Month: February 2023

Synthesis of Polysubstituted 2-Naphthols by Palladium-Catalyzed Intramolecular Arylation/Aromatization Cascade was written by Cai, Jinhui;Wang, Zhen-Kai;Zhang, Yun-Hao;Yao, Fei;Hu, Xu-Dong;Liu, Wen-Bo. And the article was included in Advanced Synthesis & Catalysis in 2020.Reference of 61150-57-0 This article mentions the following:

A palladium-catalyzed intramol. α-arylation and defluorinative aromatization strategy for the synthesis of polysubstituted 2-naphthols, e.g., 1-(3-hydroxynaphthalen-2-yl)ethan-1-one, is reported. With ortho-bromobenzyl-substituted α-fluoroketones RCH₂C(F)(C(O)R²)C(O)R¹ (R = 2-bromophenyl, 2-bromopyridin-3-yl, 6-bromo-2H-1,3-benzodioxol-5-yl, etc., R¹ = Me, Et, Ph, R² = Et, OMe, OEt, Ot-Bu) as the substrates and palladium acetate/triphenylphosphine as the catalyst system, this method features good functional group tolerance, readily available catalyst and starting materials, and high yields. The applications of the strategy are demonstrated by the synthesis of useful building blocks, such as naphtha[2,3-b]furan, naphthol AS-D, and ligands/catalysts. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0Reference of 61150-57-0).

2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Reference of 61150-57-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and gas permeation properties of poly(diarylacetylene)s having substituted and twisted biphenyl moieties was written by Hu, Yanming;Shimizu, Toshiyuki;Hattori, Kyohei;Shiotsuki, Masashi;Sanda, Fumio;Masuda, Toshio. And the article was included in Journal of Polymer Science, Part A: Polymer Chemistry in 2010.Computed Properties of C16H17Br This article mentions the following:

Diarylacetylene monomers containing substituted biphenyl (1a-f) and anthryl (1g) groups were synthesized and then polymerized with TaCl₅-n-Bu₄Sn catalyst to produce the corresponding poly(diarylacetylene)s (2a-g). Polymers 2a-f were soluble in common organic solvents such as cyclohexane, toluene, and chloroform. According to thermogravimetric anal., the onset temperatures of weight loss of the polymers were over 400° in air, indicating considerably high thermal stability. Free-standing membranes 2a and 2c-e were prepared by the solution casting method. Desilylation of Si-containing membrane 2c was carried out with trifluoroacetic acid to afford 3c. All the polymer membranes, especially those having twisted biphenyl groups, exhibited high gas permeability; for example, their oxygen permeability (PO₂) values ranged from 130 to 1400 barriers. Membrane 2d having two chlorine atoms in the biphenyl group showed the highest gas permeability (PO₂ = 1400 barriers) among the present polymers. In the experiment, the researchers used many compounds, for example, 4-Bromo-4′-tert-butylbiphenyl (cas: 162258-89-1Computed Properties of C16H17Br).

4-Bromo-4′-tert-butylbiphenyl (cas: 162258-89-1) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Computed Properties of C16H17Br

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of 3-phenylethynylphenol. (A novel high-temperature phenyl acetylene endcapper for arylene ethers) was written by Jayaraman, S.;Srinivasan, R.;McGrath, J. E.. And the article was included in Polymer Preprints (American Chemical Society, Division of Polymer Chemistry) in 1993.Safety of 3-Bromophenyl acetate This article mentions the following:

PhCCH was condensed with m-XC₆H₄OAc (X = Br, I) to give 3-(phenylethynyl)phenyl acetate, which was methanolyzed to provide 3-(phenylethynyl)phenol, an endcapping agent for aromatic polyethers. 3-Ethynylphenol was similarly obtained. In the experiment, the researchers used many compounds, for example, 3-Bromophenyl acetate (cas: 35065-86-2Safety of 3-Bromophenyl acetate).

3-Bromophenyl acetate (cas: 35065-86-2) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Safety of 3-Bromophenyl acetate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

RAFT polymerization of bromotyramine-based 4-acryloyl-1,2,3-triazole: a functional monomer and polymer family through click chemistry was written by Andjouh, Sofyane;Bressy, Christine;Blache, Yves. And the article was included in RSC Advances in 2016.Electric Literature of C10H13BrO This article mentions the following:

Four new functional acryloyl-triazole monomers derived from bromotyramine were successfully synthesized. These monomers were prepared in an efficient way from organic azides and propargyl acrylate via a copper catalyzed 1,3-dipolar cycloaddition Polymers containing bromotyramine as a pendant group were obtained via reversible addition-fragmentation chain transfer (RAFT) polymerization The influence of the chain transfer agent (CTA), solvent, temperature and the length of the linker between the triazole and bromotyramine groups on the polymerization kinetics was studied. It was found that triazoles containing acrylate monomers are characterized by fast polymerization and polymers with controlled molar masses (20 000 g mol^-1) and low dispersities (DM < 1.5) can be prepared Glass transition temperatures of these acrylic polymers ranged from 48 °C to 20 °C by controlling the length of the linker between the bromotyramine side groups and the backbone. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Electric Literature of C10H13BrO).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Electric Literature of C10H13BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes was written by Lin, Zhiyang;Jin, Youxiang;Hu, Weitao;Wang, Chuan. And the article was included in Chemical Science in 2021.Quality Control of 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

Herein, A nickel-catalyzed asym. reductive aryl-allylation of aryl iodide-tethered unactivated alkenes, wherein both acyclic allyl carbonates and cyclic vinyl ethylene carbonates was served as the coupling partners was reported. Furthermore, the direct use of allylic alcs. as the electrophilic allyl source in this reaction was also viable in the presence of BOC anhydride. Remarkably, this reaction proceeded with high linear/branched-, E/Z- and enantio-selectivity, allowing the synthesis of various chiral indanes and dihydrobenzofurans (50 examples) containing a homoallyl-substituted quaternary stereocenter with high optical purity (90-98% ee). In this reductive reaction, the use of pregenerated organometallics was circumvented, giving this process good functionality tolerance and high step-economy. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Quality Control of 1-(3-Bromopropyl)-4-methoxybenzene).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Quality Control of 1-(3-Bromopropyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Syntheses of reactive fluorescent stains derived from 5(2)-aryl-2(5)-(4-pyridyl)oxazoles and bifunctionally reactive linkers was written by Litak, Peter T.;Kauffman, Joel M.. And the article was included in Journal of Heterocyclic Chemistry in 1994.Name: 3-(Bromomethyl)benzoic acid This article mentions the following:

Several bifunctionally reactive linkers containing halide or sulfonate ester groups were prepared The linkers were used to quaternize 5-(4-methoxyphenyl)-2-(4-pyridyl)oxazole and 2-(6-chromanyl)-5-(4-pyridyl)oxazole to produce fluorescent stains that contained a reactive group such as an isothiocyanate, an N-hydroxysuccinimidyl ester, a maleimide, or an oxirane. The stains were derivatized with either PrNH₂, PrSH, or piperidine, as appropriate, to help in characterization. The stains might serve as more photostable alternatives to fluoresceins or coumarins. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8Name: 3-(Bromomethyl)benzoic acid).

3-(Bromomethyl)benzoic acid (cas: 6515-58-8) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Name: 3-(Bromomethyl)benzoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Identification of 5-benzylidene-2-phenylthiazolones as potent PRMT5 inhibitors by virtual screening, structural optimization and biological evaluations was written by Zhu, Kongkai;Tao, Hongrui;Song, Jia-Li;Jin, Lu;Zhang, Yuanyuan;Liu, Jingqiu;Chen, Zhifeng;Jiang, Cheng-Shi;Luo, Cheng;Zhang, Hua. And the article was included in Bioorganic Chemistry in 2018.Reference of 108940-96-1 This article mentions the following:

Protein arginine methyltransferase 5 (PRMT5) is an epigenetics related enzyme that has been validated as an important therapeutic target for glioblastoma and mantel cell lymphoma. In the present study, 11 novel PRMT5 inhibitors with 5-benzylidene-2-phenylthiazolone scaffold were identified by mol. docking-based virtual screening and structural optimization. Their IC₅₀ values against PRMT5 at enzymic level were ranging from 0.77 to 23 μM. As expected, the top two active hits (5 and 19) showed potent anti-proliferative activity against MV4-11 cells with EC₅₀ values lower than 10 μM and reduced the cellular sym. arginine dimethylation levels of SmD3 protein. Besides, 5 and 19 demonstrated the mechanism of cell killing in cell cycle arrest and apoptotic effect. The probable binding modes of the two compounds were explored and further verified by mol. dynamics simulation. The structure-activity relationship (SAR) of this class of structures was also discussed and further demonstrated by mol. docking simulation. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Reference of 108940-96-1).

3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Reference of 108940-96-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Presence and Absence of Excited State Intramolecular Charge Transfer with the Six Isomers of Dicyano-N,N-dimethylaniline and Dicyano-(N-methyl-N-isopropyl)aniline was written by Galievsky, Victor A.;Druzhinin, Sergey I.;Demeter, Attila;Kovalenko, Sergey A.;Senyushkina, Tamara;Mayer, Peter;Zachariasse, Klaas A.. And the article was included in Journal of Physical Chemistry A in 2011.Formula: C6H5Br2N This article mentions the following:

The excited state behavior of the six m,n-dicyano-N,N-dimethylanilines (mnDCDMA) and six m,n-dicyano-(N-methyl-N-isopropyl)anilines (mnDCMIA) is discussed as a function of solvent polarity and temperature The dicyano moiety in these electron donor (D)/acceptor (A) mols. has a considerably larger electron affinity than the benzonitrile subgroup in 4-(dimethylamino)benzonitrile (DMABN). Nevertheless, the fluorescence spectra of the mnDCDMAs and mnDCMIAs in n-hexane all consist of a single emission originating from the locally excited (LE) state, indicating that a reaction from LE to an intramol. charge transfer (ICT) state does not take place. The calculated energies E(ICT), obtained by employing the reduction potential of the dicyanobenzene subgroups and the oxidation potential of the amino substituents trimethylamine (N(Me)₃) and isopropyldimethylamine (iPrNMe₂), are lower than E(LE). The absence of an LE â†?ICT reaction therefore makes clear that the D and A units in the dicyanoanilines are not electronically decoupled. In the polar solvent acetonitrile (MeCN), dual (LE + ICT) fluorescence is found with 24DCDMA and 34DCDMA, as well as with 24DCMIA, 25DCMIA, and 34DCMIA. For all other mnDCDMAs and mnDCMIAs, only LE emission is observed in MeCN. The ICT/LE fluorescence quantum yield ratio Φ'(ICT)/Φ(LE) in MeCN at 25 °C is larger for 24DCDMA (1.2) than for 34DCDMA (0.35). The replacement of Me by iso-Pr in the amino substituent leads to a considerable increase of Φ'(ICT)/Φ(LE), 8.8 for 24DCMIA and 1.4 for 34DCMIA, showing that the LE â‡?ICT equilibrium has shifted further toward ICT. The appearance of an ICT reaction with the 2,4- and 3,4-dicyanoanilines is caused by a relatively small energy gap ΔE(S₁,S₂) between the two lowest excited singlet states as compared with the other m,n-dicyanoanilines, in accordance with the PICT model. The observation that the ICT reaction is more efficient for 24DCMIA and 34DCMIA than for their mnDCDMA counterparts is mainly caused by the fact that iPrNMe₂ is a better electron donor than N(Me)₃: E(D/D⁺) = 0.84 against 1.05 V vs SCE. That ICT also occurs with 25DCMIA, notwithstanding its large ΔE(S₁,S₂), is due to the substantial amino twist angle θ = 42.6°, which leads to partial electronic decoupling of the D and A subgroups. The dipole moments μ_e(ICT) range between 18 D for 34DCMIA and 12 D for 25DCMIA, larger than the corresponding μ_e(LE) of 16 and 11 D. The difference between μ_e(ICT) and μ_e(LE) is smaller than with DMABN (17 and 10 D) because of the noncollinear arrangement of the amino and cyano substituents (different dipole moment directions). The dicyanoanilines that do not undergo ICT, have LE dipole moments between 9 and 16 D. From plots of ln(Φ'(ICT)/Φ(LE)) vs 1000/T, the (rather small) ICT reaction enthalpies ΔH could be measured in MeCN: 5.4 kJ/mol (24DCDMA), 4.7 kJ/mol (24DCMIA), and 3.9 kJ/mol (34DCMIA). With the mnDCDMAs and mnDCMIAs only showing LE emission, the fluorescence decays are single exponential, whereas for those undergoing an LE â†?ICT reaction the LE and ICT picosecond fluorescence decays are double exponential. In MeCN at 25 °C, the decay times τ₂ have values between 1.8 ps for 24DCMIA and 4.6 ps for 34DCMIA at 25 °C. Longer times are observed at lower temperatures Arrhenius plots of the forward and backward ICT rate constants k_a and k_d of 25DCMIA in THF, obtained from the LE and ICT fluorescence decays, give the activation energies E_a = 4.5 kJ/mol and E_d = 11.9 kJ/mol, i.e., ΔH = -7.4 kJ/mol. From femtosecond transient absorption spectra of 24DCDMA and 34DCDMA at 22 °C, ICT reaction times τ₂ = 1/(k_a + k_d) of 1.8 and 3.1 ps are determined By combining these results with the data for the fluorescence decays and Φ'(ICT)/Φ(LE), the values k_a = 49 × 10¹⁰ s^-1 (24DCDMA) and k_a = 23 × 10¹⁰ s^-1 (34DCDMA) are calculated An LE and ICT excited state absorption is present even at a pump/probe delay time of 100 ps, showing that an LE â‡?ICT equilibrium is established. In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4Formula: C6H5Br2N).

3,4-Dibromoaniline (cas: 615-55-4) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Formula: C6H5Br2N

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Discovery of Novel Indoline Cholesterol Ester Transfer Protein Inhibitors (CETP) through a Structure-Guided Approach was written by Wilson, Jonathan E.;Kurukulasuriya, Ravi;Reibarkh, Mikhail;Reiter, Maud;Zwicker, Aaron;Zhao, Kake;Zhang, Fengqi;Anand, Rajan;Colandrea, Vincent J.;Cumiskey, Anne-Marie;Crespo, Alejandro;Duffy, Ruth A.;Murphy, Beth Ann;Mitra, Kaushik;Johns, Douglas G.;Duffy, Joseph L.;Vachal, Petr. And the article was included in ACS Medicinal Chemistry Letters in 2016.Formula: C8H7BrO2 This article mentions the following:

Using the collective body of known (CETP) inhibitors as inspiration for design, a structurally novel series of tetrahydroquinoxaline CETP inhibitors were discovered. An exemplar from this series, compound I, displayed potent in vitro CETP inhibition and was efficacious in a transgenic cynomologus-CETP mouse HDL PD (pharmacodynamic) assay. However, an undesirable metabolic profile and chem. instability hampered further development of the series. A three-dimensional structure of tetrahydroquinoxaline inhibitor was proposed from ¹H NMR structural studies, and this model was then used in silico for the design of a new class of compounds based upon an indoline scaffold. This work resulted in the discovery of compound II, which displayed potent in vitro CETP inhibition, a favorable PK-PD profile relative to tetrahydroquinoxaline I, and dose-dependent efficacy in the transgenic cynomologus-CETP mouse HDL PD assay. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8Formula: C8H7BrO2).

3-(Bromomethyl)benzoic acid (cas: 6515-58-8) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Formula: C8H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Hydrogen-Bonding Controlled Nickel-Catalyzed Regioselective Cyclotrimerization of Terminal Alkynes was written by Yang, Kai;Wang, Pengfei;Sun, Ze-Ying;Guo, Minjie;Zhao, Wentao;Tang, Xiangyang;Wang, Guangwei. And the article was included in Organic Letters in 2021.COA of Formula: C24H15Br3 This article mentions the following:

Herein a hydrogen-bonding controlled nickel-catalyzed regioselective cyclotrimerization of terminal alkynes in moderate to excellent yields with high regioselectivities toward 1,3,5-trisubstituted benzenes is reported. This method features a cheap catalyst, mild reaction conditions, and excellent functional group compatibility. The Ni-B(OH)₂ complex in situ generated from NiCl₂·DME and tetrahydroxydiboron might act as an active catalyst. After three consecutive cis-additions of terminal alkynes, internal migratory insertion cyclization, and β-boron elimination induced aromatization, 1,3,5-trisubstituted benzenes were selectively established. In the experiment, the researchers used many compounds, for example, 3,3”-Dibromo-5′-(3-bromophenyl)-1,1′:3′,1”-terphenyl (cas: 96761-85-2COA of Formula: C24H15Br3).

3,3”-Dibromo-5′-(3-bromophenyl)-1,1′:3′,1”-terphenyl (cas: 96761-85-2) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.COA of Formula: C24H15Br3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary