24653-75-6

Basic information

• Product Name: 2-Propanone, 1-mercapto-
• Synonyms: 2-Propanone, 1-mercapto-;1-sulfanylpropan-2-one
• CAS NO: 24653-75-6
• Molecular Formula: C₃H₆OS
• Molecular Weight: 90.1441
• Product Categories: thiol Flavor
• Mol File: 24653-75-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 45 °C
• Boiling Point: 133.6 ºC at 760 mmHg
• Flash Point: 34.6 ºC
• Appearance: colourless to pale yellow liquid
• Density: 1.01 g/cm³
• Vapor Pressure: 8.39mmHg at 25°C
• Refractive Index: 1.447
• PKA: 7.94±0.10(Predicted)
• CAS DataBase Reference: 2-Propanone, 1-mercapto-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propanone, 1-mercapto-(24653-75-6)
• EPA Substance Registry System: 2-Propanone, 1-mercapto-(24653-75-6)

Safety Data

• Hazardous Substances Data: 24653-75-6(Hazardous Substances Data)

Usage

Chemical Properties

1-Mercapto-2-propanone has a powerful, tenacious sweet odor. It is used in cooked pork and roast pork flavors.

Occurrence

Reported present in meat aroma model system and uncured boiled pork.

InChI:InChI=1/C3H6OS/c1-3(4)2-5/h5H,2H2,1H3

Synthetic route

chloroacetone (78-95-5) → 1-mercaptopropan-2-one (24653-75-6)

Conditions	Yield
With sodium hydrogen sulfide In ethanol; water at 10 - 20℃; for 1h;	99%
With sodium hydroxide; hydrogen sulfide for 1h;	71%
With sodium hydrogensulfide In water at 0℃; for 1h;	70%

chloroacetone (78-95-5) → 4-thiaheptane-2,6-dione (63578-76-7) + 1-mercaptopropan-2-one (24653-75-6)

Conditions	Yield
With sodium hydrogensulfide; water at 0℃;
With sodium hydrogensulfide; water at 0℃;

thietane-3-one (22131-92-6) → 1-mercaptopropan-2-one (24653-75-6)

Conditions	Yield
With sodium hydrogensulfide

O-ethyl S-2-oxopropyl carbonodithioate (49762-80-3) → 1-mercaptopropan-2-one (24653-75-6)

Conditions	Yield
With sodium hydroxide In dichloromethane at 20℃; for 0.25h;	80 mg

1-bromoacetone (598-31-2) → 1-mercaptopropan-2-one (24653-75-6)

Conditions	Yield
With hydrogen sulfide; sodium methylate In methanol

water (7732-18-5) + chloroacetone (78-95-5) + NaHS → 4-thiaheptane-2,6-dione (63578-76-7) + 1-mercaptopropan-2-one (24653-75-6)

Conditions	Yield
at 0℃;

2,5c-dimethyl-<1,4>dithiane-2r,5t-diol → 1-mercaptopropan-2-one (24653-75-6)

Conditions	Yield

thioacetylacetone (14660-20-9) → 1-mercaptopropan-2-one (24653-75-6)

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 3h; Inert atmosphere;

4-(4-bromo-2-methylbenzylidene)-1-methyl-3-(pyrimidin-4-yl)-1H-pyrazol-5(4H)-imine (1616360-22-5) + 1-mercaptopropan-2-one (24653-75-6) → C19H18BrN5S (1616360-21-4)

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile at 90℃; for 16h;	100%

1-chloronaphthalene-2-carbaldehyde (14304-75-7) + 1-mercaptopropan-2-one (24653-75-6) → acetylnaphtho[1,2-b]thiophene (51925-23-6)

Conditions	Yield
With potassium carbonate In water at 90℃; for 2h; Green chemistry;	99%

4-chloro-3-cyanonitrobenzene (16588-02-6) + 1-mercaptopropan-2-one (24653-75-6) → 2-acetyl-3-amino-5-nitrobenzothiophen (74617-23-5)

Conditions	Yield
With potassium carbonate In water at 90℃; for 2h; Green chemistry;	99%

2-chloro-3-pyridinecarbonitrile (6602-54-6) + 1-mercaptopropan-2-one (24653-75-6) → 2-acetyl-3-aminopyrido[2,3-b]thiophene (52505-41-6)

Conditions	Yield
With potassium carbonate In water at 90℃; for 2h; Green chemistry;	96%

2-Bromoacetylpyridine (40086-66-6) + 1-mercaptopropan-2-one (24653-75-6) → 1-(2-oxo-2-(pyridin-2-yl)ethylthio)propan-2-one (1440682-72-3)

Conditions	Yield
With sodium hydrogencarbonate In acetonitrile at 0℃; Inert atmosphere; Schlenk technique;	96%

1-mercaptopropan-2-one (24653-75-6) + ethyl N,N'-tetraethyldiamidophosphite (2632-88-4) → O-ethyl S-(2-oxopropyl) diethylphosphoramidothioite (126199-82-4)

Conditions	Yield
	95%

2-(2-bromoethyl)isoindoline-1,3-dione (574-98-1) + 1-mercaptopropan-2-one (24653-75-6) → 5-oxo-1-phthalimido-3-thiahexane (98586-88-0)

Conditions	Yield
With sodium ethanolate In ethanol for 1h; Heating;	92%

6-chloro-3,5-dicyano-2-<<(dimethylamino)methylene>amino>pyrazine (79917-06-9) + 1-mercaptopropan-2-one (24653-75-6) → 1-<<3,5-dicyano-2-<<(dimethylamino)methylene>amino>-6-pyrazinyl>thio>-2-propanone (79917-08-1)

Conditions	Yield
With triethylamine In ethanol for 0.5h;	92%

palladium(II) acetate trimer (53189-26-7) + 1-mercaptopropan-2-one (24653-75-6) → [Pd(μ-SCH2C(O)Me)2]6

Conditions	Yield
In ethanol byproducts: HOAc; Ar-atmosphere; molar ratio Pd:sulfide=1:2; slow addn. of sulfide to Pd-salt (0°C, 1 h); filtration, washing (EtOH), drying (vac.); elem. anal.;	92%

2-Chlorobenzonitrile (873-32-5) + 1-mercaptopropan-2-one (24653-75-6) → 2-acetyl-3-aminobenzothiophen (34263-61-1)

Conditions	Yield
With potassium carbonate In water at 90℃; for 2h; Green chemistry;	91%

6-bromo-1-chloro-3,4-dihydronaphthalene-2-carbaldehyde + 1-mercaptopropan-2-one (24653-75-6) → 1-(7-bromo-4,5-dihydronaphtho[1,2-b]thiophen-2-yl)ethan-1-one

Conditions	Yield
Stage #1: 1-mercaptopropan-2-one With sodium methylate In methanol at 0℃; for 0.25h; Inert atmosphere; Stage #2: 6-bromo-1-chloro-3,4-dihydronaphthalene-2-carbaldehyde In methanol at 0 - 20℃; for 3h; Inert atmosphere;	91%

2-chloro-3-methylbenzonitrile (15013-71-5) + 1-mercaptopropan-2-one (24653-75-6) → 2-acetyl-3-amino-7-methylbenzo[b]thiophene (1426444-98-5)

Conditions	Yield
With potassium carbonate In water at 90℃; for 2h; Green chemistry;	90%

ethyl 3-(trimethylsilyl)propynoate (16205-84-8) + 1-mercaptopropan-2-one (24653-75-6) → ethyl 4-methyl-2-(trimethylsilyl)thiophene-3-carboxylate

Conditions	Yield
Stage #1: ethyl 3-(trimethylsilyl)propynoate; 1-mercaptopropan-2-one With potassium tert-butylate In toluene at 20℃; for 3h; Inert atmosphere; Green chemistry; Stage #2: With acetic anhydride In toluene at 80℃; for 3h; Inert atmosphere; Green chemistry; regioselective reaction;	90%

2-bromo-2-chloro-3-[3-(trifluoromethyl)phenyl]propanenitrile + 1-mercaptopropan-2-one (24653-75-6) → 1-{3-amino-5-[3-(trifluoromethyl)phenyl]thiophen-2-yl}-ethanone

Conditions	Yield
With sodium methylate In methanol at 20℃; for 1h;	90%

3-(3-acetylphenyl)-2-bromo-2-chloropropanenitrile + 1-mercaptopropan-2-one (24653-75-6) → 1-[3-(5-acetyl-4-aminothiophen-2-yl)phenyl]ethanone

Conditions	Yield
With sodium methylate In methanol at 20℃; for 1h;	90%

6-morpholinonaphthalen-2-ol (71585-26-7) + 1-mercaptopropan-2-one (24653-75-6) → C17H19NO3S

Conditions	Yield
With cobalt phthalocyanine-tetrasodiumsulfonate; oxygen In water at 100℃; for 15h; Schlenk technique;	89%

5-chloro-8,9-dihydro-7H-benzocycloheptene-6-carbaldehyde (54949-01-8) + 1-mercaptopropan-2-one (24653-75-6) → 1-(5,6-dihydro-4H-benzo[6,7]cyclohepta[1,2-b]thiophen-2-yl)ethanone

Conditions	Yield
Stage #1: 1-mercaptopropan-2-one With sodium methylate In methanol at 0℃; for 0.25h; Inert atmosphere; Stage #2: 9-chloro-6,7-dihydro-5H-benzocycloheptene-8-carbaldehyde In methanol at 0 - 20℃; for 3h; Inert atmosphere;	89%

2,6-dichlorobenzaldehyde (83-38-5) + 1-mercaptopropan-2-one (24653-75-6) → 1-(4-chloro-1H-benzo[b]thiophen-2-yl)ethanone (66490-34-4)

Conditions	Yield
With potassium carbonate In water at 90℃; for 2h; Green chemistry;	88%

1-chloro-2-formyl-3,4-dihydronaphthalene (3262-03-1) + 1-mercaptopropan-2-one (24653-75-6) → 1-(4,5-dihydronaphtho[1,2-b]thiophen-2-yl)ethanone (62615-59-2)

Conditions	Yield
Stage #1: 1-mercaptopropan-2-one With sodium methylate In methanol at 0℃; for 0.25h; Inert atmosphere; Stage #2: 1-chloro-2-formyl-3,4-dihydronaphthalene In methanol at 0 - 20℃; for 3h; Inert atmosphere;	88%

Triethyl-[(Z)-3-(4-methoxy-phenyl)-3-oxo-propenyl]-ammonium; chloride (24477-82-5) + 1-mercaptopropan-2-one (24653-75-6) → (Z)-1-(4-Methoxy-phenyl)-3-(2-oxo-propylsulfanyl)-propenone (132039-37-3)

Conditions	Yield
In ethanol at 78℃; for 1h;	87%

2-chloro-5-nitrobenzaldehyde (6361-21-3) + 1-mercaptopropan-2-one (24653-75-6) → 1-(5-nitrobenzo[b]thiophen-2-yl)ethanone (114305-93-0)

Conditions	Yield
With potassium carbonate In water at 90℃; for 2h; Green chemistry;	86%
With potassium carbonate In water at 90℃;	86%

2-chloro-3-carbaldehydepyridine (36404-88-3) + 1-mercaptopropan-2-one (24653-75-6) → 1-(thiopheno[2,3-b]pyridin-2-yl)ethanone (18354-56-8)

Conditions	Yield
With potassium carbonate In water at 90℃; for 2h; Green chemistry;	86%

2-bromo-2-chloro-3-(4-methylphenyl)propanenitrile + 1-mercaptopropan-2-one (24653-75-6) → 1-[3-amino-5-(4-methylphenyl)thiophen-2-yl]ethanone

Conditions	Yield
With sodium methylate In methanol at 20℃; for 1h;	85%

2-chloro-benzaldehyde (89-98-5) + 1-mercaptopropan-2-one (24653-75-6) → 2-acetyl benzo[b]thiophene (22720-75-8)

Conditions	Yield
With potassium carbonate In water at 90℃; for 2h; Green chemistry;	84%

2,6-dichloro-benzonitrile (1194-65-6) + 1-mercaptopropan-2-one (24653-75-6) → 1-(3-amino-4-chloro-benzothiophen-2-yl)-ethanone (52673-88-8)

Conditions	Yield
With potassium carbonate In water at 90℃; for 2h; Green chemistry;	82%

acetyl chloride (75-36-5) + 1-mercaptopropan-2-one (24653-75-6) → 1-acetylthio-2-propanone (57360-11-9)

Conditions	Yield
With triethylamine In acetonitrile at 10℃; for 2h;	81%

1-mercaptopropan-2-one (24653-75-6) → 2,5-dimethyl-2,5-endo-oxy-1,4-dithiane (66928-24-3)

Conditions	Yield
With diethylphosphoramidous dichloride In benzene Heating;	81%
With butyl dichlorophosphite In benzene Heating;	64%

2-bromo-2-chloro-3-(4-fluorophenyl)propanenitrile + 1-mercaptopropan-2-one (24653-75-6) → 1-[3-amino-5-(4-fluorophenyl)thiophen-2-yl]ethanone

Conditions	Yield
With sodium methylate In methanol at 20℃; for 1h;	81%

Triethyl-((Z)-4-methyl-3-oxo-pent-1-enyl)-ammonium; chloride (38480-36-3) + 1-mercaptopropan-2-one (24653-75-6) → (Z)-4-Methyl-1-(2-oxo-propylsulfanyl)-pent-1-en-3-one (132039-40-8)

Conditions	Yield
In ethanol at 78℃; for 1h;	80%

Upstream product

• 78-95-5 chloroacetone 
• 22131-92-6 thietane-3-one 
• 598-31-2 1-bromoacetone 
• 7732-18-5 water 
• 14660-20-9 thioacetylacetone 
• 49762-80-3 O-ethyl S-2-oxopropyl carbonodithioate 

Downstream Products

• 17525-15-4 4-methyl-3-phenyl-3H-thiazol-2-one 
• 5316-80-3 4-methyl-3-phenyl-1,3-thiazole-2(3H)-thione 
• 41803-21-8 2-ethyl-4-methyl-3-thiazoline 
• 1826-17-1 4-methyl-2-phenyl-thiazole 
• 22057-31-4 (2,4-dinitro-phenylsulfanyl)-acetone 
• 22962-86-3 4-methyl-3-phenyl-2-(N-phenylimino)-1,3-thiazoline 
• 859301-46-5 phenyldisulfanyl-acetone 
• 103859-03-6 4-methyl-2-p-tolyl-2,5-dihydro-thiazole 
• 60755-05-7 2,4-dimethyl-3-thiazoline 
• 102598-56-1 5-(4-dimethylamino-benzyl)-2-(4-dimethylamino-phenyl)-4-methyl-thiazole 
• 100255-14-9 N,N-dimethyl-4-(4-methyl-2,5-dihydro-thiazol-2-yl)-aniline 
• 40700-12-7 4-methyl-3-phenyl-3H-thiazole-2-selone 
• 103861-07-0 4-methyl-2-m-tolyl-2,5-dihydro-thiazole 
• 103986-13-6 2-(4-methyl-2,5-dihydro-thiazol-2-yl)-benzoic acid 

Relevant articles and documents

HETEROCYCLIC COMPOUND, APPLICATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING SAME

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