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13205-48-6

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13205-48-6 Usage

Chemical Properties

light yellow to beige crystalline powder

General Description

Administration of 4-(methylthio)benzoic acid reduces cisplatin nephrotoxicity in rats. It prevents in vitro DNA binding and mutation induction in Escherichia coli K12.

Check Digit Verification of cas no

The CAS Registry Mumber 13205-48-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,2,0 and 5 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 13205-48:
(7*1)+(6*3)+(5*2)+(4*0)+(3*5)+(2*4)+(1*8)=66
66 % 10 = 6
So 13205-48-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H8O2S/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10)/p-1

13205-48-6 Well-known Company Product Price

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  • Alfa Aesar

  • (B25706)  4-(Methylthio)benzoic acid, 97%   

  • 13205-48-6

  • 1g

  • 529.0CNY

  • Detail
  • Alfa Aesar

  • (B25706)  4-(Methylthio)benzoic acid, 97%   

  • 13205-48-6

  • 5g

  • 1760.0CNY

  • Detail
  • Alfa Aesar

  • (B25706)  4-(Methylthio)benzoic acid, 97%   

  • 13205-48-6

  • 25g

  • 5541.0CNY

  • Detail

13205-48-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(METHYLTHIO)BENZOIC ACID

1.2 Other means of identification

Product number -
Other names 4-methylsulfanylbenzoic 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:13205-48-6 SDS

13205-48-6Synthetic route

4-(Methylthio)benzaldehyde
3446-89-7

4-(Methylthio)benzaldehyde

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; sodium hydroxide; (CTA)2SO4 at 20℃; for 20h;98%
With sodium hydroxide In water at 20 - 75℃; for 20h;85%
With perchloric acid; mercury(II) diacetate; N-bromoacetamide In acetic acid at 24.9℃; Kinetics; Mechanism; Thermodynamic data; other temperatures, ΔG(excit.), ΔH(excit.), ΔS(excit.);
4-(methylthio)benzyl alcohol
3446-90-0

4-(methylthio)benzyl alcohol

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
With diethylene glycol dimethyl ether at 70℃; for 0.5h; Sonication;95%
With [Rh(1,3,4,5-tetramethylimidazole-2-ylidene)(trop2NH)][trifluoromethanesulfonate]; potassium tert-butylate; dinitrogen monoxide In tetrahydrofuran; toluene at 50℃; under 750.075 Torr; Schlenk technique;90%
With oxygen at 120℃; for 11h; Green chemistry;87%
4-iodothioanisole
35371-03-0

4-iodothioanisole

diphenylmethylsilanecarboxylic acid
18414-58-9

diphenylmethylsilanecarboxylic acid

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
With potassium trimethylsilonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In toluene at 40℃; for 0.333333h;95%
1-(Bis-tert-butylperoxy-methyl)-4-methylsulfanyl-benzene
106914-57-2

1-(Bis-tert-butylperoxy-methyl)-4-methylsulfanyl-benzene

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
With copper(II) sulfate; ascorbic acid In tetrahydrofuran; water for 8h; Ambient temperature;88%
methyl 4-(methylsulfanyl)dithiobenzoate
5969-48-2

methyl 4-(methylsulfanyl)dithiobenzoate

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide In methanol; water at 20℃; for 0.0833333h;86%
carbon dioxide
124-38-9

carbon dioxide

(4-bromophenyl)thioanisole
104-95-0

(4-bromophenyl)thioanisole

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
Stage #1: (4-bromophenyl)thioanisole With n-butyllithium In diethyl ether; hexane at 0℃; for 2h;
Stage #2: carbon dioxide In diethyl ether; hexane at -78 - 20℃; for 24h; Further stages.;
85%
With [2,2]bipyridinyl; lithium chloride; cobalt(II) iodide; zinc In N,N-dimethyl-formamide; acetonitrile at 40℃; under 760.051 Torr; for 14h; Sealed tube;69%
With diethylzinc; palladium diacetate; tert-butyl XPhos In hexanes; N,N-dimethyl acetamide at 40℃; under 7600.51 Torr; Automated synthesizer;65%
4-mercaptobenzoic acid
1074-36-8

4-mercaptobenzoic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

A

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

B

methyl 4-(methylthio)benzoate
3795-79-7

methyl 4-(methylthio)benzoate

Conditions
ConditionsYield
With NaY faujasite at 150℃; for 26h;A 85%
B n/a
carbon dioxide
124-38-9

carbon dioxide

(4-thiomethoxyphenyl)boronic acid
98546-51-1

(4-thiomethoxyphenyl)boronic acid

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic 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;85%
4-iodothioanisole
35371-03-0

4-iodothioanisole

H2O*CHLiO2

H2O*CHLiO2

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
With formic acid; 1,3-bis-(diphenylphosphino)propane; nickel(II) acetate tetrahydrate; acetic anhydride In tetrahydrofuran at 100℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;81%
dimethyl{4-(methylthio)phenyl}sulfonium triflate
870081-83-7

dimethyl{4-(methylthio)phenyl}sulfonium triflate

carbon dioxide
124-38-9

carbon dioxide

A

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

B

(dimethyl)(phenyl)sulfonium trifluoromethanesulfonate
85980-21-8

(dimethyl)(phenyl)sulfonium trifluoromethanesulfonate

Conditions
ConditionsYield
With 2.9-dimethyl-1,10-phenanthroline; neocuproine; zinc In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 16h;A 73%
B 5%
4-(methylthio)benzyl alcohol
3446-90-0

4-(methylthio)benzyl alcohol

A

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

B

4-(methylsulfinyl)benzoic acid
33963-58-5

4-(methylsulfinyl)benzoic acid

C

4-methylsulfonylbenzoic acid
4052-30-6

4-methylsulfonylbenzoic acid

Conditions
ConditionsYield
With chromium(VI) oxide; sulfuric acid In water; acetone for 0.05h; Ambient temperature;A 72%
B 14%
C 14%
carbon dioxide
124-38-9

carbon dioxide

4,4,5,5-tetramethyl-2-(4-methylsulfanylphenyl)-[1,3,2]-dioxaborolane
190788-58-0

4,4,5,5-tetramethyl-2-(4-methylsulfanylphenyl)-[1,3,2]-dioxaborolane

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
With copper(l) iodide; cesium fluoride; sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride at 120℃; for 24h; Sealed tube;71%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

(4-bromophenyl)thioanisole
104-95-0

(4-bromophenyl)thioanisole

A

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

B

methyl 4-(methylthio)benzoate
3795-79-7

methyl 4-(methylthio)benzoate

Conditions
ConditionsYield
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 71h; Irradiation;A 11.5%
B 70.5%
carbon monoxide
201230-82-2

carbon monoxide

(4-bromophenyl)thioanisole
104-95-0

(4-bromophenyl)thioanisole

A

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

B

methyl 4-(methylthio)benzoate
3795-79-7

methyl 4-(methylthio)benzoate

Conditions
ConditionsYield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 71h; Irradiation;A 11.5%
B 70.5%
carbon dioxide
124-38-9

carbon dioxide

4-chlorophenyl methyl sulfide
123-09-1

4-chlorophenyl methyl sulfide

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
Stage #1: 4-chlorophenyl methyl sulfide With bis(cyclopentadienyl)titanium dichloride; butyl magnesium bromide In tetrahydrofuran at 40℃; for 6h; Inert atmosphere; Schlenk technique;
Stage #2: carbon dioxide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique;
61%
2-[4-(methylsulfanyl)phenyl]acetonitrile
38746-92-8

2-[4-(methylsulfanyl)phenyl]acetonitrile

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; copper diacetate In neat (no solvent) at 80℃; for 5h; Green chemistry;60%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

(4-thiomethoxyphenyl)boronic acid
98546-51-1

(4-thiomethoxyphenyl)boronic acid

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
Stage #1: tert-butylisonitrile; (4-thiomethoxyphenyl)boronic acid With copper diacetate; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 24h; Molecular sieve; Sealed tube;
Stage #2: With water In N,N-dimethyl-formamide Molecular sieve; Sealed tube;
57%
methyl bromide
74-83-9

methyl bromide

4-mercaptobenzoic acid
1074-36-8

4-mercaptobenzoic acid

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 12h; Williamson Ether Synthesis; Reflux;55%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

diethyl ether
60-29-7

diethyl ether

(4-bromophenyl)thioanisole
104-95-0

(4-bromophenyl)thioanisole

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
at 20℃; anschliessende Umsetzung mit CO2;
4-methylthiobenzophenone
23405-48-3

4-methylthiobenzophenone

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
With sodium amide; toluene Zersetzen des Reaktionsprodukts mit Wasser und Verseifen mit verd. Natronlauge;
diethyl ether
60-29-7

diethyl ether

(4-bromophenyl)thioanisole
104-95-0

(4-bromophenyl)thioanisole

methyllithium
917-54-4

methyllithium

A

methyl-phenyl-thioether
100-68-5

methyl-phenyl-thioether

B

4-methylphenyl methylsulfide
623-13-2

4-methylphenyl methylsulfide

C

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
anschliessendes Behandeln mit festem CO2;
(4-bromophenyl)thioanisole
104-95-0

(4-bromophenyl)thioanisole

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
With n-butyllithium; diethyl ether Eintragen der Reaktionsloesung in festes Kohlendioxid;
p-cyanophenyl methyl sulfide
21382-98-9

p-cyanophenyl methyl sulfide

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
With potassium hydroxide
4-mercaptobenzoic acid
1074-36-8

4-mercaptobenzoic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
With alkali
With potassium hydroxide In ethanol for 6h; Reflux;
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
(i) aq. HCl, NaNO2, (ii) potassium ethyl xanthate, (iii) /BRN= 635994/, aq. KOH; Multistep reaction;
p-methylthiobenzoyloxyl radical

p-methylthiobenzoyloxyl radical

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
With toluene In acetonitrile at 20℃; Kinetics; Further Variations:; Reaction partners; Reagents; hydrogen-atom abstraction;
bis(p-methylthiobenzoyl) peroxide

bis(p-methylthiobenzoyl) peroxide

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

Conditions
ConditionsYield
In acetonitrile at 20℃; Quantum yield; photolysis; UV-irradiation;
4-(Methylthio)benzaldehyde
3446-89-7

4-(Methylthio)benzaldehyde

KMnO4

KMnO4

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

4-(methylthio)benzoyl chloride
1442-06-4

4-(methylthio)benzoyl chloride

Conditions
ConditionsYield
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0℃;100%
With phosphorus trichloride In acetonitrile at 60℃; for 6h; Inert atmosphere;95%
With thionyl chloride
4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

4-(methylsulfinyl)benzoic acid
33963-58-5

4-(methylsulfinyl)benzoic acid

Conditions
ConditionsYield
With ferric(III) bromide; nitric acid In acetonitrile at 20℃; for 2.5h; chemoselective reaction;100%
With water; bromine; oxygen; sodium nitrite In acetonitrile at 25℃; for 5h;96%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water; oxygen; sodium nitrite In acetonitrile at 100℃; under 7500.75 Torr; for 3h; Autoclave; chemoselective reaction;91%
C19H29N3O4

C19H29N3O4

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

C27H35N3O5S

C27H35N3O5S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide98%
4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

descarboethoxyloratadine
100643-71-8

descarboethoxyloratadine

[4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-(4-methylsulfanyl-phenyl)-methanone
169252-29-3

[4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-(4-methylsulfanyl-phenyl)-methanone

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 4℃; for 0.5h;97%
4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

methyl 4-(methylthio)benzoate
3795-79-7

methyl 4-(methylthio)benzoate

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 16h; Inert atmosphere; Green chemistry;97%
4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

dibenzylamine
103-49-1

dibenzylamine

N,N-dibenzyl-4-(methylthio)benzamide

N,N-dibenzyl-4-(methylthio)benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;97%
4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

methyl iodide
74-88-4

methyl iodide

methyl 4-(methylthio)benzoate
3795-79-7

methyl 4-(methylthio)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 3h; Inert atmosphere;95.1%
C19H29N3O4

C19H29N3O4

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

C27H35N3O5S

C27H35N3O5S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide94%
4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

4-(Methylthio)benzaldehyde
3446-89-7

4-(Methylthio)benzaldehyde

Conditions
ConditionsYield
With 4,4'-dimethoxyphenyl disulfide; iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C20]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate; triphenylphosphine In toluene for 24h; Irradiation;94%
With 2,6-dimethylpyridine; nickel(II) bromide trihydrate; phenylsilane; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc; dimethyl dicarbonate In ethyl acetate at 60℃; for 24h; Schlenk technique; Inert atmosphere;72 %Chromat.
4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

diethylamine
109-89-7

diethylamine

N,N-diethyl-4-(methylthio)benzamide
1378313-78-0

N,N-diethyl-4-(methylthio)benzamide

Conditions
ConditionsYield
Stage #1: 4-(methylthio)benzoic acid With thionyl chloride In dichloromethane at 20℃; for 1h;
Stage #2: diethylamine With triethylamine In dichloromethane at 20℃;
93%
4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

4-methylsulfonylbenzoic acid
4052-30-6

4-methylsulfonylbenzoic acid

Conditions
ConditionsYield
With sodium hydroxide; Oxone<*>; sodium hydrogencarbonate In water; acetone for 1h; Ambient temperature;92.6%
With [Ti(η5-C5H4SiMe2OPh7Si7O11-κ2O2)Cl]; dihydrogen peroxide In methanol; water at 50℃; for 3h; chemoselective reaction;85%
With dihydrogen peroxide; acetic acid
With chromium(VI) oxide; acetic acid
4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

4-(methylthio)benzyl alcohol
3446-90-0

4-(methylthio)benzyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;90.89%
With lithium aluminium tetrahydride; diethyl ether
With diborane In tetrahydrofuran at 0℃; for 1.5h;
methanol
67-56-1

methanol

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

methyl 4-(methylthio)benzoate
3795-79-7

methyl 4-(methylthio)benzoate

Conditions
ConditionsYield
With sulfuric acid In water for 22h; Reflux;90%
With hydrogenchloride
morpholine
110-91-8

morpholine

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

(4-(methylthio)phenyl)(morpholino)methanone
675618-10-7

(4-(methylthio)phenyl)(morpholino)methanone

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;90%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;90%
With 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride In tetrahydrofuran for 2h;
C24H27F3N4O4

C24H27F3N4O4

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

C32H33F3N4O5S

C32H33F3N4O5S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide87%
C24H28F3N5O4

C24H28F3N5O4

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

C32H34F3N5O5S

C32H34F3N5O5S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide87%
4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

water
7732-18-5

water

diethylzinc
557-20-0

diethylzinc

[Zn4(μ4-O)(O2C-p-MeSC6H4)6]

[Zn4(μ4-O)(O2C-p-MeSC6H4)6]

Conditions
ConditionsYield
In tetrahydrofuran; water (N2); std. Schlenk technique; Zn compd. (2 equiv.) was added to suspn. of acid (3 equiv.) in THF at -78°C; after 4 h H2O (0.5 equiv.) wasadded; stirred for 20 h; recrystd. (THF, -20°C); elem. anal.;87%
4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

4-amino-3-mercapto-1,2,4-triazin-5(4H)-one
23702-90-1

4-amino-3-mercapto-1,2,4-triazin-5(4H)-one

C11H8N4OS2
1403747-99-8

C11H8N4OS2

Conditions
ConditionsYield
With trichlorophosphate Reflux;87%
4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

2-methoxyindolizine

2-methoxyindolizine

(2-methoxyindolizin-3-yl)(4-(methylthio)phenyl)methanone

(2-methoxyindolizin-3-yl)(4-(methylthio)phenyl)methanone

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 30℃; for 20h; Inert atmosphere;86.6%
N-(4-piperidin-4-yl-3-trifluoromethyl-benzoyl)-N'-(carbobenzyloxy)-guanidine
1204331-51-0

N-(4-piperidin-4-yl-3-trifluoromethyl-benzoyl)-N'-(carbobenzyloxy)-guanidine

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

N-{4-[1-(4-methylsulfanyl-benzoyl)-piperidin-4-yl]-3-trifluoromethyl-benzoyl}-N'-(carbobenzyloxy)-guanidine
1204331-57-6

N-{4-[1-(4-methylsulfanyl-benzoyl)-piperidin-4-yl]-3-trifluoromethyl-benzoyl}-N'-(carbobenzyloxy)-guanidine

Conditions
ConditionsYield
Stage #1: 4-(methylthio)benzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 1.5h;
Stage #2: N-(4-piperidin-4-yl-3-trifluoromethyl-benzoyl)-N'-(carbobenzyloxy)-guanidine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
85%
C23H31F3N4O4
746670-24-6

C23H31F3N4O4

4-(methylthio)benzoic acid
13205-48-6

4-(methylthio)benzoic acid

C31H37F3N4O5S
746666-66-0

C31H37F3N4O5S

Conditions
ConditionsYield
With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide85%

13205-48-6Relevant articles and documents

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Brown,F.C. et al.

