dimethoxy-pentane
F
valeric acid
Conditions | Yield |
---|---|
In methanol at 90℃; for 6h; Mechanism; Product distribution; | A 2.1% B 2.8% C 18.3% D 20.4% E 18.4% F 15.9% |
methanol
dichloromethane
A
Dimethoxymethane
B
1-((2R,4S,5R)-4-Ethoxymethoxy-5-ethoxymethoxymethyl-tetrahydro-furan-2-yl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione
Conditions | Yield |
---|---|
With sodium hydroxide at 140℃; | A n/a B 19% |
methanol
di-n-butyloxymethane
A
Dimethoxymethane
B
1-butoxy-1-methoxymethane
C
butan-1-ol
Conditions | Yield |
---|---|
at 160 - 180℃; reagiert analog mit Decylalkohol; |
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
With sodium hydroxide at 100 - 125℃; unter Druck; | |
With sodium hydroxide at 100 - 125℃; unter Druck; |
methanol
Chloromethyl acetate
A
Dimethoxymethane
B
acetic acid methyl ester
Conditions | Yield |
---|---|
at 50℃; |
Dimethoxymethane
2,2-Dimethyl-1,3-propanedithiol
5,5-Dimethyl-1,3-dithiane
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate | 100% |
With boron trifluoride diethyl etherate; acetic acid In chloroform for 0.5h; Heating; | 100% |
88.7% | |
With trifluoroborane diethyl ether; acetic acid In chloroform |
Conditions | Yield |
---|---|
100% |
Dimethoxymethane
2,2-diethyl-1,3-propanedithiol
5,5-Diethyl-1,3-dithiane
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate | 100% |
With boron trifluoride diethyl etherate; acetic acid In chloroform for 0.5h; Heating; | 100% |
Dimethoxymethane
2-(hydroxymethyl)butane-1,4-diol
5-(2-hydroxyethyl)-1,3-dioxane
Conditions | Yield |
---|---|
100% |
Dimethoxymethane
3-Phenylpropenol
γ-Phenyl-allylalkohol-methoxy-methylether
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; lithium bromide for 0.75h; Ambient temperature; | 100% |
With 12-tungstophosphoric acid immobilized on [bmim][FeCl4] at 75 - 82℃; for 0.00555556h; Microwave irradiation; | 98% |
With 1-butyl-3-methylimidazolium tetrachloroindate for 0.025h; Microwave irradiation; chemoselective reaction; | 97% |
With tin(IV)octabromotetraphenylporphyrinato trifluoromethanesulfonate at 20℃; for 0.0833333h; | 95% |
Dimethoxymethane
diethyl (2R,3R)-tartrate
(+)-(2R,3R)-diethyl 2,3-bismethoxymethoxybutanedioate
Conditions | Yield |
---|---|
With phosphorus pentaoxide In chloroform for 2.5h; Ambient temperature; | 100% |
With phosphorus pentoxide In dichloromethane for 5h; Ambient temperature; | 100% |
With phosphorus pentoxide In chloroform for 2h; Alkylation; | 97% |
With phosphorus pentoxide In dichloromethane | 96% |
With phosphorus pentoxide In dichloromethane |
Dimethoxymethane
1-Methylsulfanyl-4-phenyl-1-(toluene-4-sulfonyl)-butan-2-ol
1-(2-Methoxymethoxy-1-methylsulfanyl-4-phenyl-butane-1-sulfonyl)-4-methyl-benzene
Conditions | Yield |
---|---|
With phosphorus pentoxide In chloroform for 1h; Ambient temperature; | 100% |
Dimethoxymethane
2-Methylsulfanyl-1-phenyl-2-(toluene-4-sulfonyl)-ethanol
1-(2-Methoxymethoxy-1-methylsulfanyl-2-phenyl-ethanesulfonyl)-4-methyl-benzene
Conditions | Yield |
---|---|
With phosphorus pentoxide In chloroform for 1h; Ambient temperature; | 100% |
Dimethoxymethane
2β-bromo-1α,3β-dihydroxycycloheptane
2β-bromo-1α,3β-bis(methoxymethoxy)-cycloheptane
Conditions | Yield |
---|---|
With phosphorus pentoxide In dichloromethane | 100% |
Dimethoxymethane
L-(+)-diethyl tartrate
2,3-Bis-methoxymethoxy-succinic acid diethyl ester
Conditions | Yield |
---|---|
With phosphorus pentoxide | 100% |
Conditions | Yield |
---|---|
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide at 20℃; for 1h; | 100% |
zirconium(IV) chloride at 20℃; for 1h; | 97% |
With tin(IV)octabromotetraphenylporphyrinato trifluoromethanesulfonate at 20℃; for 0.0833333h; | 97% |
Dimethoxymethane
diethyl (2R,3R)-tartrate
trans-(4R,5R)-1,3-dioxolane-4,5-dicarboxylic acid diethyl ester
Conditions | Yield |
---|---|
