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Chemical Structure| 1643-19-2 Chemical Structure| 1643-19-2

Structure of Tetrabutylammonium bromide
CAS No.: 1643-19-2

Chemical Structure| 1643-19-2

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Chrzan, Julia ; Drabczyk, Anna Karolina ; Siemińska, Izabela ; Baj-Krzyworzeka, Monika ; Greber, Katarzyna Ewa ; Jaśkowska, Jolanta , et al.

Abstract: Colorectal cancer (CRC) remains a major global health challenge, necessitating the development of more effective and environmentally sustainable treatments. This study presents a novel green synthetic protocol for 1,3,5-triazine derivatives with anticancer potential, employing both microwave-assisted and ultrasound-assisted methods. The synthesis was optimized using 4-chloro-N-(2-chlorophenyl)-6-(morpholin-4-yl)-1,3,5-triazin-2-amine as the key intermediate, with sodium carbonate, TBAB, and DMF providing optimal yields under microwave conditions. To enhance sustainability, a modified sonochemical method was also developed, enabling efficient synthesis in aqueous media with a minimal use of organic solvents. A series of nine morpholine-functionalized derivatives were synthesized and evaluated for cytotoxic activity against SW480 and SW620 colorectal cancer cell lines. Compound 11 demonstrated superior antiproliferative activity (IC50 = 5.85 µM) compared to the reference drug 5-fluorouracil, while compound 5 showed promising dual-line activity. In silico ADME analysis supported the drug likeness of the synthesized compounds, and biomimetic chromatography analysis confirmed favorable physicochemical properties, including lipophilicity and membrane affinity. These results underscore the potential of the developed protocol to produce bioactive triazine derivatives through an efficient, scalable, and environmentally friendly process, offering a valuable strategy for future anticancer drug development.

Keywords: 1,3,5-triazine ; green chemistry ; microwave-assisted synthesis ; sonochemistry ; colorectal cancer ; anticancer agents ; phase-transfer catalysis ; cytotoxicity ; ADME ; drug likeness

Purchased from AmBeed: ; ;

Damian Kułaga ; Anna K. Drabczyk ; Przemysław Zaręba ; Jolanta Jaśkowska ; Julia Chrzan ; Katarzyna Ewa Greber , et al.

Abstract: derivatives are useful compounds with potential applications in various branches of chemical industry, including pharmaceutical chemistry, cosmetic chemistry, photochemistry, and organic chemistry. Due to the growing environmental requirements on conducting efficient, economical, and safe syntheses, development of new methods for synthesizing organic compounds is highly desirable. In this publication, we present a protocol for the synthesis of derivatives using a sonochemical approach. In as little as 5 min, it is possible to obtain most of the investigated compounds with a yield of over 75%. An undeniable advantage of this method, besides its short time, is the use of water as the solvent. Furthermore, we provide examples that the sonochemical method may be more versatile than the competing microwave method. Analysis conducted using the DOZNTM 2.0 tool revealed that in terms of the 12 principles of green chemistry, the developed sonochemical method is 13 times “greener” than the classical one. Additionally, it has been demonstrated that the investigated molecules are attractive for their application as drug-like compounds.

Keywords: Sonochemistry ; ; Green chemistry ; Eco-friendly

Purchased from AmBeed: ; ;

Brian P. Radka ; Taewoo Lee ; Ivan I. Smalyukh ; Timothy J. White ;

Abstract: Polymer stabilized cholesteric liquid crystals (PSCLCs) are electrically reconfigurable reflective elements. Prior studies have hypothesized and indirectly confirmed that the electro-optic response of these composites is associated with the electrically mediated distortion of the stabilizing polymer network. The proposed mechanism is based on the retention of structural chirality in the polymer stabilizing network, which upon deformation is spatially distorted, which accordingly affects the pitch of the surrounding low molar-mass liquid crystal host. Here, we utilize fluorescent confocal polarized microscopy to directly assess the electro-optic response of PSCLCs. By utilizing dual fluorescent probes, sequential imaging experiments confirm that the periodicity of the polymer stabilizing network matches that of the low molar-mass liquid crystal host. Further, we isolate distinct ion-polymer interactions that manifest in certain photopolymerization conditions.

Purchased from AmBeed: ; ; ; ; ;

Thomson, Brodie ;

Abstract: Sulfur(IV) fluorides are powerful synthetic reagents typically used in the fluorination of small molecules. Traditional examples, including SF4 and DAST, were primarily applied in the deoxyfluorinations of alcohols, carbonyls and carboxylic acids. More recent sulfur(IV) fluoride analogues, including thionyl fluoride and XtalFluor-E® , display unique reactivity relative to DAST and SF4, yet have rarely been applied outside of similar organic transformations. In this thesis, the unique reactivities of thionyl fluoride and XtalFluor-E® were investigated and utilised towards the synthesis of acyl fluorides, sulfonyl fluorides, sulfinyl fluorides, and arylaminooxetanes. Chapter 2 describes the utilization of thionyl fluoride in a carboxylic acid activation strategy to synthesize acyl fluorides. The desired products were synthesized in high yields (60–99%) under mild conditions and quantified either in solution using 19F NMR spectroscopy or isolated in a column-free protocol. Chapter 3 describes the efforts made in improving the synthesis of sulfonyl fluorides and sulfinyl fluorides. In one transformation, sulfonic acids were derivatized in a DMF-promoted, thionyl fluoride-mediated fluorination, affording sulfonyl fluorides in high yields (80-99%). A complementary strategy utilising XtalFluor-E® accessed the same products in good isolated yields (41-94%), but milder conditions. Thionyl fluoride was also used to transform sulfinic acids to sulfinyl fluorides in a one-pot strategy, accessing sulfinyl fluorides in high crude yields (75-98%) quantified by 19F NMR spectroscopy. This represents the first general method reported towards their synthesis. Chapter 4 describes an expedited route towards the synthesis of arylamino-oxetanes via the XtalFluor-E®-mediated activation of 3-aryloxetan-3-ols. The optimised protocol accessed arylamino-oxetanes under mild conditions and reduced the number of steps required in their syntheses (between 2-6) compared to current literature procedures. This represents the shortest and simplest route towards their synthesis, accessing the desired products in 34-97% isolated yields. Chapter 6 is a distinct chapter in collaboration with Delic Laboratories, UBC and BAT, in which the light-induced degradation of CBD solutions was investigated. CBD-hydroxyquinone was identified to undergo a light-induced photo-isomerisation to form a previously unidentified cannabinoid intermediate. Both experimental and computation studies identified this intermediate reacts rapidly with oxygen to form a multitude of products in solution.

Purchased from AmBeed: ; ; ;

Yan, Kaili ; Kwon, Hyuna ; Huddleston, Morgan ; Jiang, De-en ; Sun, Yujie ;

Abstract: Electrocatalytic biomass valorization has attracted increasing interest over the years. Amongst many possible products from biomass upgrading, pyridine-containing chems. are rarely reported. Herein, we describe an electrochem. synthesis of 3-pyridniol from biomass-derived furfurylamine in 0.1 M H2SO4, taking advantage of the Br-/Br+ redox cycle and the strong acidic condition in driving the final dehydration step. Such an electrosynthesis approach was able to achieve a 97% yield of 3-pyridinol from the nearly complete conversion of furfurylamine. A number of control experiments aided by computational investigation were carried out to elucidate the key mechanistic steps of the ''one-pot'' conversion of furfurylamine to 3-pyridinol.

Purchased from AmBeed: ; ;

BRIAN P. RADKA ;

Abstract: Dynamic reconfiguration of optical materials has and continues to be of significant interestin technological utility in displays, healthcare, automotive, aerospace, and architecture. This thesis is concerned with so-called “polymer stabilized” cholesteric liquid crystals (PSCLCs), material systems in which application of an electric field can adjust the position or bandwidth of a selective reflection. These material systems are based upon the cholesteric liquid crystal (CLC) phase, which nascently self-organizes into a periodic helical structure in which refractive index modulation results in a polarization-specific Bragg reflection. Depending on material composition, application of an electric field to a CLC can result in reflection switching or “tuning” (e.g., shift in reflection wavelength) but typically these electro-optic responses are limited in magnitude or response time (often taking days for the reflection to recover). Comparatively, the integration of small concentrations of polymer, to “stabilize” the CLC phase, creates a material system that can undergo a dynamic and reversible electro-optic response. This thesis extends upon a number of prior examinations (generally focused on phenomena or functionality) undertaken at the Air Force Research Laboratory, that have demonstrated myriad responses including reflection bandwidth broadening, reflection wavelength tuning, and switching. The systematic investigations presented in this thesis directly elucidate the underlying electromechanical mechanism that is critical to enabling further optimization and enhancement of electro-optic response necessary for implementation in functional utility in applications. More specifically, the first aim of this thesis focuses on the formation and importance of the retention of structural chirality in the polymer stabilizing network (PSN) and the intermolecular interactions between the PSN and the non-reactive CLC host. Notably, PSCLCs prepared with non-liquid-crystalline polymer networks confirm that the chiral templating does not require the monomeric precursors to be liquid crystalline. Further, the cation-mediated electromechanical response of the deformation of the polymer network was correlated to be directly associated with the host (via distinctive confocal fluorescent experiments). The second aim of this thesis is focused on identifying and understanding the interactions between the polymer network and ions, through exploring the electrochemical properties in addition to the electro-optic response. The effect of polymerization on the electrical properties was investigated through impedance spectroscopy with mixtures prepared with metallic salts, ionic liquids, and ionic polymers. The electrical properties of these formulations were then correlated to the electro-optic response of PSCLCs prepared from them. Finally, informed by these fundamental studies, this thesis explored the molecular engineering of the polymer stabilizing network. This was achieved in two ways, both focused on affecting the crosslink density of the PSN. In the first, a dithiol additive was incorporated into the polymer network through copolymerization with the acrylate functionalized liquid crystalline monomer. This reaction decreases the crosslink density through both chain extension and chain transfer. Compositional studies isolated an optimum crosslink density/concentration to retain structural chirality with maximal elasticity. Second, a monofunctional liquid crystalline monomer was incorporated into the polymer network to decrease crosslink density while retaining high liquid crystalline character in the polymer network. The electromechanical mechanism in this material system enabled the realization of a new electro-optic phenomena in PSCLCs, reflection notch splitting

Purchased from AmBeed: ; ; ;

Chapel Hill ;

Abstract: Photoredox catalysis has traditionally been accomplished by using ruthenium or iridium polypyridyl complexes. These complexes, while robust in their application, can prove to be quite cost prohibitive. Additionally, their respective redox windows are relatively narrow, limiting the scope of substrates with which they can undergo photoinduced electron transfer. Visible light absorbing organic chromophores have proven to be cost effective alternatives to precious transition metal photoredox catalysts. Additionally, the excited state redox potentials of organic photoredox catalysts can be significantly greater than that of their inorganic counterparts allowing for the development of new methodologies on substrates that could not otherwise undergo photoinduced electron transfer. In particular, organic acridinium dyes possess photophysical properties that make them extremely potent excited state oxidants. More recently it has been demonstrated that the acridine radical in the excited state possesses and excited state oxidation potential comparable to that of dissolving metal reductants making it an excellent excited state reductant. Herein, we describe methods developed that leverage the 5.51 V of redox potential that acridinium complexes can access. Nucleophilic aromatic substitution (SNAr) is a common method for arene functionalization; however, reactions of this type are typically limited to electron-deficient aromatic halides. Herein, we describe a mild, metal_x005f_x0002_free, cation-radical accelerated nucleophilic aromatic substitution (CRA-SNAr) using a potent acridinium photoredox catalyst as an excited state oxidant. Selective substitution of arene C−O bonds on a wide array of aryl ether substrates was shown with a variety of primary amine nucleophiles. Mechanistic evidence is also presented that supports the proposed CRA-SNAr pathway. Ketone–olefin coupling reactions are common methods for the formation of carbon–carbon bonds. This reaction class typically requires stoichiometric or super stoichiometric quantities of metal reductants and catalytic variations are limited in application. Photoredox catalysis has offered an alternative method towards ketone–olefin coupling reactions, although most methods are limited in scope to easily reducible aromatic carbonyl compounds. Herein, we describe a mild, metal-free ketone–olefin coupling reaction using an excited state acridine radical super reductant as a photoredox catalyst. We demonstrate both intra and intermolecular ketone–olefin couplings of aliphatic and aromatic ketones and aldehydes. Mechanistic evidence is also presented supporting an “olefin first”ketone–olefin coupling mechanism.

Purchased from AmBeed: ; ; ; ;

Alternative Products

Product Details of [ 1643-19-2 ]

CAS No. :1643-19-2
Formula : C16H36BrN
M.W : 322.37
SMILES Code : CCCC[N+](CCCC)(CCCC)CCCC.[Br-]
MDL No. :MFCD00011633
InChI Key :JRMUNVKIHCOMHV-UHFFFAOYSA-M
Pubchem ID :74236

Safety of [ 1643-19-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 1643-19-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 18
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 12
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 90.33
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

-1.49
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.62
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.01
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.13
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

4.71
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.6

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.07
Solubility 2.76 mg/ml ; 0.00856 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.23
Solubility 18.9 mg/ml ; 0.0586 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-6.35
Solubility 0.000145 mg/ml ; 0.000000449 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.12 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

1.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.93

Application In Synthesis of [ 1643-19-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 1643-19-2 ]
  • Downstream synthetic route of [ 1643-19-2 ]

[ 1643-19-2 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1643-19-2 ]
  • [ 38932-80-8 ]
YieldReaction ConditionsOperation in experiment
96.7%
Stage #1: With dihydrogen peroxide In water at 20℃; for 0.5 h;
Stage #2: With sulfuric acid; potassium bromide In water at 0℃; for 3 h;
A sample of molybdic acid monohydrate, H2MO04. H20 (0. 16MMOL, 0.029g) was taken in a 250mL glass beaker and 30percent hydrogen peroxide, H2O2 (15. 52MMOL, 1.76mL) was added to it. The mixture was stirred for 30MIN. at room temperature. The solution, which was slightly turbid, was filtered through Whatman No. L filter paper on a glass funnel. The clear filtrate was collected in a 250ML glass beaker and kept in the ice-water bath. Tetrabutylammonium bromide, TBAB (15. 51MMOL, 5G) and potassium bromide, KBr (31. 01MMOL, 3.69g) dissolved in (0. 3M) H2S04 (15. 52MMOL, 51. 70ML) was added to this solution slowly with continuous stirring leading to the formation of a yellow precipitate. The mixture was continued to stir in ice-water bath for another Nlh and then kept standing in ice- water bath for 2h to get an orange yellow compound of Tetrabutylammonium tribromide, TBATB. The compound was separated by filtration under suction using Whatman No. 1 filter paper. It was DRIED IN VACUO over fused CaCl2 and was recrystallized from acetonitrile. Y=7. 23g (96.7percent) MP : 76-77°C. The chemical analyses, IR and conductance of the compound match very well with those reported in literature. Analytical data: The compound analyzed correctly CL6H36NBR3 : Calc. C, 39.86 ; H, 7. 52 ; N, 2. 90 ; Br, 49.71percent. Found. C, 39. 41 ; H, 8. 28 ; N, 2. 78 ; Br, 49. 53. percent.
96.26% With sulfuric acid; dihydrogen peroxide; potassium bromide In water at 0 - 20℃; for 0.916667 h; Molybdic acid monohydrate, H2MO04. H20 (0. 16MMOL, 0.029g), potassium bromide, KBr (31. 01MMOL, 3.69g) and tetrabutylammonium bromide, TBAB (15. 51mmol, 5g) were powdered separately, mixed together smoothly and thoroughly. The whole was transferred to a boat kept on ice-water bath and 30percent hydrogen peroxide, H202 (15. 52MMOL, 1.76mL) was added drop wise with continuous grinding for 15 min, followed by drop wise addition of 1 OM H2S04 (15. 5MMOL, 1.55mL) leading to the formation of a yellow colored solution. It was stirred smoothly with glass rod for 10 min and then at room temperature for 30min. An exothermic reaction set in to form orange-yellow crystalline compound of tetrabutylammonium tribromide, TBATB. The compound was dried over fused CaCl2 and extracted with ethyl acetate by dissolving in minimum amount of solvent followed by filtration through Whatman No. 42 filter paper. Aqueous phase, if present, could be separated using anhydrous sodium sulphate. The organic layer was concentrated to get yellow-orange tetrabutylammonium tribromide, TBATB and the latter was recrystallized from acetonitrile. Yield: 7.2g (96.26percent) Mp: 76-77 °C. The chemical analyses, IR and conductance of the compound match very well with those reported in literature. Analytical data: The compound analyzed correctly CL6H36NBR3 : Calc. C, 39.86 ; H, 7.52 ; N, 2.90 ; Br, 49.71percent. Found. C, 39.41 ; H, 8.28 ; N, 2.78 ; Br, 49.53 percent.
96% With 3-chloro-benzenecarboperoxoic acid; potassium bromide In water for 0.0833333 h; 4. Synthesis of tetrabutyl ammonium tribromide, TBATB: 1 equiv of tetrabutyl ammonium bromide(1 mmol, 0.322 g), 2 equiv of KBr (2 mmol, 0.238 g) and 2 equiv of MCPBA (2 mmol, 0.346 g) weremixed together in 10 mL of water and stirred for ca. 5 min. The orange coloured product formed waswashed with NaHCO3 solution (10 percent solution) for several times to remove unreacted substrate. After thatthe crude product was again washed with water to remove by-products. The compound was dried invacuo and recrystallized with EtOAc; mp: 75oC. Yield: 0.462 g; 96 percent.
96%
Stage #1: With sodium bromate In water at 20℃; for 0.166667 h;
Stage #2: With hydrogen bromide In water at 20℃; for 0.5 h;
A mixture of TBAB (38.80 g, 120 mmol), sodium bromate (6.00 g, 40 mmol) and water (300 mL) was stirred at room temperature for 10 min. To this solution was added 48percent Aq. HBr (28 mL) drop wise under stirring and continued for another 30 min at room temperature. An orange colored solid precipitated out, which was filtered, washed with water (2×120 mL) and air-dried at room temperature.Yield: 55.36 g (96percent). mp 74-76°C.
91% for 0.0833333 h; Green chemistry An amount of 3.2 g (10 mmol) tetrabutylammonium bromide was added to a solution of 2.4 g (20 mmol) of KBr in 10 mL of 4N H2SO4. To the resulting solution was added 10 mL of 4 percent sodium hypochlorite. The solution was stirred for ca. 5 mins and then the bright orange-yellow colored crystalline TBATB which had separated out was isolated by suction filtration and washed with water (5 mL) three to four times and dried under vacuum over anhydrous CaCl2 to get 4.38 g of TBATB as orange crystals (yield 91percent). Mp: 74 C.
91% With periodic acid; potassium bromide In neat (no solvent) at 20℃; General procedure: 1 equiv of tetraalkylammonium bromide (10 mmol), 2 equiv of KBr (20 mmol, 2.38 g)and 2 equiv of H5IO6 (20 mmol, 4.56 g) were mixed together and ground well in a mortar ca. 5-15 minutes. The orange coloured product formed was washed with water for several times to remove by-products. After that the crude product was extracted with ethyl acetate and the organic solvent was dried in vacuo to get pure product. Yield: 82-93 percent (0.3-0.4 g).

References: [1] Patent: WO2004/54962, 2004, A1, . Location in patent: Page 10.
[2] Patent: WO2004/54962, 2004, A1, . Location in patent: Page 11-12.
[3] Catalysis Communications, 2010, vol. 11, # 11, p. 992 - 995.
[4] Synthetic Communications, 2015, vol. 45, # 6, p. 724 - 736.
[5] Arkivoc, 2018, vol. 2018, # 7, p. 172 - 185.
[6] Chemistry Letters, 2014, vol. 43, # 5, p. 631 - 633.
[7] Chemistry Letters, 2014, vol. 43, # 10, p. 1545 - 1547.
[8] Synthetic Communications, 2013, vol. 43, # 12, p. 1734 - 1742.
[9] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1987, p. 39 - 46.
[10] Bulletin of the Chemical Society of Japan, 1988, vol. 61, p. 3181 - 3186.
[11] Organic Process Research and Development, 2016, vol. 20, # 7, p. 1227 - 1238.
[12] Tetrahedron Letters, 2016, vol. 57, # 50, p. 5644 - 5648.
[13] Inorganica Chimica Acta, 2018, vol. 469, p. 583 - 587.
  • 2
  • [ 1643-19-2 ]
  • [ 1209459-16-4 ]
References: [1] Patent: US2013/190249, 2013, A1, . Location in patent: Page/Page column.
  • 3
  • [ 1643-19-2 ]
  • [ 7460-56-2 ]
  • [ 1209459-16-4 ]
References: [1] Patent: US2015/31627, 2015, A1, . Location in patent: Page/Page column.
 

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[ 1643-19-2 ]

Chemical Structure| 10549-76-5

A1006083 [10549-76-5]

Tetrabutylammonium

Reason: Free-Salt