Category: 6214-45-5

Kochansky, Jan published the artcileSubstituent effects on chemosterilant activity of 2,4-di-tert-butyl-6-(4′-substituted benzyl)phenols in the house fly (Musca domestica L.), Recommanded Product: (4-Butoxyphenyl)methanol, the main research area is chemosterilant butylbenzylphenol fly structure; Musca chemosterilant butylbenzylphenol structure.

A series of 2,4-di-tert-butyl-6-(4′-X-benzyl)phenols was prepared, analogous to the compound Jurd 2644 (X = OMe) in an attempt to establish a Hammett relationship between the 4′-substituent and the chemosterilant activity of the compounds after oral administration to adult Musca domestica. Fourteen compounds of this type were prepared, 12 of them new. Jurd 2419 (X = H) was found to be as active in our bioassay as Jurd 2644, as were four new compounds [X = N(CH3)2, CH3, SCH3, Cl]. All prevented successful reproduction at 30 mg/kg of diet. There was no correlation between Hammett σ and activity. Active compounds all had small substituents and mol. weights below 350. The activity seemed to be determined by the bulk of X rather than by its electronic properties.

Journal of Agricultural and Food Chemistry published new progress about Aralkyl alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 6214-45-5 belongs to class alcohols-buliding-blocks, name is (4-Butoxyphenyl)methanol, and the molecular formula is C11H16O2, Recommanded Product: (4-Butoxyphenyl)methanol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Hikawa, Hidemasa published the artcilePalladium-Catalyzed Benzylic C-H Benzylation via Bis-Benzylpalladium(II) Complexes in Water: An Effective Pathway for the Direct Construction of N-(1,2-Diphenylethyl)anilines, Computed Properties of 6214-45-5, the main research area is aniline diphenylethyl preparation; benzyl alc aniline benzylation palladium catalyst.

A strategy for the N-benzylation/benzylic C-H benzylation cascade of anilines by the π-benzylpalladium system using a water-soluble palladium(0)/sodium diphenylphosphinobenzene-3-sulfonate (TPPMS) catalyst and benzyl alc. in water has been developed. The nucleophilic ν1-σ-benzyl anion ligand attacks the electrophilic ν3-π-benzyl ligand to give a dibenzylated product. The intermol. competition between mono-N-benzylaniline and its monodeuterated form (monodeuterated at the benzylic group) with benzyl alc. gave a KIE = 4.6, suggesting that C-H bond cleavage was involved in the rate-determining step. Hammett studies on the rate constants of benzylation by various substituted anthranilic acids and mono-N-benzylanilines show a good correlation between the log(kX/kH) and the σ values of the resp. substituents. From the slope, neg. ρ values were obtained, suggesting that there is a build-up of pos. charge in the transition state. The reaction of anilines R1C6H4NH2 (R1 = 4-Me, 3-COOEt, 2-OPh, etc.) with electron-donating and electron-withdrawing groups R2C6H4CH2 (R2 = H, 4-MeO, 3-Me, etc.) afforded the corresponding N-(1,2-diphenylethyl)anilines I in moderate to good yields (54-86%). Interestingly, the reaction of anthranilic acids R3C6H3(COOH)NH2 (R3 = 6-Me, 5-NHAc, H, etc.) with benzylic alcs. R4CH2OH (R4 = Ph, naphthyl, 4-MeC6H4, 3-MeC6H4) proceeded smoothly to give only the corresponding dibenzylated products II in good to excellent yields (70-87%) in which carboxyl group of the anthranilic acids acts as a directing group.

Advanced Synthesis & Catalysis published new progress about Aralkyl alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 6214-45-5 belongs to class alcohols-buliding-blocks, name is (4-Butoxyphenyl)methanol, and the molecular formula is C11H16O2, Computed Properties of 6214-45-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Hikawa, Hidemasa published the artcileA Borrowing Hydrogen Strategy for Dehydrative Coupling of Aminoisoquinolines with Benzyl Alcohols in Water, Category: alcohols-buliding-blocks, the main research area is borrowing hydrogen strategy dehydrative coupling aminoisoquinoline benzylic alc.

We report a borrowing hydrogen strategy for a palladium-catalyzed dehydrative coupling of aminoisoquinolines with benzylic alcs. in water. This cascade reaction using the π-benzylpalladium system can be achieved in an atom-economic process without the need for base or other additives, furnishing the N-benzylated aminoisoquinolines in moderate to excellent yields along with water as the sole co-product. The crossover experiment using [D7]benzyl alc. and 4-methoxybenzyl alc. afforded H/D scrambled products. KIE experiments showed that benzylic C-H bond cleavage of benzyl alc. was involved in the turnover limiting step (KIE = 4.4). The coupling reaction was found to be first order in benzyl alc. with a kinetic solvent isotope effect (KSIE) of 1.6. These exptl. results are consistent with a borrowing hydrogen mechanism in water. Notably, the water-soluble Pd0/TPPMS system can be applied to the more challenging catalytic benzylic amination with aminoisoquinoline nucleophiles despite the possible deactivation of PdII species.

European Journal of Organic Chemistry published new progress about Aralkyl alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 6214-45-5 belongs to class alcohols-buliding-blocks, name is (4-Butoxyphenyl)methanol, and the molecular formula is C11H16O2, Category: alcohols-buliding-blocks.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Zhang, Lingjuan published the artcileIron-catalyzed cross etherification of alcohols to form unsymmetrical benzyl ethers, HPLC of Formula: 6214-45-5, the main research area is iron catalyst cross etherification alc; unsym benzyl ether preparation mechanism.

A Fe(II)-catalyzed direct synthesis of unsym. benzyl ethers, e.g. I, from two different alcs. has been developed. In the presence of a catalyst in situ generated by combining Fe(OTf)2 (OTf = trifluomethanesulfonate) with a pyridine bis-imidazoline ligand, benzyl alcs. underwent cross dehydrative etherification with a wide range of aliphatic alcs. in good to excellent yields under mild, operationally simple conditions with low catalyst loading. The catalyst tolerates a number of functional groups in both coupling partners, and is highly chemoselective, affording no sym. ether byproducts. Ligand is shown to play a crucial role to the success of this dehydrative transformation, and preliminary mechanistic studies indicate that a benzylic cation is involved in the cross etherification.

Molecular Catalysis published new progress about Aliphatic alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 6214-45-5 belongs to class alcohols-buliding-blocks, name is (4-Butoxyphenyl)methanol, and the molecular formula is C11H16O2, HPLC of Formula: 6214-45-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Hikawa, Hidemasa published the artcileA borrowing hydrogen methodology: palladium-catalyzed dehydrative N-benzylation of 2-aminopyridines in water, Name: (4-Butoxyphenyl)methanol, the main research area is benzyl aminopyridine green preparation KIE; aminopyridine benzyl alc dehydrative monobenzylation palladium catalyst base free.

A greener borrowing hydrogen methodol. using the π-benzylpalladium system, which offered an efficient and environmentally friendly preparation of N-benzyl aminopyridines I [R1 = H, 5-F, 3-Me, etc.; R2 = H, 3-Me, 4-t-BuO, etc.; R3 = H, Me] via dehydrative N-monobenzylation of 2-aminopyridines with benzylic alcs. in the absence of base was demonstrated. The crossover experiment using benzyl-α,α-d2 alc. and 3-methylbenzyl alc. afforded H/D scrambled products, suggesting that the dehydrative N-benzylation in the catalytic system involved a borrowing hydrogen pathway. KIE experiments showed that C-H bond cleavage at the benzylic position of benzyl alc. was involved in the rate-determining step (KIE = 2.9). This simple base-free protocol could be achieved under mild conditions in an atom-economic process, affording the desired products in moderate to excellent yields.

Green Chemistry published new progress about Benzylation. 6214-45-5 belongs to class alcohols-buliding-blocks, name is (4-Butoxyphenyl)methanol, and the molecular formula is C11H16O2, Name: (4-Butoxyphenyl)methanol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Nakayama, Taku published the artcilePalladium-Catalyzed Dehydrogenative Synthesis of Imidazoquinolines in Water, Quality Control of 6214-45-5, the main research area is imidazoquinoline preparation green chem; benzylic alc diaminoquinoline dehydrogenative coupling reaction palladium catalyst.

