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CAS No. : | 1111096-20-8 | MDL No. : | MFCD12405360 |
Formula : | C14H20BClO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 266.57 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 150℃; for 18h; | 27 [0105] 4-Chloro-3,5-dimethylphenol was synthesized as follows. The general process was applied to 2-chloro-m-xylene (141 mg, 1.0 mmol). The borylation step was carried out neat with HBPin (320 mg, 2.5 mmol, 2.5 equiv.) and dmpe (3.0 mg, 0.02 mmol, 2 mol %) at 150° for 18 hours. The oxidation step was then performed as described above, afterwhich, the crude material was dissolved in CH2Cl2 and passed through a plug of silica gel. Evaporation of solvent gave 147 mg material containing 130 mg of the phenol (83%) and 17 mg water. Sublimation at 80° C. under 0.10 mmHg afforded the analytically pure product as a slightly yellow solid; mp 112113° C. 1HNMR (300 MHz, CDCl3): δ6.55 (s, 2 H), 4.45 (s, 1 H), 2.30 (s, 6 H); 13CNMR (75 MHz, CDCl3): δ153.2, 137.4, 126.2, 115.2, 20.8; IR (neat) : 3291, 1590, 1488, 1318, 1167 cm-1. LRMS: m/e 156 (M+), 121, 91. Anal. Calcd for C8H9ClO: C, 61.35; H, 5.79. Found C, 61.57; H, 5.98. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4′-di-(tert-butyl)-2,2′-bipyridyl In tetrahydrofuran at 80℃; for 24h; High pressure; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.188 g | With copper(l) iodide; 1,10-Phenanthroline; potassium iodide In methanol; water at 80℃; for 1h; High pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 20 - 90℃; for 3h; Inert atmosphere; | 1 Step 1: 2-bromo-1,3-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzene General procedure: Step 1: 2-bromo-1,3-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzene A flask charged with a stir bar, 2-bromo-5-iodo-1,3-dimethyl-benzene (1.0 g), bis-(pinacolato)-diboron (1.0 g), potassium acetate (1.1 g) and dimethyl sulfoxide (10 mL) is purged with argon for 5 min. [1,1'-Bis(diphenylphosphino)-ferrocene]-dichloropalladium(II) (0.26 g) is added at room temperature, and the mixture is stirred at 90° C. for 3 h. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (MgSO4) and concentrated. The residue is chromatographed on reversed phase (HPLC; acetonitrile/water) to give the title compound. LC (method 9): tR=1.30 min; Mass spectrum (ESI+): m/z=311/313 (Br) [M+H]+. |
|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 90℃; for 3h; Inert atmosphere; | 1 Step 1 : 2-bromo-1 ,3-dimethyl-5-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-benzene General procedure: A flask charged with a stir bar, 2-bromo-5-iodo-1 ,3-dimethyl-benzene (1 .0 g), bis- (pinacolato)-diboron (1 .0 g), potassium acetate (1 .1 g) and dimethyl sulfoxide (10 ml_) is purged with argon for 5 min. [1 ,1 '-Bis(diphenylphosphino)-ferrocene]- dichloropalladium(ll) (0.26 g) is added at room temperature, and the mixture is stirred at 90 °C for 3 h. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (MgSO4) and concentrated. The residue is chromatographed on reversed phase (HPLC; acetonitrile/water) to give the title compound . LC (method 9): tR = 1 .30 min; Mass spectrum (ESI+): m/z = 31 1/313 (Br) [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In ethanol; water; toluene for 14h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 2,2'-iminobis[ethanol] / diethyl ether 1.2: 2 h 2.1: toluene / 5 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 2,2'-iminobis[ethanol] / diethyl ether 1.2: 2 h 2.1: toluene / 5 h / Reflux 3.1: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 2,2'-iminobis[ethanol] / diethyl ether 1.2: 2 h 2.1: toluene / 5 h / Reflux 3.1: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere 4.1: potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / tetrahydrofuran; water / 24 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 2,2'-iminobis[ethanol] / diethyl ether 1.2: 2 h 2.1: toluene / 5 h / Reflux 3.1: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere 4.1: potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / tetrahydrofuran; water / 24 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride; water / tetrahydrofuran / 48 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 2,2'-iminobis[ethanol] / diethyl ether 1.2: 2 h 2.1: toluene / 5 h / Reflux 3.1: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere 4.1: potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / tetrahydrofuran; water / 24 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 2,2'-iminobis[ethanol] / diethyl ether 1.2: 2 h 2.1: toluene / 5 h / Reflux 3.1: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere 4.1: potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / tetrahydrofuran; water / 24 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride; water / tetrahydrofuran / 48 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-chloro-1,3-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzene With 2,2'-iminobis[ethanol] In diethyl ether Stage #2: With hydrogenchloride In water for 2h; |