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619-58-9 Usage

Chemical Properties

4-Iodobenzoic acid is white to off-white powder

Uses

Different sources of media describe the Uses of 619-58-9 differently. You can refer to the following data:
1. suzuki reaction
2. 4-Iodobenzoic acid was used in the synthesis of [hydroxy(4-carboxyphenyl)iodonium]ion in situ that helps in the cleavage of a variety of alkenes.
3. 4-Iodobenzoic acid was used in the synthesis of [hydroxy(4-carboxyphenyl)iodonium]ion in situ that helps in the cleavage of a variety of alkenes. It is is used as anti-infective, contraceptive agent and x-ray contrast medium for diagnostic radiology.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 2365, 1980 DOI: 10.1021/jo01300a020

Purification Methods

Crystallise the acid repeatedly from water and EtOH. Sublime it under vacuum at 100o. [Beilstein 9 IV 1035.]

Check Digit Verification of cas no

The CAS Registry Mumber 619-58-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 9 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 619-58:
(5*6)+(4*1)+(3*9)+(2*5)+(1*8)=79
79 % 10 = 9
So 619-58-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H5IO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)/p-1

619-58-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A10730)  4-Iodobenzoic acid, 97%   

  • 619-58-9

  • 10g

  • 332.0CNY

  • Detail
  • Alfa Aesar

  • (A10730)  4-Iodobenzoic acid, 97%   

  • 619-58-9

  • 50g

  • 1167.0CNY

  • Detail
  • Alfa Aesar

  • (A10730)  4-Iodobenzoic acid, 97%   

  • 619-58-9

  • 250g

  • 3069.0CNY

  • Detail

619-58-9SDS

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 4-Iodobenzoic acid

1.2 Other means of identification

Product number -
Other names para-iodobenzoic acid

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:619-58-9 SDS

619-58-9Synthetic route

p-carboxybenzene diazonium nitrate

p-carboxybenzene diazonium nitrate

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With potassium iodide for 24h;100%
4-tolyl iodide
624-31-7

4-tolyl iodide

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; water at 20℃; for 14h; Inert atmosphere;99%
With carbon tetrabromide; oxygen In acetonitrile at 20℃; for 60h; Irradiation;82%
With carbon tetrabromide; oxygen In acetonitrile at 20℃; for 60h; UV-irradiation;81.5%
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
Stage #1: 4-amino-benzoic acid With cation-exchange resin KU-2-8; sodium nitrite In water at 20℃; for 2.33333h;
Stage #2: With potassium iodide In water at 20℃; for 10h; Further stages.;
98%
Stage #1: 4-amino-benzoic acid With sodium nitrite In neat (no solvent) at 0℃; for 0.133333h; Green chemistry;
Stage #2: With sodium iodide In neat (no solvent) at 0 - 20℃; for 0.1h; Green chemistry;
95%
Stage #1: 4-amino-benzoic acid With nicotinic acid sulfate; sodium nitrite In water at 20℃; for 0.333333h; Grinding;
Stage #2: With sodium iodide In water at 20℃;
85%
4-iodo-benzyl alcohol
18282-51-4

4-iodo-benzyl alcohol

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48h; Schlenk technique;97%
With diethylene glycol dimethyl ether at 70℃; for 0.5h; Sonication;93%
With oxygen at 120℃; for 10h; Green chemistry;92%
With C22H36IrNP(1+)*CF3O3S(1-); potassium hydroxide In toluene at 120℃; for 18h;42%
Multi-step reaction with 2 steps
1: tert.-butylnitrite; oxygen / acetonitrile / 24 h / 25 °C / 760.05 Torr / Green chemistry
2: oxygen / acetonitrile / 12 h / 80 °C / 760.05 Torr / Green chemistry
View Scheme
4-(trimethylsilyl)benzoic acid
15290-29-6

4-(trimethylsilyl)benzoic acid

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With Iodine monochloride In tetrachloromethane 1.) RT, 30 min, 2.) reflux, 1 h;95%
4-iodo-N,N-bis(pyridin-2-ylmethyl)benzamide
1314659-41-0

