Category: alcohols-buliding-blocks

Herbinski, Aurelien published the artcileEco-conception of Highly Salt-Tolerant Alkyl Ether Carboxylate Hydrotropes with a Glyceryl Spacer, Name: 3-((2-Ethylhexyl)oxy)propane-1,2-diol, the publication is Chemistry – A European Journal (2022), 28(28), e202200274, database is CAplus and MEDLINE.

New alkyl ether carboxylates with a glyceryl spacer instead of ethylene glycol units had been synthesized using environmentally friendly methodol. A cascade synthesis of acetalization and hydrogenolysis was developed to obtain products containing an alkyl chain linked to a glycerol unit bearing a polar carboxylate head. These products were methylated by using tri-Me phosphate to observe the influence of a free or methoxylated alc. on the physicochem. properties. Finally, saponification gave the carboxylate anionic group of the new hydrotropes. Studying the amphiphilicity, the tolerance to sodium and calcium ions, and the solubilizing power of these bio-based ionic/nonionic hydrotropes has shown that they exhibited significantly improved application properties compared to similar petro-based hydrotropes.

Chemistry – A European Journal published new progress about 70445-33-9. 70445-33-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is 3-((2-Ethylhexyl)oxy)propane-1,2-diol, and the molecular formula is C11H24O3, Name: 3-((2-Ethylhexyl)oxy)propane-1,2-diol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Sandanayake, K. R. A. Samankumara published the artcileMolecular fluorescence sensor for saccharides based on amino coumarin, Name: 3-(Methylamino)phenol, the publication is Chemistry Letters (1995), 139-40, database is CAplus.

The intramol. neighboring group interaction of the amino group of the 7-aminocoumarin moiety with phenylboronic acid gave fluorescence intensity and spectral changes upon saccharide binding which could be used in fluorescence mapping of saccharides in biol. cells.

Chemistry Letters published new progress about 14703-69-6. 14703-69-6 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Phenol, name is 3-(Methylamino)phenol, and the molecular formula is C7H9NO, Name: 3-(Methylamino)phenol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Hayashi, Mikihiro published the artcileAchievement of a Highly Rapid Bond Exchange for Self-Catalyzed Polyester Vitrimers by Incorporating Tertiary Amino Groups on the Network Strands, HPLC of Formula: 111-29-5, the publication is ACS Applied Polymer Materials (2021), 3(9), 4424-4429, database is CAplus.

Herein, we describe the preparation of a self-catalyzed polyester vitrimer containing tertiary amino groups on the network strands that overcomes the significantly slow bond exchange often encountered in the reported systems. Starting from a polyester precursor bearing both carboxy and tertiary amino side groups, a selective reaction of the carboxyl groups with diepoxy cross-linkers affords a network that possesses hydroxy and tertiary amino groups. The tertiary amino groups on the network strands effectively work as internal catalysts for the trans-esterification bond exchange. Because of the high mobility of the incorporated internal amine catalyst, the bond exchange in the vitrimer material was much more rapid (more than 20 times) than that in reported self-catalyzed polyester vitrimers.

ACS Applied Polymer Materials published new progress about 111-29-5. 111-29-5 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Alcohol,Ploymers, name is Pentane-1,5-diol, and the molecular formula is C5H12O2, HPLC of Formula: 111-29-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Maegawa, Yoshifumi published the artcileIridium-bipyridine periodic mesoporous organosilica catalyzed direct C-H borylation using a pinacolborane, Name: 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, the publication is Dalton Transactions (2015), 44(29), 13007-13016, database is CAplus and MEDLINE.

Heterogeneous catalysis for direct C-H borylation of arenes and heteroarenes in the combination of iridium (Ir) complex fixed on periodic mesoporous organosilica containing bipyridine ligands within the framework (Ir-BPy-PMO) and pinacolborane (HBpin) is reported. Ir-BPy-PMO showed higher catalytic activity toward the borylation of benzene with inexpensive HBpin compared to expensive bis(pinacolato)diboron (B₂pin₂). The precatalyst could be handled without the use of a glove box. The catalyst was easily recovered from reaction mixtures by simple filtration under air. The recovered catalyst still showed good catalytic activity for at least three more times for the borylation of benzene. A variety of arenes and heteroarenes were successfully borylated with high boron efficiency by Ir-BPy-PMO using HBpin, whereas almost no activity was observed for borylation of some heteroarenes with B₂pin₂. The system using Ir-BPy-PMO and HBpin was also utilized in syntheses of multi-boronated thiophene-based building blocks containing ladder-, acenefused-, and fused-thiophene skeletons. The combination of a stable and reusable solid catalyst and inexpensive HBpin is expected to be superior to conventional approaches for the development of industrial applications.

Dalton Transactions published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C20H28B2O4S2, Name: 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Zhao, Pinjing published the artcileDirect Observation of β-Aryl Eliminations from Rh(I) Alkoxides, Quality Control of 596-38-3, the publication is Journal of the American Chemical Society (2006), 128(10), 3124-3125, database is CAplus and MEDLINE.

Rhodium(I) tris-phosphine triaryl alkoxides undergo β-Ph elimination, affording phenylrhodium complexes and diaryl ketones. Ligand substitution of [(PEt₃)₂Rh[N(SiMe₃)₂]] with ROH in the presence of PEt₃ afforded either [(PEt₃)₂RhOR] (2a,c; R = CPh₃, 9-phenyl-9-xanthenyl) or [(PEt₃)₃RhOR] [3b–e; R = CMePh₂, 9-phenyl-9-xanthenyl, 9-phenyl-9H-fluoren-9-yl, CMe₂(CF₃)]. Reaction of 2a with an excess of PEt₃ gave [(PEt₃)₃RhPh] and Ph₂CO; Ph β-elimination from 3b–d gave similarly [(PEt₃)₃RhPh] and acetophenone, xanthone and 9-fluorenone, resp. Kinetic results are most consistent with irreversible β-Ph elimination from a bisphosphine-ligated rhodium alkoxide complex. Such bisphosphine complexes result from ligand dissociation from the tris-phosphine complexes and were isolated in some cases. The bisphosphine complexes are stabilized by Rh-Ph interactions, as evidenced by an x-ray structure of 2a, and this structure with a metal-aryl interaction likely illustrates the pathway for C-C bond cleavage.

Journal of the American Chemical Society published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C6H13N3O2, Quality Control of 596-38-3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Winstein, S. published the artcileThe role of neighboring groups in replacement reactions. XVIII. Migration of the methoxyl group, Safety of 2-Methyl-3-bromo-2-butanol, the publication is Journal of the American Chemical Society (1952), 1160-4, database is CAplus.

cf. C.A. 45, 4661f. A result of participation of a functional neighboring group in a replacement process is migration of the neighboring group. Such a migration of a MeO group occurs in the solvolysis of Me₂C(OMe)CHBrMe (I), which solvolyzes to give Me₂C(OH)CH(OMe)Me (II). EtMe₂COH with H₂SO₄ yielded Me₂C:CHMe (III), b₇₅₂ 38.7-8.9°, n_D²⁵ 1.3845. III (175 cc.) added dropwise to 224 g. N-bromosuccinimide (IV) in 2 1. MeOH, the mixture let stand overnight, added to 2 1. saturated NaCl, and the oil extracted with Et₂O yielded 227 g. I, b₄₀ 69-9.5°, n_D²⁵ 1.4533, d₂₅ 1.2632. MR_D is given for the compounds prepared Me₂CHCH(OH)Me, b₇₆₀ 111.8-11.9°, and 6.9 g. Na refluxed in 250 cc. petr. ether (b. 150-90°), the solution treated with 42.5 g. MeI and refluxed 1 h. yielded 13.9 g. 3-methoxy-2-methylbutane, b₇₆₀ 83-3.5°, n_D²⁰ 1.3838, n_D²⁵ 1.3812, d₂₅ 0.7542. I (36.2 g.), 250 cc. MeOH, 10 g. Pd-CaCO₃, and 17 g. KOH shaken 24 h. with H at 1 atm., the solution filtered, added to 250 cc. water, and extracted with petr. ether yielded 10.6 g. Me₂C(OMe)Et, b₇₆₀ 85-6.5°, n_D²⁰ 1.3885. III (230 cc.) added dropwise during 20 min. to 270 g. IV in 21. water, the mixture stirred 1 h., and extracted the next day with Et₂O, yielded 81.1 g. 2,3-epoxy-2-methylbutane (V), b₇₆₀ 73-3.3°, n_D²⁵ 1.3822, d₂₅ 0.8000. MeCH(OMe)CO₂Me, b₇₄₇ 129-30°, n_D²⁵ 1.3957, d₂₅ 0.9948, (0.45 mol) with 1 mol Me Grignard reagent yielded 21.8 g. II, b₇₅₂ 129.5-30°, n_D²⁵ 1.4100, d₂₅ 0.8877; V with Na yielded 53% II. V (33.2 g.) in 155 cc. MeOH treated with 2 drops H₂SO₄ yielded 34.6 g. 3-methyl-3-methoxy-2-butanol (VI), b₇₆₀ 143-4°, n_D²⁵ 1.4193, 0.9151. I (90.5 g.), 30 g. CaCO₃, and 400 cc. water treated dropwise during 20 min. with 95 g. AgNO₃, the mixture stirred 4 h. and extracted with Et₂O yielded 35.3 g. II, and 6.4 g. Me₂CHCOMe, b₇₆₀ 92-5° (2,4-dinitrophenylhydrazone, m. 122-2.5°); VI gave 80% recovered alc., b₇₆₀ 141-4°, and II gave 80.6% recovered alc., b₇₆₀ 129-30°. I (90.5 g.), 92 g. AgNO₃, and 500 cc. AcOH stirred 1 h. at 90-110°, the mixture filtered, and the filtrate neutralized with 6N KOH under Et₂O yielded 16.8 g. II, b₇₅₂ 129.5-30°. VI (20 g.), 20 g. Ac₂O, and 50 cc. pyridine refluxed 1 h. yielded 22 g. acetate, b₅₀ 85°, n_D²⁵ 1.4122, d₂₅ 0.9456. VI (32.1 g.) and 6.25 g. Na dissolved in 250 cc. refluxing petr. ether (b. 230-60°) and the solution treated with 39 g. MeI in 100 cc. Et₂O and refluxed 30 min. yielded 17.3 g. 2,3-dimethoxy-2-methylbutane (VII), b₇₆₀ 125-5.5°, n_D²⁵ 1.4026, d₂₅ 0.8571. I (95.5 g.) in 500 cc. MeOH refluxed 2 h. with 70 g. Ag₂O yielded 44.8 g. VII, b₇₆₀ 125-6°, n_D²⁵ 1.4018. III (53 cc.), 89 g. IV, and 1.5 1. water stirred 1.5 h. in an ice bath, the mixture saturated with NaCl, and extracted with Et₂O, yielded 67.33 g. trimethylethylene bromohydrin (Me₂C(OH)CHBrMe) (VIII), b₁₀ 48-51°, n_D²⁵ 1.4712. AgNO₃ (9.35 g.) in 200 cc. water added dropwise to 88.5 g. VIII and 84 g. NaHCO₃ in 300 cc. water during 1 h., the mixture stirred 1 h., extracted with Et₂O, the Et₂O partially distilled, the residue shaken with 42 g. NaHCO₃ and 47 g. AgNO₃ in 200 cc. water extracted with Et₂O, and the extract distilled, yielded 21.90 g. V, b₇₆₀ 72-3°, n_D²⁵ 1.3826, and 1.95 g. Me₂CHCOMe, b₇₆₉ 90-6° (2,4-dinitrophenylhydrazone, m. 122-2.5°).

Journal of the American Chemical Society published new progress about 2588-77-4. 2588-77-4 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is 2-Methyl-3-bromo-2-butanol, and the molecular formula is C10H15BO4, Safety of 2-Methyl-3-bromo-2-butanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Stellato, Michael J. published the artcilePore blocking by phenolates as deactivation path during the cracking of 4-propylphenol over ZSM-5, HPLC of Formula: 645-56-7, the publication is Catalysts (2021), 11(6), 721, database is CAplus.

Cracking of Pr side chains from 4-propylphenol, a model compound for lignin monomers, is studied for a com. ZSM-5 zeolite catalyst. The decline of 4-propylphenol conversion with time on stream can be delayed by co-feeding water. FTIR spectroscopy shows the formation of chemisorbed phenolates during reactions and significant amounts of phenolics are detected by GC-MS of the extract from the spent catalysts. Thus, chemisorbed phenolates are identified as the main reason for deactivation in the absence of water. Regardless of the amount of co-fed water, substituted monoaroms. and polyaromatic species are formed. Comprehensive characterization of the spent catalysts including Raman and solid-state ²⁷Al NMR spectroscopy, and thermogravimetric anal. points to a combination of deactivation processes. First, phenolates bind to Lewis acid sites within the zeolite framework and hinder diffusion unless they are hydrolyzed by water. In addition, light olefins created during the cracking process react to form a polyaromatic coke that deactivates the catalyst more permanently.

