Conditions | Yield |
---|---|
With trimethoxysilane; lithium methanolate In tetrahydrofuran for 0.5h; Ambient temperature; | 100% |
With hydrogen In 1,2-dimethoxyethane at 80℃; under 60006 Torr; for 2h; Reagent/catalyst; | 87.7% |
With sodium tetrahydroborate; C36H30F6N10Ni4O10(2+)*2C2F3O2(1-); zinc(II) chloride In tetrahydrofuran at 45℃; for 12h; | 79% |
5-[(4-methoxy-phenyl)-diphenyl-methoxy]-pentan-1-ol
1 ,5-pentanediol
Conditions | Yield |
---|---|
With methanol In chloroform-d1 for 0.25h; UV-irradiation; | 100% |
With methanol Irradiation; |
Conditions | Yield |
---|---|
With hydrogen In water at 120℃; under 150015 Torr; Compressed gas(es); | 98% |
With methanol; dmap; aluminum oxide for 0.133333h; microwave irradiation; | 90% |
With sodium tetrahydroborate In methanol at 20℃; for 1h; |
Conditions | Yield |
---|---|
With silica gel; triethylamine In diethyl ether; Petroleum ether Substitution; Detrifluoroacetylation; | 96% |
(5-Benzyloxy-pentyloxy)-diethyl-isopropyl-silane
1 ,5-pentanediol
Conditions | Yield |
---|---|
With hydrogen; palladium dihydroxide In methanol at 26℃; for 6h; | 93% |
Conditions | Yield |
---|---|
With hydrogen; sodium methylate; RuCl2(L-1) In tetrahydrofuran at 100℃; under 37503.8 Torr; for 2.5h; Product distribution / selectivity; | 93% |
With hydrogen; sodium methylate; dichloro-bis-[2-(diphenylphosphino)ethylamine]ruthenium In tetrahydrofuran at 100℃; under 37503.8 Torr; for 2.5h; Product distribution / selectivity; | 72% |
With Ag/SiO2; hydrogen In methanol at 99.84℃; under 750.075 Torr; for 12h; Microreactor; chemoselective reaction; | 100 %Chromat. |
1 ,5-pentanediol
Conditions | Yield |
---|---|
With hydrogen; palladium dihydroxide In methanol under 760 Torr; for 2h; Ambient temperature; | 91% |
Conditions | Yield |
---|---|
With hydrogen In water at 100℃; under 60006 Torr; for 24h; Temperature; Reagent/catalyst; Pressure; Time; | 90.2% |
With hydrogen In ethylenediamine at 100℃; under 60006 Torr; for 2h; Reagent/catalyst; Solvent; Temperature; | 64.6% |
With hydrogen at 285℃; under 112511 - 187519 Torr; for 5h; Reagent/catalyst; Temperature; Pressure; Time; Concentration; Inert atmosphere; Autoclave; | 57% |
A
1 ,5-pentanediol
B
5-(tert-butyldimethyl-silyloxy)pentan-1-ol
Conditions | Yield |
---|---|
With MCM-41 In methanol for 4h; Ambient temperature; | A 2% B 90% |
With mesoporous silica MCM-41 In methanol at 20℃; for 4h; | A 2% B 90% |
1,5-pentanedioic acid
A
1 ,5-pentanediol
B
pentan-1-ol
C
valeric acid
Conditions | Yield |
---|---|
With hydrogen In water at 130℃; under 37503.8 Torr; for 12h; Pressure; Reagent/catalyst; Autoclave; | A 90% B 4% C 5% |
tert-butyldimethyl[5-(tetrahydropyran-2-yloxy)pentyloxy]silane
1 ,5-pentanediol
Conditions | Yield |
---|---|
With phosphomolybdic acid hydrate; silica gel In acetonitrile at 20℃; for 0.416667h; | 89% |
Conditions | Yield |
---|---|
With titanium(III)-tris-(tetrahydridoborate) In dichloromethane at -20℃; for 6h; | 87% |
With chloro-trimethyl-silane; Benzyltriethylammonium borohydride; oxygen In dichloromethane at 0℃; for 8h; | 74% |
Stage #1: 3,4-dihydro-2H-pyran With water at 70℃; for 12h; Stage #2: With Ni-Mo/SiO2; hydrogen In water at 120℃; under 49130.4 Torr; for 1h; Reagent/catalyst; Solvent; Pressure; | |
Stage #1: 3,4-dihydro-2H-pyran With hydrogen at 70℃; under 25858.1 Torr; Stage #2: under 25858.1 Torr; |
1 ,5-pentanediol
Conditions | Yield |
---|---|
bismuth(lll) trifluoromethanesulfonate In tetrahydrofuran; water at 20℃; for 0.666667h; | 86% |
With niobium pentachloride In acetonitrile at 0 - 20℃; for 1h; | 70% |
A
1 ,5-pentanediol
B
5-(tert-butyldimethyl-silyloxy)pentan-1-ol
Conditions | Yield |
---|---|
With Ti-HMS; hydrogen; 5% Pd on active carbon In methanol under 760 Torr; for 4h; Ambient temperature; | A 15% B 82% |
1-(tert-Butyl-dimethyl-silanyloxy)-5-(diethyl-isopropyl-silanyloxy)-pentane
A
1 ,5-pentanediol
B
5-(tert-butyldimethyl-silyloxy)pentan-1-ol
C
5-(Diethyl-isopropyl-silanyloxy)-pentan-1-ol
Conditions | Yield |
---|---|
With acetic acid In tetrahydrofuran at 26℃; for 1.33333h; Product distribution; other mono-diethylisopropysilyl protected diols investigated; | A 5% B 81% C 1.3% |
With hydrogen; palladium dihydroxide In methanol at 40℃; for 1h; | A 15% B 71% C 12% |
methyl 5-hydroxypentanoate
1 ,5-pentanediol
Conditions | Yield |
---|---|
With trimethoxysilane; lithium methanolate In tetrahydrofuran for 27h; Heating; | 80% |
1-(Diethyl-isopropyl-silanyloxy)-5-triethylsilanyloxy-pentane
A
1 ,5-pentanediol
B
5-(Diethyl-isopropyl-silanyloxy)-pentan-1-ol
C
5-Triethylsilanyloxy-pentan-1-ol
Conditions | Yield |
---|---|
With acetic acid In tetrahydrofuran at 26℃; for 0.833333h; | A 9% B 75% C 1.3% |
With acetic acid In tetrahydrofuran at 26℃; for 0.833333h; Product distribution; other mono-diethylisopropysilyl protected diols investigated; | A 9% B 75% C 1.3% |
3,4,5,6-tetrahydro-2H-pyran-2-one
A
1 ,5-pentanediol
B
pentan-1-ol
C
pentane
Conditions | Yield |
---|---|
With hydrogen; (acetylacetonato)dicarbonylrhodium (l); molybdenum hexacarbonyl In 1,4-dioxane at 150℃; under 75007.5 Torr; for 3h; | A 75% B 19% C 6% |
5-(tetrahydro-2H-pyran-2-yloxy)pentan-1-ol
1 ,5-pentanediol
Conditions | Yield |
---|---|
With water; β‐cyclodextrin In methanol at 50℃; for 10h; | 75% |
1,5-pentanedioic acid
Adipic acid
succinic acid
A
1 ,5-pentanediol
B
Butane-1,4-diol
C
1,6-hexanediol
Conditions | Yield |
---|---|
With hydrogen; nitric acid; Ru-Sn-Re catalyst In water at 180℃; under 15001.5 - 112511 Torr; for 18h; | A 73% B 45 - 75 %Chromat. C 72% |
Conditions | Yield |
---|---|
With methanol; [Dy2((2-hydroxy-3-methoxyphenyl)methylene benzohydrazide)2(triflate)2(H2O)4] for 96h; Reflux; Inert atmosphere; chemoselective reaction; | 73% |
n-Pentan-1,5-di-(ol-trimethylsilylaether)
1 ,5-pentanediol
Conditions | Yield |
---|---|
With Kaolinitic clay; water for 0.0166667h; Irradiation; microwave; | 72% |
(E)-pent-2-ene-1,5-diol
carbon monoxide
A
tetrahydro-2H-2-pyranol
B
1 ,5-pentanediol
C
2,3,3aβ,4,5,6aβ-perhydrofuro<2,3b>furan
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; triphenylphosphine In dichloromethane at 120℃; under 45003.6 Torr; for 20h; Product distribution; Further Variations:; Reagents; Solvents; | A n/a B n/a C 72% D n/a |
Conditions | Yield |
---|---|
Stage #1: furfural With hydrogen In water at 39.84℃; under 45004.5 Torr; for 8h; Stage #2: In water at 99.84℃; for 72h; Reagent/catalyst; Time; Temperature; Pressure; | 71.4% |
With ethanol; platinum; iron(II) chloride under 760 - 1520 Torr; Hydrogenation; | |
With nickel at 200 - 220℃; under 29420.3 Torr; Hydrogenation; |
furfural
A
Tetrahydrofurfuryl alcohol
B
1 ,5-pentanediol
C
(+/-)-2-pentanol
D
pentan-1-ol
Conditions | Yield |
---|---|
With hydrogen In isopropyl alcohol at 150℃; under 30003 Torr; for 8h; Temperature; Pressure; Autoclave; | A 68.7% B 24.2% C n/a D n/a |
1,5-dibromo-pentane
diethyl malonate
A
TETRAHYDROPYRANE
B
1 ,5-pentanediol
C
diethyl cyclohexane-1,1-dicarboxylate
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate In N,N-dimethyl-formamide electrolysis; | A n/a B n/a C 64% |
Conditions | Yield |
---|---|
With tris(2,4,6-trimethoxyphenyl)phosphine In methanol at 80℃; for 8h; | A 10% B 62% C 4% |
Conditions | Yield |
---|---|
Stage #1: furfural With 0.5% Pd/C; hydrogen; acetic acid; scandium tris(trifluoromethanesulfonate) at 100℃; under 7600.51 Torr; for 6h; Autoclave; Stage #2: With methanol; water Reagent/catalyst; Temperature; Pressure; Reflux; | A 14% B 23% C 62% |
Conditions | Yield |
---|---|
With hydrogen at 100℃; under 25858.1 Torr; for 2h; | A 61.6% B 43.4% |
With hydrogen at 100℃; under 25858.1 Torr; for 2h; | A 39.8% B 57.7% |
Conditions | Yield |
---|---|
methyltin(IV) trichloride at 95 - 115℃; for 0.28h; | 100% |
methyltin(IV) trichloride at 95 - 115℃; for 0.28h; Mechanism; variation of catalyst, temperature, time; | 100% |
With copper(ll) bromide at 175℃; for 3h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube; | 99% |
1 ,5-pentanediol
(E)-3-phenylacrylic acid
Cinnamic acid 1,5-pentane diol monoester
Conditions | Yield |
---|---|
With sulfuric acid In toluene Heating; | 100% |
1 ,5-pentanediol
tert-butyldimethylsilyl chloride
5-(tert-butyldimethyl-silyloxy)pentan-1-ol
Conditions | Yield |
---|---|
Stage #1: 1 ,5-pentanediol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; hexane at -78 - 23℃; for 3.16667h; Inert atmosphere; | 100% |
With sodium hydride In tetrahydrofuran at 20℃; for 0.75h; | 99% |
With 1H-imidazole In dichloromethane at 0 - 20℃; for 13.5h; Inert atmosphere; | 99% |
1 ,5-pentanediol
p-methoxybenzyl chloride
5-(4-methoxybenzyloxy)-1-pentanol
Conditions | Yield |
---|---|
Stage #1: 1 ,5-pentanediol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 3h; Inert atmosphere; Reflux; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; mineral oil at 20℃; for 12h; Inert atmosphere; Reflux; | 100% |
Stage #1: 1 ,5-pentanediol With sodium hydride In tetrahydrofuran for 3h; Heating; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran for 15h; | 99% |
Stage #1: 1 ,5-pentanediol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 4.5h; Reflux; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; mineral oil for 17h; Reflux; | 97% |
1 ,5-pentanediol
(Z)-3-bromoacrylic acid
(Z)-3-Bromo-acrylic acid 5-((Z)-3-bromo-acryloyloxy)-pentyl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide Condensation; | 100% |
Conditions | Yield |
---|---|
With dmap; diisopropyl-carbodiimide In dichloromethane | 100% |
1 ,5-pentanediol
triisopropylsilyl chloride
5-((triisopropylsilanyl)oxy)pentan-1-ol
Conditions | Yield |
---|---|
Stage #1: 1 ,5-pentanediol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Inert atmosphere; Cooling with ice; Stage #2: triisopropylsilyl chloride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; | 99.6% |
Stage #1: 1 ,5-pentanediol With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: triisopropylsilyl chloride In tetrahydrofuran at 0℃; for 0.666667h; | 76% |
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 5h; | 74% |
1 ,5-pentanediol
methanesulfonyl chloride
pentane-1,5-diyl dimethanesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 2h; | 99% |
With pyridine | |
With triethylamine In dichloromethane at 0 - 20℃; | |
With TEA In dichloromethane at 0 - 10℃; |
Conditions | Yield |
---|---|
With sodium hypochlorite; sodium hydrogencarbonate; potassium bromide In dichloromethane at 0℃; for 0.5h; chemoselective reaction; | 99% |
With sodium bromite In water; acetic acid for 10h; Ambient temperature; | 98% |
With 4-hydroxy-TEMPO benzoate; sodium bromide In dichloromethane; water NaHCO3-buffered at pH 8.6; electrolysis; | 97% |
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol; chloro-(pentamethylcyclopentadienyl)-{5-methoxy-2-{1-[(4-methoxyphenyl)imino-N]ethyl}phenyl-C}-iridium(lll); potassium carbonate at 100℃; for 24h; Inert atmosphere; Sealed tube; | 99% |
With [RuCl(p-cymene)(1,3-dibenzylbenzimidazolin-2-ylidene)(PPh3)]PF6 In neat (no solvent) at 150℃; for 24h; | 98% |
With tris(triphenylphosphine)ruthenium(II) chloride In 1,4-dioxane at 150℃; for 5h; | 76% |
With Knoelker’s complex; silver fluoride In toluene at 110℃; for 24h; Inert atmosphere; Sealed tube; | 61% |
With iron(III) chloride hexahydrate In tetrachloromethane at 160 - 180℃; Autoclave; Inert atmosphere; | 5% |
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate at 85℃; for 3h; | 99% |
With triethylamine In ethyl acetate at 85℃; for 3h; | 99% |
With triethylamine In dichloromethane at 0℃; for 1h; | 96% |
1 ,5-pentanediol
[Ti(N-phenylsalicylideneimine(-H))2(O(CH2)5O)]
Conditions | Yield |
---|---|
In benzene byproducts: (CH3)2CHOH; under unhydrous atm., soln. of ligand added to soln. of Ti compd. (3.06:3.01), refluxed, monitored by isopropanol liberated; concd., crystd., elem. anal.; | 99% |
4,7-dichloroquinoline
1 ,5-pentanediol
O-(7-chloro-4-quinolyl)-1,5-pentanediol
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol at 80℃; for 18h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With iron(III) chloride; 1-(n-butyl)-3-methylimidazolium triflate at 40℃; for 4.25h; Ionic liquid; | 99% |
Conditions | Yield |
---|---|
With C24H33IrN4O3; water; sodium hydroxide for 18h; Catalytic behavior; Reagent/catalyst; Reflux; | 98% |
In water for 48h; Ambient temperature; Gluconobacter roseus IAM 1841; | 97% |
With sodium hydroxide In water at 20℃; Temperature; Concentration; Electrochemical reaction; | 91% |
Conditions | Yield |
---|---|
With iodine at 25℃; for 0.0166667h; | 98% |
With iron(III) p-toluenesulfonate hexahydrate In neat (no solvent) at 0℃; for 2h; | 96% |
With nickel dichloride at 20℃; for 0.5h; Neat (no solvent); | 95% |
Conditions | Yield |
---|---|
Stage #1: 1 ,5-pentanediol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: benzyl bromide In tetrahydrofuran at 20℃; for 20h; Further stages.; | 98% |
Stage #1: 1 ,5-pentanediol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; for 20h; Inert atmosphere; | 98% |
With sodium hydride In tetrahydrofuran at 20℃; for 5h; | 92% |
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran at 0℃; for 2h; | 98% |
With triethylamine In dichloromethane at 0 - 20℃; for 12h; | 85% |
With sodium hydride In tetrahydrofuran at 20℃; for 5h; | 78% |
1 ,5-pentanediol
[Al2(OCH(CH3)2)2(CH3COCHCOCH3)2(O(CH2)5O)]2
Conditions | Yield |
---|---|
In benzene byproducts: i-PrPH; moisture free; refluxing; solvent removal; elem. anal.; | 98% |
thionyl chloride
1 ,5-pentanediol
[(C5H5)TiCl2(C5H4C(CH3)2CH2C(O)O(CH2)3)]2
Conditions | Yield |
---|---|
With NaH In dichloromethane Ti complex was reacted with SOCl2 at room temp. for 1 h; heated at 50°C for 2 h in vac.; dissolved in CH2Cl2; transferred to mixt. of NaHand alcohol in CH2Cl2; stirred at room temp. for 16 h; filtered through Celite; crystd. (CH2Cl2/pentane); | 98% |
1 ,5-pentanediol
3-phenyl-4-benzenesulfonylfuroxan
5-(3-phenylfuroxan-4-yloxy)pentan-1-ol
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran for 0.5h; | 98% |
