7022-45-9

Basic information

• Product Name: 2-(METHYLTHIO) BENZALDEHYDE
• Synonyms: 2-(METHYLTHIO) BENZALDEHYDE;2-(Methylmercapto)-benzaldehyde;o-(Methylthio)benzaldehyde;2-(METHYLTHIO)BENZALDEHYDE / 2-THIOANISALDEHYDE;2-Methylsulfanylbenzaldehyde;2-(methylthio) Benza;2-(Methylthio)benzaldehyde 90%
• CAS NO: 7022-45-9
• Molecular Formula: C₈H₈OS
• Molecular Weight: 152.21
• Product Categories: Aldehydes;C8;Carbonyl Compounds
• Mol File: 7022-45-9.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 141-143 °C13 mm Hg(lit.)
• Flash Point: 230 °F
• Appearance: /
• Density: 1.18 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.633(lit.)
• CAS DataBase Reference: 2-(METHYLTHIO) BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(METHYLTHIO) BENZALDEHYDE(7022-45-9)
• EPA Substance Registry System: 2-(METHYLTHIO) BENZALDEHYDE(7022-45-9)

Safety Data

• RIDADR: UN 3334
• WGK Germany: 3
• Hazardous Substances Data: 7022-45-9(Hazardous Substances Data)

Usage

Uses

2-(METHYLTHIO)BENZALDEHYDE is a useful research chemical.

Synthetic route

2-(methylthio)benzyl alcohol (33384-77-9) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
With dimethylsulfide; N-succinimide; triethylamine In toluene	94%
With pyridinium chlorochromate In dichloromethane at 20℃; for 1h;	69%
With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 12h;	65%

dimethyl sulfoxide (67-68-5) + ortho-bromobenzaldehyde (6630-33-7) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide at 130℃; for 12h; Sealed tube; Inert atmosphere;	93%

2-chloro-benzaldehyde (89-98-5) + sodium thiomethoxide (5188-07-8) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
In N,N,N,N,N,N-hexamethylphosphoric triamide for 5h; Heating;	86%
In N,N-dimethyl-formamide at 20℃; for 44h;	44%

2-Fluorobenzaldehyde (446-52-6) + sodium thiomethoxide (5188-07-8) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
With potassium carbonate In dichloromethane; N,N-dimethyl-formamide at 55℃; for 24h; Inert atmosphere;	85%
In N,N-dimethyl-formamide at 0.15℃; Inert atmosphere;	85%
In acetonitrile Heating;

methylthiol (74-93-1) + 2-Fluorobenzaldehyde (446-52-6) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 24h;	85%
Stage #1: methylthiol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.5h; Inert atmosphere; Stage #2: 2-Fluorobenzaldehyde In N,N-dimethyl-formamide; mineral oil at -40℃; for 2h; Inert atmosphere;

methyl sodium sulfide + 2-Fluorobenzaldehyde (446-52-6) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
With potassium carbonate In dichloromethane; N,N-dimethyl-formamide	85%

methylthiol (74-93-1) + 2-halobenzaldehyde → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 55 - 80℃; for 24h; Inert atmosphere;	85%

dimethyl sulfoxide (67-68-5) + 2-Fluorobenzaldehyde (446-52-6) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In water at 189℃; for 24h;	64%

dimethyl sulfoxide (67-68-5) + 2-nitro-benzaldehyde (552-89-6) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In water at 189℃; for 15h;	56%

2-(Methylthio)thiobenzoesaeure-S-mesitylester (77418-23-6) → 2.2'-Bis(methylthio)benzil (53271-52-6) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) + bis(2,4,6-trimethylphenyl)disulfide (1483-92-7)

Conditions	Yield
In benzene at 20℃; for 70h; Irradiation;	A 22% B 11% C 41%

<2-methylthio-α-oxo-phenylmethan>-diphenylphosphin (75087-02-4) → 2-(methylsulfanyl)benzaldehyde (7022-45-9) + <2-Methylthio-α-hydroxyphenylmethan>-diphenyl-phosphinoxid (75087-03-5)

Conditions	Yield
In benzene at 22℃; for 120h; Irradiation;	A 16% B 14%

2-Methylthiobenzoesaeuremesitylester (77408-42-5) → 2.2'-Bis(methylthio)benzil (53271-52-6) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) + 2-Methylthio-2'.4'.6'-trimethyl-biphenyl

Conditions	Yield
In benzene at 20℃; for 77h; Irradiation;	A 9% B 7% C 5%

N'-p-Toluolsulfonyl-N-<2-methylmercapto-benzoyl>-hydrazin (92580-60-4) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
With sodium carbonate In ethylene glycol at 160℃;
With sodium carbonate In diethylene glycol

1-chloromethyl-2-methylsulfanylbenzene (26190-68-1) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
With hexamethylenetetramine; acetic acid

2-Methylmercaptobenzoesaeure-methylanilid (7022-44-8) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran
(i) LiAlH4, THF, (ii) aq. HCl; Multistep reaction;

Dimethyldisulphide (624-92-0) + 1,3-dimethyl-2-phenylimidazolidine (23229-37-0) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
Yield given. Multistep reaction;

Dimethyldisulphide (624-92-0) + 1,3-dimethyl-2-phenylimidazolidine (23229-37-0) → 2-(methylsulfanyl)benzaldehyde (7022-45-9) + 1-(Bis-methylsulfanyl-methyl)-2-methylsulfanyl-benzene

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

C8H10OS*C5H5N*Br3H → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
In acetic acid at 19.9℃; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), ΔG(excit.), var. temp.;

2-(Methylsulfinyl)thiobenzoesaeure-S-mesitylester (77408-41-4) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2 percent / benzene / 70 h / 20 °C / Irradiation 2: 11 percent / benzene / 70 h / 20 °C / Irradiation View Scheme

2-methylsulfanyl-benzoyl chloride (1442-03-1) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / toluene / 2 h / Heating 2: 7 percent / benzene / 77 h / 20 °C / Irradiation View Scheme
Multi-step reaction with 2 steps 1: 42 percent / toluene / 2 h / Heating 2: 11 percent / benzene / 70 h / 20 °C / Irradiation View Scheme
Multi-step reaction with 2 steps 1: 40 percent / diethyl ether 2: 16 percent / benzene / 120 h / 22 °C / Irradiation View Scheme
Multi-step reaction with 2 steps 1: aq. NaOH / dioxane 2: LiAlH4 / tetrahydrofuran View Scheme

ethyl 2-(methylthio)benzoate (1442-00-8) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 / tetrahydrofuran 2: SOCl2 / benzene 3: hexamethylenetetramine, aq. AcOH View Scheme

anthranilic acid (118-92-3) + deuterium oxide → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: (i) (diazotization), (ii) aq. Na2S2, (iii) aq. Na2S2O4,(iv) (methylation) 2: (i) SOCl2, (ii) /BRN= 1718733/ 3: LiAlH4 / tetrahydrofuran 4: SOCl2 / benzene 5: hexamethylenetetramine, aq. AcOH View Scheme

2-(methylthio)benzoic acid (3724-10-5) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: (i) SOCl2, (ii) /BRN= 1718733/ 2: LiAlH4 / tetrahydrofuran 3: SOCl2 / benzene 4: hexamethylenetetramine, aq. AcOH View Scheme
Multi-step reaction with 2 steps 1: (i) SOCl2, benzene, (ii) /BRN= 741982/ 2: (i) LiAlH4, THF, (ii) aq. HCl View Scheme
Multi-step reaction with 3 steps 1: SOCl2 2: aq. NaOH / dioxane 3: LiAlH4 / tetrahydrofuran View Scheme

2-methylthiobenzohydrazide (885949-42-8) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Py 2: Na2CO3 / ethane-1,2-diol / 160 °C View Scheme

[Rh(mer-κ3-DPEphos)(H)(C(O)C6H4SMe)][CB11H12] + 2-(methylthio)cyclohex-1-ene-1-carbaldehyde (49571-45-1) → 2-(methylsulfanyl)benzaldehyde (7022-45-9) + [Rh(mer-κ3-DPEphos)(H)(C(O)C6H8SMe)][CB11H12]

Conditions	Yield
at 24.84℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Glovebox;

sodium thiomethoxide (5188-07-8) + 2-halidebenzaldehyde → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
In N,N-dimethyl-formamide

methyl 2-(methylthio)benzoate (3704-28-7) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C 2: pyridinium chlorochromate / dichloromethane / 12 h / 0 - 20 °C View Scheme

2-(methylsulfanyl)benzaldehyde (7022-45-9) → 2-(methylsulfinyl)benzaldehyde (62351-49-9)

Conditions	Yield
With C42H70O35*Br3Fe; ferric nitrate In acetonitrile at 20℃; for 3h; chemoselective reaction;	100%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃;	89%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃;	89%

2-(methylsulfanyl)benzaldehyde (7022-45-9) + (1R,2R)-1,2-diaminocyclohexane (20439-47-8) → (1R,2R)-N,N'-bis[(2-(methylthio)benzylidene)]-1,2-cyclohexanediamine (1383610-91-0)

Conditions	Yield
In ethanol at 80℃;	100%

2-(methylsulfanyl)benzaldehyde (7022-45-9) + 3,4-dichloro-benzeneacetonitrile (3218-49-3) → 3-amino-2-(3,4-dichlorophenyl)-1-(2-(methylthio)phenyl)propan-1-ol

Conditions	Yield
Stage #1: 3,4-dichloro-benzeneacetonitrile With n-butyllithium In tetrahydrofuran at -75℃; for 0.333333h; Stage #2: 2-(methylsulfanyl)benzaldehyde In tetrahydrofuran at -75℃; for 0.5h; Stage #3: With borane-THF In tetrahydrofuran at -75℃; Temperature; Reflux;	100%

2-(methylsulfanyl)benzaldehyde (7022-45-9) + 4-methoxy-aniline (104-94-9) → (E)-N-(4-methoxyphenyl)-1-(2-(methylthio)phenyl)methanimine

Conditions	Yield
In dichloromethane at 20℃; for 18h; Inert atmosphere; Molecular sieve;	100%

1,1-pentamethylene-1,2-nonadiene (1173936-61-2) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) → 2-(cyclohexylidenemethyl)-1-(2-(methylthio)phenyl)octan-1-one (1173936-88-3)

Conditions	Yield
With [Rh(dppe)]ClO4 In acetone at 55℃; Inert atmosphere; regioselective reaction;	99%

C13H18O (1173936-62-3) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) → (E)-2-(2-(furan-2-yl)vinyl)-1-(2-(methylthio)phenyl)octan-1-one (1173936-89-4)

Conditions	Yield
With [Rh(dppe)]ClO4 In acetone at 55℃; Inert atmosphere; regioselective reaction;	99%

C13H18S (1173936-63-4) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) → (E)-1-(2-(methylthio)phenyl)-2-(2-(thiophen-2-yl)vinyl)octan-1-one (1173936-90-7)

Conditions	Yield
With [Rh(dppe)]ClO4 In acetone at 55℃; Inert atmosphere; regioselective reaction;	99%

2-(methylsulfanyl)benzaldehyde (7022-45-9) + (4-methylpenta-1,2-dien-1-yl)benzene (141821-03-6) → (E)-2-isopropyl-1-(2-(methylthio)phenyl)-4-phenylbut-3-en-1-one (1173936-86-1)

Conditions	Yield
With [Rh(dppe)]ClO4 In acetone at 55℃; Inert atmosphere; regioselective reaction;	99%

2-(methylsulfanyl)benzaldehyde (7022-45-9) + buta-1,2-diene-1,4-diyldibenzene (141821-06-9) → (E)-2-benzyl-1-(2-(methylthio)phenyl)-4-phenylbut-3-en-1-one (1173936-85-0)

Conditions	Yield
With [Rh(dppe)]ClO4 In acetone at 55℃; Inert atmosphere; regioselective reaction;	99%

2-(methylsulfanyl)benzaldehyde (7022-45-9) + [Rh(bis(di-tert-butylphosphino)methane)(cyclooctene)(NCCH2BF3)] (1362860-09-0) + acetone (67-64-1) → [Rh(bis(di-tert-butylphosphino)methane)(hydrido)(κ2-(S,C)-2-SMe-C6H4CO)(NCCH2BF3)]

Conditions	Yield
In acetone	99%

(4-bromo-2-ethynylphenyl)carbamic acid 1,1-dimethylethyl ester (1038779-13-3) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) → tert-butyl (E)-(4-bromo-2-(3-(2-(methylthio)phenyl)-3-oxoprop-1-en-1-yl)phenyl)carbamate

Conditions	Yield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; bis(dicyclohexylphosphino)methane In acetone at 20℃; for 0.333333h; Inert atmosphere;	99%

2-(methylsulfanyl)benzaldehyde (7022-45-9) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C14H21BO3S

Conditions	Yield
With C28H26FeN2S4 In benzene-d6 at 20℃; for 0.5h;	99%
With [CoCl2(4'-(4-pyridyl)-2,2':6',2''-terpyridine)]·2H2O; potassium tert-butylate In tetrahydrofuran at 25℃; for 16h; Inert atmosphere; Glovebox;	95 %Chromat.
With two-dimensional iron(II) coordination polymer based on a divergent 4'-(4-diphenylamino)phenyl-4,2';6',4''-terpyridine ligand; potassium tert-butylate In neat (no solvent) at 20℃; for 0.5h; Green chemistry; chemoselective reaction;	88 %Chromat.
With potassium tert-butylate; Mn(2+)*C20H14N4*2Cl(1-) In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; Glovebox;
With 0.55C27H43N3Si3V*0.45C27H44N3Si3V In diethyl ether at 20℃; for 2h; Inert atmosphere; Glovebox; Schlenk technique; chemoselective reaction;

2-(methylsulfanyl)benzaldehyde (7022-45-9) + 2-ethynyl-6-methoxynaphthalene (129113-00-4) → C21H18O2S

Conditions	Yield
Stage #1: 2-ethynyl-6-methoxynaphthalene With n-butyllithium In tetrahydrofuran Stage #2: 2-(methylsulfanyl)benzaldehyde In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;	99%

2-(methylsulfanyl)benzaldehyde (7022-45-9) + 4-trifluoromethylphenylacetylene (705-31-7) → C17H13F3OS

Conditions	Yield
Stage #1: 4-trifluoromethylphenylacetylene With n-butyllithium In tetrahydrofuran Stage #2: 2-(methylsulfanyl)benzaldehyde In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;	99%

2-(methylsulfanyl)benzaldehyde (7022-45-9) + acetylenemagnesium bromide (4301-14-8) → C10H10OS

Conditions	Yield
In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;	99%

2-tert-butyl-5-methoxy-phenylamine (478701-44-9) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) → (2-tert-butyl-5-methoxy-phenyl)-(2-thiomethyl-benzylidene)-amine

Conditions	Yield
In toluene Heating;	98%

2-(methylsulfanyl)benzaldehyde (7022-45-9) + 2-(1,1-dimethylethyl)-benzenamine (6310-21-0) → (2-tert-butylphenyl)-(2-thiomethyl-benzylidene)-amine (958877-81-1)

Conditions	Yield
In toluene Heating;	98%

oct-1-ene (111-66-0) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) → 1-(2-(methylthio)phenyl)nonan-1-one (1085561-73-4)

Conditions	Yield
With C21H44N2P2Rh*C32H12BF24 In acetone at 55℃; for 3h; Inert atmosphere;	98%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; silver perchlorate; bis[2-(diphenylphosphino)phenyl] ether In acetone at 55℃; for 24h; Inert atmosphere;	73%
With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (11aR)-(+)-10,11,12,13-tetrahydrodiindeno[7,1-de:1', 7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine In 1,2-dichloro-ethane at 70℃; for 72h; Inert atmosphere;	48%
With [Rh(η6-C6H5F)(bis(dicyclohexylphosphino)methane)][B(C6H3-3,5-(CF3)2)4] In 1,2-dichloro-ethane at 80℃; for 2h; Inert atmosphere;
With C29H39FO2P2Rh(1+)*C32H12BF24(1-) In acetone at 24.84℃; for 0.0833333h; Reagent/catalyst;

C11H20 (1173936-60-1) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) → (E)-2-(3-methylbut-1-enyl)-1-(2-(methylthio)phenyl)heptan-1-one (1173936-82-7)

Conditions	Yield
With [Rh(dppe)]ClO4 In acetone at 55℃; Inert atmosphere; regioselective reaction;	98%

N-methylmaleimide (930-88-1) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) → 1-methyl-3-(2-(methylthio)benzoyl)pyrrolidine-2,5-dione (1362860-36-3)

Conditions	Yield
With C29H39FO2P2Rh(1+)*C32H12BF24(1-) In acetone at 55℃; for 3h; Inert atmosphere; Glovebox;	98%
With C29H52N2P2Rh*C32H12BF24 In acetone at 55℃; for 3h; Inert atmosphere;	81%

(2-propenyl)propanedioic acid diethyl ester (2049-80-1) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) → 1,3-diethyl 2-(4-(2-(methylthio)phenyl)-4-oxobutyl)malonate (1362860-33-0)

Conditions	Yield
With C21H44N2P2Rh*C32H12BF24 In acetone at 55℃; for 3h; Inert atmosphere;	98%
With [Rh(η6-C6H5F)(bis(dicyclohexylphosphino)methane)][B(C6H3-3,5-(CF3)2)4] In 1,2-dichloro-ethane at 80℃; for 2h; Inert atmosphere;

2-(methylsulfanyl)benzaldehyde (7022-45-9) + tert-butyl (5-chloro-2-ethynylphenyl)carbamate → tert-butyl (E)-(5-chloro-2-(3-(2-(methylthio)phenyl)-3-oxoprop-1-en-1-yl)phenyl)carbamate

Conditions	Yield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; bis(dicyclohexylphosphino)methane In acetone at 20℃; for 2h; Inert atmosphere;	98%

2-(methylsulfanyl)benzaldehyde (7022-45-9) + tert-butyl (4-acetyl-2-ethynylphenyl)carbamate → tert-butyl (E)-(4-acetyl-2-(3-(2-(methylthio)phenyl)-3-oxoprop-1-en-1-yl)phenyl)carbamate

Conditions	Yield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; bis(dicyclohexylphosphino)methane In acetone at 20℃; for 0.5h; Inert atmosphere;	98%

2-(methylsulfanyl)benzaldehyde (7022-45-9) + tert-butyl (2-ethynyl-4-nitrophenyl)carbamate → tert-butyl (E)-(2-(3-(2-(methylthio)phenyl)-3-oxoprop-1-en-1-yl)-4-nitrophenyl)carbamate

Conditions	Yield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; bis(dicyclohexylphosphino)methane In acetone at 20℃; for 0.333333h; Inert atmosphere;	98%

2-(methylsulfanyl)benzaldehyde (7022-45-9) + ethylenediamine (107-15-3) → N,N-bis[(2-methylthio)phenylmethylene]-1,2-ethanediamine (90148-99-5)

Conditions	Yield
In acetonitrile	97%
In ethanol at 80℃; Inert atmosphere;

2-ethynyl-1-nitrobenzene (16433-96-8) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) → (E)-3-(4-methoxy-2-nitrophenyl)-1-(2-(methylthio)phenyl)prop-2-en-1-one

Conditions	Yield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; bis(dicyclohexylphosphino)methane In acetone at 55℃; for 0.25h; Inert atmosphere;	97%

1-ethynyl-4-methoxy-2-nitrobenzene (889134-73-0) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) → (E)-3-(4-methoxy-2-nitrophenyl)-1-(2-(methylthio)phenyl)prop-2-en-1-one

Conditions	Yield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; bis(dicyclohexylphosphino)methane In acetone at 55℃; for 0.333333h; Inert atmosphere;	97%

2-(methylsulfanyl)benzaldehyde (7022-45-9) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → o-Methylthio-zimtsaeure-aethylester (26833-02-3)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 12h;	97%

3-Aethyl-1.1-diphenylallen (33863-95-5) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) → 2-ethyl-1-(2-(methylthio)phenyl)-4,4-diphenylbut-3-en-1-one (1173936-87-2)

Conditions	Yield
With [Rh(dppe)]ClO4 In acetone at 55℃; Inert atmosphere; regioselective reaction;	96%

3-ethynylthiophene (67237-53-0) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) → (E)-1-(2-(methylthio)phenyl)-3-(thiophen-3-yl)prop-2-en-1-one (1311381-67-5)

Conditions	Yield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; 1,2-bis-(dicyclohexylphosphino)ethane In acetone at 20℃; for 2h; Inert atmosphere; regioselective reaction;	96%

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 5188-07-8 sodium thiomethoxide 
• 77408-41-4 2-(Methylsulfinyl)thiobenzoesaeure-S-mesitylester 
• 1442-03-1 2-methylsulfanyl-benzoyl chloride 
• 118-92-3 anthranilic acid 
• 446-52-6 2-Fluorobenzaldehyde 
• 3704-28-7 methyl 2-(methylthio)benzoate 
• 67-68-5 dimethyl sulfoxide 
• 552-89-6 2-nitro-benzaldehyde 
• 49571-45-1 2-(methylthio)cyclohex-1-ene-1-carbaldehyde 
• 74-93-1 methylthiol 
• 885949-42-8 2-methylthiobenzohydrazide 
• 3724-10-5 2-(methylthio)benzoic acid 
• 1442-00-8 ethyl 2-(methylthio)benzoate 

Downstream Products

• 70401-49-9 o-(methylthio)benzaldehyde p-tosylhydrazone 
• 118468-19-2 2-(2-methylthiophenyl)ethylamine 
• 141463-67-4 2-Chloro-N-[2-(2-methylsulfanyl-phenyl)-ethyl]-acetamide 
• 2634-33-5 1,2-benzisothiazolin-3-one 
• 30439-34-0 1-(methylsulfanyl)-2-vinylbenzene 
• 1085561-72-3 (E)-2-methyl-1-(2-(methylthio)phenyl)-3-phenylprop-2-en-1-one 
• 1085561-73-4 1-(2-(methylthio)phenyl)nonan-1-one 
• 1085561-71-2 (E)-6-chloro-1-(2-(methylthio)phenyl)hex-2-en-1-one 
• 1085561-70-1 methyl 4-(2-(methylthio)phenyl)-4-oxobutanoate 
• 1173936-82-7 (E)-2-(3-methylbut-1-enyl)-1-(2-(methylthio)phenyl)heptan-1-one 
• 1173936-88-3 2-(cyclohexylidenemethyl)-1-(2-(methylthio)phenyl)octan-1-one 
• 1173936-89-4 (E)-2-(2-(furan-2-yl)vinyl)-1-(2-(methylthio)phenyl)octan-1-one 
• 1173936-90-7 (E)-1-(2-(methylthio)phenyl)-2-(2-(thiophen-2-yl)vinyl)octan-1-one 
• 1173936-87-2 2-ethyl-1-(2-(methylthio)phenyl)-4,4-diphenylbut-3-en-1-one 

Relevant articles and documents

Rhodium(III)-Catalyzed Aldehyde C?H Activation and Functionalization with Dioxazolones: An Entry to Imide Synthesis

A rhodium(III)-based catalytic system has been used to develop a C?H bond activation of benzaldehyde derivatives and subsequent functionalization with dioxazolones in order to afford imides. The importance of the nature of the directing group to perform selectively the aldehydic C?H bond activation has been highlighted. The scope investigation showed that this transformation could be applied to various dioxazolones and many benzaldehyde derivatives as well as an acrolein derivative. Derivatization reactions of the imide products demonstrated the synthetic utility of this rhodium-catalyzed aldehydic C?H amidation.

Unexpected formation of 4,7-dihalobenzo[b]thiophenes using Ohira-Bestmann reagent and reactivity of the halogen-substituted benzo[b]thiophenes in Suzuki-Miyaura coupling with phenylboronic acid

Reaction of 2-(1-adamantylsulfanyl)-3,6-dihalobenzaldehydes with Ohira-Bestmann reagent gave 4,7-dihalobenzo[b]thiophenes along with normal alkyne products. Nine types of 4,7-dihalobenzo[b]thiophenes bearing chlorine, bromine, or iodine atoms, were prepared by this method. Regioselectivity in Suzuki-Miyaura cross coupling reactions of the 4,7-dihalobenzo[b]thiophenes with PhB(OH)2 was also studied.

A convenient method for the synthesis of aryl methyl sulfides via Cu(I)-mediated methylthiolation of haloarenes with DMSO

An efficient process for the Cu(I)-mediated methylthiolation of haloarenes using simple and readily available DMSO as a convenient and environment friendly source of SMe moiety has been developed. In the presence of CuI and DABCO, a variety of aryl/heteroaryl halides reacted with DMSO to afford corresponding aryl methyl sulfides in good to excellent yields.