631-58-3

Basic information

• Product Name: Thiopropionamide
• Synonyms: Thiopropianamide;THIOPROPIONAMIDE
• CAS NO: 631-58-3
• Molecular Formula: C₃H₇NS
• Molecular Weight: 89.16
• EINECS: 1533716-785-6
• Mol File: 631-58-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 40°C
• Boiling Point: 133.9 °C at 760 mmHg
• Flash Point: 34.8 °C
• Appearance: Solid
• Density: 1.028 g/cm³
• Vapor Pressure: 8.28mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 13.17±0.29(Predicted)
• Water Solubility: Practically insoluble in water
• CAS DataBase Reference: Thiopropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: Thiopropionamide(631-58-3)
• EPA Substance Registry System: Thiopropionamide(631-58-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36-22
• Safety Statements: 22-36/37/39-26
• Hazardous Substances Data: 631-58-3(Hazardous Substances Data)

Usage

General Description

Thiopropionamide, also known as 3-Thiopropionamide, is a chemical compound with the molecular formula C3H7NS. It is a white solid compound that is soluble in water and has a melting point of around 125 degrees Celsius. Thiopropionamide is primarily used as an intermediate in the production of pharmaceuticals and agrochemicals. It is also employed as a corrosion inhibitor, a lubricant additive, and in the synthesis of various organic compounds. Thiopropionamide is known for its strong odor and should be handled with care due to its potential irritant properties.

InChI:InChI=1/C3H7NS/c1-2-3(4)5/h2H2,1H3,(H2,4,5)

Synthetic route

propiononitrile (107-12-0) → thiopropanamide (631-58-3)

Conditions	Yield
Stage #1: propiononitrile With calcium hydride; tiolacetic acid at 80℃; for 1h; Stage #2: With water In ethyl acetate at 20℃;	84%
With diphenylphosphinodithioic acid In isopropyl alcohol at 40 - 60℃;	83%
With sodium hydrogensulfide; diethyl amine hydrochloride In 1,4-dioxane; water at 55℃; for 48h;	76%
With hexamethyldisilathiane; sodium methylate In various solvent(s) at 20℃; for 4h;	40%
With ethanol; hydrogen sulfide; sodium disulfide at 38℃; under 760 Torr;

Propionamid (79-05-0) → thiopropanamide (631-58-3)

Conditions	Yield
With Lawessons reagent In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;	61%
With diphosphorus pentasulfide; benzene
With diphosphorus pentasulfide In diethyl ether at 20℃; for 2h;
With Lawessons reagent In tetrahydrofuran at 20℃; for 0.5h;

methyl dithiopropionate (5415-95-2) → thiopropanamide (631-58-3)

Conditions	Yield
With ammonia In N,N-dimethyl-formamide; toluene at 20℃; for 48h; Substitution;	42%

thiopropionimidic acid ethyl ester (409110-06-1) → thiopropanamide (631-58-3)

Conditions	Yield
With diethyl ether; hydrogen sulfide

N,N-diethyl-propionamidine (84764-73-8) → thiopropanamide (631-58-3)

Conditions	Yield
With pyridine; hydrogen sulfide

triphenylphosphine thiocyanogen (66365-41-1) + ethylmagnesium bromide (925-90-6) → thiopropanamide (631-58-3)

ethanol (64-17-5) + hydrogen sulfide (7783-06-4) + propiononitrile (107-12-0) + sodium disulfide → thiopropanamide (631-58-3)

Conditions	Yield
at 38℃;

ethanol (64-17-5) + hydrogen sulfide (7783-06-4) + sodium ethanolate (141-52-6) + propiononitrile (107-12-0) + sodium disulfide → thiopropanamide (631-58-3)

Conditions	Yield
at 60.6℃; under 1330 Torr; Geschwindigkeit;

diethyl ether (60-29-7) + thiopropionimidic acid ethyl ester (409110-06-1) + hydrogen sulfide (7783-06-4) → thiopropanamide (631-58-3)

thiopropanamide (631-58-3) + 5-bromo-azepan-4-one hydrobromide → 2-ethyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine hydrobromide (1443256-57-2)

Conditions	Yield
With ethanol for 3h; Reflux;	100%
In ethanol for 3h; Reflux;	0.39 g

thiopropanamide (631-58-3) + 2-iodophenylamine (615-43-0) → 2-ethylbenzothiazole (936-77-6)

Conditions	Yield
With calcium oxide; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene In N,N-dimethyl-formamide at 60℃; for 1h;	99%

thiopropanamide (631-58-3) + 1-bromo-3-p-nitrophenylpropan-2-one (20772-07-0) → 2-ethyl-4-(4-nitrobenzyl)-1,3-thiazole (689251-49-8)

