Tag: M.W=100-150

Kucinski, K. published the artcileChemoselective and Catalyst-Free O-Borylation of Silanols: A Facile Access to Borasiloxanes, Application In Synthesis of 597-52-4, the publication is ChemSusChem (2017), 10(23), 4695-4698, database is CAplus and MEDLINE.

This paper demonstrates the 1st highly chemoselective syntheses of various borasiloxanes from hydroboranes and silanols, achieved through catalyst-free dehydrogenative coupling at room temperature This green protocol, which uses easily accessible reagents, allows for the obtaining of borasiloxanes under air atm. and solvent-free conditions.

ChemSusChem published new progress about 597-52-4. 597-52-4 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is Triethylsilanol, and the molecular formula is C6H16OSi, Application In Synthesis of 597-52-4.

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

Corey, E. J. published the artcileA study of the formation of halo amines and cyclic amines by the free radical chain decomposition of N-haloammonium ions (Hofmann-Löffler reaction), Recommanded Product: 4-(Butylamino)butan-1-ol, the publication is Journal of the American Chemical Society (1960), 1657-68, database is CAplus.

cf. Wawzonek and Thelen, CA 44, 9444g; W., et al., CA 46, 2058a. Cyclization of N-halo amines to pyrrolidines by heating in H₂SO₄ was a free-radical chain reaction which was initiated by ultraviolet light or by persulfate and (or) ferrous ions and was inhibited by O. The reaction was acid-catalyzed; the acid most likely accelerated chain-propagation or retarded chain-termination. Five-membered rings were formed almost exclusively. The ease of removal of H from the δ-C involved was tertiary > secondary > primary; there was virtually no competition when different types were present. No pyrrolidines were obtained when the δ-H was tertiary; solvolysis of the intermediate δ-Cl amine apparently predominated. Irradiation of dibutylchloramine in H₂SO₄ did not liberate Cl ion, indicating that a δ-Cl amine was an intermediate. The exptl. data support the Wawzonek mechanism (loc. cit.). For isotope effect and stereochem. studies, some deuteriated amines were synthesized. Valerolactone [66.2% L-(-)isomer, 33.8% D(+)-isomer] (26 g.) and liquid MeNH₂ under N for 7 days in a sealed tube gave 100% crude N-methyl-4-hydroxyvaleramide (I), which with LiAlH₄ gave 39% N-methyl-4-hydroxyamylamine (II), b₈ 97-8°, n²⁵_D 1.4460, [α]²²_D 4.23° (c 10, EtOH). II and p-MeC₆H₄SO₂Cl in pyridine gave 82% (-)-N-methyl-N-(4-p-toluenesulfonoxyamyl)-p-toluenesulfonamide (III), [α]²⁰_D -2.73° (c 10, CHCl₃). Reduction of III with LiAlD₄ gave 73% (-)-methylamylamine-4-d (IV), n²⁵_D 1.4068, α²⁰_D -0.135 ± 0.03° (1 dm.). Cyclization of IV (Coleman, et al., Organic Syntheses Collective volume III, 159(1955)) gave 43% optically inactive 1,2-dimethylpyrrolidine; analysis of the picrate showed 4.88 atom-% D, corresponding to an isotope effect (k_H/k_D) of 3.54 ± 0.5. As a check on the anal. data, 1,2-dimethylpyrrolidine-2-d (V) was synthesized and the isotope effect determined from infrared absorption. 1,2-Dimethyl-2-pyrroline (30 g.), neutralized with 3N HCl and treated with aqueous KCN gave 79% 1,2-dimethyl-2-cyanopyrrolidine (VI), b₃₆ 83-4°, n^22.5_D 1.4447; picrate m. 154.5-6.5° (C₆H₆EtOH). Reduction of VI with LiAlD₄ gave 72% V, b. 94-5°, n²⁵_D 1.4203. From the absorption band at 2040 cm.^-1, the amount of V present in the product from cyclization of IV was determined, giving an isotope effect of 3.42 ± 0.5. N-Butyl-2-pyrrolidone was hydrolyzed with Ba(OH)₂ to 4-butylaminobutyric acid, m. 145-6° (MeOH-Et₂O), which on reduction with LiAlD₄ gave 36% 4-butylaminobutanol-1,1-d₂ (VII), b₁₆ 131-2°, n^24.5_D 1.4508. VII was converted to N-butyl-N-(4-p-toluenesulfonoxybutyl)-p-toluenesulfonamide-4,4-d₂ (oil), which on reduction with LiAlD₄ gave 66% dibutylamine-4,4-d₃ (VIII), b₄₆ 76-7°; HCl salt m. 292-6° (decomposition). Cyclization of VIII after chlorination gave N-butylpyrrolidine, b₅₅ 75°; the infrared absorption showed bands corresponding to N-CD₂– and C-CD₃ groups. The isotope effect for this cyclization, calculated from infrared absorption, was approx. 2.6. Other amine derivatives synthesized for study were as follows. Isocaproyl chloride and amylamine gave 78% N-amylisocaproamide, b_0.35 103-5°, n²²_D 1.4481, which on reduction with LiAlH₄ gave amylisohexylamine, b₁₆ 99-102°, n²²_D 1.4295, yield 81%; HBr salt m. 291-2.5° (decomposition) (dioxane-EtOH). Attempted cyclization of the N-Cl derivative gave no tertiary amines. Similar failure was experienced with butyl-sohexylamine, although HCl was evolved during heating. The product amounted to 0.147 g., b₁₄ about 75°, n^21.8_D 1.4378; HBr salt (IX) m. 162-4° (dioxane). IX was not identical with N-butyl-2,2-dimethylpyrrolidine-HBr nor with N-isohexylpyrrolidine-HBr, which was prepared for comparison by LiAlH₄ reduction of N-isocaproylpyrrolidine [N-isohexylpyrrolidine b₁₅ 79-82°, n²⁵_D 1.4428; HBr salt m. 179-80° (dioxane)].

Journal of the American Chemical Society published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, Recommanded Product: 4-(Butylamino)butan-1-ol.

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

Nagasawa, Yoshiyuki published the artcileHydrogenation of 4-Propylphenol over Carbon-supported Palladium Catalyst without External Hydrogen: Effect of Carbon Support and Palladium Loading, Computed Properties of 645-56-7, the publication is Chemistry Letters (2021), 50(3), 431-434, database is CAplus.

The ring hydrogenation of 4-propylphenol in aqueous ethanol solution was studied over graphite- and activated carbon-supported palladium catalysts (Pd/G and Pd/C) with 0.1-5 wt% of palladium loadings without using external hydrogen. Decomposition of ethanol produced hydrogen which was responsible for the hydrogenation of 4-propylphenol over palladium metal particles on both the supports in aqueous medium. The different hydrogenation behaviors were discussed based on surface properties of supports.

Chemistry Letters 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 C9H12O, Computed Properties of 645-56-7.

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

Asahara, Teruzo published the artcileTelomerization of ethylene and carbon tetrachloride initiated by amines, Quality Control of 4543-95-7, the publication is Bulletin of the Japan Petroleum Institute (1965), 35-40, database is CAplus.

cf. CA 62, 1554a. In this reaction, strongly basic amines are excellent initiators. Primary amines are more effective than secondary or tertiary structures, and branched amines are inferior to n-amines. Alkanolamines are also excellent initiators. The experiments were carried out in a stainless steel autoclave in the absence of metallic salts. tert-Butanol is a preferred solvent for this reaction. Generally, the higher the dielec. constant of the hydroxylic solvent, the greater the yield of telomer. Aprotic solvents show no such regular influence. 13 references.

Bulletin of the Japan Petroleum Institute published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, Quality Control of 4543-95-7.

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

Luleburgaz, Serter published the artcileChlorodimethylsilane-Mediated Reductive Etherification Reaction: A Robust Method for Polyether Synthesis, Name: Pentane-1,5-diol, the publication is Macromolecules (Washington, DC, United States) (2022), 55(5), 1533-1543, database is CAplus.

Polyethers have always been privileged compounds in polymer chem. and have found extensive applications in both academic research and industry. However, the currently employed strategies for their synthesis require harsh conditions such as ionic polymerizations together with limited precursor monomer options. In this study, a chlorodimethylsilane (CDMS)-mediated reductive etherification reaction was introduced as a versatile strategy for polyether synthesis. Accordingly, terephthalaldehyde (TPA) and 1,4-butanediol were first reacted at room temperature in the presence of CDMS using nitromethane as the polymerization solvent to reveal the optimum conditions for the proposed system. Subsequently, a variety of diols ranging from linear to sterically congested diols were reacted with TPA (and its isomers) under the optimized conditions to create a polyether library. Meanwhile, in addition to polyether having the expected alternating units, the formation of polyether stem from the self-condensation of TPA was found to be inevitable in all cases. From the proposed strategy, polyethers with a mol. weight of up to 110.4 kDa and a high alternating unit of up to 93% were obtained. The versatile and robust character of the presented strategy was supported by a model end-group study, and the polymerization behavior was examined mechanistically. It is anticipated that the presented method might be a strong candidate for polyether synthesis with different backbones, given the unlimited sources of diols.

Macromolecules (Washington, DC, United States) 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, Name: Pentane-1,5-diol.

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

Yu, Wanwan published the artcileA Catalytic Oxidative Quinone Heterofunctionalization Method: Synthesis of Strongylophorine-26, Application of 2-Morpholinoethanol, the publication is Angewandte Chemie, International Edition (2018), 57(31), 9805-9809, database is CAplus and MEDLINE.

The preparation of heteroatom-substituted p-quinones is ideally performed by direct addition of a nucleophile followed by in situ reoxidation Albeit an appealing strategy, the reactivity of the p-quinone moiety is not easily tamed and no broadly applicable method for heteroatom functionalization exists. Shown herein is that Co(OAc)₂ and Mn(OAc)₃·2H₂O act as powerful catalysts for oxidative p-quinone functionalization with a collection of O, N, and S nucleophiles, using oxygen as the terminal oxidant. Preliminary mechanistic observations and the first synthesis of the cytotoxic natural product strongylophorine-26, I, is presented.

Angewandte Chemie, International Edition published new progress about 622-40-2. 622-40-2 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Alcohol, name is 2-Morpholinoethanol, and the molecular formula is C6H8O4, Application of 2-Morpholinoethanol.

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

Chen, Yuming published the artcileTwo-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of alcs., Computed Properties of 4410-99-5, the publication is European Journal of Organic Chemistry (2021), 2021(7), 1179-1183, database is CAplus.

We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcs. to afford products containing a C-N, C-S, or C-O bond. In the first step the alc. undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-mol. drugs containing hydroxy-group.

European Journal of Organic Chemistry published new progress about 4410-99-5. 4410-99-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Benzene, name is 2-Phenylethanethiol, and the molecular formula is C8H10S, Computed Properties of 4410-99-5.

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

Zhao, Ling published the artcileAcceptorless Dehydrogenative Cross-Coupling of Primary Alcohols Catalyzed by an N-Heterocyclic Carbene-Nitrogen-Phosphine Chelated Ruthenium(II) Complex, Safety of Pentane-1,5-diol, the publication is Journal of Organic Chemistry (2022), 87(7), 4550-4559, database is CAplus and MEDLINE.

The acceptorless dehydrogenative cross-coupling of primary alcs. to form cross-esters with the liberation of H₂ gas was enabled using a [RuCl(η⁶-C₆H₆)(κ²-CNP)][PF₆]Cl complex as the catalyst. This sustainable protocol was applicable to a broad range of primary alcs., particularly for the sterically demanding ones, featuring good functional group tolerance and high selectivity. The good catalytic performance can be attributed to the nitrogen-phosphine-functionalized N-heterocyclic carbene (CNP) ligand, which adopted a facial coordination mode as well as the facile dissociation of coordinated benzene.

Journal of Organic Chemistry 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 C8H5F3N4, Safety of Pentane-1,5-diol.

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

Forcellini, Elsa published the artcileSystematic study of the reactivity of (E)-4,4,4-trifluorobut-2-en-1-yl 4-methylbenzenesulfonate towards different classes of nucleophiles, Formula: C4H5F3O, the publication is Journal of Fluorine Chemistry (2015), 216-221, database is CAplus.

The alkylation of 4-phenylphenol, benzyl alc., thiols, primary and secondary amines, indole, and malonates by (E)-F₃CCH:CHCH₂OTs was studied; in most cases (4-phenylphenol, thiols, amines, malonates), alkylation of the nucleophiles was most effective using K₂CO₃ in MeCN, while none of the conditions tried were effective for indole and benzyl alc.

Journal of Fluorine Chemistry published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Formula: C4H5F3O.

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

Sugimoto, Kanta published the artcileVersatile tensile and fracture behaviors of dual crosslinked elastomers by postpreparation photo tuning of local crosslink density, COA of Formula: C5H12O2, the publication is Polymer (2021), 124089, database is CAplus.

This study demonstrates the postpreparation easy tuning of the Young’s modulus of elastomers by using polyesters bearing thermal and photo crosslinkable groups. In the first crosslinking step, only thermoreactive groups form crosslinks, resulting in a highly deformable soft elastomer. In the second step, photoreactive groups are crosslinked by UV irradiation, and controlling the UV irradiation time can tune the crosslink d., resulting in modulus tuning over two orders of magnitude at room temperature The use of photo reaction enables precise modulus patterning using photomasks with a series of slits. In horizontally patterned samples, the dually crosslinked stiff section shows negligible deformation, whereas large elongation is observed selectively in the single crosslinked soft sections. In vertically patterned samples, interestingly, crack propagation and complete fracture are significantly suppressed, compared with the fully dually crosslinked sample. The present data can thus provide important insight for developing new methodologies for controlling the tensile and fracture behavior of elastomers.

Polymer 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 C13H15NO6S, COA of Formula: C5H12O2.

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