FZ single-side polished silicon wafers, (100)-oriented (〈100〉 ± 0.05°), 500 ± 25 μm thick, >10 kΩ cm in resistivity, and CZ single-side polished silicon wafers (100)-oriented (〈100〉 ± 0.05°), n-type (phosphorus), 500 ± 10 μm thick, 1–3 Ω cm in resistivity, were purchased from Suzhou Resemi Semiconductor Co. Ltd., China. All chemicals, unless noted otherwise, were of analytical grade and used as received. Isopropanol, acetone, and ethanol for surface cleaning were of CMOS grade. 5-Hexenyl acetate (98%) was purchased from TCI, Shanghai. Mono-N-dodecyl phosphate (97%) was from Alfa Aesar. Dicyclohexylcarbodiimide (DCC, 99%), lithium aluminum hydride (LiAlH4 powder, reagent grade, 95%), and hydrofluoric acid (HF, 48%, CMOS grade) were from Sigma Aldrich.
Lithium aluminum hydride
Manufactured by Merck Group
Sourced in United States
Lithium aluminum hydride is a chemical compound used as a reducing agent in organic synthesis. It is a white, crystalline solid that reacts violently with water and other protic solvents. The compound is commonly used in the laboratory setting for the reduction of various functional groups such as aldehydes, ketones, and esters.
Automatically generated - may contain errors
Lab products found in correlation
Titanium 4 isopropoxide, by Merck Group (2 mentions)
Pyridine, by Merck Group (2 mentions)
Ethanol, by Merck Group (2 mentions)
Tetrahydrofuran thf, by Merck Group (2 mentions)
Diethyl ether, by Merck Group (2 mentions)
Hydrofluoric acid, by Merck Group (1 mentions)
Mono n dodecyl phosphate, by Thermo Fisher Scientific (1 mentions)
Dicyclohexylcarbodiimide, by Merck Group (1 mentions)
Dimethylformamide, by Merck Group (1 mentions)
Hydrochloric acid (hcl), by Honeywell (1 mentions)
Magnesium sulfate, by Thermo Fisher Scientific (1 mentions)
Sodium hydride, by Merck Group (1 mentions)
Dibutyltin dilaurate, by Merck Group (1 mentions)
1 bromononane, by Merck Group (1 mentions)
1 bromooctadecane, by Merck Group (1 mentions)
Diethyl malonate, by Merck Group (1 mentions)
1 bromobutane, by Merck Group (1 mentions)
1 bromooctane, by Merck Group (1 mentions)
1 bromododecane, by Merck Group (1 mentions)
3 aminopropyltriethoxysilane, by Merck Group (1 mentions)
13 protocols using lithium aluminum hydride
1
Silicon Wafer Characterization and Surface Preparation
2
Synthesis of Alkyl Bromides and Polyurethanes
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1-Bromobutane (99%), 1-bromooctane
(99%), 1-bromononane (98%), 1-bromododecane (97%), 1-bromooctadecane
(>97%), lithium aluminum hydride (LiAlH4, pellets, 95%),
sodium hydride (NaH, dispersion in mineral oil, 60%), diethyl malonate
(99%), dibutyltin dilaurate (DBTL, 95%), and dimethylformamide (DMF,
anhydrous, 99.8%) were purchased from Sigma-Aldrich. Ethyl acetate
(99%, technical), methanol (≥99.5%, technical), chloroform
(≥98%, technical), deuterated chloroform (D-chloroform, 0.03%
TMS), and deuterated dimethylsulfoxide (D-DMSO) were purchased from
VWR Chemicals. Hexamethylene diisocyanate (HDI, ≥98%) and 1,4-butanediol
(BDO, ≥99%) were purchased from TCI Europe. Hydrochloric acid
(37%) was purchased from Honeywell. Magnesium sulfate (dried, contains
approximately 1–2 mol water of hydration, ≥98%) was
purchased from Alfa Aesar. All commercial chemicals were used as received.
All reactions were carried out under a nitrogen atmosphere. The synthesis
of the diols and polymers showed high reproducibility.
(99%), 1-bromononane (98%), 1-bromododecane (97%), 1-bromooctadecane
(>97%), lithium aluminum hydride (LiAlH4, pellets, 95%),
sodium hydride (NaH, dispersion in mineral oil, 60%), diethyl malonate
(99%), dibutyltin dilaurate (DBTL, 95%), and dimethylformamide (DMF,
anhydrous, 99.8%) were purchased from Sigma-Aldrich. Ethyl acetate
(99%, technical), methanol (≥99.5%, technical), chloroform
(≥98%, technical), deuterated chloroform (D-chloroform, 0.03%
TMS), and deuterated dimethylsulfoxide (D-DMSO) were purchased from
VWR Chemicals. Hexamethylene diisocyanate (HDI, ≥98%) and 1,4-butanediol
(BDO, ≥99%) were purchased from TCI Europe. Hydrochloric acid
(37%) was purchased from Honeywell. Magnesium sulfate (dried, contains
approximately 1–2 mol water of hydration, ≥98%) was
purchased from Alfa Aesar. All commercial chemicals were used as received.
All reactions were carried out under a nitrogen atmosphere. The synthesis
of the diols and polymers showed high reproducibility.
3
Synthesis of Lithium-Ion Battery Materials
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p-Toluenesulfonyl
chloride (97%), p-toluenesulfonyl amide (97%), lithium
hydroxide monohydrate, potassium permanganate, calcium chloride, N-methyl-2-pyrrolidone (NMP, anhydrous, 99.8%), pyridine
(anhydrous, 99.8%), lithium aluminum hydride (95%), tetrahydrofuran
(THF, anhydrous, 99.8%), lithium bis(trimethylsilyl) amide solution
(1 M in THF), tributyl phosphate (≥99%), and titanium(IV) isopropoxide
(97%) were purchased from Sigma-Aldrich. Aluminum nitrate (Al(NO3)3 × 9H2O), 3-(aminopropyl)triethoxysilane,
1-propanol, and propionic acid were acquired from Merck. 4,4-(Hexa-fluoroisopropylidene)dianiline
(98%) was obtained from TCI Europe, poly(vinylidene difluoride-co-hexafluoropropylene)
(PVdF-HFP, Kynar FLEX LBG) from Arkema, and lithium
nitrate (LiNO3 × xH2O)
from Alfa Aesar. Concentrated hydrochloric acid, methanol, dimethyl
sulfoxide (DMSO), and triphenyl phosphite were acquired from VWR.
Ethylene carbonate, propylene carbonate, and NMC622 were purchased
from BASF. Carbon black (Super C65) was obtained from Imerys Graphite
& Carbon and polyvinylidene difluoride (PVdF, Solef 5130) from
Solvay. Prior to use, calcium chloride was dried at 180 °C under
reduced pressure (10–3 mbar) for 48 h.
chloride (97%), p-toluenesulfonyl amide (97%), lithium
hydroxide monohydrate, potassium permanganate, calcium chloride, N-methyl-2-pyrrolidone (NMP, anhydrous, 99.8%), pyridine
(anhydrous, 99.8%), lithium aluminum hydride (95%), tetrahydrofuran
(THF, anhydrous, 99.8%), lithium bis(trimethylsilyl) amide solution
(1 M in THF), tributyl phosphate (≥99%), and titanium(IV) isopropoxide
(97%) were purchased from Sigma-Aldrich. Aluminum nitrate (Al(NO3)3 × 9H2O), 3-(aminopropyl)triethoxysilane,
1-propanol, and propionic acid were acquired from Merck. 4,4-(Hexa-fluoroisopropylidene)dianiline
(98%) was obtained from TCI Europe, poly(vinylidene difluoride-co-hexafluoropropylene)
(PVdF-HFP, Kynar FLEX LBG) from Arkema, and lithium
nitrate (LiNO3 × xH2O)
from Alfa Aesar. Concentrated hydrochloric acid, methanol, dimethyl
sulfoxide (DMSO), and triphenyl phosphite were acquired from VWR.
Ethylene carbonate, propylene carbonate, and NMC622 were purchased
from BASF. Carbon black (Super C65) was obtained from Imerys Graphite
& Carbon and polyvinylidene difluoride (PVdF, Solef 5130) from
Solvay. Prior to use, calcium chloride was dried at 180 °C under
reduced pressure (10–3 mbar) for 48 h.
4
Functionalization of Bicomponent Nonwovens
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Bicomponent PE/PP nonwovens were kindly donated by Shalag Company (Israel). The following analytical-grade chemicals were purchased from Sigma Aldrich (St. Louis, MO) and were used without further purification: sodium borohydride (NaBH4; ≥ 98%), lithium aluminum hydride (LiAlH4; 95%), ethanol (absolute, 95%), tetrahydrofuran (THF) (HPLC-grade), (trimethoxysilyl) propyl-octadecyl-dimethyl-ammonium chloride (C18-TSA; 72%), cetyltrimethylammonium chloride (98%) and fluorescein sodium salt (≥ 98%). The commercial finishing agent PHP10 was produced by Schill + Seilacher GmbH (Germany) and was kindly donated by Avgol Ltd. (Israel).
5
Hyaluronic Acid-Based Cell Culture
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1-(2-cyanoethyl) pyrrole, lithium aluminum hydride, N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDC), N-Hydroxysuccinimide (NHS), Ammonium persulfate (APS), and diethyl ether were provided from Sigma-Aldrich (St. Louis, MO, USA). Hyaluronic acid (1 × 106 Da) was kindly provided from the LG Life Science Ltd (South Korea). Dulbecco’s modified Eagle’s medium, fetal bovine serum (FBS), and Dulbecco’s phosphate buffered saline (DPBS) were produced from Hyclone. Penicillin/Streptomycin and trypsin/EDTA were provided from Gibco (Gaithersburg, MD, USA). LIVE/DEAD viability/cytotoxicity kit and CMFDA cell tracker kit were purchased from Life Science Technology.
6
Synthesis of Pyrazole Derivatives for TLC-FAPA
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All reagents used were commercial products. Ethyl 2,4-dioxovalerate, hydrazine hydrate, 2-hydrazinopyridine, 2-hydrazinobenzothiazole, lithium aluminum hydride, nicotine, sparteine, and anhydrous tetrahydrofuran (THF) were obtained from Sigma-Aldrich (St. Louis, MO, USA). Anhydrous ethyl alcohol and all other solvents were of p.a. grade, obtained from Avantor Performance Materials Poland S.A. (Gliwice, Poland) and were used without further purification. The commonly used analgesic, consisting of paracetamol, propyphenazone, and caffeine, was obtained from the local pharmacy.
Synthesis of pyrazole derivatives used in this work as analytes for the TLC-FAPA technique has been described in detail in our previous publication [25 (link)]. For all TLC-FAPA experiments, the Merck Millipore TLC silica gel 60 F254 aluminum sheets was applied.
Synthesis of pyrazole derivatives used in this work as analytes for the TLC-FAPA technique has been described in detail in our previous publication [25 (link)]. For all TLC-FAPA experiments, the Merck Millipore TLC silica gel 60 F254 aluminum sheets was applied.
7
Synthesis of Brominated Organic Compounds
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Dichloromethane, hexane and tetrahydrofuran (THF, stabilized with BHT) were purchased from Avantor Performance Materials. o-Dichlorobenzene (o-DCB), n-butanol (n-BuOH), dioxane, mesitylene, trifluoromethanesulfonic acid, paraformaldehyde, hydrobromic acid (41%), acetic acid and hydrazobenzene were purchased from TCI Chemicals. Toluene, methanol (MeOH) and dimethylformamide (DMF) were purchased from VWR Chemicals. Potassium carbonate and potassium permanganate were purchased from Goodrich Chemical Enterprise. 1,3,6,8-Tetrabromopyrene, tetrakis(triphenylphosphine)palladium(0), 1,4-dimethoxybenzene, 4-aminobenzonitrile, 2,3,6,7,10,11-hexabromotriphenylene, 4-formylphenylboronic acid, 1,4-phenylenediamine (PDA), 2,5-dimethyl-1,4-phenylenediamine (DMePDA), 1,3,5-benzenetricarboxylic acid and N-hydroxysuccinimide (NBS) were purchased from BLDPharm. Carbazole, lithium aluminum hydride, pyridinium chlorochromate and n-butyllithium solution (2.0 M in cyclohexane) were purchased from Sigma Aldrich.
