All solvents were purified before use. N-bromosuccinimide, thiourea, 2-methylbenzyl chloride, 3-fluorobenzyl chloride, 2-chlorobenzyl chloride, 2,4-dichlorobenzyl chloride, 3,4-dichlorobenzyl chloride, 4-bromobenzyl chloride, 2-chloroacetamide, and ethyl chloroacetate were purchased from Acros Organics and used without purification. Compounds 2 , 3 , 4b , and 4h were prepared using methods described previously [10 ]. The reactions were monitored by thin-layer chromatography (TLC) using Fluka silica gel (60 F 254) plates (0.25 mm). Visualization was made with UV light. The melting points of the synthesized compounds were taken on a melting point tube. Infrared spectra were recorded on a Bruker Tensor 37 spectrometer (Germany). The 1H-NMR spectra were recorded on a Bruker WP 250 SY spectrometer (250.13 MHz) (Germany). Chemical shifts are reported relative to chloroform (δ=7.25 ppm) for 1H-NMR. The mass spectra were recorded on an Agilent LC/MSD SL 1100 instrument (USA).
N bromosuccinimide
Manufactured by Thermo Fisher Scientific
Sourced in Belgium, Germany
N-bromosuccinimide is a chemical reagent commonly used in organic synthesis. It is a source of electrophilic bromine and acts as a halogenating agent. N-bromosuccinimide is used in a variety of organic reactions, such as allylic bromination, benzylic bromination, and radical bromination.
Automatically generated - may contain errors
Lab products found in correlation
Thiourea, by Thermo Fisher Scientific (1 mentions)
Lc msd sl 1100 instrument, by Agilent Technologies (1 mentions)
Tensor 37 spectrometer, by Bruker (1 mentions)
2 chloroacetamide, by Thermo Fisher Scientific (1 mentions)
Wp 250 sy spectrometer, by Bruker (1 mentions)
Calcium hydride, by Merck Group (1 mentions)
Benzoyl peroxide, by Merck Group (1 mentions)
Triethylamine, by Merck Group (1 mentions)
Azobisisobutyronitrile, by Merck Group (1 mentions)
N hexane, by RCI Labscan (1 mentions)
Hydrochloric acid (hcl), by RCI Labscan (1 mentions)
Chloroform, by RCI Labscan (1 mentions)
Dichloromethane, by RCI Labscan (1 mentions)
Benzamide, by Merck Group (1 mentions)
Tetrahydrofuran, by Thermo Fisher Scientific (1 mentions)
Sodium carbonate, by Thermo Fisher Scientific (1 mentions)
Magnesium sulfate, by Thermo Fisher Scientific (1 mentions)
Pivalic acid, by Merck Group (1 mentions)
N n dimethylethylenediamine, by Merck Group (1 mentions)
Trimethyltin chloride, by Merck Group (1 mentions)
6 protocols using n bromosuccinimide
1
Synthesis of Benzyl Substituted Heterocycles
2
Synthesis and Characterization of Polylactide
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L-lactide (LLA) and liquid tin(II) n-butoxide (Sn(OnBu)2) were purchased from the Bioplastics Production Laboratory for Medical Applications (ISO 13485:2016 TÜV SÜD America Accredited Laboratory, Chiang Mai University, Chiang Mai, Thailand) and used as received [64 ]. Benzoyl peroxide (75%), triethylamine (≥99%), calcium hydride (90–95%), and azobisisobutyronitrile (AIBN) were purchased from Sigma-Aldrich (Saint Louis, MO, USA). N-bromosuccinimide (99%) was purchased from Acros (Geel, Belgium). Magnesium sulfate anhydrous (96%) was purchased from PanReac AppliChem (Barcelona, Spain). Sodium bisulfite (58.5–67.4%) was purchased from HiMedia (Mumbai, India). 1,2-Dichlorobenzene (≥98%) was purchased from Carlo Erba (Milano, Italy). Chloroform-d1 (99.8% CDCl3) and dimethyl sulfoxide-d6 (99.9% DMSO) were purchased from CIL (Kolkata, India). Chloroform (99.8%) and hydrochloric acid (37%) were purchased from RCI Labscan (Bangkok, Thailand). Methanol, dichloromethane, ethyl acetate, and n-hexane (RCI Labscan) were purified by distillation prior to use.
3
Synthesis of 3-Hexylthiophene Derivatives
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3-Hexylthiophene (3HT) was purchased from TCI (Tokyo, Japan). triphenylamine, benzo [c] [1,2,5] thiadiazole, tetrahydrofuran (99.9%) and N-bromosuccinimide were purchased from Acros Organics. Palladium(II) acetate (Pd(OAc)2) (98%), tricyclohexylphosphine tetrafluoroborate (97%, PCy3·HBF4), 3,3′dibromo-2,2′bithiophene, benzamide, N,N′-dimethylethylenediamine (85%, DMEDA) and pivalic acid (PivOH) were purchased from Sigma-Aldrich. Potasium acetate (KOAc), sodium carbonate (99%), magnesium sulfate (98%), and copper iodine (CuI) were purchased from Acros and used as received. Chloroform (CHCl3, 99.5%), toluene (99.5%), and dimethylacetamide (DMAc, 99%) were purchased from Fisher/Acros and dried using molecular sieves under N2. Dichloromethane (99.8%), n-heptane (99%), methanol (99.8%), ethyl acetate (99%) and diethyl ether (99%) were purchased from Fisher/Acros and used as received.
4
Synthetic Procedures for Heterocyclic Compounds
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Commercially purchased reagents were used without further purification. Chemicals were obtained from Alfa Aesar GmbH & Co. KG, Karlsruhe, Germany (N-bromosuccinimide, 3-bromoquinoline, ethenyltriethylsilane), Acros Organics [n-butyllithium solution (2.5 M in hexane), 2-butenoic acid, 4-pyridinecarbonitrile]. 1,5-di(bromomethyl)naphthalene (5) 11 2-(2methyl-(1,3)-dioxolan-2-yl)pyridine (6), 13 2-methylquinolizinium bromide (3) 25 and (E)-1,2-di(quinolin-3-yl)ethane (2a) 15
5
Synthesis of Organic Semiconductors
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Anhydrous solvents, tri(o-tolyl)phosphine, tris(dibenzylideneacetone)dipalladium(0), trimethyltin chloride, and n-Butyllithium were purchased from Sigma-Aldrich, (Seoul, Republic of Korea). N-bromosuccinimide (NBS) was purchased from Alfa Aesar (Gongduk-Dong, Mapo-Gu, Republic of Korea) a, and thienothiophene, thiophene, and tetrakis(triphenylphosphine)-palladium(0) were purchased from TCI Chemical (Tokyo Chemical Industry Co., LTD., Tokyo, Japan). All chemicals were used without further purification. 4-(2-Ethylhexyl)-2,6-bis(trimethylstannyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole) were purchased from J’s science (Daejeon, Republic of Korea).
6
Synthetic Protocols for Halogenated Organic Compounds
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Unless otherwise stated, all air sensitive manipulations were carried out inside an inertatmosphere glove box (N2) or using standard Schlenk techniques (Ar). 2,6-Dibromoaniline (AK Scientific), N-iodosuccinimide (AK Scientific), p-toluidine (Alfa Aesar), N-bromosuccinimide (Alpha Aesar), 2-formylphenyl boronic acid (Combi Blocks), Pd(PPh3)4 (Alfa Aesar), Na2CO3 (Alfa Aesar), chlorodiphenylphosphine (VWR), CuBr (Aldrich), CuI (Aldrich) and CuCl (Acros) were purchased from commercial suppliers and used as received. 2-Bromo-4-methylaniline, 48 6-bromo-2-iodo-4methylaniline, 9 4-bromo-2-methylphenanthridine, 9 8-bromo-6-methylquinoline, 48 4diphenylphosphinophenanthridine 8 (L1) and {(4diphenylphosphino)phenanthridine}CuBr (1-Br) 8 were synthesized following published procedures. Organic solvents were dried over appropriate reagents and deoxygenated prior to use, with the exception of 1,2-dimethoxyethane and water, which were simply degassed. NMR spectra were recorded on a Bruker Avance 300 MHz or Bruker Avance-III 500 MHz spectrometer as noted. Elemental analyses were performed b y Canadian Microanalytical Service Ltd., Delta, BC (Canada).
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