4-Methylthiophenylacetic acid supplier

Name
4-Methylthiophenylacetic acid
EINECS
CAS No. 16188-55-9
Article Data12
CAS DataBase
Density 1.16g/cm³
Solubility
Melting Point 97-98 ºC
Formula C9H10 O2 S
Boiling Point 274.2°Cat760mmHg
Molecular Weight 182.243
Flash Point 125.4°C
Transport Information
Appearance Cream crystalline powder
Safety S26;S36
Risk Codes R36/37/38
Molecular Structure
Hazard Symbols
Synonyms Acetic acid,[p-(methylthio)phenyl]- (6CI,7CI,8CI); (4-Methylsulfanylphenyl)acetic acid;2-[4-(Methylthio)phenyl]acetic acid; 4-(Methylthio)phenylacetic acid;[p-(Methylthio)phenyl]acetic acid
PSA 62.60000
LogP 2.03560

Synthetic route

: 53066-99-2
2-(4-(methylthio)phenyl)-2-oxoacetic acid

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

Conditions

Conditions	Yield
Stage #1: 2-(4-(methylthio)phenyl)-2-oxoacetic acid With sodium iodide In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With chloro-trimethyl-silane In dichloromethane at 20℃; for 2h; Inert atmosphere; regioselective reaction;	91%
Stage #1: 2-(4-(methylthio)phenyl)-2-oxoacetic acid With sodium hydroxide; hydrazine In water at 75℃; for 120h; Wolff-Kishner Reduction; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1.5;

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

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

Conditions

Conditions	Yield
Stage #1: 2-[4-(methylsulfanyl)phenyl]acetonitrile With potassium hydroxide; water for 8h; Reflux; Stage #2: With hydrogenchloride; water at 20℃;	82%
With sodium hydroxide In ethylene glycol; ethyl acetate
With sulfuric acid; water for 1h; Reflux;

: 1878-66-6
4-chlorophenylacetic Acid

: 5188-07-8
sodium thiomethoxide

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

Conditions

Conditions	Yield
With copper(I) bromide In N,N-dimethyl-formamide at 130℃; for 24h; Inert atmosphere;	79.3%

: 5188-07-8
sodium thiomethoxide

: 1878-68-8
2-(4-bromophenyl)-acetic acid

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

Conditions

Conditions	Yield
With copper(I) bromide In N,N-dimethyl-formamide at 130℃; Inert atmosphere;	76.1%

: 1778-09-2
4-(Methylthio)acetophenone

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

Conditions

Conditions	Yield
With morpholine; sulfur for 20h; Heating;	53%
Stage #1: 4-(Methylthio)acetophenone With morpholine; sulfur at 130℃; for 48h; Willgerodt reaction; Stage #2: With sodium hydroxide; water at 130℃; for 24h; Stage #3: With hydrogenchloride In water

: 1798-06-7
(4-iodophenyl)acetic acid

: 4856-13-7
cuprous methylmercaptide

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

Conditions

Conditions	Yield
With quinoline at 200℃;

: 110-91-8
morpholine

: 1778-09-2
4-(Methylthio)acetophenone

sulfur: sulfur

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

Conditions

Conditions	Yield
Erhitzen des Reaktionsgemisches mit wss. HCl;

...Expand

1-<4-methylsulfanyl-phenyl>-ethanone-(1): 1-<4-methylsulfanyl-phenyl>-ethanone-(1)

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

Conditions

Conditions	Yield
With morpholine; sulfur Erhitzen des Reaktionsgemisches mit wss. Salzsaeure;

: 100-68-5
methyl-phenyl-thioether

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / AlCl3 / CHCl3 / 0 - 5 °C 2: 53 percent / S8, Morpholin / 20 h / Heating View Scheme

: 67-56-1
methanol

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 70290-37-8
(4-methylsulfanyl-phenyl)-acetic acid methyl ester

Conditions

Conditions	Yield
With sulfuric acid at 50℃; for 16h;	100%
With thionyl chloride at 0 - 20℃; for 48h;	100%
With sulfuric acid for 19h; Heating / reflux;	98%
With sulfuric acid In benzene at 0 - 80℃; for 16h; Inert atmosphere;	83.1%
With hydrogenchloride

: 1006-64-0
2-(phenyl)pyrrolidine

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 2-(4-(methylthio)phenyl)-1-(2-phenylpyrrolidin-1-yl)ethan-1-one

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;	100%

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 70290-37-8
(4-methylsulfanyl-phenyl)-acetic acid methyl ester

Conditions

Conditions	Yield
With sulfuric acid In methanol	98%
With sulfuric acid In methanol	98%
With sulfuric acid In methanol	92%

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 74-88-4
methyl iodide

: 70290-37-8
(4-methylsulfanyl-phenyl)-acetic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 2-(4-(methylthio)phenyl)acetic acid With sodium hydrogencarbonate In N,N-dimethyl-formamide for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 24h;	97%
Stage #1: 2-(4-(methylthio)phenyl)acetic acid With sodium hydrogencarbonate In N,N-dimethyl-formamide for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 24h;	97%

: 64-17-5
ethanol

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 14062-27-2
ethyl 4-methylthiophenylacetate

Conditions

Conditions	Yield
With sulfuric acid for 8h; Heating;	96%
With sulfuric acid for 8h; Heating / reflux;	96%
With sulfuric acid	79%

: 524-38-9
N-hydroxyphthalimide

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 1,3-dioxoisoindolin-2-yl 2-(4-(methylthio)phenyl)acetate

Conditions

Conditions	Yield
With dmap; diisopropyl-carbodiimide In tetrahydrofuran at 20℃; Inert atmosphere;	96%
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 0.5h;	72%

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 81227-89-6
2-[4-(methylmercapto)phenyl]-1-ethanol

Conditions

Conditions	Yield
With borane In tetrahydrofuran at 0℃; for 5h;	94%
With sodium hydroxide In tetrahydrofuran; methanol; diethyl ether	84.4%

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 530-62-1
1,1'-carbonyldiimidazole

: N-methoxy-N-methyl-4-(methylthio)benzeneacetamide

Conditions

Conditions	Yield
In dichloromethane	93%

...Expand

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: N-methoxy-N-methyl-4-(methylthio)benzeneacetamide

Conditions

Conditions	Yield
Stage #1: 2-(4-(methylthio)phenyl)acetic acid With 1,1'-Carbonyl-di-(1,2,4-triazole) In dichloromethane at 20℃; for 0.333333h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 20℃;	93%

aqueous sodium chloride: aqueous sodium chloride

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 321-97-1
(1R,2R)-pseudoephedrine

: 3282-30-2
pivaloyl chloride

: 436141-37-6
N-[2(R)-hydroxy-1(R)-methyl-2(R)-phenyl-ethyl]-N-methyl-2-(4-methylsulfanyl-phenyl)-acetamide

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water; toluene	92.6%

...Expand

: 4-amino-3-(4-methylthiobenzyl)-5-mercapto-1,2,4-triazole

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 1144110-74-6
C19H18N4S3

Conditions

Conditions	Yield
With trichlorophosphate for 8h; Heating;	91%

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: monomethyl auristatin E

: C48H75N5O8S

Conditions

Conditions	Yield
With 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 dimethyl sulfoxide for 1h;	90%

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 1257393-74-0
(4-methylthiophenyl)acetic acid hydrazide

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol for 8h; Reflux;	86%
Multi-step reaction with 2 steps 1: Acidic conditions 2: hydrazine hydrate / ethanol / 8 h / Reflux View Scheme

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 103-49-1
dibenzylamine

: N,N-dibenzyl-2-(4-(methylthio)phenyl)acetamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;	86%

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 2-(pyrimidin-5-yl)phenol

: 2-(pyrimidin-5-yl)phenyl 2-(4-(methylthio)phenyl)acetate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 12h; Sealed tube;	86%

: 870-50-8
di-tert-butyl-diazodicarboxylate

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: di-tert-butyl 1-(4-(methylthio)benzyl)hydrazine-1,2-dicarboxylate

Conditions

Conditions	Yield
With iron(III) sulfate; bis[(2-pyridyl)methyl]amine In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;	86%

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 2-bromo-1-(4-fluorophenyl)-1-butanone

: 5-ethyl-4-(4-fluoro-phenyl)-5-hydroxy-3-(4-methylsulfanyl-phenyl)-5H-furan-2-one

Conditions

Conditions	Yield
Stage #1: 2-(4-(methylthio)phenyl)acetic acid With potassium hydroxide In water; N,N-dimethyl-formamide at 25 - 30℃; Stage #2: 2-bromo-1-(4-fluorophenyl)-1-butanone In water; N,N-dimethyl-formamide at 25 - 30℃;	83%

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 118362-28-0
2-(4-(methylsulfinyl)phenyl)acetic acid

Conditions

Conditions	Yield
With sodium periodate In methanol; water at 0 - 20℃; for 2h;	82%
With perchloric acid; dihydrogen peroxide In ethanol; water at 25℃; Rate constant;
With sodium periodate In ethanol at 25℃; Rate constant;
With 3-chloro-benzenecarboperoxoic acid at 25℃; Rate constant; also in the presence α-cyclodextrin; pH 1.6;

: 2700-22-3
Benzylidenemalononitrile

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 2-(2-(4-(methylthio)phenyl)-1-phenylethyl)malononitrile

Conditions

Conditions	Yield
With iron(III) sulfate; bis[(2-pyridyl)methyl]amine In 1,2-dichloro-ethane at 20℃; for 12h; Inert atmosphere; Sealed tube; Irradiation;	81%

: 2564-83-2, 45842-10-2
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: methyl 2-(4-(methylthio)phenyl)-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)acetate

Conditions

Conditions	Yield
Stage #1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2-(4-(methylthio)phenyl)acetic acid With N4,N4,N7,N7-tetramethyl-1,10-phenanthroline-4,7-diamine; iron(II) acetate In tetrahydrofuran at 60℃; for 24h; Molecular sieve; Inert atmosphere; Schlenk technique; Stage #2: diazomethyl-trimethyl-silane With methanol In tetrahydrofuran; hexane for 1h; Inert atmosphere; Stage #3: With acetic acid In tetrahydrofuran; hexane; ethyl acetate chemoselective reaction;	81%

Yield

Stage #1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2-(4-(methylthio)phenyl)acetic acid With N4,N4,N7,N7-tetramethyl-1,10-phenanthroline-4,7-diamine; iron(II) acetate In tetrahydrofuran at 60℃; for 24h; Molecular sieve; Inert atmosphere; Schlenk technique;
Stage #2: diazomethyl-trimethyl-silane With methanol In tetrahydrofuran; hexane for 1h; Inert atmosphere;
Stage #3: With acetic acid In tetrahydrofuran; hexane; ethyl acetate chemoselective reaction;

81%

...Expand

: 85-44-9
phthalic anhydride

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: (Z)-3-(4-methylsulfanylbenzylidene)isobenzofuran-1-one

Conditions

Conditions	Yield
With sodium acetate In benzene at 230 - 240℃;	80%
With sodium acetate Heating;	65%
With sodium acetate Heating;
With sodium acetate In toluene at 210 - 245℃; Inert atmosphere;
With sodium acetate In toluene at 210 - 245℃; Dean-Stark; Inert atmosphere;

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 881-43-6
2-bromo-1-(4-methoxyphenyl)butan-1-one

A: 5-ethyl-4-hydroxy-4-(4-methoxy-phenyl)-3-(4-methylsulfanyl-phenyl)-dihydro-furan-2-one

B: 5-ethyl-5-hydroxy-4-(4-methoxy-phenyl)-3-(4-methylsulfanyl-phenyl)-5H-furan-2-one

Conditions

Conditions	Yield
With potassium hydroxide In water; N,N-dimethyl-formamide at 25℃; for 6h; Product distribution; Further Variations:; Temperatures; Reagents; substrate/reagent ratios, inert/O2 atmosphere;	A 16% B 79%

...Expand

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 877-35-0
2-bromo-1-phenylbutan-1-one

: 503174-32-1
5-ethyl-5-hydroxy-3-(4-methylsulfanylphenyl)-4-phenyl-2,5-dihydro-2-furanone

Conditions

Conditions	Yield
Stage #1: 2-(4-(methylthio)phenyl)acetic acid With potassium hydroxide In water; N,N-dimethyl-formamide at 25 - 30℃; Stage #2: 2-bromo-1-phenylbutan-1-one In water; N,N-dimethyl-formamide at 25 - 30℃;	77%

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 1400872-56-1
5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-amino-2,2-dimethyl-1,3-dioxane

: 1400872-58-3
5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-{N-[(4-methylthiobenzyl)carboximido]}-2,2-dimethyl-1,3-dioxane

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 24h; Inert atmosphere;	76%

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 95-01-2
2,4-Dihydroxybenzaldehyde

: 3-(4-methylthiophenyl)-7-hydroxycoumarin

Conditions

Conditions	Yield
Stage #1: 2-(4-(methylthio)phenyl)acetic acid; 2,4-Dihydroxybenzaldehyde With sodium acetate; acetic anhydride at 160℃; for 10h; Inert atmosphere; Stage #2: With lithium hydroxide In tetrahydrofuran; methanol; water for 3h;	74.2%

: 16188-55-9
2-(4-(methylthio)phenyl)acetic acid

: 321-97-1
(1R,2R)-pseudoephedrine

: 3282-30-2
pivaloyl chloride

: 436141-37-6
N-[2(R)-hydroxy-1(R)-methyl-2(R)-phenyl-ethyl]-N-methyl-2-(4-methylsulfanyl-phenyl)-acetamide

Conditions

Conditions	Yield
Stage #1: 2-(4-(methylthio)phenyl)acetic acid With potassium carbonate In tetrahydrofuran at 25 - 26℃; for 0.5h; Stage #2: pivaloyl chloride In tetrahydrofuran at -10 - -5℃; for 1h; Stage #3: (1R,2R)-pseudoephedrine at -10 - 0℃; for 3.25h;	73.1%

...Expand

4-Methylthiophenylacetic acid Chemical Properties

Molecular Formula: C₉H₁₀O₂S
Molecular Weight: 182.24 g/mol
Canonical SMILES: O=C(O)Cc1ccc(SC)cc1
InChI: InChI=1/C9H10O2S/c1-12-8-4-2-7(3-5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)
Mol File: 16188-55-9.mol
Product Categories: C9;Carbonyl Compounds; Carboxylic Acids
Nominal Mass: 182
Average Mass: 182.2395
Monoisotopic Mass: 182.04015
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 3
Polar Surface Area: 51.6
Index of Refraction: 1.596
Molar Refractivity: 50.29 cm³
Molar Volume: 147.7 cm³
Polarizability: 19.93×10^-24cm³
Surface Tension: 51.9 dyne/cm
Density: 1.23 g/cm³
Flash Point: 157.9 °C
Enthalpy of Vaporization: 61.29 kJ/mol
Boiling Point: 337.4 °C at 760 mmHg
Melting Point: 97-98 °C(lit.)
Vapour Pressure of 4-Methylthiophenylacetic acid (CAS NO.16188-55-9): 4.1E-05 mmHg at 25 °C

4-Methylthiophenylacetic acid Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
WGK Germany of 4-Methylthiophenylacetic acid (CAS NO.16188-55-9): 3

4-Methylthiophenylacetic acid Specification

4-Methylthiophenylacetic acid (CAS NO.16188-55-9), its synonyms are (4-Methylsulfanyl-phenyl)-cetic acid ; 2-(4-(methylthio)phenyl)acetic acid ; 4-(Methylthio)benzeneacetic acid ; 4-(Methylthio)phenylacetic acid,98% . It is a cream crystalline powder.

Product Name

4-Methylthiophenylacetic acid

Synthetic route

4-Methylthiophenylacetic acid Chemical Properties

4-Methylthiophenylacetic acid Safety Profile

4-Methylthiophenylacetic acid Specification

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