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7189-69-7 Usage

Uses

1,1′-Sulfonyldiimidazole may be used in the preparation of stable 1:1 complexes of benziodoxole. It may be used in the synthesis of 2,3′-anhydro-2′-deoxyribonucleosides.

General Description

The mol-ecule of 1,1′-sulfonyldiimidazole, is reported to possess a pseudo-twofold rotation axis of symmetry passing through the S atom. It undergoes one pot Suzuki Coupling reaction to afford 1-phenylnaphthalene.

Check Digit Verification of cas no

The CAS Registry Mumber 7189-69-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,1,8 and 9 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 7189-69:
(6*7)+(5*1)+(4*8)+(3*9)+(2*6)+(1*9)=127
127 % 10 = 7
So 7189-69-7 is a valid CAS Registry Number.

7189-69-7 Well-known Company Product Price

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  • (Code)Product description
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  • Aldrich

  • (367818)  1,1′-Sulfonyldiimidazole  98%

  • 7189-69-7

  • 367818-1G

  • 491.40CNY

  • Detail
  • Aldrich

  • (367818)  1,1′-Sulfonyldiimidazole  98%

  • 7189-69-7

  • 367818-5G

  • 1,682.46CNY

  • Detail
  • Aldrich

  • (367818)  1,1′-Sulfonyldiimidazole  98%

  • 7189-69-7

  • 367818-25G

  • 3,005.73CNY

  • Detail

7189-69-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,1'-Sulfonyldiimidazole

1.2 Other means of identification

Product number -
Other names 1-imidazol-1-ylsulfonylimidazole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:7189-69-7 SDS

7189-69-7Synthetic route

1-(Trimethylsilyl)imidazole
18156-74-6

1-(Trimethylsilyl)imidazole

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

Conditions
ConditionsYield
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

1H-imidazole-1-sulfonyl fluoride

1-(Trimethylsilyl)imidazole
18156-74-6

1-(Trimethylsilyl)imidazole

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 50 - 53℃; Reagent/catalyst; Temperature;97%
1H-imidazole
288-32-4

1H-imidazole

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

Conditions
ConditionsYield
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%
1H-imidazole
288-32-4

1H-imidazole

sulfuryl dichloride
7791-25-5

sulfuryl dichloride

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 16h;87%
1H-imidazole
288-32-4

1H-imidazole

1H-imidazole-1-sulfonyl fluoride

1H-imidazole-1-sulfonyl fluoride

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50 - 70℃; for 8h; Reagent/catalyst; Temperature;80%
1-(Trimethylsilyl)imidazole
18156-74-6

1-(Trimethylsilyl)imidazole

A

1H-imidazole-1-sulfonyl fluoride

1H-imidazole-1-sulfonyl fluoride

B

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

Conditions
ConditionsYield
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%
N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

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

3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.2h;100%
In dichloromethane at 0 - 20℃; for 3h;96%
In dichloromethane at 0℃; for 3h;94%
4-methoxy-phenol
150-76-5

4-methoxy-phenol

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

4-methoxyphenyl 1H-imidazole-1-sulfonate

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran100%
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

C24H32O4

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

C27H34N2O6S

C27H34N2O6S

Conditions
ConditionsYield
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℃;
4-Iodophenol
540-38-5

4-Iodophenol

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

C9H7IN2O3S

C9H7IN2O3S

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran100%
N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

C70H76O15
218607-58-0

C70H76O15

C73H78N2O17S
218607-59-1

C73H78N2O17S

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at -40℃; for 5h;99%
Mesitol
527-60-6

Mesitol

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

2,4,6-trimethylphenyl imidazolesulfonate

Conditions
ConditionsYield
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

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

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

C23H28N2O6S

C23H28N2O6S

Conditions
ConditionsYield
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%
2-Phenylphenol
90-43-7

2-Phenylphenol

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

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

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran99%
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;98%
N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

phenol
108-95-2

phenol

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

phenyl 1H-imidazole-1-sulfonate

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran at 20℃;98%
With sodium carbonate In N,N-dimethyl-formamide at 130℃;98%
With caesium carbonate In tetrahydrofuran98%
O-methylresorcine
150-19-6

O-methylresorcine

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

3-methoxyphenyl 1H-imidazole-1-sulfonate

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran98%
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;94%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

2-methoxyphenyl 1H-imidazole-1-sulfonate

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;98%
With caesium carbonate In tetrahydrofuran90%
4-Benzyloxyphenol
103-16-2

4-Benzyloxyphenol

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

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

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;98%
C27H36O4

C27H36O4

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

C30H38N2O6S

C30H38N2O6S

Conditions
ConditionsYield
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%
N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

3,5-Dimethylphenol
108-68-9

3,5-Dimethylphenol

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

3,5-dimethylphenyl 1H-imidazole-1-sulfonate

Conditions
ConditionsYield
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%
2-hydroxypyridin
142-08-5

2-hydroxypyridin

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

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

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 130℃; for 48h;97%
4-bromo-phenol
106-41-2

4-bromo-phenol

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

4-bromophenyl 1H-imidazole-1-sulfonate

4-bromophenyl 1H-imidazole-1-sulfonate

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran97%
With caesium carbonate In tetrahydrofuran at 20℃;96%
methyl 3,4-di-O-methyl-2-O-(2,3,4-tri-O-methyl-β-D-xylopyranosyl)-α-D-galactopyranoside
94715-33-0

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

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

methyl 6-O-imidazolylsulfonyl-3,4-di-O-methyl-2-O-(2,3,4-tri-O-methyl-β-D-xylopyranosyl)-α-D-galactopyranoside
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
ConditionsYield
With sodium hydride In tetrahydrofuran 1.) 0 deg C, 2 h; 2.) -40 deg C, 20 min.-> r.t., 2 h;95%
p-cresol
106-44-5

p-cresol

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

4-methylphenyl imidazolesulfonate
1139705-26-2

4-methylphenyl imidazolesulfonate

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran95%
With caesium carbonate In tetrahydrofuran at 20℃;91%
With caesium carbonate In tetrahydrofuran at 20℃;86%
With caesium carbonate In tetrahydrofuran at 20℃;86%
N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

β-naphthol
135-19-3

β-naphthol

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

naphthalen-2-yl 1H-imidazole-1-sulfonate

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran at 20℃; for 12h; Reagent/catalyst; Temperature; Solvent;95%
With caesium carbonate In tetrahydrofuran at 20℃;91%
ortho-cresol
95-48-7

ortho-cresol

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

o-tolyl 1H-imidazole-1-sulfonate

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 130℃;95%
With caesium carbonate In tetrahydrofuran at 20℃;94%
4-Fluorophenol
371-41-5

4-Fluorophenol

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

4-fluorophenyl 1H-imidazole-1-sulfonate

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran95%
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;89%
α-naphthol
90-15-3

α-naphthol

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

naphthalene-1-yl 1H-imidazole-1-sulfonate

Conditions
ConditionsYield
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%
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
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

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

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

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;93%
4-methoxyphenyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-talopyranoside
1139852-92-8

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

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

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

Conditions
ConditionsYield
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%
[1,1'-biphenyl]-3-ol
580-51-8

[1,1'-biphenyl]-3-ol

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

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

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;92%
1,2:5,6-Di-O-isopropyliden-3-O-trimethylsilyl-D-glucofuranose
3067-62-7

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

N,N`-sulfuryldiimidazole
7189-69-7

N,N`-sulfuryldiimidazole

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

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

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

7189-69-7Relevant articles and documents

SULFONYLDIAZOLES AND N-(FLUOROSULFONYL)AZOLES, AND METHODS OF MAKING THE SAME

-

Paragraph 0148, (2020/10/21)

The present disclosure provides methods for producing N-(fluorosulfonyl)azoles, sulfonyldiazoles, or related derivatives thereof; and the related products including N- (fluorosulfonyl)azoles, sulfonyldiazoles, and related derivatives thereof. For example, an N- (fluorosulfonyl)azole is obtained by reaction of sulfuryl fluoride with an azoles, an azole anion compound, a silylazole, or a combination thereof. Symmetric and asymmetric sulfonyldiazoles are obtained by further reaction of such an N-(fluorosulfonyl)azole with azoles, azole anion compounds, or silylazoles. A sulfonyldiazole can be also produced by reacting sulfuryl fluoride with an azole, a silylazole, or a combination thereof in one pot.

Introduction of Aryl Fluorosulfates into the Realm of Catellani Reaction Substrates

Bieliū Nas, Vidmantas,De Borggraeve, Wim M.

, p. 15706 - 15717 (2019/11/21)

Application of activated phenol fluorosulfates as substrates in a Pd/NBE mediated sequential alkylation-arylation, commonly known as a Catellani reaction, is presented. These substrates provide a level of complementarity to the commonly used aryl halides and, in combination with a plethora of existing Catellani reaction variations, enable even wider application of this powerful synthetic tool.

Ex situ generation of sulfuryl fluoride for the synthesis of aryl fluorosulfates

Veryser, Cedrick,Demaerel, Joachim,Bieliunas, Vidmantas,Gilles, Philippe,De Borggraeve, Wim M.

supporting information, p. 5244 - 5247 (2017/11/06)

A convenient transformation of phenols into the corresponding aryl fluorosulfates is presented: the first protocol to completely circumvent direct handling of gaseous sulfuryl fluoride (SO2F2). The proposed method employs 1,1'-sulfonyldiimidazole as a precursor to generate near-stoichiometric amounts of SO2F2 gas using a two-chamber reactor. With NMR studies, it was shown that this ex situ gas evolution is extremely rapid, and a variety of phenols and hydroxylated heteroarenes were fluorosulfated in good to excellent yields.

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