4-iodo-N,N-bis(pyridin-2-ylmethyl)benzamide

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
Stage #1: 4-iodo-N,N-bis(pyridin-2-ylmethyl)benzamide With methanol; copper(II) bis(trifluoromethanesulfonate) at 20℃; for 16h;
Stage #2: With barium(II) hydroxide In methanol; water at 20℃; Inert atmosphere;
Stage #3: With hydrogenchloride In methanol; water Inert atmosphere;
95%
methyl 4-iodobenzoate
619-44-3

methyl 4-iodobenzoate

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With iodine; aluminium In acetonitrile at 80℃; for 18h;93%
With water; sodium hydroxide In methanol
carbon monoxide
201230-82-2

carbon monoxide

para-diiodobenzene
624-38-4

para-diiodobenzene

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With water; palladium diacetate; potassium carbonate at 20℃; under 760.051 Torr; for 7h;92%
4-carboxybenzenediazonium 4-methylbenzenesulfonate
52936-52-4

4-carboxybenzenediazonium 4-methylbenzenesulfonate

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With potassium iodide In water at 20℃; for 4h;91%
With potassium iodide In water for 0.333333h; paste form;
4-carboxyphenylboronic acid
14047-29-1

4-carboxyphenylboronic acid

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With iodine; potassium carbonate In acetonitrile at 80℃; for 8h; Inert atmosphere; Schlenk technique; Sealed tube;89%
4-iodobenzoic acid ethyl ester
51934-41-9

4-iodobenzoic acid ethyl ester

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With water; sodium hydroxide In 1,4-dioxane at 100℃; for 1.5h;89%
carbon monoxide
201230-82-2

carbon monoxide

4-iodobenzenediazonium tetrafluoroborate
1514-50-7

4-iodobenzenediazonium tetrafluoroborate

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With sodium acetate; palladium diacetate In acetonitrile under 6619.6 Torr; for 0.25h; Ambient temperature;86%
carbon dioxide
124-38-9

carbon dioxide

2-(4-iodophenyl)-5,5-dimethyl-1,3,2-dioxaborinane
5572-94-1

2-(4-iodophenyl)-5,5-dimethyl-1,3,2-dioxaborinane

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With (1,3-bis(2,6-diisopropyl-4-(morpholinomethyl)phenyl)imidazolidin-2-ylidene)copper(I) bromide; potassium tert-butylate In tetrahydrofuran under 760.051 Torr; for 24h; Inert atmosphere; Schlenk technique; Reflux; Green chemistry;86%
With potassium tert-butylate; copper(l) chloride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 70℃; under 760.051 Torr; for 24h;85%
Stage #1: carbon dioxide; 5,5-dimethyl-2-(4-iodophenyl)-1,3,2-dioxaborinane With potassium tert-butylate; silver(I) acetate; triphenylphosphine In tetrahydrofuran at 70℃; under 15201 Torr; for 16h; Inert atmosphere; Autoclave;
Stage #2: With hydrogenchloride In tetrahydrofuran; water Inert atmosphere;
79%
Stage #1: carbon dioxide; 5,5-dimethyl-2-(4-iodophenyl)-1,3,2-dioxaborinane With copper(l) iodide; 5,5-bis(4,5-dihydrooxazol-2-yl)nonane; cesium fluoride In N,N-dimethyl-formamide at 90℃; under 760.051 Torr; for 10h;
Stage #2: With hydrogenchloride; water In N,N-dimethyl-formamide
76%
4-iodo-benzyl alcohol
18282-51-4

4-iodo-benzyl alcohol

A

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

B

p-(iodophenyl)carboxaldehyde
15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions
ConditionsYield
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48h; Schlenk technique;A 86%
B 14 %Spectr.
4-carboxybenzenediazonium trifluoromethanesulfonate

4-carboxybenzenediazonium trifluoromethanesulfonate

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With potassium iodide In water at 20℃;77%
C6H4I2Zn
151073-93-7

C6H4I2Zn

carbon dioxide
124-38-9

carbon dioxide

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
Stage #1: C6H4I2Zn; carbon dioxide With lithium chloride In N,N-dimethyl-formamide at 50℃; under 760.051 Torr; for 48h;
Stage #2: With hydrogenchloride; water In N,N-dimethyl-formamide
70%
carbon dioxide
124-38-9

carbon dioxide

4-iodophenylboronic acid
5122-99-6

4-iodophenylboronic acid

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium methanolate In N,N-dimethyl acetamide at 70℃; for 24h; Schlenk technique; Sealed tube;69%
4-iodo-benzyl alcohol
18282-51-4

4-iodo-benzyl alcohol

A

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
Stage #1: 4-iodo-benzyl alcohol With [RuCl2(p-cymene)(iPr2-imy)]; tricyclohexylphosphine tetrafluoroborate; potassium hydroxide In toluene for 6h; Schlenk technique; Inert atmosphere; Reflux;
Stage #2: With hydrogenchloride In water pH=1;
A 67%
B 12%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With potassium iodide at 19.9℃; under 45003600 Torr; Product distribution; under shear deformation (360 deg); other pressures, regents, angles of rotation;3.73%
para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With potassium iodide at 19.9℃; under 45003600 Torr; Product distribution; under shear deformation (360 deg); other reagents;2.3%
4-iodobenzonitrile
3058-39-7

4-iodobenzonitrile

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With sulfuric acid at 180℃;
With potassium hydroxide
4,4'-diiodobiphenyl
3001-15-8

4,4'-diiodobiphenyl

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid
4-iodosyl-benzoic acid
4230-36-8

4-iodosyl-benzoic acid

A

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

B

4-iodylbenzoic acid
64297-66-1

4-iodylbenzoic acid

Conditions
ConditionsYield
With water at 160℃;
1,2-bis-(4-iodo-phenyl)-1,2-diphenyl-ethane-1,2-diol
861602-18-8

1,2-bis-(4-iodo-phenyl)-1,2-diphenyl-ethane-1,2-diol

acetyl chloride
75-36-5

acetyl chloride

A

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
at 100℃; nachfolgend Verseifen mit alkoh. Kalilauge;
p-(iodophenyl)carboxaldehyde
15164-44-0

p-(iodophenyl)carboxaldehyde

A

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

B

4-iodo-benzyl alcohol
18282-51-4

4-iodo-benzyl alcohol

Conditions
ConditionsYield
With potassium hydroxide auch unter Zusatz von Aethanol;
With potassium hydroxide
4-iodobenzamide
3956-07-8

4-iodobenzamide

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 90℃; for 3h; Rate constant;
methyl 4-iodobenzoate
619-44-3

methyl 4-iodobenzoate

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With 1-Benzyl-1,4-dihydronicotinamide; RhCl(PPh3)3 In acetonitrile at 69.9℃; for 6h; in the dark;A 95 % Chromat.
B n/a
C n/a
p-(iodophenyl)carboxaldehyde
15164-44-0

p-(iodophenyl)carboxaldehyde

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

Conditions
ConditionsYield
With perchloric acid; pyridinium chlorochromate In acetic acid at 29.9 - 59.9℃; Thermodynamic data; E(a), ΔH(excit.), ΔS(excit.), ΔG(excit.);
With acetic acid; quinolinium chlorochromate(VI) In water at 29.85℃; Kinetics; Further Variations:; Temperatures; Oxidation;
With oxygen In acetonitrile at 80℃; under 760.051 Torr; for 12h; Green chemistry;52 mg
2-Hydroxy-1-(4-iodo-phenyl)-2-phenyl-ethanone

2-Hydroxy-1-(4-iodo-phenyl)-2-phenyl-ethanone

A

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With sodium methylate In methanol at 30℃; Kinetics; Thermodynamic data; enthalpy-entropy relationship, ΔH(excit.), ΔS(excit.);
methanol
67-56-1

methanol

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

methyl 4-iodobenzoate
619-44-3

methyl 4-iodobenzoate

Conditions
ConditionsYield
With acetyl chloride at 60℃; for 12h;100%
With sulfuric acid for 30h; Reflux;99%
With sulfuric acid Reflux;99%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

4-iodo-benzyl alcohol
18282-51-4

4-iodo-benzyl alcohol

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran at -20 - 50℃; for 14h; Reflux;100%
With borane-THF In tetrahydrofuran at 20℃; for 16h;99%
With borane-THF In tetrahydrofuran at 20℃;99%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

4-iodobenzoic acid chloride
1711-02-0

4-iodobenzoic acid chloride

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide100%
100%
With thionyl chloride In dichloromethane for 18h; Heating;100%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

2,5-dioxopyrrolidin-1-yl 4-iodobenzoate
39028-25-6

2,5-dioxopyrrolidin-1-yl 4-iodobenzoate

Conditions
ConditionsYield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane for 2h; Heating;100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; Inert atmosphere;100%
With dicyclohexyl-carbodiimide In 1,4-dioxane at 24.85℃; for 24h;99%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

phenylboronic acid
98-80-6

phenylboronic acid

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With potassium phosphate monohydrate; 4,4'-di-tBu-2,2'-dipyridylpalladium(II) dichloride In methanol; water at 80℃; for 2h; Suzuki-Miyaura Coupling;100%
With potassium carbonate; palladium dichloride In water at 20 - 90℃; Suzuki coupling; Inert atmosphere;99%
With potassium carbonate In water at 90℃; for 0.25h; Suzuki reaction; Inert atmosphere;99%
fur-2-ylboronic acid
13331-23-2

fur-2-ylboronic acid

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

4-(furan-2-yl)benzoic acid
35461-98-4

4-(furan-2-yl)benzoic acid

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 90℃; Inert atmosphere;100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 20 - 90℃; Inert atmosphere;92%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 90℃; Inert atmosphere;92%
4-Methoxybenzenethiol
696-63-9

4-Methoxybenzenethiol

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

4-[(4-methoxyphenyl)thio]benzoic acid
252973-46-9

4-[(4-methoxyphenyl)thio]benzoic acid

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With dmap; SPPSLHMP SynPhase Lanterns(R); dacarbazine In dichloromethane; N,N-dimethyl-formamide at 50℃; for 15h;
Stage #2: 4-Methoxybenzenethiol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: With trifluoroacetic acid In dichloromethane
100%
4-Methoxybenzenethiol
696-63-9

4-Methoxybenzenethiol

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

4-((4-methoxyphenyl)thio)benzamide

4-((4-methoxyphenyl)thio)benzamide

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With SPPSLRAM SynPhase Lanterns(R); N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 45℃; for 15h;
Stage #2: 4-Methoxybenzenethiol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: With trifluoroacetic acid In dichloromethane
100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

2-Methoxybenzenethiol
7217-59-6

2-Methoxybenzenethiol

4-[(2-methoxyphenyl)thio]benzamide

4-[(2-methoxyphenyl)thio]benzamide

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With SPPSLRAM SynPhase Lanterns(R); N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 45℃; for 15h;
Stage #2: 2-Methoxybenzenethiol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: With trifluoroacetic acid In dichloromethane
100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

2-Methoxybenzenethiol
7217-59-6

2-Methoxybenzenethiol

4-[(2-methoxyphenyl)thio]benzoic acid

4-[(2-methoxyphenyl)thio]benzoic acid

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With dmap; SPPSLHMP SynPhase Lanterns(R); dacarbazine In dichloromethane; N,N-dimethyl-formamide at 50℃; for 15h;
Stage #2: 2-Methoxybenzenethiol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: With trifluoroacetic acid In dichloromethane
100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

4-trifluoromethylbenzenethiol
825-83-2

4-trifluoromethylbenzenethiol

4-{[4-(trifluoromethyl)phenyl]thio}benzoic acid

4-{[4-(trifluoromethyl)phenyl]thio}benzoic acid

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With dmap; SPPSLHMP SynPhase Lanterns(R); dacarbazine In dichloromethane; N,N-dimethyl-formamide at 50℃; for 15h;
Stage #2: 4-trifluoromethylbenzenethiol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: With trifluoroacetic acid In dichloromethane
100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

4-trifluoromethylbenzenethiol
825-83-2

4-trifluoromethylbenzenethiol

4-{[4-(trifluoromethyl)phenyl]thio}benzamide

4-{[4-(trifluoromethyl)phenyl]thio}benzamide

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With SPPSLRAM SynPhase Lanterns(R); N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 45℃; for 15h;
Stage #2: 4-trifluoromethylbenzenethiol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: With trifluoroacetic acid In dichloromethane
100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

para-thiocresol
106-45-6

para-thiocresol

4-[(4-methylphenyl)thio]benzamide

4-[(4-methylphenyl)thio]benzamide

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With SPPSLRAM SynPhase Lanterns(R); N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 45℃; for 15h;
Stage #2: para-thiocresol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: With trifluoroacetic acid In dichloromethane
100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

para-thiocresol
106-45-6

para-thiocresol

4-[(4-methylphenyl)thio]benzoic acid
22494-64-0

4-[(4-methylphenyl)thio]benzoic acid

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With dmap; SPPSLHMP SynPhase Lanterns(R); dacarbazine In dichloromethane; N,N-dimethyl-formamide at 50℃; for 15h;
Stage #2: para-thiocresol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: With trifluoroacetic acid In dichloromethane
100%
(5-mercapto-4-phenyl-4H-[1,2,4]triazol-3-ylmethyl)-carbamic acid tert-butyl ester

(5-mercapto-4-phenyl-4H-[1,2,4]triazol-3-ylmethyl)-carbamic acid tert-butyl ester

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

trifluoroacetic acid
76-05-1

trifluoroacetic acid

4-(5-aminomethyl-4-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl)-benzoic acid; compound with trifluoro-acetic acid

