Tag: M.W=250-300

Wollweber, H. published the artcile1-Phenethyl-2-iminoimidazolidines, a new class of compounds with ganglion-regulating activity, SDS of cas: 1997-80-4, the publication is Med. Chem., Abhandl. Med. Chem. Forschungsstaetten Farbwerke Hoechst A.G. (1963), 248-61, database is CAplus.

To a solution of the Grignard reagent from 225 g. 3-Br-C₆H₄CF₃, 26 g. Mg, and 500 ml. Et₂O was added dropwise a solution of 44 g. ethylene oxide in 200 ml. Et₂O to give after hydrolysis with aqueous NH₄Cl 74.9 g. 3-F₃CC₆H₄CH₂CH₂OH (I), b₁₂ 102-6°. I (38 g.) was saturated at 100° with dry HBr to give 45 g. 3-F₃CC₆H₄CH₂CH₂Br (II), b₁₂ 92-4°. A mixture of 45 g. II and 50 g. (CH₂NH₂)₂ was refluxed overnight, distilled in vacuo, the residue basified, and the oil separated to give 19.4 g. 3-F₃CC₆H₄CH₂CH₂-NHC₂H₄NH₂, b_0.15 96-8°. A mixture of 80 g. PhCH₂CH₂Cl and 160 g. H₂NCH₂CH₂NHCO₂Et was refluxed 8 hrs. to give 62 g. PhCH₂CH₂NHCH₂CH₂NHCO₂Et (III), b_0.05 140°. III (53 g.) in 500 ml. Et₂O was reduced with LiAlH₄ to give 16.1 g. PhCH₂CH₂NHCH₂CH₂NHMe, b₁₂ 84-6°. A mixture of 55 g. PhCH₂CH₂NHCH₂CH₂NH₂ (IV), 47 g. S-methylisothiuronium sulfate, 200 ml. EtOH. and 40 ml. water was refluxed 2 hrs. to give 80 g. 2PhCH₂CH₂NHCH₂CH₂NHC(:NH)NH₂.H₂SO₄ (V), m. 188° (decomposition) (EtOH-AcOEt). V (60 g.) was heated 1.5 hrs. at 150-60, 200 ml. amyl alc. added, and the mixture refluxed 6 hrs. to give 28 g. VI (R¹ = R² = R³ = R⁴ = R⁵ = R⁶ = R⁷ = H, m = n = 1, X = NH) (VII).0.5 H₂SO₄, m. 206.5-7.5°. A solution of 10.6 g. BrCN in 50 ml. benzene was added dropwise at 20-30° to a solution of 18 g. IV in 100 ml. benzene and the mixture stirred 1 hr. to give VII HBr salt, m. 144-6° (AcOEt). PhCH₂CH₂NHCH₂CH₂OH with concentrated HBr at 170° gave PhCH₂CH₂NHCH₂CH₂Br HBr salt, m. 173-5°; this (15.5 g.) in 45 ml. water treated with a solution of 4.05 g. KOCN in 10 ml. water gave an oil which slowly dissolved upon vigorous shaking. After 0.5 hr. the solution was treated with K₂CO₃ and the oil extracted with CH₂Cl₂ to give 8.5 g. X = O analog of VII, b_0.25 122-5°; HCl salt m. 178-9°. Similarly prepared were VI (R¹, R¹, R¹, R¹, R¹, R², R², n, m, m, m.p. HBr salt, and b.p./mm. of diamine corresponding to IV given): H, H, OMe, H, H, H, H, 1, 1, NH, 166-7°, 140°/0.1; H, OMe, H, H, H, H, H, 1, 1, NH, 139°, 124°/0.1; H, (R²R³ =) CH₂O₂, H, H, H, H, 1, 1, NH, 217°, 130°/0.2; H, H, Me, H, H, H, H, 1, 1, NH, 193-5°, 100°/0.2; H, Me, H, H, H, H, H, 1, 1, NH, 148-9°, 116°/0.5; Me, H, H, H, H, H, H, 1, 1, NH, 173-5°, 118°/0.2; H, H, Cl, H, H, H, H, 1, 1, NH, 187°, 112°/0.1; H, Cl, H, H, H, H, H, 1, 1, NH, 138°, 110°/0.05; H, H, H, H, H, H, H, 1, 1, NMe, 180°, 85°/12; H, H, H, H, H, H, Me, 1, 1, NH, 186-7°, 90°/0.1; H, H, H, H, H, Me, H, 1, 1, NH, 111-13°, 80°/0.1; H, OMe, H, H, Me, Me, H, 1, 1, NH, 156°, 125°/0.05; H, H, H, OH, H, H, H, 1, 1, NH, 173°, 164°/0.05; H, H, H, H, H, H, H, 1, 0, NH, 202-3°, 84°/0.2; Cl, H, H, H, H, H, H, 1, 0, NH, 270-3° (decomposition) (1/2H₂SO₄ salt), 102°/0.1. Also prepared were VIII (R¹, R², m.p. HBr salt, and b.p./mm. diamine given): H, H, 153°, 100°/0.1; H, Me, 140°, 125°/12; Me, H, 115-17°, 126°/12. Similarly prepared from α-phenyl-ethylenediamine, b_0.3 84°, was 4-phenyl-2-iminoimidazolidine HBr salt, m. 177°. Toxicity and pharmacol. data are given for all compounds

Med. Chem., Abhandl. Med. Chem. Forschungsstaetten Farbwerke Hoechst A.G. published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C12H9N3O4, SDS of cas: 1997-80-4.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Yang, Ting published the artcileDiscovery of Tertiary Amine and Indole Derivatives as Potent RORγt Inverse Agonists, Name: 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, the publication is ACS Medicinal Chemistry Letters (2014), 5(1), 65-68, database is CAplus and MEDLINE.

A novel series of tertiary amines as retinoid-related orphan receptor gamma-t (RORγt) inverse agonists was discovered through agonist/inverse agonist conversion. The level of RORγt inhibition can be enhanced by modulating the conformational disruption of H12 in RORγt LBD. Linker exploration and rational design led to the discovery of more potent indole-based RORγt inverse agonists, e.g., I.

ACS Medicinal Chemistry Letters published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C25H23NO4, Name: 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Ren, Bo published the artcileDesign, synthesis and in vitro antitumor evaluation of novel pyrazole-benzimidazole derivatives, Name: 4-Bromo-1-(bromomethyl)-2-fluorobenzene, the publication is Bioorganic & Medicinal Chemistry Letters (2021), 128097, database is CAplus and MEDLINE.

A series of novel pyrazole-benzimidazole derivatives I [R = Br, MeO; R¹ = Pr, benzyl, cinnamyl, etc.] were designed, synthesized and evaluated for their in-vitro antiproliferative activity against the HCT116, MCF-7 and Huh-7 cell lines. Among them, compounds I [R = Br, R¹ = Pr, 4-(trifluoromethyl)benzyl; R = MeO, 4-cyanomethyl] showed significant antiproliferative activity against HCT116 cell lines with the IC₅₀ values of 4.33, 5.15 and 4.84μM, resp. Moreover, fluorescent staining studies showed compound I [R = Br, R¹ = 4-(trifluoromethyl)benzyl] could induce cancer cells apoptosis. The flow cytometry assay revealed that compound I [R = Br, R¹ = 4-(trifluoromethyl)benzyl] could induce cell cycle arrest at G0/G1 phase. All in all, these consequences suggested that pyrazole-benzimidazole derivatives I could serve as promising compounds for further research to develop novel and highly potent cancer therapy agents.

Bioorganic & Medicinal Chemistry Letters published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Name: 4-Bromo-1-(bromomethyl)-2-fluorobenzene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Song, Zhidan published the artcileSynthesis and aromatase inhibitory evaluation of 4-N-nitrophenyl substituted amino-4H-1,2,4-triazole derivatives, Related Products of bromides-buliding-blocks, the publication is Bioorganic & Medicinal Chemistry (2016), 24(19), 4723-4730, database is CAplus and MEDLINE.

In this paper, 13 4-N-nitrophenyl substituted amino-4H-1,2,4-triazole derivatives were synthesized and their aromatase inhibitory activities were measured. The results show that the substitution of the groups on benzyl group can further improve their bioactivity and the compound (I) with Cl on the para position of benzyl has the highest bioactivity (IC₅₀ = 9.02 nM). A QSAR model was constructed from the 13 compounds with genetic function approximation using DS 2.1 package. This model can explain 90.09% of the variance (R²_Adj), while it can predict 84.95% of the variance (R²_cv) with the confidence interval of 95%.

Bioorganic & Medicinal Chemistry published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C15H18BF3O4, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Liu, Zhuo published the artcilePh₃P⁺CF₂CO^–₂ as an F^– and :CF₂ source for trifluoromethylthiolation of alkyl halides, COA of Formula: C8H6BrF3S, the publication is Chinese Chemical Letters (2019), 30(3), 714-716, database is CAplus.

