methanol
A
(S)-methyl 2-(2-oxopyrrolidin-1-yl)-2-butanoate
B
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
Stage #1: (-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidineacet-N-(+)-(R)-(1-phenylethyl)-amide With sulfonic acid type-ion exchange resin; water In toluene for 6h; not specified; Heating / reflux; Stage #2: methanol With sulfonic acid type-ion exchange resin In water; toluene at 60℃; for 3h; | A 100% B n/a |
Conditions | Yield |
---|---|
With ammonia at 25℃; optical yield given as %ee; | 100% |
A
(R)-1-phenyl-ethyl-amine
B
(S)‐1,4‐benzodioxane‐2‐carboxylic acid
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 90℃; | A 100% B 100% |
A
(R)-1-phenyl-ethyl-amine
B
(+)-(2R)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 90℃; | A 100% B 100% |
C12H17NOS
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
Stage #1: C12H17NOS With [RhCl2(p-cymene)]2; potassium tert-butylate; (1S,2R)-1-amino-2-indanol In isopropyl alcohol at 40℃; for 2h; Molecular sieve; Stage #2: With hydrogenchloride In methanol optical yield given as %ee; stereoselective reaction; | 99% |
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With aluminum (III) chloride; methoxybenzene In dichloromethane at 30℃; for 2h; | 98.4% |
With aluminum (III) chloride; methoxybenzene In dichloromethane at 20℃; for 2h; Inert atmosphere; enantioselective reaction; | 95% |
N-[(R)-(+)-1-phenylethyl]decanamide
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With Candida antarctica lipase B In phosphate buffer at 70℃; for 48h; pH=7; | 98% |
N-acetyl-1-phenylethylamine
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
Stage #1: N-acetyl-1-phenylethylamine With hydrogenchloride; methanol; water at 80℃; for 15h; Stage #2: With water; sodium hydroxide | 98% |
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With hydrogenchloride; D-sorbitol; choline chloride In water at 25℃; for 3h; | 98% |
Conditions | Yield |
---|---|
With Candida boidinii formate dehydrogenase; Geobacillus stearothermophilus ε‐deaminating L‐lysine dehydrogenase variant 22; nicotinamide adenine dinucleotide In aq. buffer at 50℃; for 48h; pH=8.5; Reagent/catalyst; Enzymatic reaction; | 97% |
With glucose dehydrogenase; sodium hydroxide; D-Alanine; ATA-117 transaminase; NADH; 2,3,4,5,6-pentahydroxy-hexanal; pyridoxal 5'-phosphate; lactate dehydrogenase at 30℃; for 10h; pH=7.5; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee; | 96% |
With Ru(2+)*2C2H3O2(1-)*C77H108O6P2; hydrogen; sodium acetate In 2,2,2-trifluoroethanol at 100℃; under 42754.3 Torr; for 24h; Autoclave; enantioselective reaction; | 96% |
(R(S))-N-(1-phenylethylidene)-tert-butanesulfinamide
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
Stage #1: (R(S))-N-(1-phenylethylidene)-tert-butanesulfinamide With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium tert-butylate; 2-Amino-2-methyl-1-propanol In isopropyl alcohol at 50℃; for 2h; Molecular sieve; Stage #2: With hydrogenchloride In methanol optical yield given as %ee; diastereoselective reaction; | 97% |
Stage #1: (R(S))-N-(1-phenylethylidene)-tert-butanesulfinamide With [RhCl2(p-cymene)]2; potassium tert-butylate; 2-Amino-2-methyl-1-propanol; isopropyl alcohol at 50℃; for 0.5h; Inert atmosphere; Microwave irradiation; Molecular sieve; Stage #2: With hydrogenchloride In methanol at 20℃; Catalytic behavior; Temperature; Inert atmosphere; enantioselective reaction; | 95% |
Multi-step reaction with 2 steps 1: [RhCl2(p-cymene)]2; potassium tert-butylate; 2-Amino-2-methyl-1-propanol; isopropyl alcohol / 2 h / 50 °C / Inert atmosphere; Molecular sieve 2: hydrogenchloride / methanol / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: 2-Amino-2-methyl-1-propanol; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 / isopropyl alcohol / 0.25 h / 50 °C / Inert atmosphere; Molecular sieve 1.2: 2 h / 50 °C / Inert atmosphere; Molecular sieve 2.1: hydrogenchloride / methanol; diethyl ether / 3 h / 0 - 20 °C / Inert atmosphere View Scheme |
A
(S)-1-phenyl-ethylamine
B
(R)-1-phenyl-ethyl-amine
C
(R)-(-)-o-(1-pivaloylaminoethyl)benzene sulfinic acid
Conditions | Yield |
---|---|
With trifluoroacetic acid In methanol Yields of byproduct given; | A n/a B n/a C 96% |
Conditions | Yield |
---|---|
With nickel at 110℃; for 1h; Reagent/catalyst; Inert atmosphere; | 94% |
With ωTA ATA-117 102907WW; Vibrio fluvialis Vf-ωTA 2100208MW; pyridoxal 5'-phosphate; pentan-3-one at 30℃; for 24h; pH=7; aq. phosphate buffer; Enzymatic reaction; | |
With hydrogen In toluene at 70℃; for 35h; chemoselective reaction; |
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With sodium hydroxide In water pH=11; | 94% |
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With sodium hydroxide In water pH=11; | 93.3% |
(R)-2-methoxy-N-(1-phenylethyl)acetamide
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With sodium hydroxide; triethanolamine In water at 120℃; for 6h; optical yield given as %ee; | 93% |
(RS)-2-methyl-N-((R)-1-phenylethyl)propane-2-sulfinamide
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; methanol at 25℃; for 0.5h; Inert atmosphere; | 92% |
With hydrogenchloride In methanol; diethyl ether at 0 - 20℃; for 3h; Inert atmosphere; | 88% |
Stage #1: (RS)-2-methyl-N-((R)-1-phenylethyl)propane-2-sulfinamide With thionyl chloride In methanol at 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In water Inert atmosphere; Stage #3: With ammonia; ammonium chloride In water Inert atmosphere; optical yield given as %ee; enantioselective reaction; | |
Stage #1: (RS)-2-methyl-N-((R)-1-phenylethyl)propane-2-sulfinamide With hydrogenchloride In methanol at 20℃; Stage #2: With ammonia; ammonium chloride In water |
ethanone-1-phenyl-O-(phenylmethyl)oxime
A
(S)-1-phenyl-ethylamine
B
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With sodium tetrahydroborate; (S)-valinol; zirconium(IV) chloride In tetrahydrofuran Ambient temperature; Title compound not separated from byproducts; | A 91% B n/a |
(2S)-2-phenyl-2-({[(1R)-1-phenylethyl]amino}oxy)ethanol
A
(R)-1-phenyl-ethyl-amine
B
(S)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With hexacarbonyl molybdenum In water; acetonitrile at 85℃; for 1h; | A 90% B n/a |
A
(R)-1-phenyl-ethyl-amine
B
(R)-(+)-2-methyl-2-(3-oxobutyl)cyclohexanone
Conditions | Yield |
---|---|
With acetic acid at 20℃; for 1h; Yields of byproduct given; | A n/a B 88% |
(R)-1-phenylethylamine hydrochloride
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With potassium carbonate In water at 70℃; for 1h; pH=9; | 88% |
With sodium hydroxide In dichloromethane; water pH=10 - 11; |
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With diethylamine; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 20℃; for 0.0833333h; | 85% |
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With samarium diiodide In tetrahydrofuran for 4h; Ambient temperature; | 83% |
(E)-ethanone-1-phenyl-O-(phenylmethyl)oxime
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
Stage #1: (E)-ethanone-1-phenyl-O-(phenylmethyl)oxime With C10H18BNO In tetrahydrofuran at 20℃; for 24h; Stage #2: With borane-THF In tetrahydrofuran for 24h; Reflux; optical yield given as %ee; enantioselective reaction; Further stages; | 82% |
With dimethylsulfide borane complex; (R)-(+)-2-(1,3,2-dioxaborolan-2-yloxy)-1,2,2-triphenylethanamine In toluene at 50 - 110℃; for 15h; Product distribution / selectivity; | n/a |
With dimethylsulfide borane complex; C11H14BNO3 In toluene at 50 - 110℃; for 15h; Product distribution / selectivity; | n/a |
With borane-THF; N-isopropyl-N,2-dimethylpropan-2-amine; C22H22BNO3 In 1,4-dioxane at 20℃; for 48h; Product distribution / selectivity; | 100 %Chromat. |
(R)-N-(4-methoxyphenyl)-(1-phenylethyl)amine
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
Stage #1: (R)-N-(4-methoxyphenyl)-(1-phenylethyl)amine With ammonium cerium (IV) nitrate In methanol; water at 0℃; for 6h; Stage #2: With sodium hydroxide In water | 81.3% |
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With thiophenol; zinc(II) chloride In dichloromethane at 20℃; for 6h; | 81% |
(Z)-acetophenone O-benzyloxime
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With borane-THF; C19H23BNO3(1-)*H(1+) In tetrahydrofuran; 1,4-dioxane at 0℃; Temperature; Solvent; Reagent/catalyst; Time; Inert atmosphere; enantioselective reaction; | 76% |
(R)-1-phenyl-ethyl-amine
chloroformic acid ethyl ester
(R)-(1-phenylethyl)-carbamic acid ethyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -30 - 20℃; | 100% |
With triethylamine In diethyl ether at 0 - 20℃; for 2.5h; | 95% |
Stage #1: (R)-1-phenyl-ethyl-amine With triethylamine In dichloromethane at 20℃; Inert atmosphere; Stage #2: chloroformic acid ethyl ester at -30 - 20℃; for 8h; Inert atmosphere; | 90.5% |
With sodium carbonate | |
With sodium hydroxide |
Conditions | Yield |
---|---|
at 55℃; for 2h; | 100% |
In chloroform at 0℃; | 95% |
In benzene 1.) 90 deg C, 1 h, 2.) r.t., 12 h; | 86% |
glyoxylic acid ethyl ester
(R)-1-phenyl-ethyl-amine
((R)-1-phenyl-ethylimino)-acetic acid ethyl ester
Conditions | Yield |
---|---|
In toluene for 0.333333h; Heating; | 100% |
In toluene Heating; | 100% |
In toluene at 15 - 25℃; | 95% |
(R)-1-phenyl-ethyl-amine
formic acid ethyl ester
(R)-(+)-α-methylbenzyl formamide
Conditions | Yield |
---|---|
for 8h; Reflux; | 100% |
With amberlyst 15 In tetrahydrofuran for 21h; Reflux; Inert atmosphere; | 99% |
With Novozyme 435 CALB In tetrahydrofuran at 20℃; Green chemistry; Enzymatic reaction; | 92% |
8-oxo-(E)-non-2-enoic acid methyl ester
(R)-1-phenyl-ethyl-amine
(E)-8-[(E)-(R)-1-Phenyl-ethylimino]-non-2-enoic acid methyl ester
Conditions | Yield |
---|---|
With molecular sieve In cyclohexane at 40℃; for 1h; | 100% |
(E)-9-Oxo-2-decanoic acid methyl ester
(R)-1-phenyl-ethyl-amine
(E)-9-[(E)-(R)-1-Phenyl-ethylimino]-dec-2-enoic acid methyl ester
Conditions | Yield |
---|---|
With molecular sieve In cyclohexane at 40℃; for 1h; | 100% |
(R)-1-phenyl-ethyl-amine
7-oxo-2(E)-octenoic acid methyl ester
(E)-7-[(E)-(R)-1-Phenyl-ethylimino]-oct-2-enoic acid methyl ester
Conditions | Yield |
---|---|
With molecular sieve In cyclohexane at 40℃; for 1h; | 100% |
(R)-1-phenyl-ethyl-amine
(E)-7-(2-Oxo-cyclohexyl)-hept-2-enoic acid methyl ester
(E)-7-{2-[(E)-(R)-1-Phenyl-ethylimino]-cyclohexyl}-hept-2-enoic acid methyl ester
Conditions | Yield |
---|---|
In cyclohexane for 3h; Heating; | 100% |
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
100% |
