1452-15-9

Basic information

• Product Name: 4-CYANOTHIAZOLE
• Synonyms: 4-thiazolecarbonitrile;4-CYANOTHIAZOLE;thiazole-4-carbonitrile;1,3-thiazole-4-carbonitrile
• CAS NO: 1452-15-9
• Molecular Formula: C₄H₂N₂S
• Molecular Weight: 110.14
• EINECS: 215-919-4
• Mol File: 1452-15-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 60-61℃
• Boiling Point: 100-120℃ (20 Torr)
• Flash Point: 96.1 °C
• Appearance: /
• Density: 1.393 (estimate)
• Vapor Pressure: 0.0505mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -1.45±0.10(Predicted)
• CAS DataBase Reference: 4-CYANOTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CYANOTHIAZOLE(1452-15-9)
• EPA Substance Registry System: 4-CYANOTHIAZOLE(1452-15-9)

Safety Data

• Statements: 10-20/21/22-36
• Safety Statements: 16-26-36
• RIDADR: 3275
• Hazardous Substances Data: 1452-15-9(Hazardous Substances Data)

Usage

General Description

4-Cyanothiazole is a heterocyclic chemical compound with the molecular formula C4H3NS. It is a colorless to light yellow liquid with a strong odor. 4-Cyanothiazole is mainly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It is also utilized in the manufacturing of dyes, pigments, and other industrial chemicals. The compound has potential for antimicrobial and antifungal activities, making it a valuable intermediate in the production of pharmaceuticals and agrochemicals. Additionally, 4-Cyanothiazole has been studied for its potential applications in material science and as a precursor in organic synthesis. Overall, 4-Cyanothiazole is an important chemical building block with a wide range of industrial and research applications.

InChI:InChI=1/C4H2N2S/c5-1-4-2-7-3-6-4/h2-3H

Synthetic route

1,3-thiazole-4-carbaldehyde (3364-80-5) → thiazole-4-carbonitrile (1452-15-9)

Conditions	Yield
With hydroxylamine hydrochloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate; N,N-dimethyl-formamide at 100℃;	95%

zinc(II) cyanide (557-21-1) + 4-bromo-1,3-thiazole (34259-99-9) → thiazole-4-carbonitrile (1452-15-9)

Conditions	Yield
With C12H10N(1-)*CH3O3S(1-)*Pd(2+)*C39H32OP2 In tetrahydrofuran; water at 65℃; for 4h; Micellar solution;	93%
With [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate In tetrahydrofuran; water at 40℃; for 18h; Inert atmosphere;	78%

potassiumhexacyanoferrate(II) trihydrate + 4-bromo-1,3-thiazole (34259-99-9) → thiazole-4-carbonitrile (1452-15-9)

Conditions	Yield
With C42H58NO3PPdS(2-); potassium acetate; tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; Sealed tube;	89%

1,3-thiazole-4-carboxamide (3575-09-5) → thiazole-4-carbonitrile (1452-15-9)

Conditions	Yield
at 325℃; for 1h; Temperature;	85%
With triethylamine; trifluoroacetic anhydride In tetrahydrofuran at 0 - 20℃; for 2h;	55.2%
With phosphorus pentoxide at 200℃;

Thiazole-4-carboxylic acid (3973-08-8) → thiazole-4-carbonitrile (1452-15-9)

Conditions	Yield
Stage #1: Thiazole-4-carboxylic acid With 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; ammonium chloride Stage #2: With triethylamine; trifluoroacetic anhydride at 0 - 20℃; for 6h;	83%

ethyl thioformate (29392-46-9) + N-formylamino-acetonitrile (5018-27-9) → thiazole-4-carbonitrile (1452-15-9)

Conditions	Yield
(i) Et3N, POCl3, CH2Cl2, (ii) /BRN= 1737704/, EtOH; Multistep reaction;

thiocarboxamide (115-08-2) + β,β-dichloro-α-amino-acrylonitrile (36641-13-1) → thiazole-4-carbonitrile (1452-15-9)

Conditions	Yield
With p-toluenesulfonic acid monohydrate In acetone

[11C]hydrogen cyanide (14904-70-2) + 4-bromo-1,3-thiazole (34259-99-9) → thiazole-4-carbonitrile (1452-15-9)

Conditions	Yield
Stage #1: 4-bromo-1,3-thiazole With C41H57P In toluene at 20℃; for 0.5h; Stage #2: [11C]hydrogen cyanide In tetrahydrofuran at 100℃; for 0.0166667h;

thiazole-4-carbonitrile (1452-15-9) + 1,2-diamino-benzene (95-54-5) + ascorbic acid (50-81-7) → thiabendazole (148-79-8)

Conditions	Yield
With hydrogenchloride; ethylenediaminetetraacetic acid In water	92.7%

thiazole-4-carbonitrile (1452-15-9) + o-phenylenediamine hydrochloride (39145-59-0) + 1,2-diamino-benzene (95-54-5) + ascorbic acid (50-81-7) → thiabendazole (148-79-8)

Conditions	Yield
With hydrogenchloride; ethylenediaminetetraacetic acid In methanol; water	91.7%
With hydrogenchloride; ethylenediaminetetraacetic acid In water

thiazole-4-carbonitrile (1452-15-9) + 1,2-diamino-benzene (95-54-5) + ascorbic acid (50-81-7) + butan-1-ol (71-36-3) → thiabendazole (148-79-8)

Conditions	Yield
With methanesulfonic acid In water	87.1%
With acetic acid In water	75.4%

thiazole-4-carbonitrile (1452-15-9) + aniline (62-53-3) → C10H9N3S*ClH

Conditions	Yield
With hydrogenchloride In 1,2-dichloro-benzene at 55 - 140℃;	86.83%
With hydrogenchloride In 1,2-dichloro-benzene at 135℃; for 3h;

thiazole-4-carbonitrile (1452-15-9) + aminosulfonic acid (5329-14-6) + 1,2-diamino-benzene (95-54-5) + ascorbic acid (50-81-7) + butan-1-ol (71-36-3) → thiabendazole (148-79-8)

Conditions	Yield
In water	75.7%

thiazole-4-carbonitrile (1452-15-9) + tin(II)chloride dihydrate + 1,2-diamino-benzene (95-54-5) + ascorbic acid (50-81-7) + butan-1-ol (71-36-3) → thiabendazole (148-79-8)

Conditions	Yield
In water	74.5%

thiazole-4-carbonitrile (1452-15-9) + thiosemicarbazide (79-19-6) → 5-(thiazol-4-yl)-1,3,4-thiadiazol-2-amine

Conditions	Yield
With trifluoroacetic acid at 80℃; Reflux;	72.3%

thiazole-4-carbonitrile (1452-15-9) + N-Cyanoguanidine (127099-85-8, 780722-26-1) → 6-(thiazol-4-yl)-1,3,5-triazine-2,4-diamine

Conditions	Yield
With potassium hydroxide In 2-ethoxy-ethanol at 130 - 135℃; for 10h;	65%

thiazole-4-carbonitrile (1452-15-9) + ethylmagnesium bromide (925-90-6) → 1-(thiazol-4-yl)cyclopropanamine (1240521-86-1)

Conditions	Yield
Stage #1: thiazole-4-carbonitrile; ethylmagnesium bromide With titanium(IV) isopropylate In diethyl ether; toluene at -70 - 20℃; for 1.25h; Stage #2: With boron trifluoride diethyl etherate In diethyl ether; toluene for 1.5h; Stage #3: With hydrogenchloride; water In diethyl ether; toluene	49%
Stage #1: thiazole-4-carbonitrile With titanium(IV) isopropylate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2.5h; Stage #3: With boron trifluoride diethyl etherate In tetrahydrofuran; diethyl ether for 0.25h;

thiazole-4-carbonitrile (1452-15-9) + (R)-2-methylcysteine hydrochloride methyl ester → C9H10N2O2S2 (1592904-89-6)

Conditions	Yield
With triethylamine In methanol at 50℃; for 48h;	42.7%

thiazole-4-carbonitrile (1452-15-9) + 1-amino-1-deoxy-D-fructose acetic acid salt (1201794-87-7) → (1R,2S,3R)-1-(2-(thiazol-4-yl)-1H-imidazol-4-yl)butane-1,2,3,4-tetraol (1160957-43-6)

Conditions	Yield
Stage #1: thiazole-4-carbonitrile With sodium methylate In methanol at 20℃; for 1h; Stage #2: 1-amino-1-deoxy-D-fructose acetic acid salt In methanol at 20℃; for 6h; Further stages;	9%

thiazole-4-carbonitrile (1452-15-9) → thiazole-4-carbothioamide (80653-66-3)

