Conditions | Yield |
---|---|
With 2AlBr3*CBr4; bromine at 55 - 65℃; for 18h; | 100% |
With 2AlBr3*CBr4; bromine at 55 - 65℃; for 18h; Product distribution; Mechanism; different times; | 100% |
Conditions | Yield |
---|---|
With bromine; iodobis(N,N-diisopropyldithiocarbamato)iron(III) In dichloromethane at 20℃; under 760 Torr; | 98% |
With bromine at -5℃; | 91% |
With bromine |
ethene
di(neopentyloxy)thioxophosphoranesulphenyl bromide
A
bis-(O,O-2,2-dimethylpropylthiophosphoryl)disulfide
B
ethylene dibromide
Conditions | Yield |
---|---|
In toluene at 0 - 15℃; | A 97% B n/a C 3% |
Conditions | Yield |
---|---|
With 1,2-dibromo-1,1,2,2-tetrachloroethane; triphenylphosphine In dichloromethane at 20℃; for 0.15h; Appel Halogenation; | 96% |
With phosphorus; phosphorous; bromine | |
With sulfuric acid; hydrogen bromide | |
bromination; | |
With tetrabutylammomium bromide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; | 78 % Chromat. |
N-bromo-1,8-naphthalenedicarboximide
benzene
A
2-phenylbenzo[de]isoquinoline-1,3-dione
B
ethylene dibromide
Conditions | Yield |
---|---|
With ethene In dichloromethane at 70℃; Irradiation; | A 79% B 89% |
Conditions | Yield |
---|---|
With air; bromine; sodium carbonate; adogen 464; palladium dichloride Product distribution; multistep reaction: 1.) 1,2-dichloroethane, reflux, 15 h, 2.) CCl4; reactions under var. conditions, reactions of derivatives; | A 88% B n/a |
methanol
A
Methyl 3-bromopropionate
B
methyl 3-methoxypropionate
C
ethylene dibromide
D
2-Bromoethyl methyl ether
Conditions | Yield |
---|---|
With bromine at -80℃; temperature up to 30 deg C; | A 67% B n/a C n/a D n/a |
Conditions | Yield |
---|---|
With calcium bromide; tetrahexylammonium bromide at 110℃; for 24h; | A 38% B 53% |
Conditions | Yield |
---|---|
With 1,2-dibromo-1,1,2,2-tetrachloroethane; triphenylphosphine In dichloromethane at 20℃; for 0.15h; Appel Halogenation; | A 50% B 45% |
ethene
tetrabutylammonium p-toluenesulfonate
A
2-bromoethyl p-toluenesulfonate
B
ethylene dibromide
Conditions | Yield |
---|---|
With bromine In dichloromethane at 20℃; Product distribution; Mechanism; | A 34% B 51 % Spectr. |
With bromine In dichloromethane at 20℃; | A 34% B 51 % Spectr. |
With bromine In dichloromethane Ambient temperature; |
Conditions | Yield |
---|---|
With bromine; tetrabutylammonium p-toluenesulfonate In dichloromethane at 20℃; | A 34% B 51 % Spectr. |
Conditions | Yield |
---|---|
With (tBuCH2O)2P(S)SBr In toluene at 0 - 15℃; | A n/a B 3% |
Conditions | Yield |
---|---|
With aluminum tri-bromide; bromine at 65 - 70℃; | |
With bromine at 180℃; | |
With bromine; iron at 100℃; |
Conditions | Yield |
---|---|
With hydrogen bromide | |
With hydrogen bromide at 100 - 200℃; | |
With hydrogen bromide |
Conditions | Yield |
---|---|
With magnesium hydrosilicate; hydrogen bromide |
Conditions | Yield |
---|---|
at 300 - 320℃; | |
at 300 - 315℃; |
Acetyl bromide
1,2-dibenzyloxyethane
A
Benzyl acetate
B
ethylene dibromide
ethene
potassium benzenesulfonate
A
benzenesulfonic acid-(2-bromo-ethyl ester)
B
ethylene dibromide
Conditions | Yield |
---|---|
With water; bromine |
Conditions | Yield |
---|---|
With water; bromine; iron at 100℃; |
Acetyl bromide
phenoxyethyl bromide
A
ethylene dibromide
B
Phenyl acetate
Conditions | Yield |
---|---|
With aluminum tri-bromide unterhalb des Siedepunkts; | |
With aluminum tri-bromide |
Conditions | Yield |
---|---|
With aluminum tri-bromide unterhalb des Siedepunkts; |
Conditions | Yield |
---|---|
With hydrogen bromide; pyrographite at 220℃; | |
With metal bromide-contact; hydrogen bromide at 100 - 200℃; | |
With air; hydrogen bromide; chlorine |
Conditions | Yield |
---|---|
at 30℃; |
Conditions | Yield |
---|---|
With Bis-(2-bromoethyl)selenium dibromide at 80℃; for 7h; Product distribution; Mechanism; other dialkylselenium dihalides; other alcohols; | A 98 % Chromat. B 75 % Chromat. |
ethene
dichloromethane
methylcyclopropane
2,2-dimethyl-N-bromoglutarimide
A
1-bromo-4-butene
B
2,2-dimethylglutarimide
C
bromodichloromethane
E
ethylene dibromide
F
cyclopropylcarbinyl bromide
Conditions | Yield |
---|---|
at 15℃; for 1h; Product distribution; Kinetics; Mechanism; Irradiation; | A 1.7 % Chromat. B 50.4 % Chromat. C 12.8 % Chromat. D 50.1 % Chromat. E 2.0 % Chromat. F 18.0 % Chromat. |
ethene
tetrabutylammonium methanesulfonate
A
2-bromoethyl methanesulfonate
B
ethylene dibromide
Conditions | Yield |
---|---|
With bromine In dichloromethane Ambient temperature; |
ethene
tetrabutylammonium trifluoromethylsulfonate
A
2-bromoethyl triflate
B
ethylene dibromide
Conditions | Yield |
---|---|
With bromine at -78 - 20℃; various solvents; Yield given. Yields of byproduct given; |
ethene
lithium trifluoromethanesulfonate
A
2-bromoethyl triflate
B
ethylene dibromide
Conditions | Yield |
---|---|
With bromine at -78 - 20℃; various solvents; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 24h; | 100% |
In chloroform at 20℃; for 24h; | 100% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethanol; water at 70 - 90℃; for 1h; | 100% |
With sodium hydrogencarbonate | 88% |
2-hydroxybromobenzene
ethylene dibromide
1-(2-bromoethoxy)-2-bromobenzene
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 80℃; | 100% |
With caesium carbonate In acetonitrile at 80℃; for 11h; Inert atmosphere; Schlenk technique; | 88% |
With sodium hydroxide for 6.5h; Etherification; Heating; | 72% |
carbon disulfide
ethylene dibromide
acetylacetone
3-(1,3-dithiolan-2-ylidene)pentane-2,4-dione
Conditions | Yield |
---|---|
With potassium carbonate | 100% |
Stage #1: carbon disulfide; acetylacetone With tetrabutylammomium bromide; potassium carbonate In water at 20℃; Stage #2: ethylene dibromide In water at 20℃; for 8h; | 97% |
Stage #1: carbon disulfide; acetylacetone With tetrabutylammomium bromide; potassium carbonate In water at 20℃; for 1h; Stage #2: ethylene dibromide In water at 20℃; for 8.25h; Further stages.; | 97% |
ethylene dibromide
ethanethiol
2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 1h; Heating; | 100% |
ethylene dibromide
(1R,2R)-1-(4-Methoxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-ethane-1,2-diol
Conditions | Yield |
---|---|
With sodium hydroxide; cetyltrimethylammonium chloride | 100% |
sodium ethanolate
ethylene dibromide
para-thiocresol
(2-ethoxyethyl)-para-thiocresol
Conditions | Yield |
---|---|
Stage #1: para-thiocresol With sodium ethanolate In ethanol at 20℃; Metallation; Stage #2: ethylene dibromide In ethanol at 20℃; Alkylation; Stage #3: sodium ethanolate In ethanol Substitution; Heating; | 100% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine for 18h; Heating; | 100% |
ethylene dibromide
Conditions | Yield |
---|---|
With potassium hydroxide; tetra(n-butyl)ammonium hydroxide In water at 50℃; for 15h; | 100% |
ethylene dibromide
Conditions | Yield |
---|---|
With potassium hydroxide; tetra(n-butyl)ammonium hydroxide In water at 50℃; for 15h; | 100% |
ethylene dibromide
Conditions | Yield |
---|---|
With potassium hydroxide; tetra(n-butyl)ammonium hydroxide In water at 50℃; for 15h; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 48h; Heating; | 100% |
With potassium carbonate In acetone at 55℃; | 92% |
With potassium carbonate In acetone at 0 - 55℃; Inert atmosphere; | 85% |
With potassium carbonate; potassium iodide In acetone at 60℃; | 69% |
Stage #1: 3-Iodophenol With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Stage #2: ethylene dibromide In N,N-dimethyl-formamide at 20 - 55℃; Inert atmosphere; | 38% |
1,2-bis(4,5-dihydro-1H-imidazol-1-yl)ethane
ethylene dibromide
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 3h; Heating; | 100% |
With potassium carbonate In acetonitrile for 3h; Heating; | 70% |
5-acetyl-7-(3-(4-fluorophenyl)butoxy)-6-hydroxy-4-methylbenzofuran
ethylene dibromide
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 1.5h; | 100% |
6-bromo-naphthalen-2-ol
ethylene dibromide
2-bromo-6-(2-bromoethoxy)naphthalene
Conditions | Yield |
---|---|
With potassium hydroxide; tetrabutylammomium bromide In water at 100℃; for 3h; | 100% |
With potassium carbonate In acetonitrile at 95℃; for 8h; | 50% |
With potassium carbonate In acetonitrile at 95℃; for 8h; | 50% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 37.54% |
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutylammomium bromide In water for 0.25h; | 100% |
(2,6-difluorophenyl)acetonitrile
ethylene dibromide
1-(2,6-difluorophenyl)cyclopropane-1-carbonitrile
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutylammomium bromide In water Product distribution / selectivity; | 100% |
With sodium hydroxide | 52% |
With sodium hydroxide; tetrabutylammomium bromide In water at 35 - 47℃; for 3.5h; | |
With N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide In water at 60 - 65℃; for 6h; |
Conditions | Yield |
---|---|
In methanol to soln. Ru complex in MeOH Br(CH2)2Br was added and stirred for 2 h, NH4PF6 was added and stirred for 1 h; react. mixt. was evacuated to dryness, residue was extd. with MeCN, filtered through Celite, evacuated to dryness, residue was dissolved in MeNO2, layered with ether andkept at -30°C for 3 days; elem. anal.; | 100% |
ethylene dibromide
Conditions | Yield |
---|---|
With LisBu In diethyl ether; cyclohexane (inert atm.); Ru complex in Et2O cooled to -78°C, treated with LisBu in cyclohexane (1:1.70) at -78°C within 20-30 s, stirred at -78°C for 3.5 h, treated with suspn. of ligand in Et2O, warmed to room temp. within 2.5 h, stirred for; evapd.(vac.), extd.(pentane), filtered (kieselghur), freed of volatiles,elem. anal.; | 100% |
1-methyl-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine
ethylene dibromide
1-methyl-4-(5-vinylpyridin-2-yl)piperazine
Conditions | Yield |
---|---|
Stage #1: ethylene dibromide With potassium hydroxide In tetrahydrofuran at 95℃; for 1.16667h; Inert atmosphere; Microwave irradiation; Stage #2: 1-methyl-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine With triphenylphosphine; palladium diacetate In tetrahydrofuran; methanol at 95℃; for 1h; Microwave irradiation; | 100% |
Stage #1: ethylene dibromide With potassium hydroxide In tetrahydrofuran at 95℃; for 1.16667h; Microwave irradiation; Inert atmosphere; Stage #2: 1-methyl-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine With palladium diacetate; triphenylphosphine In tetrahydrofuran at 95℃; for 1h; Microwave irradiation; Inert atmosphere; | 93% |
5-chloro-3-bromo-2-hydroxyacetophenone
ethylene dibromide
3'-bromo-2'-(2-bromoethoxy)-5'-chloroacetophenone
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50℃; | 100% |
1,1,2,5,6,6-hexamethyl-1,6-dihydronaphtho<2,1-b:3,4-b'>dipyrrole
ethylene dibromide
Conditions | Yield |
---|---|
at 160℃; for 8h; sealed tube; | 100% |
ethylene dibromide
5-nitro-2H-pyrazole-3-carboxylic acid methyl ester
methyl 1-(2-bromoethyl)-3-nitro-1H-pyrazole-5-carboxylate
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 0 - 100℃; for 4h; | 100% |
Stage #1: 5-nitro-2H-pyrazole-3-carboxylic acid methyl ester With caesium carbonate In N,N-dimethyl-formamide at 98℃; for 0.0833333h; Stage #2: ethylene dibromide at 0 - 20℃; for 5h; | 92% |
With potassium carbonate In acetone for 2h; Reflux; | 77% |
With potassium carbonate In acetone for 2h; Product distribution / selectivity; Reflux; | 63% |
With potassium carbonate In acetone at 60℃; for 1h; | 41.1 mmol |
ethylene dibromide
ethyl 1-(3-methylisoxazol-5-yl)cyclopropanecarboxylate
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutyl ammonium fluoride In toluene at 20℃; for 1h; | 100% |
Conditions | Yield |
---|---|
Stage #1: 3-trifluoromethylphenylacetonitrile With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: ethylene dibromide In N,N-dimethyl-formamide at 20℃; for 3h; | 100% |
Estrone
ethylene dibromide
3-(2’-bromoethoxy)estra-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; water Reflux; | 100% |
With sodium hydroxide In tetrahydrofuran; water Reflux; | 84% |
Conditions | Yield |
---|---|
With magnesium Heating; | 100% |
(1,4-diazepan-1-yl)(phenyl)methanone
ethylene dibromide
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethanol for 16h; Heating; | 100% |
Conditions | Yield |
---|---|
With sodium hydrogensulfide; oxygen In ethanol; water at 76℃; for 8h; Temperature; Reflux; | 100% |
The IUPAC name of 1,2-Dibromoethane is 1,2-dibromoethane. With the CAS registry number 106-93-4, it is also named as Aadibroom; Celmide. The product's categories are organics and bromine chemicals. It is colorless to light yellow liquid with a sweetish odor. And it is slightly soluble in water, and soluble in most organic solvents and thinners. In addition, this chemical slowly decomposes in the presence of light and heat, so it may turn brown upon exposure to light. It is corrosive to iron and other metals and may decompose upon contact with alkalis. Furthermore, it is incompatible with oxidizing agents. Reacts with sodium, potassium, calcium, powdered aluminum, zinc, magnesium and liquid ammonia.
The other characteristics of 1,2-Dibromoethanecan be summarized as:
(1)ACD/LogP: 2.08; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.08; (4)ACD/LogD (pH 7.4): 2.08; (5)ACD/BCF (pH 5.5): 22.42; (6)ACD/BCF (pH 7.4): 22.42; (7)ACD/KOC (pH 5.5): 322.43; (8)ACD/KOC (pH 7.4): 322.43; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.521; (13)Molar Refractivity: 26.77 cm3; (14)Molar Volume: 87.9 cm3; (15)Polarizability: 10.61×10-24 cm3; (16)Surface Tension: 36.4 dyne/cm; (17)Enthalpy of Vaporization: 34.77 kJ/mol; (18)Vapour Pressure: 12 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 187.865929; (21)MonoIsotopic Mass: 185.867975; (22)Heavy Atom Count: 4.
Preparation of 1,2-Dibromoethane:
It can be obtained by ethene petroleum ether and bromine under Geschwindigkeit der Reaktion at -80 - -100°C.
Uses of 1,2-Dibromoethane:
It can be used as ethyl reagents and solvents.In agriculture, it is used as a nematicide and synthetic plant growth regulator. And it is also used as intermediate in synthesis of diethyl-bromophenyl acetonitrile, and fire retardant of vinyl bromide in medicine. In addition, it is used in gasoline to eliminate lead in seismic liquid agent, metal surface treatment agent and fire-fighting agent. It reacts with 2,4,5-tribromo-1H-imidazole to get 2,4,5-tribromo-1-vinylimidazole. This reaction needs reagent aq. tetrabutylammonium bromide and aq. NaOH by heating. The reaction time is 3 hours. The yield is 90 %.
Safety informationg of 1,2-Dibromoethane:
When you are using this chemical, please be cautious about it as the following:It is highly flammable, so it is toxic by inhalation, in contact with skin and if swallowed. And it is irritating to eyes, respiratory system and skin. In addition, this chemical may cause cancer and is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
(1)SMILES:BrCCBr;
(2)Std. InChI:InChI=1S/C2H4Br2/c3-1-2-4/h1-2H2;
(3)Std. InChIKey:PAAZPARNPHGIKF-UHFFFAOYSA-N.
The following are the toxicity data of 1,2-Dibromoethane:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
chicken | LD50 | oral | 79mg/kg (79mg/kg) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 6, Pg. 158, 1952. | |
guinea pig | LCLo | inhalation | 400ppm/3H (400ppm) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 6, Pg. 158, 1952. | |
guinea pig | LCLo | inhalation | 400ppm/3H (400ppm) | LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 6, Pg. 158, 1952. |
guinea pig | LD50 | oral | 110mg/kg (110mg/kg) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 6, Pg. 158, 1952. | |
man | TDLo | oral | 43uL/kg (0.043mL/kg) | LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | Human & Experimental Toxicology. Vol. 19, Pg. 152, 2000. |
mouse | LD50 | intraperitoneal | 220mg/kg (220mg/kg) | Journal fuer Praktische Chemie. Vol. 320, Pg. 133, 1978. | |
mouse | LD50 | unreported | 146mg/kg (146mg/kg) | "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 38, 1971. | |
mouse | LDLo | oral | 250mg/kg (250mg/kg) | Toxicology and Applied Pharmacology. Vol. 23, Pg. 288, 1972. | |
quail | LD50 | oral | 130mg/kg (130mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | British Poultry Science. Vol. 22, Pg. 355, 1981. |
rabbit | LD50 | oral | 55mg/kg (55mg/kg) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 6, Pg. 158, 1952. | |
rabbit | LD50 | skin | 300mg/kg (300mg/kg) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 6, Pg. 158, 1952. | |
rabbit | LD50 | skin | 300mg/kg (300mg/kg) | SKIN AND APPENDAGES (SKIN): CORROSIVE: AFTER TOPICAL EXPOSURE | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 6, Pg. 158, 1952. |
rabbit | LDLo | rectal | 2500mg/kg (2500mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" | Journal of Pharmacology and Experimental Therapeutics. Vol. 34, Pg. 223, 1928. |
rat | LC50 | inhalation | 14300mg/m3/30 (14300mg/m3) | PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Farmakologiya i Toksikologiya Vol. 8, Pg. 140, 1973. |
rat | LD50 | oral | 108mg/kg (108mg/kg) | Special Publication of the Entomological Society of America. Vol. 78-1, Pg. 17, 1978. | |
rat | LD50 | skin | 300mg/kg (300mg/kg) | "Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976Vol. -, Pg. -, 1971/1976. | |
women | LDLo | oral | 90mg/kg (90mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 257, 1969. |
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