106-45-6

Basic information

• Product Name: p-Toluenethiol
• Synonyms: p-Toluenethiol(7CI,8CI);1-Mercapto-4-methylbenzene;4-Mercaptotoluene;4-Methyl-1-thiophenol;4-Methylbenzenethiol;4-Methylphenyl mercaptan;4-Methylphenylthiol;4-Methylthiophenol;4-Thiocresol;4-Toluenethiol;NSC2227;NSC 229565;p-Mercaptotoluene;p-Methylbenzenethiol;p-Methylbenzenthiol;p-Methylphenyl mercaptan;p-Methylphenylthiol;p-Methylthiophenol;p-Thiocresol;p-Tolyl mercaptan;p-Tolylthiol;Benzenethiol, 4-methyl-
• CAS NO: 106-45-6
• Molecular Formula: C₇H₈S
• Molecular Weight: 123.196
• EINECS: 203-399-1
• Product Categories: Intermediates;Phenol&Thiophenol&Mercaptan
• Mol File: 106-45-6.mol
• Article Data: 211

Chemical Properties

• Melting Point: 40-44℃
• Boiling Point: 195 °C at 760 mmHg
• Flash Point: 69.5 °C
• Appearance: White or colorless solid melt
• Density: 1.049 g/cm³
• Vapor Density: 6.2 (vs air)
• Vapor Pressure: 0.601mmHg at 25°C
• Refractive Index: 1.5420 (estimate)
• Storage Temp.: Store at RT.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: pK1:6.52 (25°C)
• Water Solubility: slightly soluble
• Stability: Smelly, Air Sensitive
• Merck: 14,9325
• BRN: 605761
• CAS DataBase Reference: p-Toluenethiol(CAS DataBase Reference)
• NIST Chemistry Reference: p-Toluenethiol(106-45-6)
• EPA Substance Registry System: p-Toluenethiol(106-45-6)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:; R36/37/38:
• Safety Statements: S26:; S36/37/39:
• RIDADR: 2811
• WGK Germany: 3
• RTECS: XT8925000
• F: 13
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 106-45-6(Hazardous Substances Data)

Usage

Chemical Properties

White or colorless solid melt

Uses

p-Thiocresol is used as a pharmaceutical intermediate.

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 1235, 1980 DOI: 10.1016/S0040-4039(00)71380-3

Safety Profile

Poison by intraperitoneal route. A flammable liquid. When heated to decomposition it emits toxic fumes of SOx. See also a- TOLUENETHIOL and MERCAPTANS.

Purification Methods

Crystallise the thiol from pet ether (b 40-70o). The 2,4-dinitrophenyl thioether has m 103o (from EtOH), and the 2,4-dinitrophenyl sulfone has m 190o (from EtOH). [Beilstein 6 IV 2153.]

InChI:InChI=1/C7H8S/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3/p-1

Synthetic route

4-tolyl iodide (624-31-7) → para-thiocresol (106-45-6)

Conditions	Yield
With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 90℃; for 20h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;	99%
With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 90℃; for 20h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	97%
With sodiumsulfide nonahydrate; copper; ethane-1,2-dithiol In dimethyl sulfoxide at 100℃; for 20h; Inert atmosphere; Sealed tube;	97%

p-toluenesulfonyl chloride (98-59-9) → para-thiocresol (106-45-6)

Conditions	Yield
With potassium sulfide; acetic acid; triphenylphosphine; zinc In chloroform; water at 60℃; for 0.5h; Solvent; Reagent/catalyst;	97.5%
With ISOPROPYLAMIDE; dimethylsilicon dichloride; zinc In 1,2-dichloro-ethane at 75℃; for 1.5h;	96%
With formic acid; 6% Pd/C; triphenylphosphine at 60℃; for 8h;	92%

di(p-tolyl) disulfide (103-19-5) → para-thiocresol (106-45-6)

Conditions	Yield
With indium; ammonium chloride In ethanol for 1h; Reduction; Heating;	96%
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 35℃; for 0.25h; Reduction;	95%
With ammonia; aluminium; sodium chloride at 25℃; for 1h;	94%

