Sulfolane supplier | CasNO.126-33-0

Name
Sulfolane
EINECS 204-783-1
CAS No. 126-33-0
Article Data98
CAS DataBase
Density 1.261 g/cm³
Solubility soluble in water
Melting Point 27.4 °C
Formula C₄H₈O₂S
Boiling Point 285.568 °C at 760 mmHg
Molecular Weight 120.172
Flash Point 170.678 °C
Transport Information
Appearance colourless crystals
Safety 23-25
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms 1,1-Dioxothiolan;Bondelane A;Bondolane A;Cyclic tetramethylene sulfone;Cyclotetramethylenesulfone;NSC 46443;Sulfolan;Sulpholane;Tetrahydrothiophene1,1-dioxide;Tetrahydrothiophene S,S-dioxide;Tetrahydrothiophene dioxide;tetramethylene sulfone;Thiacyclopentane dioxide;Thiolane 1,1-dioxide;Thiophane 1,1-dioxide;Thiophane dioxide;
PSA 42.52000
LogP 1.27580

Synthetic route

: 110-01-0
thiophene

: 126-33-0
sulfolane

Conditions

Conditions	Yield
With silica gel; magnesium monoperoxyphthalate hexahydrate In dichloromethane for 0.833333h; Heating;	100%
With sodium tungstate (VI) dihydrate; dihydrogen peroxide In methanol; water at 40℃;	100%
With selenium(IV) oxide; dihydrogen peroxide In water; ethyl acetate chemoselective reaction;	99%

: 77-79-2
3-Sulfolene

: 126-33-0
sulfolane

Conditions

Conditions	Yield
With triethylsilane; 1% Pd on activated carbon In water at 45℃; for 20h; Green chemistry; chemoselective reaction;	100%
With ethanol; platinum Hydrogenation;
With water; palladium Hydrogenation;

: 110-01-0
thiophene

A: 1600-44-8
1-oxothiolane

B: 126-33-0
sulfolane

Conditions

Conditions	Yield
With urea-hydrogen peroxide at 85℃; for 0.116667h;	A 87% B 9%
With dihydrogen peroxide In water at 30 - 35℃; for 24h; Sealed tube; Green chemistry;	A 66% B 60%
With dihydrogen peroxide; titanium(IV) isopropylate; L-Tartaric acid; silica gel In methanol; water at 25℃; for 4h; Title compound not separated from byproducts;	A 96 % Spectr. B 2%

: 1600-44-8
1-oxothiolane

: 126-33-0
sulfolane

Conditions

Conditions	Yield
With nitronium tetrafluoborate In dichloromethane at 25℃; for 5h;	68%
With peroxynitrous acid at 25℃; for 0.166667 - 4h; pH=7.4 - 12.7; Reactivity; phosphate buffer;	3.14%
With bromine In water at 20℃; Equilibrium constant; Thermodynamic data; ΔH, ΔS, various temperature;

tetramethylenebis(dimethylglyoximato)(pyridine)cobalt(III) (45): tetramethylenebis(dimethylglyoximato)(pyridine)cobalt(III) (45)

A: 126-33-0
sulfolane

B mono- and bis(sulfur dioxide) insertion products: mono- and bis(sulfur dioxide) insertion products

Conditions

Conditions	Yield
With sulfur dioxide for 24h; Ambient temperature;	A 20% B n/a

: 17200-23-6
3-Isopropoxythiolane 1,3-dioxide

: 126-33-0
sulfolane

Conditions

Conditions	Yield
With nickel; isopropyl alcohol at 175℃; under 51485.6 Torr; Hydrogenation;

: 110-52-1
1,4-dibromo-butane

A: 126-33-0
sulfolane

B: 24308-29-0
1,2-oxathiane-2-oxide

Conditions

Conditions	Yield
With sulfur dioxide; tetraethylammonium bromide In acetonitrile at 60 - 80℃; electrolysis;	A 45 % Turnov. B 54 % Turnov.

: 1192-16-1
2,3-dihydrothiophene-1,1-dioxide

: 126-33-0
sulfolane

Conditions

Conditions	Yield
With hydrogen; nickel at 20℃; Kinetics; rate of hydrogenation as a function of deformation of crystal structure of the catalyst; other catalysts : Rh, Pd and Pt;

: 4724-56-5
1,4-ditosyloxybutane

A: 126-33-0
sulfolane

B: 24308-29-0
1,2-oxathiane-2-oxide

Conditions

Conditions	Yield
With sulfur dioxide; tetraethylammonium bromide In acetonitrile at 60 - 80℃; electrolysis;	A 45 % Turnov. B 45 % Turnov.

: 110-01-0
thiophene

ozone containing oxygen: ozone containing oxygen

: 126-33-0
sulfolane

Conditions

Conditions	Yield
With chloroform

: 110-01-0
thiophene

A: 1600-44-8
1-oxothiolane

B: 126-33-0
sulfolane

C: 102244-56-4
4-butanal disulfide

Conditions

Conditions	Yield
With oxygen; methylene blue In acetonitrile Pummerer rearrangement; Photolysis;

...Expand

: 26978-64-3
4-hydroxy-butane-1-sulfonic acid

: 126-33-0
sulfolane

Conditions

Conditions	Yield
With acetic acid In water at 135 - 155℃; under 1 - 3 Torr; for 0.8h; Temperature;	113.5 g

: 126-33-0
sulfolane

: 7651-83-4
isoquinolin-7-ol

: 56623-93-9
8-nitroisoquinolin-7-ol

Conditions

Conditions	Yield
With nitronium tetrafluoroborate In methanol	100%
With nitronium tetrafluoroborate In methanol	100%

: 96-43-5
2-thienyl chloride

: 126-33-0
sulfolane

: 79-37-8
oxalyl dichloride

: 42518-98-9
5-chlorothiophene-2-carbonyl chloride

Conditions

Conditions	Yield
at 165℃; for 17.5h; Temperature;	100%

...Expand

: 126-33-0
sulfolane

: 20627-71-8
Sulfolane-2,2-5,5-d4

Conditions

Conditions	Yield
With potassium tert-butylate; water-d2 at 120℃; for 24h;	98.5%
With water-d2; sodium at 40℃; for 48h;

: 126-33-0
sulfolane

: 314-41-0
1,2,3,5-tetrafluoro-4-nitrobenzene

: 7697-37-2
nitric acid

: 20002-14-6
2,4,5,6-Tetrafluoro-1,3-dinitrobenzene

Conditions

Conditions	Yield
With boron trifluoride at 65-70°C 7 d;	98%
With BF3 at 65-70°C 7 d;	98%

...Expand

: 126-33-0
sulfolane

: 14965-49-2
methylamine hydroiodide

: lead(II) iodide

: CH6N(1+)*Pb(2+)*3I(1-)*C4H8O2S

Conditions

Conditions	Yield
at 80℃; for 0.5h;	97%

...Expand

: (R)-4-methyl-benzenesulfinic acid (2,2-dimethyl-propylidene)-amide

: 126-33-0
sulfolane

: (1R,2S,4R)-4-methyl-benzenesulfinic acid [1-(1,1-dioxo-tetrahydro-1λ6-thiophen-2-yl)-2,2-dimethyl-propyl]-amide

Conditions

Conditions	Yield
Stage #1: sulfolane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Stage #2: (R)-4-methyl-benzenesulfinic acid (2,2-dimethyl-propylidene)-amide In tetrahydrofuran; hexane at -78℃; for 0.333333h;	92%

: 126-33-0
sulfolane

: 25899-50-7
cis-2-pentenenitrile

: 26294-98-4
2-pentenenitrile

: 3009-88-9
5-cyanopentanoic acid methyl ester

Conditions

Conditions	Yield
In methanol	92%

...Expand

: 126-33-0
sulfolane

: 74-88-4
methyl iodide

: 7560-59-0
1-methanesulfonyl-butane

Conditions

Conditions	Yield
With potassium In toluene at 0℃; for 4h; Irradiation; other cyclic sulfones;	91%
With 1.)K 1.) toluene, 4h, 0 deg C, ultrasonic irradiation, 2.) 30 min, RT; Yield given. Multistep reaction;
With water; potassium 1) toluene, THF 2) heating; Yield given. Multistep reaction;

: 126-33-0
sulfolane

: 121-91-5
isophthalic acid

: 506-77-4
cyanogen chloride

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
	91%

...Expand

: 126-33-0
sulfolane

: 115812-33-4
2,3,4-trifluoro-5-chloro-trifluoromethylbenzene

: 2H-tetrachlorobenzotrifluoride

: 2751-90-8
tetraphenylphosphonium bromide

: 2H-tetrafluorobenzotrifluoride

Conditions

Conditions	Yield
With potassium fluoride	90.5%

...Expand

: 126-33-0
sulfolane

: 71-36-3
butan-1-ol

: 542-52-9
Dibutyl carbonate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 190℃; under 1125.11 Torr; for 70h; Temperature; Pressure; Solvent;	89.4%

: 126-33-0
sulfolane

: formamidinium iodide

: lead(II) iodide

: CH5N2(1+)*Pb(2+)*3I(1-)*C4H8O2S

Conditions

Conditions	Yield
at 90℃; for 0.5h;	89%

...Expand

: 126-33-0
sulfolane

: 99-54-7
3,4-dichloronitrobenzene

: 5137-55-3
Aliquat 336

: 350-30-1
3-chloro-4-fluoronitrobenzene

Conditions

Conditions	Yield
With potassium fluoride; AlCl3	85%

...Expand

: 126-33-0
sulfolane

: 593-53-3
Methyl fluoride

: tetrahydro-1-methoxythiophenium 1-oxide hexafluoroantimonate

Conditions

Conditions	Yield
With sulfur dioxide; antimony pentafluoride for 0.25h; Ambient temperature; NMR study of products;	82%

: 126-33-0
sulfolane

: 363-72-4
Pentafluorobenzene

: 7697-37-2
nitric acid

: 880-78-4
pentafluoronitrobenzen

Conditions

Conditions	Yield
With boron trifluoride In not given with BF3 satd. mixture of tetramethylene sulfon and 95% HNO3 and C6F5H at 60-70°C 2 h;	82%
With BF3 In not given with BF3 satd. mixture of tetramethylene sulfon and 95% HNO3 and C6F5H at 60-70°C 2 h;	82%

...Expand

: 126-33-0
sulfolane

: 4231-62-3
1-benzoyl-1H-benzotriazole

: 24463-84-1
2-benzoyltetrahydrothiophene-1,1-dione

Conditions

Conditions	Yield
Stage #1: sulfolane With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; Stage #2: 1-benzoyl-1H-benzotriazole In tetrahydrofuran; hexane at -78 - 20℃; Further stages.;	81%

: 126-33-0
sulfolane

: 1028-19-9
1-(4'-methylbenzenesulfonyl)-1H-benzo[d][1.2.3]triazole

: 2-(toluene-4-sulfonyl)tetrahydrothiophene-1,1-dione

Conditions

Conditions	Yield
Stage #1: sulfolane With n-butyllithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: 1-(4'-methylbenzenesulfonyl)-1H-benzo[d][1.2.3]triazole In tetrahydrofuran; pentane at -78 - 20℃; for 10h;	78%

: 126-33-0
sulfolane

: 26294-98-4
2-pentenenitrile

: 3009-88-9
5-cyanopentanoic acid methyl ester

Conditions

Conditions	Yield
In methanol	78%

: 126-33-0
sulfolane

: 7440-47-3
chromium

: bis(tetramethylene sulfone)chromium(III)chloride trihydrate

Conditions

Conditions	Yield
With CCl4 In tetrachloromethane; ethanol added sulfolane, CCl4 and EtOH to Cr powder; heated to 120-140°C for several hours; filtered; evapd.; cooled; washed with acetone and ether; dried; elem.anal.;	78%

: 126-33-0
sulfolane

: 59046-28-5
p-toluoyl-1H-1,2,3-benzotriazole

: 2-(4-methylbenzoyl)tetrahydrothiophene-1,1-dione

Conditions

Conditions	Yield
Stage #1: sulfolane With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; Stage #2: p-toluoyl-1H-1,2,3-benzotriazole In tetrahydrofuran; hexane at -78 - 20℃; Further stages.;	77%

: 126-33-0
sulfolane

: 1953-99-7
tetrachlorophthalonitrile

: 1835-65-0
Tetrafluorophthalonitrile

Conditions

Conditions	Yield
With potassium fluoride In water	74%

: 126-33-0
sulfolane

: 7355-58-0
N-(2-chloro-ethyl)-acetamide

: 1120-64-5
2-methyl-4,5-dihydro-1,3-oxazole

Conditions

Conditions	Yield
	73%

: 126-33-0
sulfolane

: 143-15-7
1-dodecylbromide

: 2-n-dodecyltetrahydrothiophene-1, 1-dioxide

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane; water; ethyl acetate; toluene	73%

: 126-33-0
sulfolane

: 301164-69-2
(1H-benzo[d][1,2,3]triazol-1-yl)(thiophen-2-yl)methanone

: 2-(2-thienylcarbonyl)tetrahydrothiophene-1,1-dione

Conditions

Conditions	Yield
Stage #1: sulfolane With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; Stage #2: (1H-benzo[d][1,2,3]triazol-1-yl)(thiophen-2-yl)methanone In tetrahydrofuran; hexane at -78 - 20℃; Further stages.;	72%

: 126-33-0
sulfolane

: 34973-43-8
hexachloro-phthalide

: 1024-59-5
3,4,5,6-tetrafluoro-1,2-benzenedicarboxylic acid,dimethyl ester

Conditions

Conditions	Yield
With hydrogenchloride; potassium fluoride; triethylamine In methanol; n-heptane; water; toluene	72%
With hydrogenchloride; potassium fluoride; triethylamine In methanol; water	65%

: 126-33-0
sulfolane

: 13499-05-3
hafnium tetrachloride

: 760976-01-0
[HfCl4(tetrahydrothiophene-1,1-dioxide)2]

Conditions

Conditions	Yield
In dichloromethane (N2); dropwise addn. of a soln. of ligand in CH2Cl2 to a suspn. of HfCl4in CH2Cl2 at room temp.; filtration, concn., addn. of hexane, filtration, washing with hexane, drying in vac. at room temp.; elem. anal.;	71%
In sulfolane (N2); addn. of sulfolane to HfCl4; filtration, addn. of CH2Cl2, then toluene, then hexane, standing for 15 d, filtration, washing with hexane, drying in vac.; elem. anal.;	21%

: 126-33-0
sulfolane

: (3R)-4-[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl]-3-methylmorpholine

: 2-(6-((R)-3-methylmorpholino)-2-(methylthio)pyrimidin-4-yl)tetrahydrothiophene 1,1-dioxide

Conditions

Conditions	Yield
Stage #1: sulfolane With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 1.5h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran at 0℃; for 1.5h; Inert atmosphere; Stage #3: (3R)-4-[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl]-3-methylmorpholine With palladium diacetate; XPhos In tetrahydrofuran at 65℃; for 16h; Negishi Coupling; Inert atmosphere;	71%

Sulfolane Consensus Reports

Reported in EPA TSCA Inventory.

Sulfolane Specification

The Sulfolane is an organic compound with the formula C₄H₈O₂S. The IUPAC name of this chemical is thiolane 1,1-dioxide. With the CAS registry number 126-33-0, it is also named as 2,3,4,5-Tetrahydrothiophene-1,1-dioxide. The product's category is Organics. Besides, it is a colourless crystal.

Physical properties about Sulfolane are: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 13.961; (4)ACD/KOC (pH 7.4): 13.961; (5)#H bond acceptors: 2; (6)Polar Surface Area: 42.52 Å²; (7)Index of Refraction: 1.486; (8)Molar Refractivity: 27.337 cm³; (9)Molar Volume: 95.289 cm³; (10)Polarizability: 10.837×10^-24cm³; (11)Surface Tension: 35.61 dyne/cm; (12)Density: 1.261 g/cm³; (13)Flash Point: 170.678 °C; (14)Enthalpy of Vaporization: 50.357 kJ/mol; (15)Boiling Point: 285.568 °C at 760 mmHg; (16)Vapour Pressure: 0.005 mmHg at 25°C.

Preparation: the original method was to first allow butadiene to react with sulfur dioxide. This yields sulfolene, which was then hydrogenated using Raney nickel as a catalyst to give sulfolane.

Uses of Sulfolane: it is widely used as an industrial solvent, especially in the extraction of aromatic hydrocarbons from hydrocarbon mixtures and to purify natural gas. Sulfolane was found to be highly effective in separating high purity aromatic compounds from hydrocarbon mixtures using liquid-liquid extraction. This process is still widely used today in refineries and the petrochemical industry. Because sulfolane is one of the most efficient industrial solvents for purifying aromatics, the process operates at a relatively low solvent-to-feed ratio, making sulfolane relatively cost effective compared to similar-purpose solvents. In addition, it is selective in a range that complements distillation; where sulfolane can't separate two compounds, distillation easily can and vice versa, keeping sulfolane units useful for a wide range of compounds with minimal additional cost.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. When you are using it, do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) and avoid contact with eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: C1CCS(=O)(=O)C1
(2)InChI: InChI=1/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2
(3)InChIKey: HXJUTPCZVOIRIF-UHFFFAOYAA
(4)Std. InChI: InChI=1S/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2
(5)Std. InChIKey: HXJUTPCZVOIRIF-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	1250mg/kg (1250mg/kg)		Russian Pharmacology and Toxicology Vol. 42, Pg. 97, 1979.
mouse	LD50	intravenous	1080mg/kg (1080mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 119, Pg. 423, 1959.
mouse	LD50	oral	1900mg/kg (1900mg/kg)		"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 560, 1969.
rabbit	LD50	skin	3180uL/kg (3.18mL/kg)	LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	National Technical Information Service. Vol. OTS0535072,
rat	LC	inhalation	> 250mg/m³/8H (250mg/m³)		National Technical Information Service. Vol. OTS0535072,
rat	LD50	intraperitoneal	1600mg/kg (1600mg/kg)		Toxicologist. Vol. 4, Pg. 22, 1984.
rat	LD50	oral	1540uL/kg (1.54mL/kg)		American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
rat	LD50	skin	> 3800mg/kg (3800mg/kg)		British Journal of Industrial Medicine. Vol. 23, Pg. 302, 1966.
rat	LD50	subcutaneous	1620uL/kg (1.62mL/kg)		National Technical Information Service. Vol. OTS0535072,

Product Name

Sulfolane

Synthetic route

Sulfolane Consensus Reports

Sulfolane Specification

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