A synthesis of imidazoquinolines I (R = Me, iso-Bu, Ph, etc.; Ar = Ph, 3-fluorophenyl, naphthalen-1-yl, etc.) via dehydrogenative coupling of 3,4-diaminoquinolines II with benzylic alcs. ArCH2OH utilizing π-benzylpalladium(II) system in water was reported. Readily available benzylic alcs. initially undergo catalytic dehydrogenation to form benzaldehydes, which are then reacted with 3,4-diaminoquinolines II via sequential cyclocondensation/aromatization, leading to the formation of imidazoquinolines I. This exptl. simple and practical one-pot procedure provides direct access to the desired products I without adding strong bases, toxic oxidants or other additives. Several experiments were carried out toward an understanding of the reaction mechanism to propose plausible catalytic cycles. The dehydrogenative coupling was found to be first order with respect to the benzyl alc. and Pd catalyst, and zero order with respect to the 3,4-diaminoquinoline substrate. A kinetic isotope effect of 3.1 was observed by sep. determining the reaction rates of benzyl alc. and benzyl-α,α-d2 alc. Water mols. accelerate the catalytic dehydrogenative coupling, suggesting that they act as a proton donor to activate the benzylic alcs. by a hydrogen-bonding network.

Asian Journal of Organic Chemistry published new progress about Aralkyl alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 6214-45-5 belongs to class alcohols-buliding-blocks, name is (4-Butoxyphenyl)methanol, and the molecular formula is C11H16O2, Quality Control of 6214-45-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Lopez, Jhon J. published the artcileNew convergent one pot synthesis of amino benzyl ethers bearing a nitrogen-containing bicycle, Recommanded Product: (4-Butoxyphenyl)methanol, the main research area is benzyl alc azabicyclooctanyl alc one pot etherification; benzyloxy azabicyclooctane preparation.

A new convergent one pot method for the synthesis of amino benzyl ethers containing a bicyclic amines, derived from different substituted benzyl alcs. and bicyclic amino alcs. such as tropine, pseudotropine and 3-quinuclidinol using chlorotrimethylsilane and sodium iodide was reported. In order to avoid the competitive reaction with the nitrogen atom, a solution of the sep. prepared alkoxide of tropine, pseudotropine and 3-quinuclidinol was added to the preformed substituted benzyl iodides and allowed to reflux at 90° for 15 h under nitrogen atm. This method provided an efficient alternative of the preparation of amino benzyl ethers in organic synthesis with good yields in comparison with existed methods.

Synthetic Communications published new progress about Benzaldehydes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 6214-45-5 belongs to class alcohols-buliding-blocks, name is (4-Butoxyphenyl)methanol, and the molecular formula is C11H16O2, Recommanded Product: (4-Butoxyphenyl)methanol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Hikawa, Hidemasa published the artcileA palladium-catalyzed dehydrative N-benzylation/C-H benzylation cascade of 2-morpholinoanilines on water, SDS of cas: 6214-45-5, the main research area is morpholinoaniline benzyl alc palladium catalyst tandem chemoselective dehydrative benzylation; diphenylethyl morpholinoaniline preparation green chem.

A strategy for the palladium-catalyzed dehydrative tandem benzylation of 2-morpholinoanilines with benzyl alcs. was developed. This cascade reaction was devised as a straightforward and efficient synthetic route for N-(1,2-diphenylethyl)-2-morpholinoanilines in moderate to good yields (50-81%). The dehydrative sp3 C-H bond benzylation proceeded chemoselectively at the benzylic position of N-benzyl-2-morpholinoaniline to form a new C(sp3)-C (sp3) bond. KIE experiments showed that C-H bond activation was involved in the rate-determining step (KIE = 2.7). A Hammett study of 2-morpholinoanilines gave a neg. ρ value, suggested that there was a build-up of pos. charge in the transition state. A “”on water”” protocol, which afforded the corresponding desired products with water as the sole co-product, can be achieved under mild reaction conditions without the need for bases or other additives in an atom-economical process.