1-pentyl tosylate (4450-76-4) → amyl iodide (628-17-1) + para-thiocresol (106-45-6)

Conditions	Yield
With iodine; triphenylphosphine In benzene for 0.166667h; Heating;	A 90% B 95%

(4-methylpyridyl)(4-methylphenyl)sulfide (128916-30-3) → para-thiocresol (106-45-6)

Conditions	Yield
With magnesium In methanol at 20℃; for 4h;	92%

4-methylphenyl methylsulfide (623-13-2) → para-thiocresol (106-45-6)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; diethylamine In xylene for 6h; Heating;	90%
With sodium methylselenide In N,N-dimethyl-formamide for 8h; Heating;	55%

di(p-tolyl) disulfide (103-19-5) + toluene-4-sulfonic acid (104-15-4) + triphenylphosphine (603-35-0) → para-thiocresol (106-45-6) + Triphenylphosphine oxide (791-28-6)

Conditions	Yield
In benzene for 23.5h; Product distribution; Mechanism; Heating; further reaction partners - various diaryl disulfides, diphenyl diselenide, tetrabutylammonium iodide, tributylphosphine;	A 90% B 90%

sodium 4-methylbenzenesulfinate (824-79-3) → para-thiocresol (106-45-6)

Conditions	Yield
With iodine; triphenylphosphine In 1,4-dioxane; benzene for 2h; Heating;	88%
With hydrogenchloride; tin In water for 24h; Heating;	81%
Multi-step reaction with 2 steps 1: iodine; triphenylphosphine / ethanol / 2 h / Reflux; Green chemistry 2: indole; iodine; triphenylphosphine / ethanol / 2 h / Reflux; Green chemistry View Scheme
Multi-step reaction with 2 steps 1: sulfur dioxide / water / 9.5 h / 110 °C / Inert atmosphere 2: sodium tetrahydroborate; sodium hydroxide / water; tetrahydrofuran / 3 h / 65 - 67 °C / Inert atmosphere View Scheme

toluene-4-sulfonic acid (104-15-4) → para-thiocresol (106-45-6)

Conditions	Yield
With 6% Pd/C; iodine; triphenylphosphine; isopropyl alcohol for 6h; Reflux;	88%
With triphenylphosphine; iodine In benzene for 2.5h; Heating;	89 % Chromat.
With diphosphorus pentasulfide; lithium aluminium tetrahydride 1.) sulfolane, 90 deg C for 24 h 2.) ether, room temperature for 30 min; Yield given. Multistep reaction;

3,5-diphenyl-5-(p-tolylthio)oxazolidine-2,4-dione → 2-oxo-N,2-diphenylacetamide (4732-66-5) + para-thiocresol (106-45-6)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane Schlenk technique; Inert atmosphere;	A 83% B 75%

para-chlorotoluene (106-43-4) → para-thiocresol (106-45-6)

Conditions	Yield
Stage #1: para-chlorotoluene With water; palladium diacetate; caesium carbonate; sodium thiosulfate; XPhos In toluene; tert-butyl alcohol at 80℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride; zinc In water for 1h; Cooling with ice;	82%
With sodium hydroxide; 1-thiopropane 1) N-methyl-2-pyrrolidone, removal of water by toluene reflux, 2) reflux (ca. 186 deg C), 20 h; other reagent: n-butyl mercaptan; Yield given. Multistep reaction;
With pumice stone; hydrogen sulfide; thorium dioxide at 700℃;
With hydrogen sulfide at 700℃;

para-bromotoluene (106-38-7) → para-thiocresol (106-45-6)

Conditions	Yield
Stage #1: para-bromotoluene With water; caesium carbonate; sodium thiosulfate; bis(dibenzylideneacetone)-palladium(0); XPhos In toluene; tert-butyl alcohol at 80℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride; zinc In water for 1h; Cooling with ice;	81%
With sodium thiomethoxide In N,N-dimethyl acetamide at 150℃;
With sodiumsulfide nonahydrate; copper; ethane-1,2-dithiol In dimethyl sulfoxide at 100℃; for 20h; Inert atmosphere; Green chemistry;	14 %Chromat.

4-methylphenylboronic acid (5720-05-8) → para-thiocresol (106-45-6)

Conditions	Yield
Stage #1: 4-methylphenylboronic acid With copper (II)-fluoride; sulfur In dimethyl sulfoxide at 100℃; for 12h; Chan-Lam Coupling; Inert atmosphere; Stage #2: With sodium tetrahydroborate In dimethyl sulfoxide at 40℃; for 5h; Inert atmosphere;	79%

p-toluenesulfonic acid monohydrate (6192-52-5) + trifluoroacetic anhydride (407-25-0) → S-(trifluoroacetyl)-p-methylthiophenol (75072-07-0) + para-thiocresol (106-45-6)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In dichloromethane for 20h; Product distribution; Ambient temperature;	A 78% B 11%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide 1.) CH2Cl2, 20h, room temp.; 2.) MeOH, 30 min, room temp.; Yield given. Multistep reaction. Further byproducts given;
With sodium hydroxide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; tetra-(n-butyl)ammonium iodide 1.) CH2Cl2, 20h, room temp.; 2.) 0 deg C; Yield given. Multistep reaction. Further byproducts given;

1-<α-(p-tolylsulfonyl)ethyl>-4-methoxybenzene (122948-71-4) + methylmagnesium bromide (75-16-1) → (4,4'-dimethyl-1,1'-biphenyl) (613-33-2) + 4-Methylbiphenyl (644-08-6) + 4-methylphenyl methylsulfide (623-13-2) + 1-isopropenyl-4-methoxybenzene (1712-69-2) + 1-methoxy-4-(1-methylethyl)benzene (4132-48-3) + para-thiocresol (106-45-6)

Conditions	Yield
With bis(triphenylphosphine)nickel(II) diiodide; tricyclohexylphosphine; phenylboronic acid In tetrahydrofuran at 70℃; Kumada Cross-Coupling; Inert atmosphere;	A 11% B 31% C 12% D 78% E 10% F 7%

toluene-4-sulfonamide (70-55-3) → para-thiocresol (106-45-6)

Conditions	Yield
With ammonium formate at 100 - 200℃; for 7h; neat (no solvent);	77%
With phosphorus; phosphoric acid; potassium iodide
With phosphonium iodide; hydrogen iodide at 75 - 100℃;
With diphosphorus pentasulfide; lithium aluminium tetrahydride 1.) sulfolane, 90 deg C for 60 h 2.) ether, room temperature for 30 min; Yield given. Multistep reaction;

1-phenyl-2-(p-tolylthio)ethanone (33046-45-6) → di(p-tolyl) disulfide (103-19-5) + para-thiocresol (106-45-6) + acetophenone (98-86-2)

Conditions	Yield
With electrolysis on Pt electrode In acetonitrile Product distribution; other electrode (Hg), other solvent (aq. ethanol), influence of phenol;	A n/a B n/a C 72%

3-[(4-methylphenyl)sulfanyl]-1-propanol (3147-28-2) → di(p-tolyl) disulfide (103-19-5) + 4-methylphenyl propyl sulfide (24599-52-8) + para-thiocresol (106-45-6)

Conditions	Yield
PPA In carbon disulfide for 40h; Ambient temperature;	A 72% B 21% C 4%

sodium tosylate (657-84-1) → di(p-tolyl) disulfide (103-19-5) + para-thiocresol (106-45-6)

Conditions	Yield
With sulfuric acid; triphenylphosphine In water at 20℃; for 10h;	A 30% B 68%

p-toluenesulfonyl chloride (98-59-9) → di(p-tolyl) disulfide (103-19-5) + para-thiocresol (106-45-6)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran for 4h; Heating;	A 60.2% B 27%
With sodium tetrahydroborate In tetrahydrofuran for 2h; Heating;	A 30.9% B 27%
With sodium tetrahydroborate In tetrahydrofuran Product distribution; Heating; effect of reaction time;
With water; triphenylphosphine In tetrahydrofuran at 20℃;

γ-chloropropyl 4-methylphenyl sulphide (3147-30-6) → 6-Methyl-3,4-dihydro-2H-1-benzothiopyran (71153-74-7) + 4-methylphenyl propyl sulfide (24599-52-8) + para-thiocresol (106-45-6)

Conditions	Yield
aluminium trichloride In carbon disulfide for 3h; Heating;	A 60% B 15% C 9%

p-Tolyl-thionitrit (64732-71-4) + methyllithium (917-54-4) → 4-methylphenyl methylsulfide (623-13-2) + di(p-tolyl) disulfide (103-19-5) + para-thiocresol (106-45-6)

Conditions	Yield
In diethyl ether at -70℃; for 0.05h;	A 57% B n/a C n/a

p-Tolyl-thionitrit (64732-71-4) + phenylmagnesium bromide → di(p-tolyl) disulfide (103-19-5) + 4-tolyl phenyl sulfide (3699-01-2) + para-thiocresol (106-45-6)

Conditions	Yield
In diethyl ether at -70℃; for 0.05h;	A n/a B 57% C n/a

2-(p-tolylthio)-ethanol (13290-16-9) → di(p-tolyl) disulfide (103-19-5) + p-methyl-2-phenylethyl chloride (32327-68-7) + 1,2-bis(p-tolylthio)ethane (3238-95-7) + para-thiocresol (106-45-6)

Conditions	Yield
aluminium trichloride; nitromethane In carbon disulfide for 40h; Ambient temperature;	A 2.1% B 54% C 43% D 0.3%

4-(phenyldisulfanyl)toluene (29627-34-7) + diphenyldisulfane (882-33-7) → para-thiocresol (106-45-6)

Conditions	Yield
With triphenylphosphine In 1,4-dioxane; water	53%

sodium tosylate (657-84-1) → para-thiocresol (106-45-6)

Conditions	Yield
With 18-crown-6 ether; iodine; triphenylphosphine In benzene for 5h; Heating;	50%
With triphenylphosphine; 18-crown-6 ether; iodine In benzene for 30.5h; Heating;	85 % Chromat.
With diphosphorus pentasulfide; lithium aluminium tetrahydride 1.) sulfolane, 90 deg C for 24 h 2.) ether, room temperature for 30 min; Yield given. Multistep reaction;

N-(4-methylphenylthiomethyl)benzamide (103603-53-8) → benzonitrile (100-47-0) + 2-phenyl-6-methyl-4H-1,3-benzothiazine (124778-69-4) + para-thiocresol (106-45-6) + 2,8-dimethyl-6H,12H-dibenzo<1,5>dithiocin

Conditions	Yield
With trichlorophosphate for 1h; Heating;	A 49% B 9.8% C 16% D 11%

4-(phenyldisulfanyl)toluene (29627-34-7) + diphenyldisulfane (882-33-7) → phenyl toluene-4-thiosulfonate (3541-14-8) + para-thiocresol (106-45-6)

Conditions	Yield
With PPE	A 4% B 46%

3-[(4-methylphenyl)sulfanyl]-1-propanol (3147-28-2) → ethyl p-tolyl sulfide (622-63-9) + di(p-tolyl) disulfide (103-19-5) + para-thiocresol (106-45-6) + 4-Methyl-2-propyl-1-p-tolyldisulfanyl-benzene

Conditions	Yield
sulfuric acid In carbon disulfide for 40h; Ambient temperature;	A 4% B 45% C 3% D 42%
sulfuric acid In carbon disulfide for 40h; Product distribution; Ambient temperature; further catalysts;	A 4% B 45% C 3% D 42%
sulfuric acid In carbon disulfide for 40h; Ambient temperature;	A 4% B 45% C 3% D 42%

sodium tosylate (657-84-1) + trifluoroacetic anhydride (407-25-0) → S-(trifluoroacetyl)-p-methylthiophenol (75072-07-0) + para-thiocresol (106-45-6)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In dichloromethane for 19h; Product distribution; Ambient temperature;	A 44% B 26%
With sodium hydroxide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; tetra-(n-butyl)ammonium iodide 1.) CH2Cl2, 22h, room temp.; 2.) 0 deg C; Yield given. Multistep reaction. Further byproducts given;

allyl bromide (106-95-6) + para-thiocresol (106-45-6) → allyl (p-tolyl)sulfide (1516-28-5)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃;	100%
Stage #1: para-thiocresol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Stage #2: allyl bromide In tetrahydrofuran; mineral oil for 0.4h;	95%
With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 4.33333h;	95%

para-thiocresol (106-45-6) → di(p-tolyl) disulfide (103-19-5)

Conditions	Yield
With bis dichromate In dichloromethane at 0 - 5℃; for 1h;	100%
With bromine; potassium hydrogencarbonate In dichloromethane	100%
With N-phenyltriazolinedione In toluene at 20℃; for 0.166667h;	100%

1,3-chlorobromopropane (109-70-6) + para-thiocresol (106-45-6) → γ-chloropropyl 4-methylphenyl sulphide (3147-30-6)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;	100%
With sodium hydroxide In ethanol at 100℃;	65%
With potassium hydroxide

methyl vinyl ketone (78-94-4) + para-thiocresol (106-45-6) → 4-(p-tolylthio)butan-2-one (6110-02-7)

Conditions	Yield
With zirconium In acetonitrile Michael Addition; Electrolysis; diastereoselective reaction;	100%
With triethylammonium acetate at 25℃; for 0.0166667h; Thia-Michael reaction; chemoselective reaction;	99%
Mg-La mixed oxides In N,N-dimethyl-formamide at 24.85℃; for 0.45h; Michael addition;	97%

(methoxycarbonyl)disulfanyl chloride (88766-29-4) + para-thiocresol (106-45-6) → Methoxycarbonyl 4-methylphenyl trisulfane (94839-62-0)

Conditions	Yield
In dichloromethane at -78℃; for 1h;	100%

4-tosylacetonitrile (16192-07-7) + para-thiocresol (106-45-6) → 3-p-tolylsulphonyl-2-p-tolylthiopropene (97479-48-6)

Conditions	Yield
With triethylamine In methanol for 1.75h; Ambient temperature;	100%
With triethylamine In benzene for 2h; Ambient temperature;	65%
With triethylamine In benzene for 18h; Ambient temperature;	55%
With triethylamine In benzene

p-toluene(N-phenylsulfonyl)iminosulfinyl chloride (33840-84-5) + para-thiocresol (106-45-6) → benzenesulfonamide (98-10-2) + di(p-tolyl) disulfide (103-19-5)

Conditions	Yield
In benzene at 20℃; for 2.5h; Mechanism;	A 100% B 95%

2,3-dicyanobenzaldehyde (129221-76-7) + para-thiocresol (106-45-6) → 3-Oxo-1-p-tolylsulfanyl-2,3-dihydro-1H-isoindole-4-carbonitrile (129221-84-7)

Conditions	Yield
With triethylamine In chloroform at 20℃; for 4h;	100%

(methoxy)diphenyl-λ6-sulfanenitrile (127022-75-7) + para-thiocresol (106-45-6) → 4-methylphenyl methylsulfide (623-13-2) + S,S-diphenylsulphoximine (22731-83-5)

Conditions	Yield
In benzene at 30℃; for 6h; Rate constant; Product distribution;	A 77% B 100%
In benzene at 30℃; for 6h; Yields of byproduct given;	A 77% B n/a

vinylidene-1,1-diphosphonic acid (34162-79-3) + para-thiocresol (106-45-6) → (1-Phosphono-2-p-tolylsulfanyl-ethyl)-phosphonic acid (87774-69-4)

Conditions	Yield
With acetic acid; triethylamine at 110℃; for 15h;	100%

p-toluene(N-benzoyl)iminosulfinyl chloride (70925-53-0) + para-thiocresol (106-45-6) → di(p-tolyl) disulfide (103-19-5) + benzamidene hydrochloride (15934-46-0)

Conditions	Yield
In benzene at 20℃; for 2.5h; Mechanism;	A 90% B 100%

para-thiocresol (106-45-6) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 1-(4-fluorophenyl)-4-(p-tolylthio)butan-1-one (132427-90-8)

Conditions	Yield
	100%
With triethylamine In tetrahydrofuran for 16h; Ambient temperature;	99%

para-thiocresol (106-45-6) → toluene-4-sulfonic acid (104-15-4)