With 3 A molecular sieve; Amberlyst 15 ion-exchange resin In ethyl acetate for 24h; Heating; | 100% |
With boron trifluoride diethyl etherate In Isopropyl acetate | 100% |
Conditions | Yield |
---|---|
With phosphorus pentoxide In dichloromethane at 20℃; for 2h; | 100% |
Dimethoxymethane
3,3'-Dimethyl-biphenyl-2,2'-dithiol
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane for 12h; Ambient temperature; | 100% |
Dimethoxymethane
Conditions | Yield |
---|---|
With phosphorus pentoxide at 20℃; for 0.166667h; | 100% |
With phosphorus pentoxide In dichloromethane at 20℃; | 89% |
Dimethoxymethane
diethyl (2S,3S)-tartrate
diethyl (2S,3S)-2,3-di-O-methoxymethyl-tartrate
Conditions | Yield |
---|---|
With phosphorus pentoxide In dichloromethane | 100% |
With phosphorus pentoxide In dichloromethane for 3h; | 100% |
With phosphorus pentoxide In chloroform for 2h; Alkylation; | 84% |
With phosphorus pentoxide In dichloromethane | |
With phosphorus pentoxide In dichloromethane at 0℃; for 10h; Inert atmosphere; |
Dimethoxymethane
Conditions | Yield |
---|---|
With phosphorus pentoxide at 0℃; Condensation; Cyclization; | 100% |
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate at 0 - 20℃; for 12h; | 100% |
Dimethoxymethane
methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate
Conditions | Yield |
---|---|
With phosphorus pentoxide In dichloromethane for 1h; | 100% |
Dimethoxymethane
(2R,3S)-2,3-Dihydroxy-butyric acid methyl ester
Conditions | Yield |
---|---|
With phosphorus pentoxide In dichloromethane for 1h; | 100% |
Dimethoxymethane
(R)-2,3-dihydroxy-2-methyl-propionic acid methyl ester
Conditions | Yield |
---|---|
With phosphorus pentoxide In dichloromethane for 1h; | 100% |
Dimethoxymethane
(2R,3S)-4-Benzyloxy-2,3-dihydroxy-butyric acid methyl ester
Conditions | Yield |
---|---|
With phosphorus pentoxide In dichloromethane for 1h; | 100% |
Dimethoxymethane
(-)-(2S)-5-benzenesulfonyl-1-tosyloxy-pent-3-ene-2-ol
(+)-(2S)-5-benzenesulfonyl-2-methoxymethoxy-1-tosyloxy-pent-3-ene
Conditions | Yield |
---|---|
With phosphorus pentoxide In chloroform at 20℃; for 1h; | 100% |
Dimethoxymethane
(2S)-2-hydroxy-1,4-bis<(methansulfonyl)oxy>butane
(S)-1,4-di-O-mesyl-O-(methoxymethyl)-1,2,4-butanetriol
Conditions | Yield |
---|---|
With phosphorus pentoxide In chloroform at 20℃; for 0.75h; | 100% |
Dimethoxymethane
para-Chlorobenzyl alcohol
1-chloro-4-[(methoxymethoxy)methyl]benzene
Conditions | Yield |
---|---|
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide at 20℃; for 1.2h; | 100% |
With zirconyl triflate at 20℃; for 0.166667h; neat (no solvent); chemoselective reaction; | 100% |
With 12-tungstophosphoric acid immobilized on [bmim][FeCl4] at 75 - 82℃; for 0.00555556h; Microwave irradiation; | 98% |
Conditions | Yield |
---|---|
With phosphorus pentoxide | 100% |
With phosphorus pentoxide at 20℃; for 1h; | 89% |
Dimethoxymethane
ethyl 4,7-dihydro-4β,7β-ethano-2H-isoindole-1-carboxylate
bis(3-ethoxycarbonyl-4,7-dihydro-4,7-ethano-2H-isoindol-1-yl)methane
Conditions | Yield |
---|---|
With sulfuric acid In dichloromethane; acetic acid at 20℃; for 1h; | 100% |
1-(3-bromo-4-hydroxyphenyl)-acetone
Dimethoxymethane
1-[3-bromo-4-(methoxymethoxy)phenyl]acetone
Conditions | Yield |
---|---|
With phosphorus pentoxide In toluene at -5 - 5℃; for 17h; Product distribution / selectivity; | 100% |
Dimethoxymethane
2,4,6-trihydroxyacetophenone
2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone
Conditions | Yield |
---|---|
Stage #1: Dimethoxymethane With acetyl chloride; zinc dibromide In dichloromethane at 20 - 30℃; for 3.5h; Stage #2: 2,4,6-trihydroxyacetophenone With N-ethyl-N,N-diisopropylamine In dichloromethane at 5 - 10℃; | 100% |
Stage #1: Dimethoxymethane With acetyl chloride; zinc dibromide at 20℃; for 2h; Inert atmosphere; Stage #2: 2,4,6-trihydroxyacetophenone With diisopropylamine In dichloromethane for 3h; Inert atmosphere; Cooling with ice; regioselective reaction; | 50% |