Green Chemistry published new progress about Benzylation (chemoselective, dehydrative). 6214-45-5 belongs to class alcohols-buliding-blocks, name is (4-Butoxyphenyl)methanol, and the molecular formula is C11H16O2, SDS of cas: 6214-45-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 6214-45-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 6214-45-5 as follows.

Example 45{6-[(4-Butoxybenzyl)(pyridin-2-ylsulfonyl)aminomethyl]pyridin-2-ylamino}acetic acid(Exemplary compound No. 899)45-(a): Ethyl {6-[(4-Butoxybenzyl)(pyridin-2-ylsulfonyl)aminomethyl]pyridin-2-ylamino}acetateTo 2.5 ml of a tetrahydrofuran solution containing 158 mg (0.451 mmol) of ({6-[(pyridin-2-ylsulfonyl)aminomethyl]pyridin-2-yl}amino)ethyl acetate obtained in Reference example 34 were added 89.2 mg (0.495 mmol) of 4-butoxybenzyl alcohol, 169 mul (0.677 mmol) of tri-n-butylphosphine and 116 mg (0.674 mmol) of N,N,N’,N’-tetramethylazodicarboxamide, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was applied to silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1?1:4 (V/V)), and the fractions containing the objective material were concentrated under reduced pressure to obtain 212 mg of the title compound as colorless oily product. (Yield: 92%)Mass Spectrum (FAB, m/z): 513 (M++1).1H-NMR Spectrum (CDCl3, delta ppm): 8.60 (ddd, J=4.8, 1.7, 1.0 Hz, 1H), 7.81 (ddd, J=7.8, 1.3, 1.0 Hz, 1H), 7.74 (ddd, J=7.8, 7.6, 1.7 Hz, 1H), 7.37 (ddd, J=7.6, 4.8, 1.3 Hz, 1H), 7.23 (dd, J=8.3, 7.2 Hz, 1H), 7.20-7.16 (m, 2H), 6.79-6.73 (m, 2H), 6.49 (d, J=7.2 Hz, 1H), 6.22 (d, J=8.3 Hz, 1H), 4.71-4.65 (m, 1H), 4.68 (s, 2H), 4.36 (s, 2H), 4.23 (q, J=7.1 Hz, 2H), 3.96 (d, J=5.6 Hz, 2H), 3.92 (t, J=6.5 Hz, 2H), 1.80-1.69 (m, 2H), 1.54-1.42 (m, 2H), 1.29 (t, J=7.1 Hz, 3H), 0.97 (t, J=7.4 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6214-45-5, its application will become more common.

Reference:
Patent; UBE INDUSTRIES, LTD.; US2012/259123; (2012); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Related Products of 6214-45-5, Adding some certain compound to certain chemical reactions, such as: 6214-45-5, name is (4-Butoxyphenyl)methanol,molecular formula is C11H16O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6214-45-5.

Under nitrogen atmosphere, to a stirred mixture of commercially available (4-butoxyphenyl)-methanol (0.30 g, 1.66 mmol) in dry CH2C12 (8.0 mL), DMAP (0.020 g, 0.17 mmol) and 2-DPC (0.43 g, 1.99 mmol) were added. The reaction mixture was left at r.t. for 16 h, then diluted with CH2C12 (50 mL) and sequentially washed with sat. NH4C1 solution (50 mL), sat. NaHCO3 solution (3 x 50 mL) and brine (50 mL). The organic layer was dried over Na2504, filtered and concentrated to dryness to afford an oily product (0.423 g), as a mixture (1.7:1 ratio)of (4-butoxyphenyl)-methyl-2-pyridyl carbonate and (4-butoxyphenyl)-methyl-2-oxopyridine- 1- carboxylate. The mixture of isomers was not separated and used in the next step without any further purification. R = 2.61 mm; MS (ESI) m/z: 340 [M-K].

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 6214-45-5, (4-Butoxyphenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; PIOMELLI, Daniele; BANDIERA, Tiziano; BERTOZZI, Fabio; NUZZI, Andrea; FIASELLA, Annalisa; PONZANO, Stefano; PAGLIUCA, Chiara; REGGIANI, Angelo Mario; WO2014/144836; (2014); A2;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts