4-(Methylthio)benzoic acid supplier

Name
4-(METHYLTHIO)BENZOIC ACID
EINECS 236-171-5
CAS No. 13205-48-6
Article Data70
CAS DataBase
Density 1.28 g/cm³
Solubility
Melting Point 192-196 °C(lit.)
Formula C₈H₈O₂S
Boiling Point 319 °C at 760 mmHg
Molecular Weight 168.216
Flash Point 146.7 °C
Transport Information
Appearance light yellow to beige crystalline powder
Safety 22-26-37/39-24/25
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms Benzoicacid, p-(methylthio)- (6CI,7CI,8CI);4-(Methylsulfanyl)benzoic acid;4-Carboxyphenyl methyl sulfide;NSC 400301;p-(Methylthio)benzoic acid;p-Carboxyphenyl methyl sulfide;p-Carboxythioanisole;
PSA 62.60000
LogP 2.10670

Synthetic route

: 3446-89-7
4-(Methylthio)benzaldehyde

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

Conditions

Conditions	Yield
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.);

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

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

Conditions

Conditions	Yield
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%

: 35371-03-0
4-iodothioanisole

: 18414-58-9
diphenylmethylsilanecarboxylic acid

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

Conditions

Conditions	Yield
With potassium trimethylsilonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In toluene at 40℃; for 0.333333h;	95%

: 106914-57-2
1-(Bis-tert-butylperoxy-methyl)-4-methylsulfanyl-benzene

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

Conditions

Conditions	Yield
With copper(II) sulfate; ascorbic acid In tetrahydrofuran; water for 8h; Ambient temperature;	88%

: 5969-48-2
methyl 4-(methylsulfanyl)dithiobenzoate

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

Conditions

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In methanol; water at 20℃; for 0.0833333h;	86%

: 124-38-9
carbon dioxide

: 104-95-0
(4-bromophenyl)thioanisole

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

Conditions

Conditions	Yield
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%

: 1074-36-8
4-mercaptobenzoic acid

: 616-38-6
carbonic acid dimethyl ester

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

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

Conditions

Conditions	Yield
With NaY faujasite at 150℃; for 26h;	A 85% B n/a

...Expand

: 124-38-9
carbon dioxide

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

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

Conditions

Conditions	Yield
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%

: 35371-03-0
4-iodothioanisole

: H2O*CHLiO2

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

Conditions

Conditions	Yield
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%

: 870081-83-7
dimethyl{4-(methylthio)phenyl}sulfonium triflate

: 124-38-9
carbon dioxide

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

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

Conditions

Conditions	Yield
With 2.9-dimethyl-1,10-phenanthroline; neocuproine; zinc In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 16h;	A 73% B 5%

...Expand

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

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

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

C: 4052-30-6
4-methylsulfonylbenzoic acid

Conditions

Conditions	Yield
With chromium(VI) oxide; sulfuric acid In water; acetone for 0.05h; Ambient temperature;	A 72% B 14% C 14%

...Expand

: 124-38-9
carbon dioxide

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

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

Conditions

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

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 104-95-0
(4-bromophenyl)thioanisole

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

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

Conditions

Conditions	Yield
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%

...Expand

: 201230-82-2
carbon monoxide

: 104-95-0
(4-bromophenyl)thioanisole

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

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

Conditions

Conditions	Yield
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%

...Expand

: 124-38-9
carbon dioxide

: 123-09-1
4-chlorophenyl methyl sulfide

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

Conditions

Conditions	Yield
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%

: 38746-92-8
2-[4-(methylsulfanyl)phenyl]acetonitrile

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

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; copper diacetate In neat (no solvent) at 80℃; for 5h; Green chemistry;	60%

: 119072-55-8, 7188-38-7
tert-butylisonitrile

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

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

Conditions

Conditions	Yield
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%

: 74-83-9
methyl bromide

: 1074-36-8
4-mercaptobenzoic acid

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

Conditions

Conditions	Yield
With potassium hydroxide In ethanol for 12h; Williamson Ether Synthesis; Reflux;	55%

: 109-72-8, 29786-93-4
n-butyllithium

: 60-29-7
diethyl ether

: 104-95-0
(4-bromophenyl)thioanisole

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

Conditions

Conditions	Yield
at 20℃; anschliessende Umsetzung mit CO2;

...Expand

: 23405-48-3
4-methylthiobenzophenone

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

Conditions

Conditions	Yield
With sodium amide; toluene Zersetzen des Reaktionsprodukts mit Wasser und Verseifen mit verd. Natronlauge;

: 60-29-7
diethyl ether

: 104-95-0
(4-bromophenyl)thioanisole

: 917-54-4
methyllithium

A: 100-68-5
methyl-phenyl-thioether

B: 623-13-2
4-methylphenyl methylsulfide

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

Conditions

Conditions	Yield
anschliessendes Behandeln mit festem CO2;

...Expand

: 104-95-0
(4-bromophenyl)thioanisole

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

Conditions

Conditions	Yield
With n-butyllithium; diethyl ether Eintragen der Reaktionsloesung in festes Kohlendioxid;

: 21382-98-9
p-cyanophenyl methyl sulfide

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

Conditions

Conditions	Yield
With potassium hydroxide

: 1074-36-8
4-mercaptobenzoic acid

: 77-78-1
dimethyl sulfate

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

Conditions

Conditions	Yield
With alkali
With potassium hydroxide In ethanol for 6h; Reflux;

: 150-13-0
4-amino-benzoic acid

: 77-78-1
dimethyl sulfate

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

Conditions

Conditions	Yield
(i) aq. HCl, NaNO2, (ii) potassium ethyl xanthate, (iii) /BRN= 635994/, aq. KOH; Multistep reaction;

: p-methylthiobenzoyloxyl radical

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

Conditions

Conditions	Yield
With toluene In acetonitrile at 20℃; Kinetics; Further Variations:; Reaction partners; Reagents; hydrogen-atom abstraction;

: bis(p-methylthiobenzoyl) peroxide

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

Conditions

Conditions	Yield
In acetonitrile at 20℃; Quantum yield; photolysis; UV-irradiation;

: 3446-89-7
4-(Methylthio)benzaldehyde

KMnO4: KMnO4

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

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

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

Conditions

Conditions	Yield
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

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

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

Conditions

Conditions	Yield
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

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

: C27H35N3O5S

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide	98%

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

: 100643-71-8
descarboethoxyloratadine

: 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

Conditions	Yield
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%

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

: 616-38-6
carbonic acid dimethyl ester

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

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 16h; Inert atmosphere; Green chemistry;	97%

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

: 103-49-1
dibenzylamine

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

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;	97%

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

: 74-88-4
methyl iodide

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

Conditions

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

: C19H29N3O4

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

: C27H35N3O5S

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide	94%

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

: 3446-89-7
4-(Methylthio)benzaldehyde

Conditions

Conditions	Yield
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.

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

: 109-89-7
diethylamine

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

Conditions

Conditions	Yield
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%

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

: 4052-30-6
4-methylsulfonylbenzoic acid

Conditions

Conditions	Yield
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

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

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

Conditions

Conditions	Yield
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;

: 67-56-1
methanol

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

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

Conditions

Conditions	Yield
With sulfuric acid In water for 22h; Reflux;	90%
With hydrogenchloride

: 110-91-8
morpholine

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

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

Conditions

Conditions	Yield
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

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

: C32H33F3N4O5S

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide	87%

: C24H28F3N5O4

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

: C32H34F3N5O5S

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide	87%

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

: 7732-18-5
water

: 557-20-0
diethylzinc

: [Zn4(μ4-O)(O2C-p-MeSC6H4)6]

Conditions

Conditions	Yield
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%

...Expand

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

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

: 1403747-99-8
C11H8N4OS2

Conditions

Conditions	Yield
With trichlorophosphate Reflux;	87%

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

: 2-methoxyindolizine

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

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 30℃; for 20h; Inert atmosphere;	86.6%

: 1204331-51-0
N-(4-piperidin-4-yl-3-trifluoromethyl-benzoyl)-N'-(carbobenzyloxy)-guanidine

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

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

Conditions

Conditions	Yield
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%

: 746670-24-6
C23H31F3N4O4

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

: 746666-66-0
C31H37F3N4O5S

Conditions

Conditions	Yield
With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide	85%

4-(Methylthio)benzoic acid Specification

The CAS registry number of Benzoic acid,4-(methylthio)- is 13205-48-6. Its EINECS registry number is 236-171-5. The IUPAC name is 4-methylsulfanylbenzoic acid. In addition, the molecular formula is C₈H₈O₂S and the molecular weight is 168.21. What's more, it is a kind of light yellow to beige crystalline powder and belongs to the classes of Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Organic Acids.

Physical properties about this chemical are: (1)ACD/LogP: 2.74; (2)ACD/LogD (pH 5.5): 1.5; (3)ACD/LogD (pH 7.4): -0.09; (4)ACD/BCF (pH 5.5): 4.11; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 42.57; (7)ACD/KOC (pH 7.4): 1.08; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 51.6 Å²; (12)Index of Refraction: 1.612; (13)Molar Refractivity: 45.66 cm³; (14)Molar Volume: 131.2 cm³; (15)Polarizability: 18.1 ×10^-24cm³; (16)Surface Tension: 54.4 dyne/cm; (17)Density: 1.28 g/cm³; (18)Flash Point: 146.7 °C; (19)Enthalpy of Vaporization: 59.18 kJ/mol; (20)Boiling Point: 319 °C at 760 mmHg; (21)Vapour Pressure: 0.000145 mmHg at 25°C.

Preparation of Benzoic acid,4-(methylthio)-: it can be prepared by 4-methylsulfanyl-benzaldehyde. This reaction will need reagents 1 M aq. NaOH, (CTA)₂SO₄ and aq. TBHP. The reaction time is 20 hours at reaction temperature of 20 °C. The yield is about 98%.

Benzoic acid,4-(methylthio)- can be prepared by 4-methylsulfanyl-benzaldehyde.

Uses of Benzoic acid,4-(methylthio)-: it can be used to get 4-methanesulfonyl-benzoic acid. This reaction will need reagents sodium hydroxide, sodium bicarbonate and oxone<*>, and solvents H₂O and acetone. The reaction time is 1 hour with ambient temperature. The yield is about 92.6%.

Benzoic acid,4-(methylthio)- can be used to get 4-methanesulfonyl-benzoic acid

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed and irritating to eyes, respiratory system and skin. During using it, wear suitable gloves and eye/face protection and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. In addition, you should not breathe dust.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)c1ccc(SC)cc1
(2)InChI: InChI=1/C8H8O2S/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10)
(3)InChIKey: KWHCPERWLHBLOT-UHFFFAOYAJ

Product Name

4-(METHYLTHIO)BENZOIC ACID

Synthetic route

4-(Methylthio)benzoic acid Specification

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