• Name

  5-FLUORO-1H-BENZOTRIAZOLE

• EINECS
• CAS No. 18225-90-6
• Article Data9
• CAS DataBase
• Density 1.482 g/cm³
• Solubility
• Melting Point
• Formula C₆H₄FN₃
• Boiling Point 280.881 °C at 760 mmHg
• Molecular Weight 137.116
• Flash Point 123.672 °C
• Transport Information
• Appearance
• Safety
• Risk Codes 22
• Molecular Structure
• Hazard Symbols Xn
• Synonyms 1H-Benzotriazole,5-fluoro- (8CI,9CI);Benzotriazole, 5-fluoro- (6CI);5-Fluoro-1H-benzo[d][1,2,3]triazole;
• PSA 41.57000
• LogP 1.09700

Synthetic route

367-31-7

4-fluoro-1,2-phenylenediamine

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

Conditions

Conditions	Yield
With tert.-butylnitrite In acetonitrile at 27 - 29℃; for 0.25h;	95%
With acetic acid; sodium nitrite In water at 0 - 20℃;	85%
With acetic acid; sodium nitrite In water at 20℃; Cooling with ice;	85%
With acetic acid; sodium nitrite In water at 4 - 50℃;	60%

85862-81-3

1-azido-2-bromo-4-fluorobenzene

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -85 - 20℃;	92%

4-fluoro-2-(trimethylsilyl)phenyl trifluoromethanesulfonate

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

Conditions

Conditions	Yield
With sodium azide; 18-crown-6 ether; cesium fluoride In acetonitrile at 70℃; for 12h; Inert atmosphere;	50%

367-31-7

4-fluoro-1,2-phenylenediamine

A

6-fluoro-1H-benzotriazole

B

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

Conditions

Conditions	Yield
With acetic acid; sodium nitrite In water at 4 - 70℃; stereoselective reaction;

371-40-4

4-fluoroaniline

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / dichloromethane / 0 - 5 °C / Schlenk technique; Inert atmosphere 2.1: sulfuric acid / water / Heating 2.2: 1 h / 0 - 5 °C 2.3: 4 h / 10 - 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / -85 - 20 °C View Scheme

1003-98-1

2-bromo-4-fluoroaniline

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / water / Heating 1.2: 1 h / 0 - 5 °C 1.3: 4 h / 10 - 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / -85 - 20 °C View Scheme

22979-35-7

Methyl phenyldiazoacetate

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

methyl 2-(5-fluoro-1H-benzo[d][1,2,3]triazol-1-yl)-2-phenylacetate

Conditions

Conditions	Yield
With tert.-butylnitrite; p-benzoquinone In dichloromethane at 20℃; for 48h; Irradiation;	86%

1746-23-2

4-tert-Butylstyrene

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

A

2-(1-(4-tert-butylphenyl)vinyl)-5-fluoro-2H-benzo[d][1,2,3]triazole

B

1-(1-(4-tert-butylphenyl)vinyl)-5-fluorobenzo[d][1,2,3]triazole

Conditions

Conditions	Yield
Stage #1: 4-tert-Butylstyrene; 5-fluoro-1H-benzo[d][1,2,3]triazole With N-iodo-succinimide In chloroform at 30℃; for 0.0833333h; Stage #2: With potassium carbonate In methanol for 12h; Reflux; Overall yield = 80 %; regioselective reaction;	A 75% B n/a

...Expand

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

109-70-6

1,3-chlorobromopropane

1-(3-chloropropyl)-5-fuloro-1H-benzo[d]-[1,2,3]triazole

Conditions

Conditions	Yield
With potassium carbonate In MeCN at 20℃; for 72h;	65%

86386-76-7, 123632-22-4, 141113-42-0, 150024-48-9

1-[2-(2,4-difluorophenyl)-2,3-epoxypropyl]-1H-1,2,4-triazole

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

A

1228885-19-5

2-(2,4-difluorophenyl)-1-(6-fluoro-1H-benzo[d][1,2,3]-triazol-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol

B

1228885-18-4

2-(2,4-difluorophenyl)-1-(5-fluoro-1H-benzo[d][1,2,3]-triazol-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40 - 80℃;	A 14.9% B 35.7%

...Expand

C23H37BrO3

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

A

C29H40FN3O3

B

C29H40FN3O3

C

C29H40FN3O3

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	A 33% B 22% C 18%

...Expand

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

1240784-77-3

5-fluoro-4,6,7-tribromo-1H-benzotriazole

Conditions

Conditions	Yield
With bromine; nitric acid In water at 130℃; for 15h;	22%

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

206193-17-1

(2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide

(S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(5-fluoro-1H-benzo[d][1,2,3]triazol-1-yl)propanamide

Conditions

Conditions	Yield
Stage #1: 5-fluoro-1H-benzo[d][1,2,3]triazole With sodium hydride In tetrahydrofuran; mineral oil for 3h; Inert atmosphere; Cooling with ice; Stage #2: (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;	12.6%

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

3-(5-fluoro-1H-benzo[d][1,2,3]triazol-1-yl)-N,N,N-trimethylpropan-1-aminium iodide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / MeCN / 72 h / 20 °C 2.1: potassium iodide / acetone / 2 h 2.2: 72 h / 60 °C View Scheme

603-76-9

1-methylindole

18225-90-6

5-fluoro-1H-benzo[d][1,2,3]triazole

A

5-fluoro-1-(3-iodo-1-methyl-1H-indol-2-yl)-1H-benzo[d][1,2,3]triazole

B

C15H10FIN4

C

C15H10FIN4

Conditions

Conditions	Yield
With ammonium iodide In dimethyl sulfoxide; acetonitrile at 20℃; Electrochemical reaction; Green chemistry; Overall yield = 35 percent; Overall yield = 27.3 mg;

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1H-Benzotriazole,6-fluoro- Specification