Conditions | Yield |
---|---|
With thionyl chloride In toluene for 12h; | 98% |
With thionyl chloride In chloroform at 5 - 30℃; | 98.4% |
With pyridine; thionyl chloride In diethyl ether at -5 - 25℃; for 12h; | 98% |
1-(dimethoxymethyl)naphthalene
1-Chloromethylnaphthalene
Conditions | Yield |
---|---|
With triethylsilane; acetyl chloride; tin(ll) chloride In dichloromethane at 0℃; for 2h; | 92% |
Conditions | Yield |
---|---|
With bis(tri-ortho-tolylphosphine)palladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine In toluene at 130℃; for 20h; Inert atmosphere; Glovebox; | 92% |
1-naphthalene methanol
Benzotrichlorid
A
benzylidene dichloride
B
1-Chloromethylnaphthalene
Conditions | Yield |
---|---|
With TOP; phenylsilane In neat (no solvent) at 100℃; for 24h; Appel Halogenation; Inert atmosphere; | A n/a B 81% |
1-tributylstannyl-methylnaphthalene
A
1-naphthalenecarboxylic acid
B
1-naphthalene methanol
C
1-naphthaldehyde
D
1-Chloromethylnaphthalene
Conditions | Yield |
---|---|
With C2H2Cl2F3O2V; oxygen In tert-butyl alcohol at 50℃; for 24h; | A 38% B n/a C 58% D n/a |
With C2H2Cl2F3O2V; oxygen In tert-butyl alcohol at 50℃; for 24h; | A 28% B 5% C 58% D 4% |
Conditions | Yield |
---|---|
With hydrogenchloride; phosphoric acid; acetic acid In water for 6h; Reflux; | 56% |
With hydrogenchloride; zinc(II) chloride; Petroleum ether | |
With hydrogenchloride at 60 - 65℃; |
1-Methylnaphthalene
A
4-chloro-1-methyl-naphthalene
B
1-Chloromethylnaphthalene
Conditions | Yield |
---|---|
With N-chloro-succinimide; barium(II) chloride at 102℃; under 2625.26 Torr; for 0.0666667h; Microwave irradiation; Darkness; chemoselective reaction; | A 45% B 18% |
With aluminum oxide; iron(III) chloride Irradiation; Title compound not separated from byproducts; | |
With aluminum oxide; iron(III) chloride Irradiation; Title compound not separated from byproducts; |
dichloromethane
(naphthalene-1,8-diyl)dilithium
A
naphthalene
B
1,1'-cis-ethene-1,2-diyl-bis-naphthalene
C
(E)-1,2-bis(1-naphthyl)ethene
D
1H-Cyclobutanaphthalene
E
1-Chloromethylnaphthalene
F
acenaphthylene
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine In diethyl ether at -100 - -60℃; Product distribution; Mechanism; var. of temp., further with CD2Cl2; | A 42% B n/a C n/a D 21% E n/a F n/a |
tetrachloromethane
1-Methylnaphthalene
A
bis-chloromethylnaphthalene
B
1-Chloromethylnaphthalene
Conditions | Yield |
---|---|
at 250℃; under 52505.3 Torr; for 7h; Inert atmosphere; | A 37% B 36% |
1-Methylnaphthalene
A
bis-chloromethylnaphthalene
B
1-Chloromethylnaphthalene
Conditions | Yield |
---|---|
With tetrachloromethane at 250℃; for 7h; Inert atmosphere; Autoclave; | A 37% B 36% |
Conditions | Yield |
---|---|
With N-chloro-succinimide; N-hydroxyphthalimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 80℃; for 3h; Time; Sealed tube; Inert atmosphere; | 16% |
With N-hydroxyphthalimide; carbon tetrabromide; trichloroisocyanuric acid; copper(II) acetate monohydrate In dichloromethane at 25℃; for 21h; | 15% |
With chlorine at 260℃; | |
With chlorine | |
With sodium hypochlorite; tetrabutyl-ammonium chloride In dichloromethane at 20℃; for 12h; Catalytic behavior; Inert atmosphere; Sealed tube; | 20 %Chromat. |
Conditions | Yield |
---|---|
With chlorobenzene unter Einwirkung von UV-Licht; |
Conditions | Yield |
---|---|
With hydrogenchloride; formaldehyd; arsenic trichloride | |
With hydrogenchloride; formaldehyd; arsenic(III) trioxide |
Conditions | Yield |
---|---|
With acetic acid at 65℃; |
Conditions | Yield |
---|---|
With hydrogenchloride; formaldehyd; acetic acid |
Conditions | Yield |
---|---|
With diethyl ether; tin(IV) chloride |
naphthalene
chloromethyl isocyanate
A
2-naphthylmethylisocyanate
B
1-isocyanatomethyl-naphthalene
C
1-Chloromethylnaphthalene
D
1-chloromethylnaphthalene
Conditions | Yield |
---|---|
With iron(III) chloride at 140 - 150℃; for 2h; | A 10 % Spectr. B 85 % Spectr. C n/a D n/a |
With iron(III) chloride at 40 - 150℃; for 2h; | A 10 % Spectr. B 85 % Spectr. C n/a D n/a |
1-(diazomethyl)naphthalene
1-Chloromethylnaphthalene
Conditions | Yield |
---|---|
With 1,1,2-Trichloro-1,2,2-trifluoroethane Irradiation; |
1-Chloromethylnaphthalene
Conditions | Yield |
---|---|
With phosphorus pentachloride |
1-Chloromethylnaphthalene
Conditions | Yield |
---|---|
With phosphorus pentachloride Destillieren des Reaktionsgemisches im Vakuum; |
1-Chloromethylnaphthalene
Conditions | Yield |
---|---|
With phosphorus pentachloride Destillieren des Reaktionsgemisches im Vakuum; |
formaldehyd
naphthalene
(E)-3-Ureido-but-2-enoic acid ethyl ester
1-Chloromethylnaphthalene
naphthalene
diethyl ether
ethyl chloromethyl ether
1-Chloromethylnaphthalene
hydrogenchloride
formaldehyd
naphthalene
water
A
1,4-bis(chloromethyl)naphthalene
B
1,5-bis(chloromethyl)naphthalene
C
1-Chloromethylnaphthalene
phosphorus pentachloride
bis(α-naphthylmethyl) ether
1-Chloromethylnaphthalene
1-naphthalene methanol
A
bis(α-naphthylmethyl) ether
B
1-Chloromethylnaphthalene
Conditions | Yield |
---|---|
With hydrogenchloride In water at 120℃; under 5171.62 Torr; for 0.25h; Flow reactor; | A n/a B 90 %Spectr. |
A
(naphtalen-1-yl)methyl iodide
C
1-Chloromethylnaphthalene
Conditions | Yield |
---|---|
With Iodine monochloride In dichloromethane at 20℃; Inert atmosphere; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h 2: bis(tri-ortho-tolylphosphine)palladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine / toluene / 20 h / 130 °C / Inert atmosphere; Glovebox View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 0.5 h / 0 °C 2: pyridine; thionyl chloride / diethyl ether / 12 h / -5 - 25 °C View Scheme |
1-Chloromethylnaphthalene
triethyl phosphite
diethyl 1-naphthylmethylphosphonate
Conditions | Yield |
---|---|
at 160℃; for 7h; Reflux; | 100% |
at 150℃; |
(N-benzoyl-anilino)-phenyl-acetonitrile
1-Chloromethylnaphthalene
N-(1-Cyano-2-naphthalen-1-yl-1-phenyl-ethyl)-N-phenyl-benzamide
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide for 96h; | 100% |
2-<(tetrahydrofur-2-yl)methyl>propanedionate de dimethyle
1-Chloromethylnaphthalene
2-<(naphth-1-yl)methyl>-2-<(tetrahydrofur-2-yl)methyl>propanedioate de dimethyle
Conditions | Yield |
---|---|
With sodium methylate; carbonic acid dimethyl ester for 42h; Heating; | 100% |
2-<(tetrahydrofur-2-yl)methyl>propanedionate de dimethyle
1-Chloromethylnaphthalene
2-<(naphth-1-yl)methyl>-2-<(tetrahydrofur-2-yl)methyl>propanedioate de dimethyle
Conditions | Yield |
---|---|
With sodium methylate; carbonic acid dimethyl ester for 42h; Heating; | 100% |
O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate)
propylene sulphide
1-Chloromethylnaphthalene
polymer, three-armed star-shaped, Mn 11900 Da, Mw/Mn 1.14; monomer(s): 1,3,5-tri[2-(benzylaminothiocarbonyloxy)-3-mercaptopropyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; propylene sulfide; 1-(chloromethyl)naphthalene
Conditions | Yield |
---|---|
Stage #1: O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate) With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at -78℃; for 0.5h; Stage #2: propylene sulphide In N,N-dimethyl-formamide at 0℃; for 2h; Stage #3: 1-Chloromethylnaphthalene With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h; | 100% |
O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate)
propylene sulphide
1-Chloromethylnaphthalene
polymer, three-armed star-shaped, Mn 15500 Da, Mw/Mn 1.17; monomer(s): 1,3,5-tri[2-(benzylaminothiocarbonyloxy)-3-mercaptopropyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; propylene sulfide; 1-(chloromethyl)naphthalene
Conditions | Yield |
---|---|
Stage #1: O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate) With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at -78℃; for 0.5h; Stage #2: propylene sulphide In N,N-dimethyl-formamide at 0℃; for 2h; Stage #3: 1-Chloromethylnaphthalene With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h; | 100% |
Conditions | Yield |
---|---|
for 2.5h; Heating; | 100% |
1-Chloromethylnaphthalene
C22H24N2O
Conditions | Yield |
---|---|
Stage #1: N-tert-butyl-3-methylpyridine-2-carboxamide With n-butyllithium; sodium bromide In tetrahydrofuran; hexane at -40℃; for 0.5h; Stage #2: 1-Chloromethylnaphthalene In tetrahydrofuran; hexane at -40℃; for 1.5h; | 100% |
4-nitro-aniline
1-Chloromethylnaphthalene
bis(naphthalen-1-ylmethyl)(4-nitrophenyl)amine
Conditions | Yield |
---|---|
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; | 100% |
4-nitro-phenol
1-Chloromethylnaphthalene
1-(4-nitrophenoxymethyl)naphthalene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; | 99.1% |
1-Chloromethylnaphthalene
1,2-di(1-naphthyl)ethane
Conditions | Yield |
---|---|
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; zinc In tetrahydrofuran at 23 - 25℃; for 5h; Irradiation; Inert atmosphere; | 99% |
With magnesium In tetrahydrofuran at 20℃; for 2.5h; Reflux; | 96% |
With copper(I) bromide In water at 20℃; for 0.416667h; under air; | 88% |
1-Chloromethylnaphthalene
1-(azidomethyl)naphthalene
Conditions | Yield |
---|---|
With sodium azide In acetonitrile for 16h; Reflux; | 99% |
With sodium azide In dimethyl sulfoxide | 91% |
With sodium azide In dimethyl sulfoxide | 91% |
1-Chloromethylnaphthalene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 4h; Ambient temperature; | 99% |
1H-imidazole
1-Chloromethylnaphthalene
1-(naphthalen-1-ylmethyl)-1H-imidazole
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran Heating; | 99% |
With potassium carbonate In acetonitrile Reflux; | 90% |
Stage #1: 1H-imidazole With sodium hydride In 1,2-dimethoxyethane at 0℃; for 0.75h; Stage #2: 1-Chloromethylnaphthalene In 1,2-dimethoxyethane at 20℃; for 4h; Further stages.; | |
In dichloromethane | |
Stage #1: 1H-imidazole With sodium hydride In 1,4-dioxane at 90℃; for 1h; Stage #2: 1-Chloromethylnaphthalene In 1,4-dioxane at 90℃; for 22h; |
O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate)
propylene sulphide
1-Chloromethylnaphthalene
polymer, three-armed star-shaped, Mn 8500 Da, Mw/Mn 1.06; monomer(s): 1,3,5-tri[2-(benzylaminothiocarbonyloxy)-3-mercaptopropyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; propylene sulfide; 1-(chloromethyl)naphthalene
Conditions | Yield |
---|---|
Stage #1: O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate) With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at -78℃; for 0.5h; Stage #2: propylene sulphide In N,N-dimethyl-formamide at 0℃; for 2h; Stage #3: 1-Chloromethylnaphthalene With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h; | 99% |
potassium phtalimide
1-Chloromethylnaphthalene
2-[(1-naphthyl)methyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
In DMF (N,N-dimethyl-formamide) at 100℃; | 99% |
In N,N-dimethyl-formamide | 99% |
In N,N-dimethyl-formamide at 20℃; for 10h; Inert atmosphere; |
1-Chloromethylnaphthalene
(2E)-3-phenyl-2-propen-1-ol
(E)-3-phenyl-2-propenyl 1-naphthylmethyl ether
Conditions | Yield |
---|---|
Stage #1: (2E)-3-phenyl-2-propen-1-ol With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: 1-Chloromethylnaphthalene In tetrahydrofuran at 20℃; for 24h; | 99% |
(S)-4-benzyl-1-(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazole
1-Chloromethylnaphthalene
(S)-4-benzyl-1-(2,6-diisopropylphenyl)-3-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazol-3-ium chloride
Conditions | Yield |
---|---|
In acetonitrile at 110℃; for 5h; | 99% |
N-formyldiethylamine
1-Chloromethylnaphthalene
1-<(N,N-diethylamino)methyl>naphthalene
Conditions | Yield |
---|---|
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique; | 99% |
With potassium hydroxide In water at 50℃; for 3h; Green chemistry; | 85% |
t-butyl malonate
1-Chloromethylnaphthalene
di-t-butyl (1-naphthylmethyl)malonate
Conditions | Yield |
---|---|
In tetrahydrofuran; ethyl acetate | 98.4% |
triphenylphosphine
1-Chloromethylnaphthalene
1-naphthylmethyltriphenylphosphonium chloride
Conditions | Yield |
---|---|
In toluene Reflux; | 98% |
In acetonitrile for 8h; Heating; | 94% |
In N,N-dimethyl-formamide for 5h; Heating; | 91% |
1-Chloromethylnaphthalene
trimethylamine
N,N,N-trimethyl-1-(naphthalene-1-yl)methanaminium chloride
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 60℃; for 12h; | 98% |
In ethanol | 80% |
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 3h; | 98% |
With ammonia fluess. Ammoniak; | |
With hydrogenchloride; hexamethylenetetramine 1) CH2Cl2, 12 h, 2) ethanol; Yield given. Multistep reaction; | |
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 10 h / 20 °C / Inert atmosphere 2: hydrazine hydrate / ethanol / 4 h / Inert atmosphere; Reflux View Scheme |
Conditions | Yield |
---|---|
With potassium formate; PdCl22 In benzene at 60℃; for 4h; | 98% |
With potassium formate; PdCl22 In benzene at 60℃; for 4h; Product distribution; further catalyst, reagent; solid or aqueous solution of reagent; | 98% |
With sodium tetrahydroborate; water In methanol at 20℃; for 0.333333h; | 94% |
O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate)
propylene sulphide
1-Chloromethylnaphthalene
polymer, three-armed star-shaped, Mn 5700 Da, Mw/Mn 1.10; monomer(s): 1,3,5-tri[2-(benzylaminothiocarbonyloxy)-3-mercaptopropyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; propylene sulfide; 1-(chloromethyl)naphthalene
Conditions | Yield |
---|---|
Stage #1: O,O',O''-((2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tris(1-mercaptopropane-3,2-diyl))tris(benzylcarbamothioate) With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at -78℃; for 0.5h; Stage #2: propylene sulphide In N,N-dimethyl-formamide at 0℃; for 2h; Stage #3: 1-Chloromethylnaphthalene With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h; | 98% |