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
100% |
(R)-1-phenyl-ethyl-amine
benzaldehyde
(R)-1-phenylethyl(benzylidene)amine
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; for 12h; | 100% |
In benzene for 2h; Condensation; Heating; | 96% |
With magnesium sulfate In tetrahydrofuran for 3.5h; | 83% |
succinic acid anhydride
(R)-1-phenyl-ethyl-amine
1-[(1R)-1-phenylethyl]pyrrolidine-2,5-dione
Conditions | Yield |
---|---|
Stage #1: succinic acid anhydride; (R)-1-phenyl-ethyl-amine In toluene for 18h; Reflux; Stage #2: In acetic anhydride for 2h; Reflux; | 100% |
Stage #1: succinic acid anhydride; (R)-1-phenyl-ethyl-amine In tetrahydrofuran Heating; Stage #2: With acetic anhydride In tetrahydrofuran for 2h; Heating; | 60% |
With acetic anhydride 1.) THF, reflux, 2 h, 2.) reflux, 2 h; Yield given. Multistep reaction; |
glyoxylic acid ethyl ester
(R)-1-phenyl-ethyl-amine
<(R)-(1-phenylethyl)imino>acetic acid ethyl ester
Conditions | Yield |
---|---|
In toluene for 1.5h; Heating; | 100% |
With molecular sieve In dichloromethane at 0℃; |
di-tert-butyl dicarbonate
(R)-1-phenyl-ethyl-amine
(R)-(1-phenylethyl)carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With indium(III) bromide at 30 - 35℃; for 0.0333333h; | 100% |
With perchloric acid at 30 - 35℃; for 0.0166667h; | 100% |
With sulfonic-acid-functionalized silica In dichloromethane at 20℃; for 0.0833333h; | 99% |
ethyl trifluoroacetate,
(R)-1-phenyl-ethyl-amine
N-<(R)-(+)-α-phenylethyl>-2,2,2-trifluoroacetamide
Conditions | Yield |
---|---|
With sodium hydride In diethyl ether at 0 - 20℃; Condensation; | 100% |
at 25℃; for 20h; Sealed tube; | 100% |
at 20℃; for 0.05h; Acylation; | 89% |
(R)-1-phenyl-ethyl-amine
1-(trifluoroacetyl)benzotriazole
A
1,2,3-Benzotriazole
B
N-<(R)-(+)-α-phenylethyl>-2,2,2-trifluoroacetamide
Conditions | Yield |
---|---|
In tetrahydrofuran for 4h; Ambient temperature; | A n/a B 100% |
pyridine-2-carbaldehyde
(R)-1-phenyl-ethyl-amine
(R,E)-N-(1-phenylethyl)-1-(pyridin-2-yl)methanimine
Conditions | Yield |
---|---|
In toluene Reflux; Inert atmosphere; Dean-Stark; | 100% |
With magnesium sulfate In diethyl ether for 4h; Ambient temperature; | 90% |
With aluminum oxide | |
In diethyl ether for 1h; Molecular sieve; Inert atmosphere; |
(R)-1-phenyl-ethyl-amine
chloroacetyl chloride
(R)-N-(α-methylbenzyl)chloroacetamide
Conditions | Yield |
---|---|
In dichloromethane | 100% |
With potassium carbonate In acetonitrile | 98% |
With triethylamine In dichloromethane at 0 - 20℃; for 6h; | 86.07% |
carbon disulfide
(R)-1-phenyl-ethyl-amine
(R,R)-N,N'-bis[α-methylbenzyl]thiourea
Conditions | Yield |
---|---|
aluminum oxide; zinc(II) oxide at 100℃; for 2h; Condensation; | 100% |
at 47℃; | 97% |
In ethanol Inert atmosphere; Reflux; | 95% |
MCM-41-TBD; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine at 90℃; for 15h; | 91% |
In ethanol at 88℃; for 24h; | 74% |
(R)-1-phenyl-ethyl-amine
5,5'-(2,2'-bipyridine)diacid chloride
Conditions | Yield |
---|---|
Condensation; | 100% |
(R)-1-phenyl-ethyl-amine
(SS)-(+)-2-(p-Tolylsulfinyl)prop-2-en-1-ol
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; | 100% |
Conditions | Yield |
---|---|
at 20℃; for 6h; | 100% |
(R)-1-phenyl-ethyl-amine
ethyl 4-allyloxy-3-oxobutanoate
(Z)-4-Allyloxy-3-((R)-1-phenyl-ethylamino)-but-2-enoic acid ethyl ester
Conditions | Yield |
---|---|
With acetic acid In tetrahydrofuran at 60℃; | 100% |
4,5-Dihydro-2-methylthiophen-3-(2H)-on
(R)-1-phenyl-ethyl-amine
(R)-(2-methyl-dihydrothiophen-3-ylidene)(1-phenylethyl)amine