8
Synthesis and Characterization of Novel Carbazole Derivatives
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Deoxycholic acid (DCA),
9-carbazoleacetic acid (Cbz-CH2-COOH), 9H-carbazol-9-ethanol (Cbz-(CH2)2-OH), thymine
1-acetic acid (Thy-CH2-CO2H), benzyl bromide,
1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), N,N-diisopropylethylamine (DIEA), 4-dimethylaminopyridine
(4-DMAP), lithium aluminum hydride (LiAlH4), O-(benzotriazol-1-yl)-N,N,N,N′-tetramethyluronium tetrafluoroborate
(TBTU), 2,4,6-trichlorobenzoyl chloride, benzyl alcohol, titanium(IV)
isopropoxide, triethylamine, acetonitrile, dimethylformamide (DMF),
and tetrahydrofuran (THF) were purchased from Sigma-Aldrich. Experimental
procedures and methods for characterization are reported in theSupporting Information . Structural assignments
were made with additional information from gCOSY, gHSQC, and gHMBC
experiments. The assignment of hydrogen and carbon signals was based
on a combination of 1D and 2D NMR experiments (1H; 13C; 1H,1H COSY; and 1H,13C HSQC).
9-carbazoleacetic acid (Cbz-CH2-COOH), 9H-carbazol-9-ethanol (Cbz-(CH2)2-OH), thymine
1-acetic acid (Thy-CH2-CO2H), benzyl bromide,
1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), N,N-diisopropylethylamine (DIEA), 4-dimethylaminopyridine
(4-DMAP), lithium aluminum hydride (LiAlH4), O-(benzotriazol-1-yl)-N,N,N,N′-tetramethyluronium tetrafluoroborate
(TBTU), 2,4,6-trichlorobenzoyl chloride, benzyl alcohol, titanium(IV)
isopropoxide, triethylamine, acetonitrile, dimethylformamide (DMF),
and tetrahydrofuran (THF) were purchased from Sigma-Aldrich. Experimental
procedures and methods for characterization are reported in the
were made with additional information from gCOSY, gHSQC, and gHMBC
experiments. The assignment of hydrogen and carbon signals was based
on a combination of 1D and 2D NMR experiments (1H; 13C; 1H,1H COSY; and 1H,13C HSQC).
9
Comprehensive Chemical Characterization
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The following chemicals were acquired from Sigma-Aldrich (Oakville ON, Canada) and used without further purification: chloroform (≥99%, with 0.75% ethanol as stabilizer), ethanol (≥99.8%, HPLC grade), pyridine (≥99.8%, anhydrous), N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA, GC grade), acetic anhydride (≥98%), diethyl ether (≥99.7%, anhydrous, 1 ppm BHT as inhibitor), lithium aluminum hydride (≥95%), sulphuric acid (95–98%), O-methylhydroxylamine hydrochloride (≥98%), boron trifluoride-methanol solution (14%), primuline (50% dye content), acetone (≥99.9%, HPLC grade). n-Tetracosane (≥99%) was from Alfa Aesar (Ward Hill MA, USA). Gases were acquired from Praxair Canada (Vancouver BC, Canada): nitrogen (≥99.998%), helium (≥99%), and hydrogen (≥99.95%).
10
Heterocyclic Compound Synthesis by Azide-Alkyne Cycloaddition
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Allyl chloride, 98% (CAS 107-05-1), tetra-n-butylammonium fluoride (1 M solution in THF, CAS 429-41-4), copper (I) iodide, 98% (CAS 7681-65-4) and N,N-Dimethylformamide, 99.9% (CAS 68-12-2) were obtained from ABCR. Sodium azide (CAS 26628-22-8), diphenylether, 99% (CAS 101-84-8) and triethylamine, 99% (CAS 121-44-8) were obtained from Acros Organics. Karstedt’s catalyst (CAS 11057-89-9), diphenylacetylene, 98% (CAS 501-65-5), chlorodimethylsilane, 98% (CAS 1066-35-9) and lithium aluminum hydride (CAS 16853-85-3) were obtained from Sigma-Aldrich. All chemicals were used as received.
The solvents were purified by distillation under reduced pressure in argon.
The solvents were purified by distillation under reduced pressure in argon.
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