Catalysts published new progress about 645-56-7. 645-56-7 belongs to alcohols-buliding-blocks, auxiliary class Liquid Crystal &OLED Materials, name is 4-Propylphenol, and the molecular formula is C7H7ClN2S, HPLC of Formula: 645-56-7.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kobayashi, Takashi published the artcileNovel 2-amino-1,4-dihydropyridine calcium antagonists. II. Synthesis and antihypertensive effects of 2-amino-1,4-dihydropyridine derivatives having N,N-dialkylaminoalkoxycarbonyl groups at 3- and/or 5-position, COA of Formula: C10H15NO, the publication is Chemical & Pharmaceutical Bulletin (1995), 43(5), 797-817, database is CAplus and MEDLINE.

Novel 2-amino-1,4-dihydropyridine derivatives, e.g. I (R¹ and R² = N,N-dialkylaminoalkyl, 1-benzylpiperidin-3-yl, 1-benzhydrylazetidin-3-yl, Me, iso-Pr, R³ = 3-NO₂C₆H₄, 2,3-Cl₂C₆H₃, 3-CF₃C₆H₄, R⁴= NH₂, CH₃) were synthesized and their antihypertensive effects were evaluated in spontaneously hypertensive rats. Remarkably prolonged duration of antihypertensive action was observed when a tertiary amino group was introduced into either the 3- and 5-ester side-chain of the 1,4-dihydropyridine ring. In particular, the compounds containing cyclic amino moieties at the 3-position showed greater potency than those with acyclic amino moieties. Chem. modification studies indicated that the two ester side-chains of 1,4-dihydropyridine at the 3- and 5-position might function in a different manner in relation to the antihypertensive activities. CS-905, I (R¹ = 1-benzhydrylazetidin-3-yl, R² = iso-Pr, R³ = 3-NO₂C₆H₄, R⁴ = NH₂) exhibited potent and long-lasting antihypertensive effects with gradual onset of action, and is a promising candidate as an antihypertensive drug.

Chemical & Pharmaceutical Bulletin published new progress about 101-98-4. 101-98-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Alcohol, name is 2-(Benzyl(methyl)amino)ethanol, and the molecular formula is C10H15NO, COA of Formula: C10H15NO.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kobayashi, Takashi published the artcileNovel 2-amino-1,4-dihydropyridine calcium antagonists. I. Synthesis and antihypertensive effects of 2-amino-1,4-dihydropyridine derivatives having nitroxyalkoxycarbonyl groups at 3- and/or 5-position, Name: 2-(Benzyl(methyl)amino)ethanol, the publication is Chemical & Pharmaceutical Bulletin (1995), 43(5), 788-96, database is CAplus and MEDLINE.

Novel 2-amino-1,4-dihydropyridine derivatives, e.g. I (R¹ and R² = nitroxyalkyl, alkyl, N-methyl-N-benzylaminoethyl, R³ = 2- or 3-NO₂C₆H₄, 2,3-Cl₂C₆H₃, 2- or 3-CF₃C₆H₄) were synthesized and their pharmaceutical effect was evaluated in spontaneously hypertensive rats. The structure-activity relationships are discussed in terms of potency, onset-rapidity, and duration of antihypertensive activity. Remarkably prolonged duration of antihypertensive action was observed when a tertiary amino group was introduced on either side of an ester chain.

Chemical & Pharmaceutical Bulletin published new progress about 101-98-4. 101-98-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Alcohol, name is 2-(Benzyl(methyl)amino)ethanol, and the molecular formula is C10H15NO, Name: 2-(Benzyl(methyl)amino)ethanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kato, Yuichi published the artcileDeoxygenation of tertiary and secondary alcohols with sodium borohydride, trimethylsilyl chloride, and potassium iodide in acetonitrile, Name: 9-Phenyl-9H-xanthen-9-ol, the publication is Tetrahedron Letters (2021), 153519, database is CAplus.

In this study, a deoxygenation method was developed for tertiary and secondary alcs., ROH [R = triphenylmethyl, 9-phenyl-9H-xanthen-9-yl, bis(4-methoxyphenyl)(thiophen-2-yl)methyl, etc.] using trimethylsilane and trimethylsilyl iodide generated in situ from sodium borohydride and trimethylsilyl chloride, and trimethylsilyl chloride and potassium iodide, resp. In this method, tertiary and secondary alcs., which provided stable carbocations, were converted into the corresponding alkanes RH. This paper also presents the optimization of the reaction conditions, the reaction mechanism, as well as the scope and limitations of the method.

Tetrahedron Letters published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Name: 9-Phenyl-9H-xanthen-9-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts