32503-27-8

Basic information

• Product Name: Tetrabutylammonium hydrogen sulfate
• Synonyms: 1-Butanaminium,N,N,N-tributyl-,sulfate(1:1);n,n,n-tributyl-1-butanaminiusulfate(1:1);TETRABUTYLAMM.HYDROGENSULPHATE;TETRABUTYLAMMONIUM HYDROGEN SULFATE 98+%;Tetrabutylammonium bisulfate solution;TETRABUTYLAMMONIUM HYDROGENSULFATE 97%;Tetrabutylammonium bisulfate, Concentrate;TetrabutylAmmoniumHydrogenSulfateForSynthesis
• CAS NO: 32503-27-8
• Molecular Formula: C16H37NO4S
• Molecular Weight: 339.53
• EINECS: 251-068-5
• Product Categories: quarternary ammonium salts;Ammonium Polyhalides, etc. (Quaternary);Analytical Chemistry;HPLC Ion-Pair Reagents for Acidic Samples;Ion-Pair Reagents for HPLC;Quaternary Ammonium Compounds;Ion-pair Reagents;Miscellaneous Reagents;Pharmaceutical intermediates
• Mol File: 32503-27-8.mol

Chemical Properties

• Melting Point: 171-174 °C
• Boiling Point: 213.3-593.92℃[at 101 325 Pa]
• Appearance: White to beige/Solution
• Density: 1.01
• Vapor Pressure: 0Pa at 25℃
• Storage Temp.: Refrigerator
• Solubility: H2O: soluble10% (w/v), clear, colorless
• Water Solubility: Soluble
• Sensitive: Hygroscopic
• Stability: Stable, but moisture sensitive. Incompatible with strong oxidizing agents.
• BRN: 3599663
• CAS DataBase Reference: Tetrabutylammonium hydrogen sulfate(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrabutylammonium hydrogen sulfate(32503-27-8)
• EPA Substance Registry System: Tetrabutylammonium hydrogen sulfate(32503-27-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 8-10
• TSCA: Yes
• Hazardous Substances Data: 32503-27-8(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 32503-27-8 differently. You can refer to the following data:
1. Displays antibacterial properties due to the presence of the quaternary amine and the counter ion.
2. A compound that displays antibacterial properties
3. Phase transfer catalyst Tetra-n-butylammonium hydrogen sulfate shows antibacterial properties due to the presence of the quaternary amine and the counter ion. It serves as a phase-transfer catalyst, surface-active agent, solvent, intermediate, active ingredient for conditioners, antistatic agent, detergent sanitizers, softener for textiles and paper products, emulsifying agents and pigment dispersers. It is used as an efficient catalyst in the N-alkylation reactions of benzanilides, cyclization of beta-amino acids to beta-lactams, conversion of nitriles to amides, dehydrohalogenation of aryl 2-haloethyl ethers to give vinyl ethers and in the oxidation of alcohols.

General Description

Tetrabutylammonium bisulfate, a quaternary ammonium salt, is a phase-transfer reagent.

Purification Methods

The sulfate crystallises from acetone. It has been used as a phase transfer catalyst.

InChI:InChI=1/C16H36N.H2O4S/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-5(2,3)4/h5-16H2,1-4H3;(H2,1,2,3,4)/q+1;/p-2

Synthetic route

tetrabutylammonium thiocyanate (3674-54-2) → tetra(n-butyl)ammonium hydrogensulfate (32503-27-8)

Conditions	Yield
With sulfuric acid In water at 75℃; for 1h;	83%

C18H30N4OS2*C16H36N(1+)*HO4S(1-) → tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) + 1-butyl-3-{3-[(3-butyl-thioureido)-methyl]-2-hydroxy-benzyl}-thiourea (321898-65-1)

Conditions	Yield
In chloroform-d1 at 20℃; Equilibrium constant;

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) + 6,7,8,9,10,11-hexahydro-2-methylthiocyclohepta<1,2,4>triazolo<1,5-a>pyrimidin-5-one (135119-21-0) → 6,7,8,9,10,11-hexahydro-2-methylthiocyclohepta<1,2,4>triazolo<1,5-a>pyrimidin-5-one tetrabutylammonium salt

