Category: 55376-31-3

Traynham, J. G. published the artcileEffects of ring size on the reactions of cyclic olefins. Halohydrins from methylene cycloalkanes, Name: 2-Bromo-2-methylpropan-1-ol, the publication is Tetrahedron (1959), 165-72, database is CAplus.

cf. C.A. 51, 12835c. Addition of HOCl to methylene cycloalkanes, (CH₂)_n.C:CH₂ (I) (n = 3-6) gave mixtures of (CH₂)_n.C(OH)CH₂Cl (II) and (CH₂)_n.CClCH₂OH (III) with III predominating with n = 3 or 5. Addition of HOBr to I gave only (BrCH₂OH (IV) together with (HCHO (V) in amounts dependent on n. The appropriate 1-chloro-1-(chloromethyl)cycloalkane and an approx. equimolar amount of CaCO₃ in H₂O refluxed 6 hrs. gave 28-39% yields of authentic II. II with aqueous KOH gave the corresponding methylenecycloalkane oxide (VI), (H₂ (n, b.p./mm., n_D³⁰, and MR found given): 3, 90-2°/760, 1.4207, -; 4, 43-4°/62, 1.4290, 27.4; 5, 62-3°/37, 1.4470, -; 6, 84-5°/40, 1.4552, 36.5. VI (0.01-0.06 mole) dripped into 20 ml. concentrated HCl at below 5° and stirred 1 hr., poured onto ice, and the product extracted gave poor yields of III, giving immediate precipitates with alc. AgNO₃, but none with NaI in Me₂CO, reducing KMnO₄, giving neg. tests with Lucas reagent, showing no infrared absorption near 7.25 μ. VI treated with chilled 48% HBr and the mixture stirred 1 hr., neutralized with solid Na₂CO₃ and extracted with Et₂O, the washed and dried extract evaporated, and the residue distilled gave IV, forming an immediate precipitate with alc. AgNO₃, and giving neg. tests with Lucas reagent and with NaI in Me₂CO. IV (n = 4, 5, 6) refluxed 5-6 hrs. with 5M HCl gave good yields of V [n, b.p./mm., n_D²⁰, d₂₀, m.p. of semicarbazone (or 2,4-dinitrophenylhydrazone) given]: 4, 55-6°/36, 1.4343, 0.920, 123-4°; 5, 49.5°/10, 1.4490, 0.930, – (172-3°); 6, 45.5-46°/4, 1.4621, -, 154-5°. Except for preparation from VI (n = 3), the initial product mixtures contained appreciable amounts of V, estimated by infrared determination of the composition of the Et₂O extract residue, confirmed by fractional distillation (n, total % yield from HBr and VI, % IV and % V given): 4, 45, 65, 35; 5, 68, 95, 5; 7, 87, 68, 32. Cl and Br added with stirring to chilled aqueous suspensions of HgO and Ag₂SO₄, resp., and the approx. 1.8M solutions distilled at 40° in vacuo in the dark gave HOCl and HOBr solutions (exact. concentrations determined iodometrically). I (0.12 mole) in 200 ml. H₂O was stirred below 15° with addition of 20% excess cold HOCl or HOBr until the mixture no longer turned acidified starch-iodide paper blue and the process repeated until all acid solution was added, the mixture stirred 1 hr. and saturated with NaCl, the aqueous layer extracted with Et₂O and the combined organic product fractionated through a Vigreux column, the product components identified by comparison with authentic samples, and the product distributions estimated by comparison with known mixtures and results of fractional distillation Me₃CH (0.16 mole) with HOBr yielded 77% product containing 97% Me₂C(CH₂Br)OH, b₃₁ 66-6.5°, n_D²⁰ 1.4722, d₂₀ 1.451, and not more than 3% Me₂CBr-CH₂OH. The product distributions in hypohalous acid additions to I were tabulated (n, total % yield with HOCl, % III, % II, total % yield with HOBr, % IV and % V given): 3, 72, 60, 40, 78, 99, -; 4, 64, 41, 58, 67, 91, -; 5, 92, 67, 32, 89, 98, 2; 6, 86, 35, 64, 87, 87, 13. The phys. properties of authentic halohydrins were tabulated (halohydrin, n, b.p./mm., d₂₀, and n_D²⁰ given): II, 3, 56-60°/20, 1.135, 1.4688; III, 3, 69-70°/20, 1.154, 1.4760; II, 4, 57-8°/6, 1.143, 1.4841; III, 4, 62-3°/3, 1.182, 1.5036; II, 5, 54-5°/4, 1.127, 1.5024; III, 5, 53-4°/2, 1.113, 1.4905; II, 6, 56-8°/2, 1.118, 1.4997; III, 6, 70-1°/2, 1.128, 1.5114; IV, 3, 64-5°/10, 1.506, 1.5041; IV, 4, 45-6°/2, 1.463, 1.5126; IV, 5, 55-6°/2, – (m. 82.3°), -; IV, 6, 73-4°/3, 1.339, 1.5232. The results were discussed and an interpretation included.

Tetrahedron published new progress about 55376-31-3. 55376-31-3 belongs to alcohols-buliding-blocks, auxiliary class Polymerization Reagents,ATRP Initiators, name is 2-Bromo-2-methylpropan-1-ol, and the molecular formula is C18H28B2O4, Name: 2-Bromo-2-methylpropan-1-ol.

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

Tudorascu, Marius published the artcileEnzymes in organic syntheses. I. Olefin transformation to addition products catalyzed by chloroperoxidase, SDS of cas: 55376-31-3, the publication is Progress in Catalysis (1993), 63-70, database is CAplus.

Chloroperoxidase in free or immobilized form catalyzed the addition reactions of olefins with hypohalous acids generated from metal halides and H₂O₂. Thus, the reaction of propylene with LiBr-H₂O₂ afforded 1-bromo-2-propanol (92-3%) and 2-bromo-1-propanol.

Progress in Catalysis published new progress about 55376-31-3. 55376-31-3 belongs to alcohols-buliding-blocks, auxiliary class Polymerization Reagents,ATRP Initiators, name is 2-Bromo-2-methylpropan-1-ol, and the molecular formula is C16H14O6, SDS of cas: 55376-31-3.

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

Tudorascu, Marius published the artcileEnzymes in organic syntheses. I. Olefin transformation to addition products catalyzed by chloroperoxidase, SDS of cas: 55376-31-3, the publication is Progress in Catalysis (1993), 63-70, database is CAplus.

Chloroperoxidase in free or immobilized form catalyzed the addition reactions of olefins with hypohalous acids generated from metal halides and H₂O₂. Thus, the reaction of propylene with LiBr-H₂O₂ afforded 1-bromo-2-propanol (92-3%) and 2-bromo-1-propanol.

Progress in Catalysis published new progress about 55376-31-3. 55376-31-3 belongs to alcohols-buliding-blocks, auxiliary class Polymerization Reagents,ATRP Initiators, name is 2-Bromo-2-methylpropan-1-ol, and the molecular formula is C16H14O6, SDS of cas: 55376-31-3.

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

Guo, Chuangxing published the artcileDiscovery of 3-aryloxy-lactam analogs as potent androgen receptor full antagonists for treating castration resistant prostate cancer, COA of Formula: C4H9BrO, the publication is Bioorganic & Medicinal Chemistry Letters (2012), 22(2), 1230-1236, database is CAplus and MEDLINE.

High throughput cell-based screening led to the identification of 3-aryloxy lactams as potent androgen receptor (AR) antagonists. Refinement of these leads to improve the ADME profile and remove residual agonism led to the discovery of 12, a potent full antagonist with greater oral bioavailability. Improvements in the ADME profile were realized by designing more ligand-efficient mols. with reduced mol. weights and lower lipophilicities.

Bioorganic & Medicinal Chemistry Letters published new progress about 55376-31-3. 55376-31-3 belongs to alcohols-buliding-blocks, auxiliary class Polymerization Reagents,ATRP Initiators, name is 2-Bromo-2-methylpropan-1-ol, and the molecular formula is C4H9BrO, COA of Formula: C4H9BrO.

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

Roque, Ana Carolina Abbud Hanna published the artcileConformational analysis for infrared spectroscopy and theoretical calculations of some 2-bromo-2-propyl 2-aryl-acetates, ibuprofen and naproxen analogs, SDS of cas: 55376-31-3, the publication is Journal of Molecular Structure (2021), 130027, database is CAplus.

Conformational anal. of new para-substituted 2-bromo-2-Pr 2-aryl-acetates (Y = H, OMe, Cl, and NO₂) (R1), ibuprofen (R2), and naproxen (R3) analogs using IR (IR) spectroscopy and theor. calculations was performed to determine the preferential conformers of these compounds in solvents with increasing polarity (CCl₄, CH₃Cl, and CH₃CN). The aryl-bromo-esters were synthesized via the esterification of 2-bromo-2-methylpropan-1-ol and the corresponding carboxylic acids, with good yields (∼36-70%). The IR spectra showed that these compounds presented only one conformation, and the exptl. data were supported by the theor. results obtained by d. functional theory (DFT) calculations using the 6311+G (2df, 2p) basis set. The calculations revealed that all the studied compounds presented two stable geometric conformations, which agrees with the data obtained exptl. in CCl₄. Theses conformers are stabilized by intramol. hydrogen bonds. However, the orbital interaction calculations using the natural bond orbital (NBO) method showed that the η_O→σ*_C-C,η_O→σ*_C-O, η_O→σ*_C-O and η_O→π*_C-O hyper-conjugations are the main interactions that stabilize the conformations. The compounds preferentially adopt the anti-conformation because the steric effect between the gauche bromo and oxygen atoms overrides the hyper-conjugative interactions, in addition to the stabilizing σ_C-H→ σ*_C-Br interactions in the conformers.

Journal of Molecular Structure published new progress about 55376-31-3. 55376-31-3 belongs to alcohols-buliding-blocks, auxiliary class Polymerization Reagents,ATRP Initiators, name is 2-Bromo-2-methylpropan-1-ol, and the molecular formula is C4H9BrO, SDS of cas: 55376-31-3.

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

Tiollais, Rene published the artcileSeveral physical and chemical properties of aliphatic enamines, Application of 2-Bromo-2-methylpropan-1-ol, the publication is Bulletin de la Societe Chimique de France (1964), 1205-6, database is CAplus.

RR’C:CHNR”₂ prepared by known methods were [R, R’, NR”₂, % yield, b.p. (mm.), density (temperature), and n_D listed]: Me, H, NMe₂, 33, 82° (760), 0.754 (23°), 1.4275; Et, H, NMe₂ 74, 107° (760), 0.768 (20°), 1.4345; Pr, H, NMe₂, 79, 59° (60), 0.776 (20°), 1.4390; Am, H, NMe₂, 71, 67° (15), 0.789 (20°), 1.4440; Et, H, NEt₂, 53, 37° (12), 0.786 (22°), 1.4448; Am, H, NEt₂, 57, 93° (13), 0.800 (16.8°), 1.4500; Et, H, NMeBu, 53, 65° (15), 0.786 (20.4°), 1.4492; Et, H, NMeBu-iso, 76, 82° (51), 0.779 (21°), 1.4460; Me, Me, NMe₂, 64, 87° (760), 0.745 (19.6°), 1.4212; Me, Me, NEt₂, 57, 57° (68), 0.761 (20°), 1.4268; Et, H, morpholino, 65, 72° (12), 0.935 (22°), 1.4750; Me, Me, morpholino, 61, 65° (18), 0.922 (20.4°), 1.4669. Bromination of the enamines in ether gave, after hydrolysis, α-bromo aldehydes (product, % yield, phys. properties, and m.p. 2,4-dinitrophenylhydrazone listed): 2-bromobutanal, 64, b₂₅ 42°, n^21.5_D 1.4595, d_21.5 1.4531, 93-4°; 2-bromo-2-methylpropanol, 60, b₇₀ 47°, n²¹_D 1.4522, d₂₁ 1.389, 115-16°; 2-bromoheptanal, 60, b₁₂ 80-1°, n^22.5_D 1.4621, d_22.5 1.249, 105-6°.

Bulletin de la Societe Chimique de France published new progress about 55376-31-3. 55376-31-3 belongs to alcohols-buliding-blocks, auxiliary class Polymerization Reagents,ATRP Initiators, name is 2-Bromo-2-methylpropan-1-ol, and the molecular formula is C35H35ClN6O5, Application of 2-Bromo-2-methylpropan-1-ol.

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

Helal, Mustafa R. published the artcileConformational analysis of some β-halohydrins via G3 calculations, Synthetic Route of 55376-31-3, the publication is Jordan Journal of Chemistry (2013), 8(1), 19-30, database is CAplus.

The conformational anal. of fifteen β-halohydrins, XCR₁R₂CR₃R₄OH, (X = F, Cl and Br) had been studied by ab initio G3 method. The enthalpies of formation values were calculated for nine conformers of each β-halohydrin. The (g^–, g⁺) and (g⁺, g^–) conformers are the most stable due to intramol. H-bond formation. These H-bonds are weaker than intermol. H-bonds formed between alkyl halides and alcs. This trend is more obvious in fluoro-species. The rotation of C- X bond of (g^–, g⁺) conformers by 360° gives three transition states, this rotation was found to require 6-7 kcal/mol.

Jordan Journal of Chemistry published new progress about 55376-31-3. 55376-31-3 belongs to alcohols-buliding-blocks, auxiliary class Polymerization Reagents,ATRP Initiators, name is 2-Bromo-2-methylpropan-1-ol, and the molecular formula is C4H9BrO, Synthetic Route of 55376-31-3.

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