Conditions	Yield
With dinitrogen tetraoxide In tetrachloromethane; diethyl ether for 2.5h; Ambient temperature;	100%
With dihydrogen peroxide; trichlorophosphate In water at 80℃; for 1.16667h; Micellar solution;	95%
With HOF* CH3CN In dichloromethane at 0℃;	90%
With dihydrogen peroxide; methyltrioxorhenium(VII) In acetonitrile at 20℃;	87%
Multi-step reaction with 2 steps 1: pyridine / acetonitrile / Heating 2: hydrogenchloride; water / 40 °C View Scheme

1-Bromo-3-phenylpropane (637-59-2) + para-thiocresol (106-45-6) → (3-phenylpropyl)(p-tolyl)sulfane (38644-97-2)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 12h;	100%
With potassium hydroxide
With potassium carbonate In acetone at 45℃;

D-Mannose pentaacetate (83-87-4, 604-68-2, 604-69-3, 2152-77-4, 4026-35-1, 4163-59-1, 4163-60-4, 4163-61-5, 4163-65-9, 4257-94-7, 4257-96-9, 16299-15-3, 19186-39-1, 19189-55-0, 25878-60-8, 25941-03-1, 32445-48-0, 32445-49-1, 32445-53-7, 32445-54-8, 34685-58-0, 34685-59-1, 43168-42-9, 43168-44-1, 43169-22-8, 43169-25-1, 66966-07-2, 70749-17-6, 80184-01-6, 93221-01-3, 93221-02-4, 99630-88-3, 109215-53-4, 115792-70-6, 115792-73-9, 139894-92-1, 139973-25-4, 144071-49-8, 147648-81-5) + para-thiocresol (106-45-6) → 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside (211801-79-5)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃;	100%
With trifluorormethanesulfonic acid In dichloromethane at 0℃; for 2.5h; Molecular sieve; Inert atmosphere; stereoselective reaction;	88%
With boron trifluoride diethyl etherate In dichloromethane	87%

1-iodo-2,4-dimethylbenzene (4214-28-2) + para-thiocresol (106-45-6) → (2,4‑dimethylphenyl)(4‑methylphenyl) sulfide (16704-46-4)

Conditions	Yield
With 1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2λ5,4λ5-catenadi(phosphazene); copper(I) bromide In toluene Substitution; Heating;	100%
Stage #1: para-thiocresol With potassium hydroxide In methanol at 70℃; for 0.25h; Inert atmosphere; Schlenk technique; Green chemistry; Stage #2: 1-iodo-2,4-dimethylbenzene With copper(l) iodide In methanol at 110℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;

3,5-dimethylphenyl iodide (22445-41-6) + para-thiocresol (106-45-6) → (3,5‑dimethylphenyl)(4‑methylphenyl) sulfide

Conditions	Yield
Stage #1: para-thiocresol With potassium hydroxide In methanol at 70℃; for 0.25h; Inert atmosphere; Schlenk technique; Green chemistry; Stage #2: 3,5-dimethylphenyl iodide With copper(l) iodide In methanol at 110℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;	100%
With 1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2λ5,4λ5-catenadi(phosphazene); copper(I) bromide In toluene Substitution; Heating;	92%
With copper(l) iodide; 1,10-Phenanthroline In 1-methyl-pyrrolidin-2-one; methanol at 25℃; for 36h; Inert atmosphere;	50%
With C15H16N3Ni(1+)*BF4(1-); sodium t-butanolate In acetonitrile at 100℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique;	0.20 g

sodium ethanolate (141-52-6) + ethylene dibromide (106-93-4) + para-thiocresol (106-45-6) → (2-ethoxyethyl)-para-thiocresol (57023-03-7)

Conditions	Yield
Stage #1: para-thiocresol With sodium ethanolate In ethanol at 20℃; Metallation; Stage #2: ethylene dibromide In ethanol at 20℃; Alkylation; Stage #3: sodium ethanolate In ethanol Substitution; Heating;	100%

para-thiocresol (106-45-6) + 2-chloro-ethanol (107-07-3) → (2-chloro-ethyl)-p-tolyl sulfide (20761-71-1)

Conditions	Yield
Stage #1: para-thiocresol With sodium ethanolate In ethanol at 20℃; for 0.5h; Metallation; Stage #2: 2-chloro-ethanol In ethanol for 3.5h; Alkylation; Heating; Stage #3: With hydrogenchloride In ethanol; water Chlorination; 15 h, r.t., 4.5 h, reflux;	100%

N-(2-bromo-ethyl)-ethylenediamine; dihydrobromide (23545-41-7) + para-thiocresol (106-45-6) → S-2-(2-aminoethylamino)ethyl 4-tolyl sulfide (115335-17-6)

Conditions	Yield
With triethylamine In chloroform at 0 - 5℃; for 3h;	100%

N-(2-bromo-ethyl)-butanediyldiamine; dihydrobromide (23545-43-9) + para-thiocresol (106-45-6) → S-2-(4-aminobutylamino)ethyl 4-tolyl sulfide

Conditions	Yield
With triethylamine In chloroform at 0 - 5℃; for 3h;	100%

dibromohydrate du N-(bromoethyl-2)diamino-1,3 propane (23545-42-8) + para-thiocresol (106-45-6) → S-2-(3-aminopropylamino)ethyl 4-tolyl sulfide

Conditions	Yield
With triethylamine In chloroform at 0 - 5℃; for 3h;	100%

2-phenyl-1,2-benzoisoselenazol-3(2H)-one (60940-34-3) + para-thiocresol (106-45-6) → C20H17NOSSe

Conditions	Yield
In dichloromethane at 20℃; for 1h;	100%

4-iodobenzoic acid (619-58-9) + para-thiocresol (106-45-6) → 4-[(4-methylphenyl)thio]benzamide

Conditions

Yield

Stage #1: 4-iodobenzoic acid With SPPSLRAM SynPhase Lanterns(R); 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 dichloromethane; N,N-dimethyl-formamide at 45℃; for 15h; Stage #2: para-thiocresol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h; Stage #3: With trifluoroacetic acid In dichloromethane

100%

4-iodobenzoic acid (619-58-9) + para-thiocresol (106-45-6) → 4-[(4-methylphenyl)thio]benzoic acid (22494-64-0)

Conditions	Yield
Stage #1: 4-iodobenzoic acid With dmap; SPPSLHMP SynPhase Lanterns(R); dacarbazine In dichloromethane; N,N-dimethyl-formamide at 50℃; for 15h; Stage #2: para-thiocresol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h; Stage #3: With trifluoroacetic acid In dichloromethane	100%

3-iodo-4-toluic acid (82998-57-0) + para-thiocresol (106-45-6) → 4-methyl-3-[(4-methylphenyl)thio]benzoic acid

Conditions	Yield
Stage #1: 3-iodo-4-toluic acid With dmap; SPPSLHMP SynPhase Lanterns(R); dacarbazine In dichloromethane; N,N-dimethyl-formamide at 50℃; for 15h; Stage #2: para-thiocresol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h; Stage #3: With trifluoroacetic acid In dichloromethane	100%

4-iodo-3-methylbenzoic acid (52107-87-6) + para-thiocresol (106-45-6) → 3-methyl-4-[(4-methylphenyl)thio]benzoic acid

Conditions	Yield
Stage #1: 4-iodo-3-methylbenzoic acid With dmap; SPPSLHMP SynPhase Lanterns(R); dacarbazine In dichloromethane; N,N-dimethyl-formamide at 50℃; for 15h; Stage #2: para-thiocresol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h; Stage #3: With trifluoroacetic acid In dichloromethane	100%

crotonic acid methyl ester (623-43-8) + para-thiocresol (106-45-6) → 4-(4-mercapto-phenyl)-3-methyl-butyric acid methyl ester

Conditions	Yield
With magnesium oxide In toluene at 20℃; for 0.5h; Michael addition;	100%

acrylic acid methyl ester (292638-85-8) + para-thiocresol (106-45-6) → 3-(4-methylphenylsulfanyl)propionic acid methyl ester

Conditions	Yield
With sodium acetate In tetrahydrofuran; water at 25℃; for 18h;	100%
With phosphotungstic acid In water at 20℃; for 2.5h; Michael addition;	98%
In water at 30 - 35℃; for 0.25h; thia-Michael addition;	95%

2-(4-bromophenyl)benzo[d][1,2]selenazol-3(2H)-one (944719-58-8) + para-thiocresol (106-45-6) → C20H16NOSSeBr

Conditions	Yield
In dichloromethane at 20℃; for 1h;	100%

Upstream product

• 106455-75-8 Carbamic acid, [1-(3-butenyl-4,4-d2)cyclopropyl]-, methyl ester (9CI) 
• 106455-44-1 7-({[(3S)-2,3-dihydroxy-2-(propan-2-yl)butanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizinium chloride 
• 106455-06-5 estatin A 
• 106454-69-7 N-Boc-D-Phenylalaninol 
• 106454-65-3 1S,3R,αR-DeltaMethrin 
• 106451-92-7 6-N-BIOTINYLAMINOHEXANOL 
• 106450-30-0 Bis(trimethylsilyl) 1,2-cyclohexanedicarboxylate 
• 106450-27-5 Bis(trimethylsilyl) 4-cyclohexene-1,2-dicarboxylate 
• 106450-25-3 1,11-Undecanedioic acid, di(trimethylsilyl) ester 
• 1064-50-2 trityrosine 
• 106449-56-3 2'-DEOXYISOGUANOSINE 
• 106449-21-2 methotrexate 5-aminoallyl-2'-deoxyuridine 5'-monophosphate 
• 106449-07-4 S-Bacampicillin 
• 106449-06-3 R-Bacampicillin 

Downstream Products

• 1064-56-8 4-bromo-2,5,7-trinitro-9H-fluoren-9-one - 1-(cyclohex-1-en-1-yl)naphthalene (1:1) 
• 106456-81-9 5 10 15 20-TETRAKIS(4-(ALLYLOXY)PHENYL)& 
• 106456-85-3 4-(1,3-DITHIOLAN-2-YL)BENZONITRILE 
• 106456-88-6 Benzaldehyde, 4-(5,5-dimethyl-1,3-dioxan-2-yl)- 
• 106460-50-8 4-(3,6-DIHYDROXY-10,13-DIMETHYL-2,3,6,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-17-YL)PENTANOIC ACID 
• 106461-00-1 4-[1-(4-{4-nitrophenoxy}phenyl)-1-methylethyl]phenol 
• 106461-41-0 2,4-DIHYDRO-4-[(4-(4-HYDROXYPHENYL)-1-PIPERAZINYL)PHENYL]-2-(1-METHYLPROPYL)-3H-1,2,4-TRIAZOLE-3-ONE 
• 106461-62-5 2-chloro-1-benzofuran 
• 106461-96-5 6-METHOXY-2,5,7,8-TETRAMETHYL-CHROMAN-2-CARBOXYLIC ACID 
• 106462-18-4 (R)-(-)-2,2-Dimethylcyclopropane-1-carboxamide 
• 106462-85-5 1-CHLORO-5-METHOXYISOQUINOLINE 
• 106463-17-6 Tamsulosin hydrochloride 
• 106463-19-8 (S)-Tamsulosin Hydrochloride 
• 106463-20-1 1-Allyl-3,3-diethyl-5-methyl-2,4-piperidinedione 

Recommend Products

• 56015-78-2  2-p-tolylsulfanyl-ethanethiol 
• 420-12-2  thirane 
• 25508-63-8  1-(p-tolylmercapto-methyl)-piperidine 
• 110-89-4  piperidine 
• 50-00-0  formaldehyd 
• 87184-65-4  trans-2-(p-tolylthio)cyclopentanol 
• 285-67-6  Cyclopentene oxide 
• 2943-42-2  di(4-methyl)phenylthiosulfonate 
• 110-86-1  pyridine 
• 98-59-9  p-toluenesulfonyl chloride 
• 71-43-2  benzene 
• 109845-78-5  4-methylphenyl 2-(2-pyridyl)ethyl sulfide 
• 100-69-6  2-vinylpyridine 
• 140-76-1  2-methyl-5-vinylpyridine