Conditions	Yield
With sodium hydroxide In water below 10 deg C;	100%

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) + 6,7,8,9,10,11,12,13,14,15-decahydro-2-morpholinocyclododeca<1,2,4>triazolo<1,5-a>pyrimidin-5(16H)-one (135119-51-6) → 6,7,8,9,10,11,12,13,14,15-decahydro-2-morpholinocyclododeca<1,2,4>triazolo<1,5-a>pyrimidin-5(16H)-one tetrabutylammonium salt

Conditions	Yield
With sodium hydroxide In water below 10 deg C;	100%

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → tetrabutyl ammonium fluoride (429-41-4)

Conditions	Yield
With potassium fluoride; potassium hydroxide for 0.333333h; Ambient temperature;	100%
With potassium fluoride; potassium hydroxide In dichloromethane; water

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → tetrabutylammonium hydrogen bifluoride (193819-24-8)

Conditions	Yield
With potassium hydrogen bifluoride; potassium hydrogencarbonate In chloroform 1.) room temp, 10 min, 2.) 1 h;	100%
Stage #1: tetra(n-butyl)ammonium hydrogensulfate With potassium hydrogencarbonate In water at 20℃; for 0.166667h; Stage #2: With potassium hydrogen bifluoride at 20℃; for 1h;	98%

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → tetra-n-butyl-ammonium dihydrogentrifluoride (148305-65-1, 148305-68-4, 148305-70-8)

Conditions	Yield
With potassium hydrogen bifluoride; potassium hydrogencarbonate In chloroform 1.) room temp., 10 min, 2.) 1 h;	100%

potassium hexachlororhodate(III) + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → 3(C4H9)4N(1+)*[Rh2Cl9](3-)=[(C4H9)4N]3[Rh2Cl9]

Conditions	Yield
In dichloromethane; water aq. soln. of K3(RhCl6) shaken with a soln. of (TBA)HSO4 in CH2Cl2 until the brown-red color disappeared; extracts washed with ice-cold H2O, org. layer dried over Na2SO4, solvent removed, CH2Cl2 added, ether added dropwise for pptn.;	100%

3K(1+)*{RhBr6}(3-)=K3{RhBr6} + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → 3(C4H9)4N(1+)*[Rh2Br9](3-)=[(C4H9)4N]3[Rh2Br9]

Conditions	Yield
In dichloromethane aq. soln. of K3(RhBr6) shaken with a soln. of (TBA)HSO4 in CH2Cl2 until the brown-red color disappeared; extracts washed with ice-cold H2O, org. layer dried over Na2SO4, solvent removed, CH2Cl2 added, ether added dropwise until ppt.;	100%

2NH4(1+)*{Os(CO)Br5}(2-)=(NH4)2{Os(CO)Br5} + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → 2N(CH2CH2CH2CH3)4(1+)*{Os(CO)Br5}(2-)=(N(C4H9)4)2{Os(CO)Br5}

Conditions	Yield
In water cooling (0°C); extraction (CH2Cl2), pptn. (Et2O);;	100%

potassium hexabromoplatinate(IV) + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → fac-(Bu4N)2-trichlorotribromoplatinate(IV)

Conditions

Yield

With bromine; chlorine In hydrogenchloride K2(PtBr6) was changed to Na2(PtBr6) in bromine-water with strong acidicion exchanger, dissolved in conc. HCl, Cl2 was led in for 2-4 h at 20°C, precipitated as K-salt; dissolved 4N H2SO4/Br2 (ion exchanger), separated (diethylaminoethylcellulose-ion exchanger, -8°C), eluated ((C4H9)4N)HSO4 in CH2Cl2, evapd., dissolved (CH2Cl2), shaked (H2O), dried (Na2SO4), diethylether/petroleum ether added, elem. anal.;

100%

tert-butyl 4-((2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamido)piperidine-1-carboxylate hydrate (1174020-64-4) + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → tetrabutyl ammonium salt (25,5R)-4-tert-butyl{(6-sulfooxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-ylcarbonyl)amino}piperidine-1-carboxylate (1174020-24-6)

Conditions	Yield
Stage #1: tert-butyl 4-((2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamido)piperidine-1-carboxylate hydrate With α-picoline; sulfur trioxide pyridine complex In tetrahydrofuran for 15h; Inert atmosphere; Stage #2: tetra(n-butyl)ammonium hydrogensulfate With dipotassium hydrogenphosphate In tetrahydrofuran; dichloromethane at -10℃; for 0.666667h;	100%
Stage #1: tert-butyl 4-((2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamido)piperidine-1-carboxylate hydrate With sulfur trioxide pyridine complex; triethylamine In dichloromethane at 35℃; for 4h; Stage #2: With potassium dihydrogenphosphate In water for 1h; Stage #3: tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water at 35℃; for 14h;	62%
Stage #1: tert-butyl 4-((2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamido)piperidine-1-carboxylate hydrate With pyridine; sulfur trioxide pyridine complex at 20℃; Stage #2: for 4h; Molecular sieve; Stage #3: tetra(n-butyl)ammonium hydrogensulfate With potassium dihydrogenphosphate In water for 0.166667h; Product distribution / selectivity;
Stage #1: tert-butyl 4-((2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamido)piperidine-1-carboxylate hydrate With α-picoline; sulfur trioxide pyridine complex In tetrahydrofuran for 15h; Stage #2: tetra(n-butyl)ammonium hydrogensulfate With dipotassium hydrogenphosphate In tetrahydrofuran; dichloromethane; water for 0.666667h; Product distribution / selectivity;
Stage #1: tert-butyl 4-((2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamido)piperidine-1-carboxylate hydrate With α-picoline; sulfur trioxide pyridine complex In tetrahydrofuran for 15h; Inert atmosphere; Stage #2: tetra(n-butyl)ammonium hydrogensulfate With dipotassium hydrogenphosphate In tetrahydrofuran; dichloromethane; water at -10℃; for 0.666667h;

2Cs(1+)*B9H9(2-)=Cs2{B9H9} + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → (n-Bu4N)2B9H9 (68380-71-2)

Conditions	Yield
In sodium hydroxide aq. NaOH; B compd. was dissolved in aq. NaOH at 333 K; soln. of Bu4NHSO4 in aq. NaOH was added with stirring; filtered; washed with mother liquor; dried (vac.);	100%

ammonium methyl-H-phosphonate + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → tetra-N-butylammonium methyl H-phosphonate (1598426-47-1)

Conditions	Yield
With sodium hydroxide In water at 0 - 20℃; for 0.333333h; Inert atmosphere;	100%

tert-butyl (2S)-2-[(2-{[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}hydrazinyl)carbonyl]piperidine-1-carboxylate (1452467-80-9) + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → tetrabutylammonium tert-butyl (2S)-2-[(2-{[(2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}hydrazinyl)carbonyl]piperidine-1-carboxylate

Conditions	Yield
Stage #1: tert-butyl (2S)-2-[(2-{[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}hydrazinyl)carbonyl]piperidine-1-carboxylate With sulfur trioxide pyridine complex In pyridine at 20℃; Stage #2: tetra(n-butyl)ammonium hydrogensulfate With sodium dihydrogenphosphate In water; ethyl acetate for 0.166667h;	100%

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) + disodium 4-[7-(4-sulfonatophenyl)-1,10-phenanthrolin-4-yl]benzenesulfonate → bathophenanthroline sulfonate tetrabutylammonium salt

Conditions	Yield
In water at 20℃; for 2h; Inert atmosphere; Schlenk technique;	100%

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) + 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline 4',4''-disulfonic acid disodium salt → C26H18N2O6S2(2-)*2C16H36N(1+)

Conditions	Yield
In water at 20℃; for 2h; Inert atmosphere; Schlenk technique;	100%

potassium (2,5-dimethoxyphenyl)trifluoroborate + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → tetrabutylammonium (2,5-dimethoxyphenyl)trifluoroborate

Conditions	Yield
In dichloromethane; water Schlenk technique; Glovebox;	100%

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) + Sodium 2-(perfluorohexyl)ethanesulfinate → Tetrabutylammonium 2-(perfluorohexyl)ethanesulfinate

Conditions	Yield
In dichloromethane at 25℃; for 17.5h; Substitution;	99.6%

tricarbonyl(η5-1-phenylborole)iron (103652-93-3) + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → tetra-n-butylammonium {dicarbonylhydrido(η5-(1-phenylborole))ferrate} (141293-59-6)

Conditions	Yield
In sodium hydroxide; benzene N2 atmosphere; layering of soln. of NBu4HSO4 in aq. NaOH with soln. of Fe-compd. in benzene, stirring (15 h, room temp.); evapn. to dryness of org. layer, washing of residue (pentane), drying (vac.); elem. anal.;	99%

4N((CH2)3CH3)4(1+)*2H(1+)*Nb3PW9O40(6-)=[N((CH2)3CH3)4]4H2[Nb3PW9O40] + tetrabutylammomium bromide (1643-19-2) + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → 3N((CH2)3CH3)4(1+)*3H(1+)*Nb6P2W18O77(6-)=[N((CH2)3CH3)4]3H3[Nb6P2W18O77]

Conditions	Yield
With AcOH In acetonitrile byproducts: water; dropwise addn. of AcOH to heteropolysalt (stirring), stirring for 15 min, addn. of mixt. of Bu4N-salts; pptn. on standing at 0°C; elem. anal.;	99%

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → tetrabutylammonium dihydrogen trifluoride

Conditions	Yield
Stage #1: tetra(n-butyl)ammonium hydrogensulfate With potassium hydrogencarbonate In chloroform; water at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With potassium hydrogenfluoride In chloroform; water at 20℃; for 1h; Inert atmosphere;	99%

tert-butyl (1-hydroxy-2-oxo-1-azaspiro[3.5]nonan-3-yl)carbamate + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → tetrabutylammonium 3-((tert-butoxycarbonyl)amino)-2-oxo-1-azaspiro[3.5]nonan-1-yl sulfate

Conditions	Yield
Stage #1: tert-butyl (1-hydroxy-2-oxo-1-azaspiro[3.5]nonan-3-yl)carbamate With pyridine; sulfur trioxide pyridine complex at 60℃; for 3h; Stage #2: tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water	98.5%

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) + 6,7,8,9,10,11-hexahydro-2-methylthiocycloocta<1,2,4>triazolo<1,5-a>pyrimidin-5(12H)-one (135119-31-2) → 6,7,8,9,10,11-hexahydro-2-methylthiocycloocta<1,2,4>triazolo<1,5-a>pyrimidin-5(12H)-one tetrabutylammonium salt

Conditions	Yield
With sodium hydroxide In water below 10 deg C;	98%

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) + [2-(2-Chloro-acetylamino)-thiazol-4-yl]-[(Z)-methoxyimino]-acetic acid (R)-1-((2S,3S)-2-acetoxymethyl-4-oxo-1-sulfo-azetidin-3-yl)-ethyl ester → (2S,3S)-2-Acetoxymethyl-3-((R)-1-{2-[2-(2-chloro-acetylamino)-thiazol-4-yl]-2-[(Z)-methoxyimino]-acetoxy}-ethyl)-4-oxo-azetidine-1-sulfonatetetrabutyl-ammonium;

Conditions	Yield
for 18h; Ambient temperature;	98%

(2S,5R)-2-([1,3,4]oxadiazol-2-yl)-6-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → (2S,5R)-sulfuric acid mono-(2-[1,3,4]oxadiazol-2-yl-7-oxo-1,6-diaza-bicyclo[3.2.1]oct-6-yl) ester tetrabutylammonium salt

Conditions	Yield
Stage #1: (2S,5R)-2-([1,3,4]oxadiazol-2-yl)-6-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane With sulfur trioxide pyridine complex; triethylamine In dichloromethane for 2h; Stage #2: tetra(n-butyl)ammonium hydrogensulfate In dichloromethane for 1.5h;	98%
Stage #1: (2S,5R)-2-([1,3,4]oxadiazol-2-yl)-6-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane With pyridine; sulfur trioxide pyridine complex at 20℃; for 8h; Stage #2: tetra(n-butyl)ammonium hydrogensulfate With sodium dihydrogenphosphate In water at 20℃; for 0.333333h;	97%
Stage #1: (2S,5R)-2-([1,3,4]oxadiazol-2-yl)-6-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane With pyridine; sulfur trioxide pyridine complex at 20℃; for 8h; Stage #2: tetra(n-butyl)ammonium hydrogensulfate With sodium dihydrogenphosphate In water at 20℃; for 0.333333h;	97%
Stage #1: (2S,5R)-2-([1,3,4]oxadiazol-2-yl)-6-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane With pyridine; sulfur trioxide pyridine complex In pyridine at 20℃; for 8h; Stage #2: tetra(n-butyl)ammonium hydrogensulfate With sodium dihydrogenphosphate In water at 20℃; for 0.333333h;	97%

HAuCl4 + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → tert-butylamonium tetrachloroaurate(III)

Conditions	Yield
In water	97.2%

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) + 6,7,8,9,10,11-hexahydro-2-morpholinocyclohepta<1,2,4>triazolo<1,5-a>pyrimidin-5-one (135119-26-5) → 6,7,8,9,10,11-hexahydro-2-morpholinocyclohepta<1,2,4>triazolo<1,5-a>pyrimidin-5-one tetrabutylammonium salt

Conditions	Yield
With sodium hydroxide In water below 10 deg C;	97%

C29H31N5O8 (1186386-28-6) + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → C16H36N(1+)*C29H30N5O8(1-) (1186386-31-1)

Conditions	Yield
With sodium hydrogencarbonate In chloroform; water for 0.0833333h;	97%

C27H28N6O10S (1186386-33-3) + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → C16H36N(1+)*C27H27N6O10S(1-) (1186386-35-5)

Conditions	Yield
With sodium hydrogencarbonate In chloroform; water for 0.0833333h;	97%

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) + potassium phenyltrifluoborate → tetra-n-butylammonium phenyltrifluoroborate

Conditions	Yield
In dichloromethane; water at 20℃; for 0.0833333h;	97%

{4-[(E)-2-phenylethenyl]phenyl}methanesulfonic acid sodium salt (1496554-27-8) + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → N,N,N-tributyl-1-butanaminium {4-[(E)-2-phenylethenyl]phenyl}methanesulfonate

Conditions	Yield
With sodium hydroxide In dichloromethane at 20℃; for 0.25h;	96%

Upstream product

• 3674-54-2 tetrabutylammonium thiocyanate 
• 2052-49-5 tetra(n-butyl)ammonium hydroxide 

Downstream Products

• 68695-48-7 di-tert-butyl phosphoric acid tetra-n-butylammonium salt 
• 110680-04-1 tetrabutylammonium (Z)-2-phenyl-1-propenesulphonate 
• 110679-90-8 tetrabutylammonium (E)-2,3-dimethyl-1-butenesulphonate 
• 74830-30-1 tetra-N-butylammonium salt of succinimide 
• 34851-41-7 tetrabutyl ammonium methoxide 
• 114086-83-8 tetrabutylammonium 2,2-diphenylvinylsulphonate 
• 87353-15-9 tetrabutylammonium benzylglutarate 
• 87353-23-9 tetrabutylammonium benzyladipate 
• 123963-80-4 tetrabutylammonium benzyl 2,2-dimethylmalonate 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 130163-85-8 tetrabutylammonium (3S,4S)-3-<(R)-1-(benzyloxycarbonyloxy)ethyl>-4-<(S)-1-carbamoyloxyethyl>-2-azetidinone-1-sulfonate 
• 130163-87-0 tetrabutylammonium (3S,4S)-3-<(R)-1-(benzyloxycarbonyloxy)ethyl>-4-<(S)-1-(N-methylcarbamoyloxy)ethyl>-2-azetidinone-1-sulfonate 
• 130163-89-2 tetrabutylammonium (3S,4S)-3-<(R)-1-(benzyloxycarbonyloxy)ethyl>-4-<(S)-1-(N,N-dimethylcarbamoyloxy)ethyl>-2-azetidinone-1-sulfonate 
• 130164-24-8 C₁₇H₂₁N₂O₁₀S^(1-)*C₁₆H₃₆N⁽¹⁺⁾ 

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