, p. 4707 - 4708 (1961)

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Benzoin type photoinitiator for free radical polymerization

Esen, Duygu Sevinc,Arsu, Nergis,Da Silva, Jose P.,Jockusch, Steffen,Turro, Nicholas J.

, p. 1865 - 1871 (2013)

Benzoin, a popular photoinitiator for free radical polymerization of vinyl monomers, was improved by introduction of two methyl thioether substituents. This new benzoin derivative showed an about 50 times higher light absorption in the near-UV spectral region and performed better than the unsubstituted benzoin in polymerization experiments in bulk solutions or films of acrylate monomers when low initiator concentrations are used. Laser flash photolysis, low temperature luminescence experiments and photoproduct studies by mass spectrometry suggest that a slow α-cleavage mechanism (kα = 2.2 × 105 s-1) from the electronic triplet state with a quantum yield of 0.1 is the primary photoreaction to generate the initiating free radicals.

Baliah et al.

, p. 1013 (1957)

Mechanochemical Grignard Reactions with Gaseous CO2 and Sodium Methyl Carbonate**

Pfennig, Victoria S.,Villella, Romina C.,Nikodemus, Julia,Bolm, Carsten

supporting information, (2022/01/22)

A one-pot, three-step protocol for the preparation of Grignard reagents from organobromides in a ball mill and their subsequent reactions with gaseous carbon dioxide (CO2) or sodium methyl carbonate providing aryl and alkyl carboxylic acids in up to 82 % yield is reported. Noteworthy are the short reaction times and the significantly reduced solvent amounts [2.0 equiv. for liquid assisted grinding (LAG) conditions]. Unexpectedly, aryl bromides with methoxy substituents lead to symmetric ketones as major products.

Direct 3-Acylation of Indolizines by Carboxylic Acids for the Practical Synthesis of Red Light-Releasable Caged Carboxylic Acids

Watanabe, Kenji,Terao, Nodoka,Niwa, Takashi,Hosoya, Takamitsu

, p. 11822 - 11834 (2021/07/31)

To enhance the practicality of photouncaging system using 3-acyl-2-methoxyindolizines, direct acylation of indolizines with carboxylic acids was developed using condensation reagents, generally used for peptide coupling. This method allowed for caging a broad range of carboxylic acids with indolizines. The method enabled a facile synthesis of water-soluble caged bioactive carboxylic acids having an intramolecular photosensitizer. The efficient release of carboxylic acids from the synthesized caged compounds upon red light irradiation was confirmed in neutral buffered solutions.

Mirror Symmetry Breaking and Network Formation in Achiral Polycatenars with Thioether Tail

Alaasar, Mohamed,Darweesh, Ahmed F.,Cai, Xiaoqian,Liu, Feng,Tschierske, Carsten

, p. 14921 - 14930 (2021/10/14)

Mirror symmetry breaking in systems composed of achiral molecules is of importance for the design of functional materials for technological applications as well as for the understanding of the mechanisms of spontaneous emergence of chirality. Herein, we report the design and molecular self-assembly of two series of rod-like achiral polycatenar molecules derived from a π-conjugated 5,5’-diphenyl-2,2’-bithiophene core with a fork-like triple alkoxylated end and a variable single alkylthio chain at the other end. In both series of liquid crystalline materials, differing in the chain length at the trialkoxylated end, helical self-assembly of the π-conjugated rods in networks occurs, leading to wide temperature ranges (>200 K) of bicontinuous cubic network phases, in some cases being stable even around ambient temperatures. The achiral bicontinuous cubic Ia (Formula presented.) d phase (gyroid) is replaced upon alkylthio chain elongation by a spontaneous mirror symmetry broken bicontinuous cubic phase (I23) and a chiral isotropic liquid phase (Iso1[*]). Further chain elongation results in removing the I23 phase and the re-appearance of the Ia (Formula presented.) d phase with different pitch lengths. In the second series an additional tetragonal phase separates the two cubic phase types.

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