1-Chloromethylnaphthalene
2-Amino-5-nitrophenol
2-(α-naphthylmethoxy)-4-nitroaniline
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 98% |
(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol
1-Chloromethylnaphthalene
(R)-1-O-(1-naphthylmethyl)glycerol
Conditions | Yield |
---|---|
Stage #1: (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol; 1-Chloromethylnaphthalene With potassium hydroxide In 1,4-dioxane; toluene for 2h; Heating; Stage #2: With acetic acid at 20℃; for 6h; Further stages.; | 98% |
Stage #1: (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol; 1-Chloromethylnaphthalene With potassium hydroxide In 1,4-dioxane; toluene at 120℃; for 2h; Stage #2: With water; acetic acid at 20℃; for 6h; | 98% |
carbon disulfide
1-amino-2-propene
1-Chloromethylnaphthalene
2-(naphthalen-1-yl)methyl N-allylcarbamodithioate
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; for 3h; | 98% |
4-morpholinecarboxaldehyde
1-Chloromethylnaphthalene
4-(naphthalene-1-ylmethyl)morpholine
Conditions | Yield |
---|---|
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique; | 98% |
With potassium hydroxide In water at 80℃; for 3h; Temperature; Green chemistry; | 87% |
Molecular Structure of 1-Chloromethyl naphthalene (CAS NO.86-52-2):
IUPAC Name: 1-(chloromethyl)naphthalene
Empirical Formula: C11H9Cl
Molecular Weight: 176.6422
H bond acceptors: 0
H bond donors: 0
Freely Rotating Bonds: 1
Polar Surface Area: 0Å2
Index of Refraction: 1.63
Molar Refractivity: 53.86 cm3
Molar Volume: 151.2 cm3
Surface Tension: 42.5 dyne/cm
Density: 1.167 g/cm3
Flash Point: 129.9 °C
Enthalpy of Vaporization: 50.97 kJ/mol
Boiling Point: 291.5 °C at 760 mmHg
Vapour Pressure: 0.00339 mmHg at 25°C
EINECS: 201-678-2
Melting point: 32 °C(lit.)
Storage temp: Refrigerator
InChI
InChI=1/C11H9Cl/c12-8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2
Smiles
c12c(cccc1CCl)cccc2
Product Categories: Naphthalene derivatives; API intermediates; Naphthalene series
1. | orl-rat LD50:890 mg/kg | IHFCAY Industrial Hygiene Foundation of America, Chemical and Toxicological Series, Bulletin. 6 (1967),1. | ||
2. | skn-rbt LD50:2000 mg/kg | IHFCAY Industrial Hygiene Foundation of America, Chemical and Toxicological Series, Bulletin. 6 (1967),1. |
Reported in EPA TSCA Inventory.
Moderately toxic by ingestion and skin contact. See also CHLORINATED HYDROCARBONS, AROMATIC. Combustible when exposed to heat or flame. To fight fire, use dry chemical, spray or mist, CO2. When heated to decomposition it emits toxic fumes of Cl−.
The Hazard Codes of 1-Chloromethyl naphthalene (CAS NO.86-52-2): C, Xn
HazardClass: 8
The Risk Statements information:
34: Causes burns
20/21: Harmful by inhalation and in contact with skin
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
The Safety Statements information:
20: When using, do not eat or drink
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
27: Take off immediately all contaminated clothing
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
60: This material and/or its container must be disposed of as hazardous waste
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
RIDADR: UN 3261 8/PG 2
WGK Germany: 3
1-Chloromethyl naphthalene , with CAS number of 86-52-2, can be called 1-(Chloromethyl)naphthalene ; 1-Naphthalenylmethyl chloride ; 1-Naphthylmethylchloride ; a-Naphthylmethyl chloride .
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