Conditions	Yield
In ethanol for 2h; Heating / reflux;	96%

thiopropanamide (631-58-3) + (3RS,4RS)-4-chloroacetyl-1-(4-methoxyphenyl)-3-phthalimidoazetidin-2-one → (3RS,4RS)-1-(4-methoxyphenyl)-4-(2-methylthiazol-4-yl)-3-phthalimidoazetidin-2-one

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 10h;	95%

thiopropanamide (631-58-3) + benzyl chloride (100-44-7) → dibenzyl sulfide (538-74-9) + propiononitrile (107-12-0)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In water; benzene at 30℃; for 2h; Product distribution;	A 92% B 94 % Chromat.

thiopropanamide (631-58-3) + 2-bromomethylnaphthyl bromide (939-26-4) → 2-naphthylmethyl propanimidothioate hydrobromide (616893-70-0)

Conditions	Yield
In chloroform at 80℃; for 2h;	92%

Upstream product

• 79-05-0 Propionamid 
• 84764-73-8 N,N-diethyl-propionamidine 
• 5415-95-2 methyl dithiopropionate 
• 64-17-5 ethanol 
• 7783-06-4 hydrogen sulfide 
• 107-12-0 propiononitrile 
• 141-52-6 sodium ethanolate 
• 60-29-7 diethyl ether 
• 409110-06-1 thiopropionimidic acid ethyl ester 
• 66365-41-1 triphenylphosphine-thiocyanogen 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 324-84-5 2-ethyl-4-(4-fluoro-phenyl)-thiazole 
• 15679-09-1 2-ethylthiazole 
• 32272-42-7 2-Aethyl-4-hydroxy-4-isopropyl-thiazolin-Δ2 
• 98095-50-2 N-(Phenyl-{[1-phenyl-meth-(E)-ylidene]-amino}-methyl)-thiopropionamide 
• 41795-83-9 methyl thiopropionimidate hydroiodide 
• 177561-40-9 2-ethyl-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole 
• 76706-67-7 2-ethylthiazole-4-carboxylic acid ethyl ester 
• 325769-17-3 2-ethyl-4-(3-methylphenyl)-5-(4-pyridyl)-1,3-thiazole 
• 689251-49-8 2-ethyl-4-(4-nitrobenzyl)-1,3-thiazole 
• 365428-57-5 2-ethyl-5-(2-fluoro-pyridin-4-yl)-4-(3-methylphenyl)-1,3-thiazole 
• 15729-76-7 2,5-diethylthiazole 
• 32272-49-4 2,4-diethylthiazole 
• 303162-39-2 4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-pyridin-2-ylamine 
• 1160625-42-2 N-(3-(5-(2-chloro-4-pyrimidinyl)-2-ethyl-1,3-thiazol-4-yl)phenyl)-2,6-difluorobenzamide 

Relevant articles and documents

Gold(I)-catalyzed, one-pot, oxidative formation of 2,4-disubstituted thiazoles: Application to the synthesis of a pateamine-related macrodiolide

Thiazoles are important heterocyclic motifs in many target molecules. Extension of a reported gold(I)-catalyzed oxidative coupling of alkynes and thioamides to the synthesis of functionalized thiazole-containing products is presented, including the compatibility of this reaction with ester, protected hydroxyl, alkene and thioether groups. The utility of this one-pot process is demonstrated in the preparation of the thiazole-containing macrodiolide of a simplified analogue of pateamine A.

A mild and versatile synthesis of thioamides

Aliphatic and aromatic nitriles react with thioacetic acid in the presence of calcium hydride to give the corresponding thioamides in good to excellent yields. The examples studied include haloaryl nitriles in which the halogen is facile towards SNAr reactions under other conditions. Georg Thieme Verlag Stuttgart.

NEW SUBSTITUTED 1,3-THIAZOLE DERIVATIVES OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF HAVING IMMUNOSUPPRESSION AND INFLAMMATION INHIBITORY ACITIVITY, INTERMEDIATE COMPOUNDS OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, A PROCESS FOR THE PREPARATION THEREOF, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

Disclosed relates to new substituted 1,3-thiazole derivatives or pharmaceutically acceptable salts thereof having immunosuppresion and inflammation inhibitory activity, intermediate compounds or pharmaceutically acceptable salts thereof, a process for the preparation thereof, and a pharmaceutical composition comprising the same. The compound of the present invention having excellent TNF-α inhibitory activity and inflammation inhibitory activity can be effectively used in the prevention and treatment of TNF-α related diseases.