1,1'-Sulfonyldiimidazole supplier

Name
1,1'-Sulfonyldiimidazole
EINECS 230-554-0
CAS No. 7189-69-7
Article Data18
CAS DataBase
Density 1.6 g/cm³
Solubility
Melting Point 135-137 °C(lit.)
Formula C₆H₆N₄O₂
Boiling Point 471 °C at 760 mmHg
Molecular Weight 198.205
Flash Point 238.7 °C
Transport Information
Appearance light cream crystalline powder
Safety 26-36-36/37/39
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms Imidazole,1,1'-sulfonyldi- (7CI,8CI);1,1'-Sulfonylbis(1H-imidazole);1,1'-Sulphonylbis-1H-imidazole;
PSA 78.16000
LogP 0.80160

Synthetic route

: 18156-74-6
1-(Trimethylsilyl)imidazole

: 7189-69-7
N,N`-sulfuryldiimidazole

Conditions

Conditions	Yield
With sulfuryl dichloride In toluene at -10℃; for 4h;	98%
With fluorosulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at -1 - 26℃; under 35.2535 - 697.57 Torr; for 0.566667h; Temperature; Pressure; Reagent/catalyst; Autoclave; Cooling with ice;	92%

: 1H-imidazole-1-sulfonyl fluoride

: 18156-74-6
1-(Trimethylsilyl)imidazole

: 7189-69-7
N,N`-sulfuryldiimidazole

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 50 - 53℃; Reagent/catalyst; Temperature;	97%

: 288-32-4
1H-imidazole

: 7189-69-7
N,N`-sulfuryldiimidazole

Conditions

Conditions	Yield
With sulfuryl dichloride In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	92%
With sulfuryl dichloride In dichloromethane at 0 - 20℃; for 15h;	90%
With sulfuryl dichloride In dichloromethane at 0 - 20℃;	90%

: 288-32-4
1H-imidazole

: 7791-25-5
sulfuryl dichloride

: 7189-69-7
N,N`-sulfuryldiimidazole

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; for 16h;	87%

: 288-32-4
1H-imidazole

: 1H-imidazole-1-sulfonyl fluoride

: 7189-69-7
N,N`-sulfuryldiimidazole

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 50 - 70℃; for 8h; Reagent/catalyst; Temperature;	80%

: 18156-74-6
1-(Trimethylsilyl)imidazole

A: 1H-imidazole-1-sulfonyl fluoride

B: 7189-69-7
N,N`-sulfuryldiimidazole

Conditions

Conditions	Yield
With fluorosulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene under 0.750075 - 697.57 Torr; for 1.5h; Cooling;	A 57% B 33%

: 7189-69-7
N,N`-sulfuryldiimidazole

: 333-27-7
methyl trifluoromethanesulfonate

: 489471-57-0
3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate

Conditions

Conditions	Yield
In dichloromethane at 0℃; for 0.2h;	100%
In dichloromethane at 0 - 20℃; for 3h;	96%
In dichloromethane at 0℃; for 3h;	94%

: 150-76-5
4-methoxy-phenol

: 7189-69-7
N,N`-sulfuryldiimidazole

: 1139705-25-1
4-methoxyphenyl 1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran	100%
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;	98%
With caesium carbonate In tetrahydrofuran at 20℃;	93%
With sodium carbonate In N,N-dimethyl-formamide at 130℃;	90%
Inert atmosphere; Basic conditions;

: C24H32O4

: 7189-69-7
N,N`-sulfuryldiimidazole

: C27H34N2O6S

Conditions

Conditions	Yield
Stage #1: C24H32O4 With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5h; Stage #2: N,N`-sulfuryldiimidazole In tetrahydrofuran at -10 - 23℃; for 12h;	100%
Stage #1: C24H32O4 With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: N,N`-sulfuryldiimidazole In tetrahydrofuran at 23℃; for 12h; Inert atmosphere;	100%
Stage #1: C24H32O4 With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; Stage #2: N,N`-sulfuryldiimidazole In tetrahydrofuran at -10 - 20℃;

: 540-38-5
4-Iodophenol

: 7189-69-7
N,N`-sulfuryldiimidazole

: C9H7IN2O3S

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran	100%

: 7189-69-7
N,N`-sulfuryldiimidazole

: 218607-58-0
C70H76O15

: 218607-59-1
C73H78N2O17S

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at -40℃; for 5h;	99%

: 527-60-6
Mesitol

: 7189-69-7
N,N`-sulfuryldiimidazole

: 1139705-27-3
2,4,6-trimethylphenyl imidazolesulfonate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;	99%
With caesium carbonate In tetrahydrofuran at 20℃;	91%

: (1R,2S,5S,6S)-6-hydroxy-1-isopropyl-5-methyl-8-oxabicyclo[3.2.1]octan-2-yl cinnamate

: 7189-69-7
N,N`-sulfuryldiimidazole

: C23H28N2O6S

Conditions

Conditions	Yield
Stage #1: (1R,2S,5S,6S)-6-hydroxy-1-isopropyl-5-methyl-8-oxabicyclo[3.2.1]octan-2-yl cinnamate With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: N,N`-sulfuryldiimidazole In tetrahydrofuran at -10 - 20℃; Inert atmosphere;	99%

: 90-43-7
2-Phenylphenol

: 7189-69-7
N,N`-sulfuryldiimidazole

: (1,1'-biphenyl)-2-yl 1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran	99%
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;	98%

: 7189-69-7
N,N`-sulfuryldiimidazole

: 108-95-2
phenol

: 1198183-95-7
phenyl 1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran at 20℃;	98%
With sodium carbonate In N,N-dimethyl-formamide at 130℃;	98%
With caesium carbonate In tetrahydrofuran	98%

: 150-19-6
O-methylresorcine

: 7189-69-7
N,N`-sulfuryldiimidazole

: 1198184-04-1
3-methoxyphenyl 1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran	98%
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;	94%

: 90-05-1
2-methoxy-phenol

: 7189-69-7
N,N`-sulfuryldiimidazole

: 1207429-55-7
2-methoxyphenyl 1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;	98%
With caesium carbonate In tetrahydrofuran	90%

: 103-16-2
4-Benzyloxyphenol

: 7189-69-7
N,N`-sulfuryldiimidazole

: 4-(benzyloxy)phenyl 1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;	98%

: C27H36O4

: 7189-69-7
N,N`-sulfuryldiimidazole

: C30H38N2O6S

Conditions

Conditions	Yield
Stage #1: C27H36O4 With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: N,N`-sulfuryldiimidazole In tetrahydrofuran at -10 - 23℃; for 18h; Inert atmosphere;	98%

: 7189-69-7
N,N`-sulfuryldiimidazole

: 108-68-9
3,5-Dimethylphenol

: 1342307-08-7
3,5-dimethylphenyl 1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;	97%
With caesium carbonate In tetrahydrofuran at 20℃;	90%
With sodium carbonate In N,N-dimethyl-formamide at 130℃;	90%

: 142-08-5
2-hydroxypyridin

: 7189-69-7
N,N`-sulfuryldiimidazole

: pyridin-2-yl 1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 130℃; for 48h;	97%

: 106-41-2
4-bromo-phenol

: 7189-69-7
N,N`-sulfuryldiimidazole

: 4-bromophenyl 1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran	97%
With caesium carbonate In tetrahydrofuran at 20℃;	96%

: 94715-33-0
methyl 3,4-di-O-methyl-2-O-(2,3,4-tri-O-methyl-β-D-xylopyranosyl)-α-D-galactopyranoside

: 7189-69-7
N,N`-sulfuryldiimidazole

: 94715-20-5
methyl 6-O-imidazolylsulfonyl-3,4-di-O-methyl-2-O-(2,3,4-tri-O-methyl-β-D-xylopyranosyl)-α-D-galactopyranoside

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran 1.) 0 deg C, 2 h; 2.) -40 deg C, 20 min.-> r.t., 2 h;	95%

: 106-44-5
p-cresol

: 7189-69-7
N,N`-sulfuryldiimidazole

: 1139705-26-2
4-methylphenyl imidazolesulfonate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran	95%
With caesium carbonate In tetrahydrofuran at 20℃;	91%
With caesium carbonate In tetrahydrofuran at 20℃;	86%
With caesium carbonate In tetrahydrofuran at 20℃;	86%

: 7189-69-7
N,N`-sulfuryldiimidazole

: 135-19-3
β-naphthol

: 1139705-29-5
naphthalen-2-yl 1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran at 20℃; for 12h; Reagent/catalyst; Temperature; Solvent;	95%
With caesium carbonate In tetrahydrofuran at 20℃;	91%

: 95-48-7
ortho-cresol

: 7189-69-7
N,N`-sulfuryldiimidazole

: 1232660-55-7
o-tolyl 1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 130℃;	95%
With caesium carbonate In tetrahydrofuran at 20℃;	94%

: 371-41-5
4-Fluorophenol

: 7189-69-7
N,N`-sulfuryldiimidazole

: 1207429-53-5
4-fluorophenyl 1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran	95%
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;	89%

: 90-15-3
α-naphthol

: 7189-69-7
N,N`-sulfuryldiimidazole

: 1139705-28-4
naphthalene-1-yl 1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;	93%
With caesium carbonate In tetrahydrofuran at 20℃;	91%
With caesium carbonate In tetrahydrofuran at 20℃;	76%

: 1198753-53-5
2-naphthylmethyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl-(1->2)-3,4-di-O-benzyl-5a-carba-α-L-rhamnopyranoside

: 7189-69-7
N,N`-sulfuryldiimidazole

: 1198753-54-6
2-naphthylmethyl 3-O-benzyl-4,6-O-benzylidene-2-O-(N-imidazole-1-sulfonyl)-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl-(1->2)-3,4-di-O-benzyl-5a-carba-α-L-rhamnopyranoside

Conditions

Conditions	Yield
Stage #1: 2-naphthylmethyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl-(1->2)-3,4-di-O-benzyl-5a-carba-α-L-rhamnopyranoside With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: N,N`-sulfuryldiimidazole In N,N-dimethyl-formamide at -40℃; for 5h; Inert atmosphere;	93%

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 7189-69-7
N,N`-sulfuryldiimidazole

: (S)-methyl 3-(4-(1H-imidazol-1-ylsulfonyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;	93%

: 1139852-92-8
4-methoxyphenyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-talopyranoside

: 7189-69-7
N,N`-sulfuryldiimidazole

: 1139852-94-0
4-methoxyphenyl 2-O-(1-imidazolylsulfonyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-talopyranoside

Conditions

Conditions	Yield
Stage #1: 4-methoxyphenyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-talopyranoside With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: N,N`-sulfuryldiimidazole In N,N-dimethyl-formamide; mineral oil at -30℃; for 0.333333h; Inert atmosphere;	92%

: 580-51-8
[1,1'-biphenyl]-3-ol

: 7189-69-7
N,N`-sulfuryldiimidazole

: (1,1'-biphenyl)-3-yl 1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;	92%

: 3067-62-7
1,2:5,6-Di-O-isopropyliden-3-O-trimethylsilyl-D-glucofuranose

: 7189-69-7
N,N`-sulfuryldiimidazole

: 80667-81-8
1,2:5,6-di-O-isopropylidene-3-O-(N-imidazole-1-sulfonyl)-α-D-glucofuranose

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 4h; Heating;	91%
With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane for 4h; Heating; Yield given;

1,1'-Sulfonyldiimidazole Specification

The CAS registry number of 1,1'-Sulfonyldiimidazole is 7189-69-7. The IUPAC name is 1,1'-sulfonylbis(1H-imidazole). Its EINECS registry number is 230-554-0. In addition, the formula is C₆H₆N₄O₂ and the molecular weight is 198.20244. What's more, it belongs to the classes of Imidazoles; Building Blocks; Heterocyclic Building Blocks. What's more, it is a kind of light cream crystalline powder.

Physical properties about this chemical are: (1)ACD/LogP: -0.86; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.86; (4)ACD/LogD (pH 7.4): -0.86; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 8.12; (8)ACD/KOC (pH 7.4): 8.12; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 78.16 Å²; (13)Index of Refraction: 1.722; (14)Molar Refractivity: 48.86 cm³; (15)Molar Volume: 123.4 cm³; (16)Polarizability: 19.37 ×10^-24cm³; (17)Surface Tension: 76.7 dyne/cm; (18)Density: 1.6 g/cm³; (19)Flash Point: 238.7 °C; (20)Enthalpy of Vaporization: 73.37 kJ/mol; (21)Boiling Point: 471 °C at 760 mmHg; (22)Vapour Pressure: 4.82E-09 mmHg at 25°C.

Preparation 1,1'-Sulfonyldiimidazole: it can be prepared by 1-trimethylsilanyl-1H-imidazole. This reaction will need reagent SO₂Cl₂ and solvent toluene. The reaction time is 4 hours at temperature of -10 °C. The yield is about 98%.

1,1'-Sulfonyldiimidazole can be prepared by 1-trimethylsilanyl-1H-imidazole.

Uses of 1,1'-Sulfonyldiimidazole: it can react with 2-(4-chlorophenyl)-1-(4-methoxyphenyl)ethanol to get 1-[2-(4-chloro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-1H-imidazole. This reaction will need reagent acetonitrile. The reaction time is 2 hours with ambient temperature and the yield is about 61.6%.

1,1'-Sulfonyldiimidazole can react with 2-(4-chlorophenyl)-1-(4-methoxyphenyl)ethanol to get 1-[2-(4-chloro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-1H-imidazole

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin and harmful by inhalation, in contact with skin and if swallowed. You should wear suitable protective clothing, gloves and eye/face protection when you are using it. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(n1ccnc1)n2ccnc2
(2)InChI: InChI=1/C6H6N4O2S/c11-13(12,9-3-1-7-5-9)10-4-2-8-6-10/h1-6H
(3)InChIKey: ZLKNPIVTWNMMMH-UHFFFAOYAJ

Product Name

1,1'-Sulfonyldiimidazole

Synthetic route

1,1'-Sulfonyldiimidazole Specification

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