Conditions | Yield |
---|---|
With aluminum oxide; 5A molecular sieve; silica gel In cyclohexane at 20℃; for 144h; | 100% |
With aluminum oxide; silica gel In cyclohexane at 20℃; for 100h; |
(R)-1-phenyl-ethyl-amine
4-(((tert-butyldimethylsilyl)oxy)methyl)cyclohexane carbaldehyde
(R)-N-[(4'-tert-butyldimethylsilyloxymethyl-cyclohexyl)methylidene]-1-phenylethanamine
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; | 100% |
With magnesium sulfate In dichloromethane |
Conditions | Yield |
---|---|
In butan-1-ol for 0.166667h; Zincke's reaction; microwave irradiation; | 100% |
pyridine-4-carbaldehyde
(R)-1-phenyl-ethyl-amine
((R)-1-Phenyl-ethyl)-[1-pyridin-4-yl-meth-(E)-ylidene]-amine
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; for 12h; | 100% |
With boron trifluoride diethyl etherate at 20℃; for 0.0166667h; |
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
In chloroform-d1 at 24℃; | 100% |
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
In chloroform-d1 at 24℃; | 100% |
(R)-1-phenyl-ethyl-amine
ethyl (E,E)-4-oxo-2-styrylbut-2-enoate
Conditions | Yield |
---|---|
In chloroform-d1 at 24℃; | 100% |
IUPAC Name: 1-phenylethanamine
Empirical Formula: C8H11N
Molecular Weight: 121.1796g/mol
EINECS: 223-423-4
Structure of Benzenemethanamine, a-methyl-, (aR)- (CAS NO.3886-69-9):
Index of Refraction: 1.533
Molar Refractivity: 39.34 cm3
Molar Volume: 126.6 cm3
Polarizability: 15.59×10-24cm3
Surface Tension: 36.5 dyne/cm
Density: 0.956 g/cm3
Flash Point: 75.8 °C
Enthalpy of Vaporization: 41.93 kJ/mol
Melting Point: -10 °C
Boiling Point: 183 °C at 760 mmHg
Vapour Pressure: 0.788 mmHg at 25°C
Water Solubility: 40 g/L (20 ºC)
Sensitive: Air Sensitive
Product Categories: Benzene derivatives;chiral;Amines (Chiral);Analytical Chemistry;Asymmetric Synthesis;Chiral Building Blocks;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination;for Resolution of Acids;Optical Resolution;Synthetic Organic Chemistry;Chiral Compound;Amines;Aromatics;Chiral Reagents
Canonical SMILES: CC(C1=CC=CC=C1)N
InChI: InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3
InChIKey: RQEUFEKYXDPUSK-UHFFFAOYSA-N
RTECS#: CAS# 3886-69-9: None listed
LD50/LC50: RTECS: Not available. Other: CAS 3886-69-9: supplier info (prod 15182) Oral, rat LD50: 950 mg/kg. Skin, rabbit LD50: 730 mg/kg. Inh, rat: no acute danger.
Carcinogenicity: (R)-(+)-1-Phenylethylamine - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.
Other: The toxicological properties have not been fully investigated. Mutagenicity: Ames-test: negative.
Hazard Codes: C
Risk Statements: 21/22-34
R21/22:Harmful in contact with skin and if swallowed.
R34:Causes burns.
Safety Statements: 26-28-36/37/39-45-27
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S28:After contact with skin, wash immediately with plenty of soap-suds.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S27:Take off immediately all contaminated clothing.
RIDADR: UN 2735 8/PG 2
WGK Germany: 3
F: 3-10-23-34
HazardClass: 8
PackingGroup: III
HS Code: 29214980
Benzenemethanamine, a-methyl-, (aR)- , its cas register number is 3886-69-9. It also can be called (+/-)-alpha-Methylbenzylamine ; (R,S)-(+/-)-1-Phenylethylamine ; alpha.-Methylbenzylamine ; alpha.-Phenylethylamine ; 1-Phenylethanamin ; 1-Phenylethanamine ; (R)-alpha-Methylbenzenemethanamine .
Benzenemethanamine, a-methyl-, (aR)- (CAS NO.3886-69-9) is a colorless to light yellow liquid.
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