3446-89-7

Basic information

• Product Name: 4-(Methylthio)benzaldehyde
• Synonyms: 4-(methylthio)-benzaldehyd;p-Methylmercaptobenzaldehyde;METHYLMERCAPTOBENZALDEHYDE(4-);4-ALDEHYDE THIOANISOLE;4-METHYLMERCAPTOBENZALDEHYDE;(4-METHYLTHIOCYCLOHEXYL)METHANOL;4-(METHYLTHIO)BENZALDEHYDE;AKOS BBS-00003173
• CAS NO: 3446-89-7
• Molecular Formula: C₈H₈OS
• Molecular Weight: 152.21
• EINECS: 222-365-7
• Product Categories: Aromatic Aldehydes & Derivatives (substituted)
• Mol File: 3446-89-7.mol
• Article Data: 160

Chemical Properties

• Melting Point: 6 °C
• Boiling Point: 86-90 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow/Liquid
• Density: 1.144 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.324mmHg at 25°C
• Refractive Index: n20/D 1.646(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: Not miscible in water.
• Sensitive: Stench
• BRN: 636158
• CAS DataBase Reference: 4-(Methylthio)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Methylthio)benzaldehyde(3446-89-7)
• EPA Substance Registry System: 4-(Methylthio)benzaldehyde(3446-89-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26-7/9
• RIDADR: UN 3334
• WGK Germany: 3
• F: 13
• TSCA: Yes
• Hazardous Substances Data: 3446-89-7(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow liquid

Uses

4-(Methylthio)benzaldehyde is a building block for the synthesis of various pharmaceutical and biologically active compounds. It can be used for the synthesis of sulfur-containing terpyridine ligands. It is the intermediate for the synthesis of a class of pyrrole derivatives showing analgesic/anti-inflammatory activity.

Synthesis Reference(s)

Synthetic Communications, 24, p. 2665, 1994 DOI: 10.1080/00397919408010580

InChI:InChI=1/C8H8S/c1-7-2-4-8(6-9)5-3-7/h2-6H,1H3

Synthetic route

4-(methylthio)benzyl alcohol (3446-90-0) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With cobalt(II) nitrate hexahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; manganese (II) nitrate tetrahydrate; oxygen; acetic acid at 40℃; under 760.051 Torr; for 0.75h;	100%
With N,N,N',N'-tetramethylguanidine In dichloromethane at 20℃; for 1h;	99%
With hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium nitrite In dichloromethane; water at 20℃; under 760.051 Torr; for 11h; in air;	99%

p-methylsulfinylbenzaldehyde (37794-15-3) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With indium; tungsten(VI) chloride In tetrahydrofuran at 20℃; for 0.0833333h;	95%
With niobium pentachloride; sodium iodide In acetonitrile at 20℃; for 0.0833333h;	95%
With iododioxobis(triphenylphosphine)rhenium(V); phenylsilane In tetrahydrofuran at 20℃; for 2.25h; chemoselective reaction;	92%

1,1-diacetoxy-1-(4-methylthiophenyl)methane → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With H6P2W18O62 In toluene at 100℃; for 0.0833333h;	95%

4-(methylthio)benzoic acid (13205-48-6) → 4-(Methylthio)benzaldehyde (3446-89-7)

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.

2-(4-(methylthio)phenyl)-1,3-dithiane → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With 1,3,5-trichloro-2,4,6-triazine; dimethyl sulfoxide In dichloromethane at 20℃; for 1h;	93%

dimethyl sulfoxide (67-68-5) + 4-bromo-benzaldehyde (1122-91-4) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide at 130℃; for 12h; Sealed tube; Inert atmosphere;	92%
With copper(l) iodide; zinc(II) fluoride at 150℃; for 36h; Sealed tube; Under air;	85%
With copper(l) iodide; zinc diacetate at 135℃; for 36h; regioselective reaction;	70%

2-<4-(methylthio)phenyl>-1,3-dithiolane → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With iodosylbenzene In dichloromethane at 20℃; for 0.333333h;	90%

methyl-phenyl-thioether (100-68-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With trichlorophosphate at -5 - 45℃; for 7h;	89.2%

2-(4-(methylsulfinyl)phenyl)-1,3-dioxolane → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With 1,2,3-trimethoxybenzene; oxalyl dichloride In dichloromethane at 0℃; for 0.00166667h; Inert atmosphere; chemoselective reaction;	89%

carbon monoxide (201230-82-2) + (4-bromophenyl)thioanisole (104-95-0) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium diacetate; propyl di-tert-butylphosphinite In toluene at 100℃; under 3750.38 Torr; for 20h; Inert atmosphere;	88%

4-(methylthio)benzyl bromide (38185-19-2) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With benzo[c]cinnoline In N,N-dimethyl-formamide at 80℃; Kornblum Aldehyd Synthesis;	87%

4-(Methylthio)acetophenone (1778-09-2) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With copper(l) iodide; oxygen In dimethyl sulfoxide at 120℃; for 25h; chemoselective reaction;	85%

4-(methylthio)benzyl alcohol (3446-90-0) → 4-(Methylthio)benzaldehyde (3446-89-7) + 4-(methylthio)benzyl 4-(methylthio)benzoate

Conditions	Yield
With [Rh(1,3,4,5-tetramethylimidazole-2-ylidene)(trop2NH)][trifluoromethanesulfonate]; potassium tert-butylate; dinitrogen monoxide In tetrahydrofuran; water; toluene at 50℃; under 750.075 Torr; Schlenk technique; Molecular sieve; Overall yield = 88 %; Overall yield = 165 mg;	A 3% B 85%

4-(Methylthio)-N-methylbenzenemethanamine (84212-03-3) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere; Green chemistry;	85%

4-(methylthio)benzyl alcohol (3446-90-0) → (4-(methylsulfinyl)phenyl)methanol (93183-64-3, 106732-70-1) + 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In neat (no solvent) at 70℃; for 6h; Irradiation; Green chemistry;	A 15% B 85%

(4-thiomethoxyphenyl)boronic acid (98546-51-1) + Glyoxilic acid (298-12-4) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With 1,2,3,4-tetrahydroisoquinoline In acetonitrile at 20℃; Green chemistry;	77%

1-(azidomethyl)-4-methylsulfanylbenzene (142070-82-4) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
Stage #1: 1-(azidomethyl)-4-methylsulfanylbenzene With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 4h; Inert atmosphere; Stage #2: With water In dimethyl sulfoxide; mineral oil for 0.25h; Inert atmosphere;	75%

3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide (50978-45-5) + 4-(methylthio)phenyl trifluoromethanesulfonate (57728-76-4) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With triethylsilane; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium carbonate In acetonitrile at 80℃; for 16h; Inert atmosphere; Sealed tube;	73%

formaldehyd (50-00-0) + (4-bromophenyl)thioanisole (104-95-0) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With triethylsilane; dichloro bis(acetonitrile) palladium(II); sodium carbonate; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 20 - 100℃; under 15001.5 Torr; for 20h; Inert atmosphere; Autoclave;	69%

formaldehyd (50-00-0) + 4-(methylthio)benzylamine (83171-39-5) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With iron(III) chloride hexahydrate In 1,4-dioxane; water at 80 - 100℃; for 18h;	66%

(E)-4-(methylthio)benzaldehyde oxime (93033-60-4) → 4-(methylsulfinyl)benzaldehyde oxime + p-methylsulfinylbenzaldehyde (37794-15-3) + 4-(methylsulfonyl)benzaldehyde oxime (53147-98-1) + 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With dihydrogen peroxide; bis(acetylacetonato)dioxidomolybdenum(VI) In acetone at 20℃; Product distribution; Further Variations:; Catalysts; Solvents;	A 5% B 3% C 3% D 60%

4-fluorobenzaldehyde (459-57-4) + dimethyl sulfoxide (67-68-5) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In water at 189℃; for 48h;	60%

4-(methylthio)benzyl alcohol (3446-90-0) → p-methylsulfinylbenzaldehyde (37794-15-3) + 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In n-heptane at 80℃; under 760.051 Torr; for 24h;	A 21% B 59%
With polystyrene-supported hypervalent iodine(V) reagent In 1,2-dichloro-ethane at 85℃; for 1h;
With N-(2-iodylphenyl)glutarylamide supported on amonomethylpolystyrene resin In 1,2-dichloro-ethane at 85℃; for 1h;	A 7 %Spectr. B 85 %Spectr.

2-nitropropane (79-46-9) + 4-(methylthio)benzyl bromide (38185-19-2) → 2-methyl-1-(4-methylsulfanyl-phenyl)-2-nitro-propan-1-ol + 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran Hass-Bender/Henry reaction;	A 57% B n/a

4-(methylthio)benzyl bromide (38185-19-2) → 4-(methylthio)benzyl alcohol (3446-90-0) + 1-bromomethyl-4-methanesulfinylbenzene (51927-46-9) + 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With dihydrogen peroxide at 70℃; for 1h;	A n/a B 52% C n/a

4-methylphenyl methylsulfide (623-13-2) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With 9-(benzoyl(cyclohexyl)carbamoyl)-10-phenylacridinium perchlorate In water; acetonitrile at 20℃; for 18h; Irradiation; Green chemistry; chemoselective reaction;	49%

4-(methylthio)benzyl alcohol (3446-90-0) → p-methylsulfinylbenzaldehyde (37794-15-3) + (4-(methylsulfinyl)phenyl)methanol (93183-64-3, 106732-70-1) + 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With 1-iodyl-2-butoxybenzene In acetonitrile for 15h; Heating;	A 16% B 46% C 32%
With 4-(2-iodylphenoxy)butanoylaminomethylated polystyrene In 1,2-dichloro-ethane for 3h; Heating;

p-methylsulfinylbenzaldehyde (37794-15-3) → (R)-4-(methylsulfinyl)benzaldehyde + 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With DL-dithiothreitol; methionine sulfoxide reductase A from Pseudomonas alcaliphila In aq. phosphate buffer at 30℃; for 1h; pH=8; Resolution of racemate; Enzymatic reaction; enantioselective reaction;	A 43% B n/a
With recombinant methionine sulfoxide reductase A from Pseudomonas monteilii; diothiothreitol In aq. phosphate buffer at 30℃; for 4h; pH=8; Sealed tube; Resolution of racemate; Green chemistry; Enzymatic reaction; enantioselective reaction;	A n/a B n/a

methyl-phenyl-thioether (100-68-5) → 4-(Methylthio)benzaldehyde (3446-89-7)

Conditions	Yield
With N,N-dimethyl-formamide; trichlorophosphate
Multi-step reaction with 2 steps 1: acetic acid 2: hexamethylenetetramine; acetic acid / Erhitzen des Reaktionsprodukts mit H2O View Scheme

4-(Methylthio)benzaldehyde (3446-89-7) → 4-methylsulfonylbenzoic acid (4052-30-6)

Conditions	Yield
With tert.-butylhydroperoxide; sodium hydroxide at 70℃; for 2h;	100%
With oxone In tetrahydrofuran; water at 20℃; for 24h;	94%
With sodium perborate In acetic acid at 45 - 50℃;	90%
With oxygen at 100℃; for 20h; Reagent/catalyst; Schlenk technique; chemoselective reaction;	87%

4-(Methylthio)benzaldehyde (3446-89-7) → 4-(methylthio)benzamide (90005-49-5)

Conditions	Yield
With tert.-butylhydroperoxide; sodium hydroxide; (CTA)2SO4 at 50℃; for 2h;	100%
With nitromethane; trifluoromethylsulfonic anhydride; acetic acid In formic acid at 80 - 120℃;	57%
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; pyridine / methanol / 24 h / 20 °C 2: [RuCl2(η2-C6H6){P(NMe2)3}]; water / 3 h / 100 °C / Inert atmosphere; Sealed tube View Scheme

4-(Methylthio)benzaldehyde (3446-89-7) + trimethyl orthoformate (149-73-5) → 1-(1,1-dimethoxy-methyl)-4-methylsulfanyl-benzene (100515-17-1)

Conditions	Yield
With potassium tert-butylate; toluene-4-sulfonic acid In methanol at 20℃; for 1.5h; Inert atmosphere;	100%
With toluene-4-sulfonic acid In methanol for 1.5h; Ambient temperature;	83%
With toluene-4-sulfonic acid In methanol at 20℃; for 1h;

4-(Methylthio)benzaldehyde (3446-89-7) → 4-(methylthio)benzyl alcohol (3446-90-0)

Conditions	Yield
With hydrogen; phosphotungstic acid 44-hydrate; [Fe(C5H4P(i-Pr)2)2Rh(C8H12)]BF4 In water; isopropyl alcohol at 20℃; under 5171.62 Torr; for 16h;	100%
With isopropyl alcohol; hydrotalcite at 81.84℃; for 3h; Kinetics; Further Variations:; Temperatures; Reagents;	100%
Stage #1: 4-(Methylthio)benzaldehyde With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); phenylsilane at 80℃; for 0.666667h; Stage #2: With tetrabutyl ammonium fluoride at 20℃; for 0.5h; Reagent/catalyst; Temperature; Time; Solvent; chemoselective reaction;	98%

ethyl acetoacetate (141-97-9) + urea (57-13-6) + 4-(Methylthio)benzaldehyde (3446-89-7) → ethyl 6-methyl-4-[4-(methylsulfanyl)phenyl]-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate (423737-44-4)

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In ethanol at 100℃; for 1h; Biginelli reaction; Microwave irradiation; Inert atmosphere;	100%
Wells-Dawson heteropolyacid catalyst at 80℃; for 1.5h; Biginelli reaction;	92%
With 25,26,27,28-terahydroxycalix[4]arene-5,11,7,23-tetrasulfonic acid In ethanol for 8h; Biginelli reaction; Reflux;	92%

4-(Methylthio)benzaldehyde (3446-89-7) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → 4-BOC-1-(4-methylthio)-benzylpiperazine

Conditions	Yield
Stage #1: 4-(Methylthio)benzaldehyde; 1-t-Butoxycarbonylpiperazine In methanol for 0.5h; Stage #2: With borohydride; polymer-supported In methanol for 24h;	100%

1,4-Diacetylbenzene (1009-61-6) + 4-(Methylthio)benzaldehyde (3446-89-7) → C26H22O2S2 (404585-30-4)

Conditions	Yield
With sodium hydroxide In water; isopropyl alcohol at 0 - 20℃; for 5h;	100%
With sodium hydroxide In water; isopropyl alcohol at 0 - 20℃;	100%

1,1′-(9-ethyl-9H-carbazole-3,6-diyl)diethanone (1483-97-2) + 4-(Methylthio)benzaldehyde (3446-89-7) → C34H29NO2S2 (1104847-99-5)

Conditions	Yield
With sodium hydroxide In water; tert-butyl alcohol at 0 - 20℃; for 5h;	100%
With sodium hydroxide In water; tert-butyl alcohol at 0 - 20℃;	100%

ethyl acetoacetate (141-97-9) + 1,3-cylohexanedione (504-02-9) + 4-(Methylthio)benzaldehyde (3446-89-7) → 2-Methyl-4-(4-methylsulfanyl-phenyl)-5-oxo-1,4, 5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester (312527-79-0)

Conditions	Yield
With Cu(OTf)2; ammonium acetate In ethanol at 100℃; for 0.25h; Hantzsch reaction; Microwave irradiation;	100%

2-Amino-5-chlorobenzophenone (719-59-5) + 4-(Methylthio)benzaldehyde (3446-89-7) → 6-chloro-2-[4-(methylsulfanyl)phenyl]-4-phenylquinazoline

Conditions	Yield
With copper(II) choride dihydrate; ammonium acetate In ethanol for 4h; Reflux;	100%
With 1,1,1,3',3',3'-hexafluoro-propanol; ammonium acetate at 55℃; for 1.5h;	84%

semicarbazide hydrochloride (563-41-7) + 4-(Methylthio)benzaldehyde (3446-89-7) → 1-(4-(methylthio)benzylidene)semicarbazide

Conditions	Yield
With sodium acetate In ethanol; water at 20℃;	100%

4-(Methylthio)benzaldehyde (3446-89-7) → p-methylsulfinylbenzaldehyde (37794-15-3)

Conditions	Yield
With phthaloyl peroxide In dichloromethane at 25℃; for 8h; Schlenk technique; chemoselective reaction;	99%
Stage #1: 4-(Methylthio)benzaldehyde With aluminum (III) chloride In methanol; dichloromethane at 20℃; for 0.0166667h; Stage #2: With [bis(acetoxy)iodo]benzene In methanol; dichloromethane at 20℃; for 12h;	99%
With nitric acid; phosphorus pentoxide; silica gel In water for 0.0833333h;	97%

4-(Methylthio)benzaldehyde (3446-89-7) + γ-aminopropyl-2-methyl-6-phenyl-1,3-dioxa-6-aza-2-silacyclooctane (389082-07-9) → γ-N-(p-methylthiobenzylidene)aminopropyl-2-methyl-6-phenyl-1,3-dioxa-6-aza-2-silacyclooctane

Conditions	Yield
With potassium carbonate In benzene at 20℃; for 6h;	99%

Methyltriphenylphosphonium bromide (1779-49-3) + 4-(Methylthio)benzaldehyde (3446-89-7) → 4-methythiostyrene (18760-11-7)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; Wittig reaction;	99%
With sodium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	99%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 2h; Wittig Olefination; Inert atmosphere; Stage #2: 4-(Methylthio)benzaldehyde In tetrahydrofuran; hexane at 0 - 20℃; for 16h; Wittig Olefination; Inert atmosphere;	96%

1,2-diamino-benzene (95-54-5) + 4-(Methylthio)benzaldehyde (3446-89-7) → 2-(4-(methylthio)phenyl)-1H-benzo[d]imidazole

Conditions	Yield
With sodium metabisulfite In N,N-dimethyl-formamide at 80℃; for 0.1h; Microwave irradiation;	99%
Stage #1: 4-(Methylthio)benzaldehyde In N,N-dimethyl-formamide at 240℃; under 7500.75 Torr; for 0.0833333h; Microwave irradiation; Stage #2: 1,2-diamino-benzene In N,N-dimethyl-formamide at 240℃; under 7500.75 Torr; for 0.0833333h; Microwave irradiation;

1-Methyl-4-piperidone (1445-73-4) + 4-(Methylthio)benzaldehyde (3446-89-7) → 3,5-Bis((E)-4-methylthiobenzylidene)-1-methylpiperidin-4-one

Conditions	Yield
With sodium hydroxide In water at 20℃; Aldol Condensation;	99%

4-methoxy-aniline (104-94-9) + phosphonic acid diethyl ester (762-04-9) + 4-(Methylthio)benzaldehyde (3446-89-7) → C19H26NO4PS

Conditions	Yield
With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) In neat (no solvent) at 80℃; for 0.166667h; chemoselective reaction;	99%

4-(Methylthio)benzaldehyde (3446-89-7) → 4-(methylthio)benzoic acid (13205-48-6)

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.);

4-(Methylthio)benzaldehyde (3446-89-7) → para-methanesulfonylbenzaldehyde (5398-77-6)

Conditions	Yield
With sodium hydroxide; 3-chloro-benzenecarboperoxoic acid at 1 - 3℃; for 2h;	98%
With Oxone In neat (no solvent) for 1.5h; Milling; Green chemistry; chemoselective reaction;	97%
With C2MoO9(2-)*H2O*2C19H42N(1+); dihydrogen peroxide In water at 20℃; for 0.0166667h; chemoselective reaction;	97%

Bromoform (75-25-2) + 4-(Methylthio)benzaldehyde (3446-89-7) → 2-hydroxy-2-(4-methylthiophenyl)ethanoic acid (109086-16-0)

Conditions	Yield
With sodium hydroxide; lithium bromide In 1,4-dioxane	98%
With potassium hydroxide; lithium bromide In 1,4-dioxane; water 1.) 0 deg C, 18 h, 2.) 23 deg C, 24 h;	7.6 g

4-(Methylthio)benzaldehyde (3446-89-7) → 4-(methylthio)benzaldehyde oxime (93033-60-4)

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol at 80℃; for 4h; Inert atmosphere;	98%
With sodium hydroxide; hydroxylamine hydrochloride In ethanol; water at 0℃;	46%
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water for 24h;

N-methylhydroxyamine hydrochloride (4229-44-1) + 4-(Methylthio)benzaldehyde (3446-89-7) → N-[4-(methylthio)benzylidene]methylamine N-oxide (41105-92-4, 107379-09-9)

Conditions	Yield
With sodium sulfate; sodium carbonate at 20℃; for 0.0833333h; Neat (no solvent);	98%
With sodium hydrogencarbonate In dichloromethane at 20℃;	82%
With sodium acetate In ethanol at 50 - 60℃; for 3h;	78%

piperidine (110-89-4) + (4-methoxyphenyl)zinc(II) bromide (82303-13-7) + 4-(Methylthio)benzaldehyde (3446-89-7) → 1-((4-methoxyphenyl)(4-(methylthio)phenyl)methyl)piperidine

Conditions	Yield
With copper(l) iodide In acetonitrile at 20℃; for 3h;	98%

3-bromopropylamine hydrochloride (5003-71-4) + 4-(Methylthio)benzaldehyde (3446-89-7) → 4-(thiomethyl)benzylidene-(3-bromo-1-propylamine)

Conditions	Yield
With triethylamine In chloroform at 20℃; for 16h;	98%

hydrogen cyanide (74-90-8) + 4-(Methylthio)benzaldehyde (3446-89-7) → 2-hydroxy-2-(4-(methylthio)phenyl)acetonitrile (895570-68-0)

Conditions	Yield
With Prunus communis L. (R)-hydroxynitrile lyase In various solvent(s) at 20℃; for 12h;	98%
With hydroxynitrile lyase isozyme 5 from Prunus communis In tert-butyl methyl ether at 25℃; for 4h; pH=5; pH-value; Temperature; Reagent/catalyst; Solvent; Enzymatic reaction;	94%
With hydroxynitrile lyase PcHNL5, L343F mutant at 10℃; for 12h; pH=2.5; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;	n/a

4-chloro-aniline (106-47-8) + 4-(Methylthio)benzaldehyde (3446-89-7) → 4-chloro-N-[4-methylsulfanylbenzylidene]aniline (22116-72-9)

Conditions	Yield
	98%
In methanol for 4h; Reflux;	88%
With acetic acid In ethanol at 78℃; for 10h;

2-hydroxy-2-phenylacetophenone (119-53-9) + 4-(Methylthio)benzaldehyde (3446-89-7) → 2-(4-(methylthio)phenyl)-4,5-diphenyl-1H-imidazole (36755-90-5)

Conditions	Yield
With P2O5/SiO2; ammonium acetate at 100℃; for 2h;	98%
With triphenyl(propyl-3-sulphonyl)phosphonium toluenesulfonate; ammonium acetate at 100℃; for 2h; neat (no solvent);	98%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate at 100℃; for 2.5h; Neat (no solvent);	95%
With ammonium acetate at 130℃; for 1.33333h; Neat (no solvent);	90%

4-(Methylthio)benzaldehyde (3446-89-7) + N-phenyl-1,2-benzenediamine (534-85-0) → 2-[4-(methylthio)phenyl]-1-phenyl-1H-benzo[d]imidazole (1412893-57-2)

Conditions	Yield
With sodium metabisulfite In N,N-dimethyl-formamide at 100℃; for 0.1h; Microwave irradiation;	98%

1,3-cylohexanedione (504-02-9) + 2,4-diamino-6-hydroxypyrimidine (56-06-4) + 4-(Methylthio)benzaldehyde (3446-89-7) → 2-amino-8,9-dihydro-5-(4-(methylthio)phenyl)pyrimido[4,5-b]quinoline 4,6(1H,5H,7H,10H)-dione

Conditions	Yield
With zirconium(IV) oxide In ethylene glycol at 120℃; for 0.133333h; Green chemistry;	98%

Upstream product

• 79-46-9 2-nitropropane 
• 38185-19-2 4-(methylthio)benzyl bromide 
• 3446-90-0 4-(methylthio)benzyl alcohol 
• 180143-69-5 4-methylthiobenzaldehyde ethylene acetal 
• 67-68-5 dimethyl sulfoxide 
• 1122-91-4 4-bromo-benzaldehyde 
• 37794-15-3 p-methylsulfinylbenzaldehyde 
• 75-09-2 dichloromethane 
• 104-88-1 4-chlorobenzaldehyde 
• 84212-03-3 4-(Methylthio)-N-methylbenzenemethanamine 
• 127743-98-0 4-(methylthio)benzoyl fluoride 
• 100-68-5 methyl-phenyl-thioether 
• 68-12-2 N,N-dimethyl-formamide 
• 1778-09-2 4-(Methylthio)acetophenone 

Downstream Products

• 30117-67-0 1-(4-Methylthiobenzyliden)inden 
• 83319-94-2 3,5-Bis-[1-(4-methylsulfanyl-phenyl)-meth-(Z)-ylidene]-tetrahydro-thiopyran-4-one 
• 88251-94-9 6-[2-Hydroxy-2-(4-methylsulfanyl-phenyl)-ethyl]-2-oxo-1,2-dihydro-pyridine-3-carbonitrile 
• 162274-50-2 4-<(Diphenylphosphinoyl)(4-(methylthio)phenyl)methyl>morpholine 
• 127086-52-6 1-(p-thiomethylphenylmethylidene)-1H-cyclopropa[b]naphthalene 
• 189501-35-7 1-[4-(methylthio)phenyl]hexane-1,4-dione 
• 119984-89-3 p-(thiomethyl)-p'-nitrodiphenylacetylene 
• 140423-20-7 (E)-3-(4-Methylsulfanyl-phenyl)-2-(4-nitro-phenyl)-acrylic acid 
• 189955-86-0 1-(4-(methylthio)phenyl)-5-phenoxy-1,4-pentadione 
• 215256-88-5 1-(4-methylsulfanylphenyl)but-3-yn-1-ol 
• 219788-93-9 1-(4-Methylsulfanylphenyl)but-3-en-1-ol 

Relevant articles and documents

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