Conditions | Yield |
---|---|
With hydrogenchloride; ammonium chloride In water at 60 - 100℃; for 3h; | 97.8% |
With hydrogenchloride at 80℃; for 48h; | 59% |
With tetrachloromethane; phosphorus pentachloride | |
With hydrogenchloride; water at 170℃; | |
With pyridine; thionyl chloride |
Conditions | Yield |
---|---|
With air; hydrido(triphenylphosphine)copper(I) hexamer In benzene for 5h; Ambient temperature; | 97% |
1 ,5-pentanediol
(S)-2-methylbutyl tosylate
(S)-5-(2-methylbutoxy)pentan-1-ol
Conditions | Yield |
---|---|
Stage #1: 1 ,5-pentanediol With sodium In tetrahydrofuran at 20℃; Stage #2: (S)-2-methylbutyl tosylate In tetrahydrofuran at 70 - 80℃; | 97% |
Stage #1: 1 ,5-pentanediol With sodium In tetrahydrofuran at 20℃; Stage #2: (S)-2-methylbutyl tosylate In tetrahydrofuran at 70 - 80℃; | 85% |
Conditions | Yield |
---|---|
With caesium carbonate In water; dimethyl sulfoxide at 120℃; for 8h; Time; Reagent/catalyst; Inert atmosphere; Green chemistry; | 97% |
1 ,5-pentanediol
Conditions | Yield |
---|---|
With pyridine In 1,4-dioxane Heating; | 96.3% |
1. Introduction of 1,5-Pentanediol
1,5-Pentanediol with the CAS registry number of 111-29-5, is also named as 1,5-Dihydroxypentane. The product's categories are Alpha,omega-Alkanediols; Alpha,omega-Bifunctional Alkanes; Monofunctional & Alpha,omega-Bifunctional Alkanes. Besides, it is clear colorless oily liquid, which should be stored in tightly closed containers in a cool, dry place away from sources of ignition. When you are using this chemical, please avoid contact with skin and eyes. In addition, its molecular formula is C5H12O2 and molecular weight is 104.15.
2. Properties of 1,5-Pentanediol
The other characteristics of 1,5-Pentanediol can be summarized as: (1)EINECS: 203-854-4; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 11.833; (6)ACD/KOC (pH 7.4): 11.833; (7)#H bond acceptors: 2; (8)#H bond donors: 2; (9)#Freely Rotating Bonds: 6; (10)Index of Refraction: 1.446; (11)Molar Refractivity: 28.283 cm3; (12)Molar Volume: 106.081 cm3; (13)Surface Tension: 38.673 dyne/cm; (14)Density: 0.982 g/cm3; (15)Flash Point: 129.444 °C; (16)Melting Point: -18 °C; (17)Enthalpy of Vaporization: 55.306 kJ/mol; (18)Boiling Point: 238.999 °C at 760 mmHg; (19)Vapour Pressure: 0.007 mmHg at 25 °C.
3. Structure Descriptors of 1,5-Pentanediol
(1)SMILES: C(CCO)CCO
(2)InChI: InChI=1/C5H12O2/c6-4-2-1-3-5-7/h6-7H,1-5H2
(3)InChIKey: ALQSHHUCVQOPAS-UHFFFAOYAE
4. Toxicity of 1,5-Pentanediol
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | oral | 4600mg/kg (4600mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: EXCITEMENT BEHAVIORAL: MUSCLE WEAKNESS | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(9), Pg. 14, 1973. |
mouse | LD50 | intraperitoneal | 2250mg/kg (2250mg/kg) | Toxicology and Applied Pharmacology. Vol. 49, Pg. 385, 1979. | |
mouse | LD50 | oral | 6300mg/kg (6300mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: EXCITEMENT BEHAVIORAL: MUSCLE WEAKNESS | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(9), Pg. 14, 1973. |
rabbit | LD50 | oral | 6300mg/kg (6300mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: EXCITEMENT BEHAVIORAL: MUSCLE WEAKNESS | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(9), Pg. 14, 1973. |
rabbit | LD50 | skin | > 20mL/kg (20mL/kg) | Union Carbide Data Sheet. Vol. 5/22/1959, | |
rat | LD50 | oral | 2gm/kg (2000mg/kg) | Journal of Agricultural and Food Chemistry. Vol. 23, Pg. 418, 1975. |
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