777-12-8

Basic information

• Product Name: 2-AMINO-6-(TRIFLUOROMETHYL)BENZOTHIAZOLE
• Synonyms: BUTTPARK 13\02-10;6-(TRIFLUOROMETHYL)-1,3-BENZOTHIAZOL-2-AMINE;2-AMINO-6-(TRIFLUOROMETHYL)BENZOTHIAZOLE;6-(trifluoromethyl)-1,3-benzothiazol-2-ylamine;2-Benzothiazolamine,6-(trifluoromethyl)-(9CI);2-Amino-6-(trifluoromethyl)-1,3-benzothiazole;6-(trifluoromethyl)benzo[d]thiazol-2-amine;2-BenzothiazolaMine, 6-(trifluoroMethyl)-
• CAS NO: 777-12-8
• Molecular Formula: C₈H₅F₃N₂S
• Molecular Weight: 218.2
• Product Categories: BENZOTHIAZOLE;Amines;Thiazoles, Isothiazoles &Benzothiazoles;Heterocyclic Compounds;Thiazoles, Isothiazoles & Benzothiazoles;Building Blocks;C8 to C9;Chemical Synthesis;Heterocyclic Building Blocks;Thiazoles
• Mol File: 777-12-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 120-124 °C
• Boiling Point: 306.7 °C at 760 mmHg
• Flash Point: 139.3 °C
• Appearance: /
• Density: 1.536 g/cm³
• Storage Temp.: 2-8°C(protect from light)
• Solubility: soluble in Methanol
• PKA: 2.52±0.10(Predicted)
• Sensitive: Stench
• CAS DataBase Reference: 2-AMINO-6-(TRIFLUOROMETHYL)BENZOTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-6-(TRIFLUOROMETHYL)BENZOTHIAZOLE(777-12-8)
• EPA Substance Registry System: 2-AMINO-6-(TRIFLUOROMETHYL)BENZOTHIAZOLE(777-12-8)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-25
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 777-12-8(Hazardous Substances Data)

Synthetic route

4-trifluoromethylphenylamine (455-14-1) + potassium thioacyanate (333-20-0) → 2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8)

Conditions	Yield
With sodium iodide dichloride at 70℃; for 2h;	99%
With 6-methylbenzothiazol-2-ylamine; N,N,N,N,-tetramethylethylenediamine; oxygen; copper(II) bis(trifluoromethanesulfonate) In dimethyl sulfoxide at 100℃; for 24h; regioselective reaction;	80%
With bromine In acetic acid for 24h;	20%
With bromine; acetic acid for 21h; Ambient temperature;
With bromine In acetic acid Cooling with ice;

4-trifluoromethylphenylamine (455-14-1) + ammonium thiocyanate (1147550-11-5) → 2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8)

Conditions	Yield
With bromine In acetic acid at 10℃; for 12h;	90%
With tris(2,2'-bipyridyl)ruthenium dichloride In acetonitrile at 20℃; for 18h; Irradiation;	74%
With bromine In acetic acid
With hydrogenchloride; bromine; acetic acid

4-trifluoromethylphenylamine (455-14-1) + sodium thiocyanide (540-72-7) → 2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8)

Conditions	Yield
With bromine; acetic acid
With bromine; acetic acid

1-(4-(trifluoromethyl)phenyl)thiourea (1736-72-7) → 2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8)

Conditions	Yield
With bromine In chloroform for 4h; Heating;
With bromine; acetic acid; lithium bromide at 40℃;

4-aminobenzotrifluoride hydrochloride (90774-69-9) → 2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrochloric acid / H2O / 4 h / Heating 2: bromine / CHCl3 / 4 h / Heating View Scheme

4-trifluoromethylphenylamine (455-14-1) → 2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic acid / Isopropyl acetate / 16 h / Reflux 2: acetic acid; lithium bromide; bromine / 40 °C View Scheme

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + 4-chlorophenacetyl chloride (25026-34-0) → 2-(4-chlorophenyl)-N-(6-(trifluoromethyl)benzothiazol-2-yl)acetamide (1579991-05-1)

Conditions	Yield
In neat (no solvent) at 110℃; for 0.0833333h; Microwave irradiation;	95%
at 150℃; for 0.0833333h; Microwave irradiation;	95%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) → 2-chloro-6-(trifluoromethyl)benzothiazole (159870-86-7)

Conditions	Yield
Stage #1: With tert.-butylnitrite; copper dichloride In acetonitrile at 20℃; for 0.166667h; Stage #2: 2-amino-6-trifluoromethyl-1,3-benzothiazole In acetonitrile at 65℃; for 0.5h; Stage #3: With hydrogenchloride In water; acetonitrile	92%
With hydrogenchloride; tert.-butylnitrite; copper dichloride In acetonitrile at 20℃;

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + benzaldehyde (100-52-7) → (E)-1-phenyl-N-(6-(trifluoromethyl)benzo[d]thiazol-2-yl)methanimine

Conditions	Yield
In diethyl ether at 20℃; Molecular sieve;	84%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + 2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetic acid (763903-09-9) → N1-(6-(trifluoromethyl)-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide (1392441-94-9)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	83%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 24h;	80%
Stage #1: 2-amino-6-trifluoromethyl-1,3-benzothiazole With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Stage #2: 2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetic acid In dichloromethane at 25℃; for 24h;	80%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + (E)-2-(2-methoxy-5-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)phenoxy)acetic acid (1357099-42-3) → N1-(6-(trifluoromethyl)-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxyphenyl)-1-propenyl]phenoxy}acetamide (1379509-98-4)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	81%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 24h;	80%
Stage #1: 2-amino-6-trifluoromethyl-1,3-benzothiazole With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Stage #2: (E)-2-(2-methoxy-5-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)phenoxy)acetic acid In dichloromethane at 25℃; for 24h;	80%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + 2-{5-[1-acetyl-3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-5-pyrazolyl]-2-methoxyphenoxy}acetic acid (1392443-96-7) → N1-(6-(trifluoromethyl)-1,3-benzothiazol-2-yl)-2-{5-[1-acetyl-3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-5-pyrazolyl]-2-methoxyphenoxy}acetamide (1392442-05-5)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 24h;	80%
Stage #1: 2-amino-6-trifluoromethyl-1,3-benzothiazole With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Stage #2: 2-{5-[1-acetyl-3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-5-pyrazolyl]-2-methoxyphenoxy}acetic acid In dichloromethane at 25℃; for 24h;	80%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + 2-bromo-1-(1-hydroxycyclohexyl)ethanone (23386-72-3) → 1-(7-(trifluoromethyl)benzo[d]imidazo[2,1-b]thiazol-2-yl)cyclohexanol

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane at 110℃; for 12h; Sealed tube; Inert atmosphere;	76%

4-bromophthalic anhydride (86-90-8) + 2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) → 5-bromo-2-(6-(trifluoromethyl)benzo[d]thiazol-2-yl)isoindolin-1,3-dione

Conditions	Yield
In N,N-dimethyl-formamide at 150℃; for 24h; Inert atmosphere;	76%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + 4-chlorobenzaldehyde (104-88-1) → 4-chloro-N-(6-(trifluoromethyl)benzo[d]thiazol-2-yl)benzamide

Conditions	Yield
With 2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; caesium carbonate In dichloromethane at 25℃; for 12h; Inert atmosphere; Sealed tube;	75%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + 3-(3,4-dimethoxyphenyl)-1H-pyrazole-5-carbaldehyde → (E)-N-[(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)methylene]-6-(trifluoromethyl)benzo[d]thiazol-2-amine

Conditions	Yield
In ethanol for 6h; Reflux;	75%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + 3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazole-5-carbaldehyde → (E)-N-[(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)methylene]-6-(trifluoromethyl)benzo[d]thiazol-2-amine

Conditions	Yield
In ethanol for 6h; Reflux;	75%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) → 2-iodo-6-(trifluoromethyl)-1,3-benzothiazole

Conditions	Yield
With diiodomethane; isopentyl nitrite In N,N-dimethyl-formamide at 60℃; for 0.5h;	74%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(6-(trifluoromethyl)benzo[d]thiazol-2-yl)acetamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h;	74%

4-chlorophthalic anhydride (118-45-6) + 2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) → 5-chloro-2-(6-(trifluoromethyl)benzo[d]thiazol-2-yl)isoindolin-1,3-dione

Conditions	Yield
In N,N-dimethyl-formamide at 150℃; for 24h; Inert atmosphere;	72%

suberic acid monomethyl ester (3946-32-5) + 2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) → methyl 7-(6-(trifluoromethyl)benzo[d]thiazol-2-yl-carbamoyl)heptanoate (1526909-84-1)

Conditions	Yield
Stage #1: suberic acid monomethyl ester With 1,1'-carbonyldiimidazole In dichloromethane for 0.166667h; Stage #2: 2-amino-6-trifluoromethyl-1,3-benzothiazole In dichloromethane; N,N-dimethyl-formamide at 50 - 60℃; for 24h;	70%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + 2-(2-bromoethyl)benzaldehyde (22901-09-3) → N-(isochroman-1-yl)-6-(trifluoromethyl)benzo[d]thiazol-2-amine + 2-(6-(trifluoromethyl)benzo[d]thiazol-2-yl)-3,4-dihydroisoquinolin-1(2H)-one

Conditions	Yield
With acetic acid at 80℃; for 4h;	A 70% B 18%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + 2-(3,4-dichlorophenyl)acetyl chloride (6831-55-6) → 2-(3,4-dichlorophenyl)-N-(6-(trifluoromethyl)benzothiazol-2-yl)acetamide (1579991-11-9)

Conditions	Yield
In tetrahydrofuran at 110℃; for 0.166667h; Microwave irradiation;	65%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + cyclohexanone (108-94-1) → 3-(trifluoromethyl)-7,8,9,10-tetrahydrobenzo[d]benzo[4,5]imidazo[2,1-b]thiazole

Conditions	Yield
With oxygen; sulfur In cyclohexane; dimethyl sulfoxide at 130℃; for 24h; Sealed tube; Green chemistry;	64%

4-(dimethylamino)benzoyl chloride (4755-50-4) + 2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) → 4-(dimethylamino)-N-(6-(trifluoromethyl)benzo[d]thiazol-2-yl)benzamide

Conditions	Yield
With dmap In 1,4-dioxane for 24h; Reflux;	64%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + acetic anhydride (108-24-7) → N-(6-(trifluoromethyl)benzo[d]thiazol-2-yl)acetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 2h; Microwave irradiation;	63%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + 1-bromo-5-methoxy-2,4-bis(trifluoromethyl)benzene → N-(5-methoxy-2,4-bis(trifluoromethyl)phenyl)-6-(trifluoromethyl)benzo[d]thiazol-2-amine

Conditions	Yield
With dmap; potassium phosphate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; molybdenum hexacarbonyl In 1,4-dioxane at 120℃; for 0.5h; Inert atmosphere; Microwave irradiation;	63%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + 3,4-dichlorophenylisocyanate (102-36-3) → 1-(3,4-dichlorophenyl)-3-(6-(trifluoromethyl)benzo[d]thiazol-2-yl)urea

Conditions	Yield
In tetrahydrofuran at 20℃; for 8h;	62%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + 5-chloro-2-methoxy-3-ethylbenzoic acid → 5-chloro-3-ethyl-2-hydroxy-N-(6-(trifluoromethyl)benzo[d]thiazol-2-yl)benzamide

Conditions	Yield
Stage #1: 5-chloro-2-methoxy-3-ethylbenzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 2-amino-6-trifluoromethyl-1,3-benzothiazole In N,N-dimethyl-formamide at 120℃; for 24h;	62%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + phenylacetyl chloride (103-80-0) → N-(6-(trifluoromethyl)benzothiazol-2-yl)-2-phenylacetamide (1579991-10-8)

Conditions	Yield
In neat (no solvent) at 150℃; for 0.0833333h; Microwave irradiation;	61%

3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxaldehyde (1072138-63-6) + 2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + β-naphthol (135-19-3) → 1-((3-bromo-1-(3-chloropyridine-2-yl)-1H-pyrazol-5-yl)((6-trifluoromethylbenzo[d]thiazol-2-yl)amino)methyl)naphthalene-2-ol

Conditions	Yield
at 120℃; for 2h;	60%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + cyclopropanecarboxylic acid chloride (4023-34-1) → N-(6-(trifluoromethyl)benzothiazol-2-yl)-cyclopropanecarboxamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃; Cooling with ice;	59%

7‐(4‐bromobutoxy)‐5‐hydroxy‐2‐phenyl‐4H‐chromen‐4‐one (873302-27-3) + 2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) → 5-hydroxy-2-phenyl-7-(4-(6-(trifluoromethyl)benzo[d]thiazol-2-ylamino)butoxy)-4H-chromen-4-one

Conditions	Yield
In acetonitrile Reflux;	58%

2-amino-6-trifluoromethyl-1,3-benzothiazole (777-12-8) + 2-fluoro-2-methylpropanoic acid (63812-15-7) → 2-fluoro-2-methyl-N-(6-(trifluoromethyl)benzothiazol-2-yl)-propanamide

Conditions	Yield
With 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 N,N-dimethyl-formamide at 0 - 20℃;	58%

Upstream product

• 455-14-1 4-trifluoromethylphenylamine 
• 333-20-0 potassium thioacyanate 
• 90774-69-9 4-aminobenzotrifluoride hydrochloride 
• 1736-72-7 1-(4-(trifluoromethyl)phenyl)thiourea 
• 1147550-11-5 ammonium thiocyanate 
• 540-72-7 sodium thiocyanide 

Downstream Products

• 2193-90-0 2,2'-[3-methyl-4-(6-trifluoromethyl-benzothiazol-2-ylazo)-phenylazanediyl]-bis-ethanol 
• 3879-63-8 N,N-dimethyl-4-(6-trifluoromethyl-benzothiazol-2-ylazo)-aniline 
• 182554-22-9 2-phenyl-7-(trifluoromethyl)benzo[d]imidazo[2,1-b]thiazole 
• 131106-70-2 6-(trifluoromethyl)benzo[d]thiazole 
• 131105-90-3 2-Amino-3-trifluoromethyl-benzenethiol 

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