4-(5-aminomethyl-4-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl)-benzoic acid; compound with trifluoro-acetic acid

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With dmap; SPPSLHMP SynPhase Lanterns(R); dacarbazine In dichloromethane; N,N-dimethyl-formamide at 50℃; for 15h;
Stage #2: (5-mercapto-4-phenyl-4H-[1,2,4]triazol-3-ylmethyl)-carbamic acid tert-butyl ester With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: trifluoroacetic acid In dichloromethane
100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

2-thiocresol
137-06-4

2-thiocresol

4-[(2-methylphenyl)thio]benzamide

4-[(2-methylphenyl)thio]benzamide

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With SPPSLRAM SynPhase Lanterns(R); N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 45℃; for 15h;
Stage #2: 2-thiocresol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: With trifluoroacetic acid In dichloromethane
100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

2-thiocresol
137-06-4

2-thiocresol

4-[(2-methylphenyl)thio]benzoic acid

4-[(2-methylphenyl)thio]benzoic acid

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With dmap; SPPSLHMP SynPhase Lanterns(R); dacarbazine In dichloromethane; N,N-dimethyl-formamide at 50℃; for 15h;
Stage #2: 2-thiocresol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: With trifluoroacetic acid In dichloromethane
100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole
890005-22-8, 35179-55-6

3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole

4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]benzoic acid

4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]benzoic acid

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid; 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole With potassium carbonate; copper(l) iodide; dimethylaminoacetic acid In dimethyl sulfoxide at 130℃; for 3.25h;
Stage #2: With hydrogenchloride In water pH=~ 2; Product distribution / selectivity;
100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

p-(iodophenyl)carboxaldehyde
15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With borane-THF at 20℃; Inert atmosphere; Cooling with ice;
Stage #2: With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 3.5h;
100%
Stage #1: 4-iodobenzoic acid With borane-THF
Stage #2: With pyridinium chlorochromate In chloroform
92%
Multi-step reaction with 2 steps
1: 99 percent / BH3*THF / tetrahydrofuran / 16 h / 20 °C
2: 99 percent / MnO2 / CHCl3 / 72 h / Heating
View Scheme
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

4-iodo-N,N-dimethylbenzamide
24167-53-1

4-iodo-N,N-dimethylbenzamide

Conditions
ConditionsYield
Stage #1: N,N-dimethylammonium chloride With triethylamine In dichloromethane for 0.5h;
Stage #2: 4-iodobenzoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 8h;
100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

1-[(1R,3R,4R,7S)-1-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-7-hydroxy-2-oxa-5-azabicyclo[2.2.1]hepta-3-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

1-[(1R,3R,4R,7S)-1-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-7-hydroxy-2-oxa-5-azabicyclo[2.2.1]hepta-3-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

(1R,3R,4R,7S)-1-(4,4'-Dimethoxytrityloxymethyl)-7-hydroxy-5-(4-iodobenzoyl)-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane
1260237-90-8

(1R,3R,4R,7S)-1-(4,4'-Dimethoxytrityloxymethyl)-7-hydroxy-5-(4-iodobenzoyl)-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: 1-[(1R,3R,4R,7S)-1-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-7-hydroxy-2-oxa-5-azabicyclo[2.2.1]hepta-3-yl]-5-methylpyrimidine-2,4(1H,3H)-dione In N,N-dimethyl-formamide at 20℃; for 0.5h;
100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

sodium 4-iodo-benzoate
1005-30-7

sodium 4-iodo-benzoate

Conditions
ConditionsYield
With sodium hydroxide In water at 70℃;100%
With sodium hydroxide In water at 80℃; for 0.5h;
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

acrylic acid
79-10-7

acrylic acid

4-(2-carboxyvinyl)benzoic acid
19675-63-9, 56148-65-3

4-(2-carboxyvinyl)benzoic acid

Conditions
ConditionsYield
With D-glucose; palladium diacetate; triethylamine In water; acetonitrile at 100℃; for 16h; Sealed tube;100%
With sodium carbonate In water at 100℃; for 24h; Mizoroki-Heck reaction;94.9%
With tributyl-amine; potassium carbonate In N,N-dimethyl-formamide Heck Reaction; Green chemistry;73%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

potassium tert-butylate
865-47-4

potassium tert-butylate

tert-butyl 4-iodobenzoate
120363-13-5

tert-butyl 4-iodobenzoate

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With thionyl chloride; N,N-dimethyl-formamide at 75℃; for 1h; Inert atmosphere;
Stage #2: potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h;
99.9%
Stage #1: 4-iodobenzoic acid With thionyl chloride In N,N-dimethyl-formamide at 70℃;
Stage #2: potassium tert-butylate In tetrahydrofuran at 20℃;
97%
Stage #1: 4-iodobenzoic acid With thionyl chloride In N,N-dimethyl-formamide at 75℃; for 0.75h; Schlenk technique; Inert atmosphere;
Stage #2: potassium tert-butylate In dichloromethane at 0 - 20℃; Schlenk technique; Inert atmosphere;
92%
Stage #1: 4-iodobenzoic acid With thionyl chloride for 1h; Reflux;
Stage #2: potassium tert-butylate In tetrahydrofuran at 0℃; for 2h;
91%
2-amino-3-hydroxypyridine
16867-03-1

2-amino-3-hydroxypyridine

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

C12H7IN2O

C12H7IN2O

Conditions
ConditionsYield
With polyphosphoric acid trimethylsilyl ester at 180℃; for 4h;99.78%
With trichlorophosphate at 90℃; for 12h;73.5%
With trichlorophosphate at 90℃; for 12h;73.5%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

oxalyl dichloride
79-37-8

oxalyl dichloride

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

1-[(4-iodophenyl)carbonyl]-4-methylpiperazine
102294-90-6

1-[(4-iodophenyl)carbonyl]-4-methylpiperazine

Conditions
ConditionsYield
In N,N-dimethyl-formamide99.2%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

1-[(4-iodophenyl)carbonyl]-4-methylpiperazine
102294-90-6

1-[(4-iodophenyl)carbonyl]-4-methylpiperazine

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.5h;
Stage #2: 1-methyl-piperazine With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h;
99.2%
ethanol
64-17-5

ethanol

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

4-iodobenzoic acid ethyl ester
51934-41-9

4-iodobenzoic acid ethyl ester

Conditions
ConditionsYield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 5h;99%
With sulfuric acid for 24h; Inert atmosphere; Reflux;98%
With hydrogenchloride In water for 2h; Reflux;96.1%

619-58-9Relevant articles and documents

Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process

Fu, Qiang,Liang, Fu-Shun,Lou, Da-Wei,Pan, Gao-Feng,Wang, Rui,Wu, Min,Xie, Kai-Jun

supporting information, p. 2020 - 2024 (2022/03/31)

A visible-light-promoted atomic substitution reaction for transforming thiocacids into carboxylic acids with dimethyl sulfoxide (DMSO) as the oxygen source has been developed, affording various alkyl and aryl carboxylic acids in over 90% yields. The atomic substitution process proceeds smoothly through the photochemical reactivity of the formed hydrogen-bonding adduct between thioacids and DMSO. A DMSO-involved proton-coupled electron transfer (PCET) and the simultaneous generation of thiyl and hydroxyl radicals are proposed to be key steps for realizing the transformation.

Photo-tunable oxidation of toluene and its derivatives catalyzed by TBATB

Mardani, Atefeh,Kazemi, Foad,Kaboudin, Babak

, (2021/05/04)

In this report, tetrabutylammonium tribromide (TBATB) was introduced as an efficient visible light active catalyst to carry out the aerobic oxidation of toluene, its derivatives, and some of methyl arenes to benzaldehydes, benzoic acids and ketones in good to high yields. All the oxidation reactions were performed under mild conditions using oxygen as a green oxidant, a catalytic amount of TBATB under blue (460 nm), royal blue (430 nm), and violet LED (400 nm) irradiation. It was found that the reactions selectivity was significantly affected by changing the solvent (from CH3CN to EtOAc) and LED wavelength (from blue to violet). In the following, our mechanistic studies revealed that the visible light oxidation of toluenes and methyl arenes over TBATB could be following a benzyl peroxy radical intermediate.

1,2-Dibutoxyethane-Promoted Oxidative Cleavage of Olefins into Carboxylic Acids Using O2 under Clean Conditions

Ou, Jinhua,Tan, Hong,He, Saiyu,Wang, Wei,Hu, Bonian,Yu, Gang,Liu, Kaijian

, p. 14974 - 14982 (2021/10/25)

Herein, we report the first example of an effective and green approach for the oxidative cleavage of olefins to carboxylic acids using a 1,2-dibutoxyethane/O2 system under clean conditions. This novel oxidation system also has excellent functional-group tolerance and is applicable for large-scale synthesis. The target products were prepared in good to excellent yields by a one-pot sequential transformation without an external initiator, catalyst, and additive.

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