Conditions	Yield
With hydrogen sulfide; diethylamine; benzene
With hydrogen sulfide; triethylamine In ethanol

thiazole-4-carbonitrile (1452-15-9) + 4,5-pyrimidinediamine (13754-19-3)

Conditions	Yield
With PPA at 180 - 210℃;

thiazole-4-carbonitrile (1452-15-9) + methyl magnesium iodide (917-64-6) → 1-(thiazol-4-yl)ethan-1-one (38205-66-2)

Conditions	Yield
In diethyl ether Heating;

thiazole-4-carbonitrile (1452-15-9) + 4,5-diamino-6-methylthiopyrimidine (6965-92-0) → 6-methylsulfanyl-8-thiazol-4-yl-7(9)H-purine (65911-14-0)

Conditions	Yield
With PPA at 180 - 210℃;

thiazole-4-carbonitrile (1452-15-9) + 6-methyl-2,4,5-triaminopyrimidine (60914-71-8) → 6-methyl-8-thiazol-4-yl-7(9)H-purin-2-ylamine (65911-19-5)

Conditions	Yield
With PPA at 180 - 210℃;

thiazole-4-carbonitrile (1452-15-9) + 2,6-bis(methylthio)pyrimidine-4,5-diamine (61772-85-8) → 2,6-bis-methylsulfanyl-8-thiazol-4-yl-7(9)H-purine (65911-18-4)

Conditions	Yield
With PPA at 180 - 210℃;

thiazole-4-carbonitrile (1452-15-9) + 4,5-diamino-6-hydroxypyrimidine (1672-50-0) → 8-thiazol-4-yl-1,7(9)-dihydro-purin-6-one (65911-13-9)

Conditions	Yield
With PPA at 180 - 210℃;

thiazole-4-carbonitrile (1452-15-9) + 4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → 8-thiazol-4-yl-1,7(9)-dihydro-purine-6-thione (65911-27-5)

Conditions	Yield
With PPA at 180 - 210℃;

thiazole-4-carbonitrile (1452-15-9) + 4,5-diamino-2,6-dimercaptopyrimidine (31295-41-7) → 8-thiazol-4-yl-3,7(9)-dihydro-purine-2,6-dithione (136068-15-0)

Conditions	Yield
With PPA at 180 - 210℃;

thiazole-4-carbonitrile (1452-15-9) + 6-methylsulfanyl-pyrimidine-2,4,5-triamine (4765-67-7) → 6-methylsulfanyl-8-thiazol-4-yl-7(9)H-purin-2-ylamine (65911-16-2)

Conditions	Yield
With PPA at 180 - 210℃;

thiazole-4-carbonitrile (1452-15-9) + 2,5,6-triamino-4-hydroxypyrimidine (1004-75-7) → 2-amino-8-thiazol-4-yl-1,7(9)-dihydro-purin-6-one (65911-15-1)

thiazole-4-carbonitrile (1452-15-9) + 2,5,6-triamino-3H-pyrimidine-4-thione (54-19-3) → 2-amino-8-thiazol-4-yl-1,7(9)-dihydro-purine-6-thione (65911-28-6)

Conditions	Yield
With PPA at 180 - 210℃;

thiazole-4-carbonitrile (1452-15-9) → N-hydroxy-thiazole-4-carboximidic acid amide (89829-63-0)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol

Upstream product

• 3575-09-5 1,3-thiazole-4-carboxamide 
• 115-08-2 thiocarboxamide 
• 36641-13-1 β,β-dichloro-α-amino-acrylonitrile 
• 3973-08-8 Thiazole-4-carboxylic acid 
• 3364-80-5 1,3-thiazole-4-carbaldehyde 
• 29392-46-9 ethyl thioformate 
• 5018-27-9 N-formylamino-acetonitrile 
• 557-21-1 zinc(II) cyanide 
• 34259-99-9 4-bromo-1,3-thiazole 
• 14904-70-2 [11C]hydrogen cyanide 

Downstream Products

• 80653-66-3 thiazole-4-carbothioamide 
• 7728-74-7 4-TEA 
• 148-79-8 thiabendazole 
• 38205-66-2 1-(thiazol-4-yl)ethan-1-one 

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