Stage #1: Dimethoxymethane With acetyl chloride; zinc dibromide In dichloromethane at 20℃; for 3.5h; Stage #2: 2,4,6-trihydroxyacetophenone With N-ethyl-N,N-diisopropylamine In dichloromethane at 5℃; |
Dimethoxymethane
(2,6-dibromo-3,5-dihydroxyphenyl)(3,5-dichloro-2-hydroxy-6-methoxy-4-methylphenyl)methanone
(2,6-dibromo-3,5-bis(methoxymethoxy)phenyl)(3,5-dichloro-2-hydroxy-6-methoxy-4-methylphenyl)methanone
Conditions | Yield |
---|---|
With phosphorus pentoxide at 20℃; for 3h; | 100% |
The Dimethoxymethane , with cas registry number of 109-87-5, is a clear colorless flammable liquid with a chloroform-like odor and a pungent taste. Its IUPAC name and systematic name are called the same which is dimethoxymethane . The superlist names about this chemical include Dimethoxymethane ; Methane, dimethoxy- ; Methylal ; Methylal [UN1234] [Flammable liquid] ; UN1234 . This compound is soluble in three parts water and miscible with most common organic solvents. It is sensitive to moisture. May form explosive peroxides upon exposure to air. It is incompatible with strong oxidizing agents, strong acids. It should be stored at temp. 2-8°C.
Physical properties about Dimethoxymethane are:
(1) # of Rule of 5 Violations: 0 ; (2) ACD/BCF (pH 5.5): 1 ; (3) ACD/BCF (pH 7.4): 1 ; (4) ACD/KOC (pH 5.5): 17.09 ; (5) ACD/KOC (pH 7.4): 17.09 ; (6) #H bond acceptors: 2 ; (7) #H bond donors: 0 ; (8) #Freely Rotating Bonds: 2 ; (9) Polar Surface Area: 18.46 Å2 ; (10) Index of Refraction: 1.348 ; (11) Molar Refractivity: 19.43 cm3 ; (12) Molar Volume: 90.7 cm3 ; (13) Surface Tension: 19.5 dyne/cm ; (14) Density: 0.838 g/cm3 ; (15) Enthalpy of Vaporization: 27.72 kJ/mol ; (16) Boiling Point: 45.2 °C at 760 mmHg ; (17) Vapour Pressure: 365 mmHg at 25°C ; (18) Refractive index: n20/D 1.354.
Preparation of Dimethoxymethane:
there are two simple ways. One is it is prepared by oxidation of methanol . The other way is by the reaction of formaldehyde with methanol.
Uses information of Dimethoxymethane:
This chemical mainly used in organic synthesis. Here is an example, it can be used to prepared 1,3-dithia-5-cycloheptene with but-2c-ene-1,4-dithiol .
This reaction just needs a reagent boron trifluoride . The yield is about 37%.
Safety information of Dimethoxymethane:
When you are using this chemical, please be cautious about it as the following:
Moderately toxic by subcutaneous route. Mildly toxic by ingestion and inhalation. Can cause injury to lungs, liver, kidneys, and the heart. A narcotic and anesthetic in high concentrations. A very dangerous fire hazard when exposed to heat, flame, or oxidizers. Moderately explosive when exposed to heat or flame. May ignite or explode when heated with oxygen. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.
You can still convert the following datas into molecular structure:
(1) SMILES:COCOC;
(2) InChI:InChI=1/C3H8O2/c1-4-3-5-2/h3H2,1-2H3;
(3) InChIKey:NKDDWNXOKDWJAK-UHFFFAOYAE
The toxicity data of Dimethoxymethane is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LC50 | inhalation | 57gm/m3/7H (57000mg/m3) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 259, 1986. | |
rabbit | LD | skin | > 16mL/kg (16mL/kg) | SENSE ORGANS AND SPECIAL SENSES: IRITIS: EYE LIVER: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | National Technical Information Service. Vol. OTS0536049, |
rabbit | LD50 | oral | 5708mg/kg (5708mg/kg) | Proceedings of the Society for Experimental Biology and Medicine. Vol. 29, Pg. 730, 1932. | |
rat | LC50 | inhalation | 15000ppm (15000ppm) | Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 73, 1974. | |
rat | LDLo | intraperitoneal | 5gm/kg (5000mg/kg) | National Technical Information Service. Vol. OTS0524346, |
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