Trifluoromethylthiolation of alkyl halides RX (R = naphthalen-1-ylethyl, 5-chlorobenzothiophen-3-yl, phenylpropyl, etc.; X = Br, Cl) by using Ph₃P⁺CF₂CO^–₂ as a fluoride and difluorocarbene source has been described. Difluorocarbene is a versatile intermediate, but its side reactions are usually ignored and byproducts would therefore be discarded. In this work, side reaction of difluorocarbene and generation of a fluoride anion from the difluorocarbene were developed into a synthetic tool. Although the trifluoromethylthiolation reaction involved multi-sequential steps, the cleavage of C-F bond and the formation of CF₂=S bond, F-C(S)F₂ bond, and C-SCF₃ bond were proceeded fast and completed within 10 min.

Chinese Chemical Letters published new progress about 21101-63-3. 21101-63-3 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,sulfides,Benzyl bromide,Benzene, name is (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane, and the molecular formula is C8H6BrF3S, COA of Formula: C8H6BrF3S.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Behnke, Nicole Erin published the artcileTitanium-Mediated Synthesis of Spirocyclic NH-Azetidines from Oxime Ethers, Related Products of bromides-buliding-blocks, the publication is Angewandte Chemie, International Edition (2019), 58(40), 14219-14223, database is CAplus and MEDLINE.

The Ti^IV-mediated synthesis of spirocyclic NH-azetidines from oxime ethers using either an alkyl Grignard reagent or terminal olefin ligand exchange coupling partner is described. Through a proposed Kulinkovich-type mechanism, a titanacyclopropane intermediate forms and serves as a 1,2-aliphatic dianion equivalent, inserting into the 1,2-dielectrophilic oxime ether to ultimately give rise to the desired N-heterocyclic four-membered ring. This transformation proceeds in moderate yield to furnish previously unreported and structurally diverse NH-azetidines in a single step. Thus, e.g., cyclohexanone O-methyloxime + phenethylmagnesium bromide → I (51%) in presence of Ti(Oi-Pr)₄ in Et₂O.

Angewandte Chemie, International Edition published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H8BrF3, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Xiao, Yang published the artcileThermally stable red electroluminescent hybrid polymers derived from functionalized silsesquioxane and 4,7-bis(3-ethylhexyl-2-thienyl)-2,1,3-benzothiadiazole, Synthetic Route of 303734-52-3, the publication is Journal of Polymer Science, Part A: Polymer Chemistry (2009), 47(21), 5661-5670, database is CAplus.

Hyperbranched organic-inorganic hybrid conjugated polymers P1 and P2 were prepared via FeCl₃-oxidative polymerization of 4,7-bis(3-ethylhexyl-2-thienyl)-2,1,3-benzothiadiazole (A) and octa(3-ethylhexyl-2-thienyl-phenyl)polyhedral oligomeric silsesquioxane (POSS) (B) at different POSS concentrations Compared to linear polymer PM derived from A, P1, and P2 exhibit much higher PL quantum efficiency (ϕ_PL-f) in condensed state with improved thermal stability. ϕ_PL-f of P1 and P2 increased by 80% and 400%, and the thermal degradation temperatures of P1 and P2 are increased by 35° and 46°, resp. Light-emitting diodes were fabricated using P1, P2, and PM. While the electroluminescent spectra of both P1 and PM show λ_max at 660 nm, P1 exhibits a much narrower EL spectrum and higher electroluminescence (∼500%) compared with PM at a same voltage and film thickness. The maximum current efficiency of P1 is more than seven times of that of PM. The turn-on voltages of the LEDs are in the order of P2>PM>P1. LED prepared by blending P1 with MEH-PPV shows a maximum luminescence of 2.6 × 10³ cd/m² and a current efficiency of 1.40 cd/A, which are more than twice (1.1 × 10³ cd/m²) and five times (0.27 cd/A) of LED of PM/MEH-PPV blend, resp.

Journal of Polymer Science, Part A: Polymer Chemistry published new progress about 303734-52-3. 303734-52-3 belongs to bromides-buliding-blocks, auxiliary class Thiophene,Bromide, name is 2-Bromo-3-(2-ethylhexyl)thiophene, and the molecular formula is C14H31NO2, Synthetic Route of 303734-52-3.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Li, Yangyang published the artcileNickel-catalyzed migratory alkyl-alkyl cross-coupling reaction, Recommanded Product: 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, the publication is Chemical Science (2020), 11(38), 10461-10464, database is CAplus and MEDLINE.

A migratory cross-coupling strategy, which can overcome this obstacle to access the desired cross-coupling products ArCH(R)(CH₂)_nCR¹R²R³ (Ar = Ph, 4-fluorophenyl, indol-3-yl, etc.; R = cyclopentyl, cyclohexyl, cycloheptyl, N-benzyl-piperidin-4-yl, 2-methyl-propan-1-yl; R¹ = H, D; R² = H, D; R³ = H; n = 0-3, 5), 1-cyclopentyl-indan, 1-cycloheptyl-indan, (1-cyclopentyl-3-methyl-pentyl)benzene was described. Accordingly, a selective migratory cross-coupling of two alkyl electrophiles (RBr, ArCH(R)(CH₂)_nCR¹R²R³ (R³ = Br or Cl), 2-bromoindan, (5-bromo-1-cyclopentyl-3-methyl-pentyl)benzene) has been accomplished by nickel catalysis. Remarkably, this alkyl-alkyl cross-coupling reaction provides a platform to prepare 2°-2° carbon-carbon bonds from 1° and 2° carbon coupling partners. Preliminary mechanistic studies suggest that chain-walking occurs at both alkyl halides in this reaction, thus a catalytic cycle with the key step involving two alkylnickel(II) species is proposed for this transformation.

Chemical Science published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H8BrF3, Recommanded Product: 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Li, Minglei published the artcileSynthesis and fungicidal activities of (E)-α-oxocyclododecanone oxime ethers, COA of Formula: C7H5Br2F, the publication is Nongyaoxue Xuebao (2006), 8(3), 209-213, database is CAplus.

A series of (E)-α-oxocyclododecanone oxime ethers were synthesized by etherification of corresponding hydroxylimines in yields of 59%-92%. The (E)-configuration was confirmed by single X-ray diffraction anal. of a representative compound Bioassay results showed that most of the synthesized compounds present good fungicidal activities against Rhizoctonia solani, Cladosporium cucumerinum, Colletotrichum orbiculare, Botrytis cinerea, Fusarium oxysporum, and Phomopsis asparagi. For example, the EC₅₀ values of I against mentioned-above six fungi were 13, 9, 12, 19, 14, 3 mg/L, resp.

Nongyaoxue Xuebao published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, COA of Formula: C7H5Br2F.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Chen, Hung-Yang published the artcilePolymer side-chain substituents elucidate thermochromism of benzodithiophene-dithiophenylacrylonitrile copolymers – polymer solubility correlation of thermochromism and photovoltaic performance, Recommanded Product: 2-Bromo-3-(2-ethylhexyl)thiophene, the publication is Polymer Chemistry (2017), 8(24), 3689-3701, database is CAplus.

Nine pBCNx polymers based on a donor-π-acceptor benzo[1,2-b:4,5-b’]dithiophene-(E)-2,3-di(thiophen-2-yl)acrylonitrile main-chain structure and n-octyl/2-ethylhexyl as the side-chain substituents have been designed and synthesized. The thermochromism of the pBCNx polymers has been carefully examined in both solution and the thin-film state. With addnl. evidences from Raman spectroscopy and AFM microscopy, we have deciphered the varied colors of nine pBCNx polymers in solution and the pronounced thin-film thermochromism only observed for certain pBCNx polymers, i.e., pBCN4, pBCN5, pBCN6, and pBCN8. The alkyl side-chain, and hence the solubility or aggregation of pBCNx polymers, is a main factor of the varied color in solution and the varied thermochromism in the thin film. We have identified that a stronger main-chain and main-chain interaction are present on the (E)-2,3-di(thiophen-2-yl)acrylonitrile moiety, whereas the poor to moderate solubility pBCN3, pBCN5′ and pBCN7 exhibit pronounced thermochromism in solution, and pBCN4, pBCN5, pBCN6 and pBCN8 are four polymers which have good solubility in solution and show thermochromism in the thin-film state. We took navy blue pBCN3 (poor solubility), magenta pBCN4 (good solubility), and reddish purple pBCN5′ (moderate solubility) for the fabrication of bulk heterojunction organic photovoltaics (OPVs). With a solvent annealing treatment, the power conversion efficiency of the OPVs has been improved significantly from 4.7% to 6.2% for the good solubility pBCN4, but there is little and no improvement for the moderate solubility pBCN5′ and poor solubility pBCN3, resp. Our study verifies that the good OPV performance of the pBCNx polymers can be correlated to the pronounced thin-film thermochromism. A good solubility of the polymer is a common characteristic of a material with significant thin-film thermochromism and good OPV performance.

Polymer Chemistry published new progress about 303734-52-3. 303734-52-3 belongs to bromides-buliding-blocks, auxiliary class Thiophene,Bromide, name is 2-Bromo-3-(2-ethylhexyl)thiophene, and the molecular formula is C12H19BrS, Recommanded Product: 2-Bromo-3-(2-ethylhexyl)thiophene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary