4-Fluoro-bicyclo[2.2.2]octan-1-aMine

Base Information

• Chemical Name: 4-Fluoro-bicyclo[2.2.2]octan-1-aMine
• CAS No.: 78385-91-8
• Molecular Formula: C₈H₁₄FN
• Molecular Weight: 143.204
• Mol file: 78385-91-8.mol

Synonyms:4-fluorobicyclo[2.2.2]octan-1-amine;4-fluorobicyclo-[2.2.2]-octane-1-amine;1-amino-4-fluorobicyclo[2.2.2]octane;amino-4-fluorobicyclo[2.2.2]octane;

Chemical Property of 4-Fluoro-bicyclo[2.2.2]octan-1-aMine

Chemical Property:

• PSA: 26.02000
• LogP: 2.46030

Purity/Quality:

97% ^*data from raw suppliers

4-Fluorobicyclo[2.2.2]octan-1-amine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Fluoro-bicyclo[2.2.2]octan-1-aMine

There total 17 articles about 4-Fluoro-bicyclo[2.2.2]octan-1-aMine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

ethyl 1-acetyl-4-oxocyclohexane-1-carboxylate (72653-21-5) → amino-4-fluorobicyclo[2.2.2]octane (78385-91-8)

Guidance literature:

Multi-step reaction with 12 steps

1: methanol

2: H₂O/KOH / ethanol / 16 h / Ambient temperature

3: hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 10 h / Heating

4: 91 percent / concn H₂SO₄ / 1,2-dichloro-ethane / 20 h / Heating

5: 92 percent / BF₃*OEt₂ / Ambient temperature

6: 94 percent / NaOMe / methanol / 2 h / Heating

7: 92 percent / SF₄ / 24 h / Ambient temperature

8: 96 percent / H₂O/KOH / ethanol / 16 h / Ambient temperature

9: thionyl chloride

10: NaN₃ / acetone; H₂O / 1 h / 0 - 5 °C

11: CH₂Cl₂; benzene / 2 h / Heating

12: concn HCl / CH₂Cl₂; benzene / 3 h / Heating

With hydrogenchloride; potassium hydroxide; thionyl chloride; sodium azide; sulfuric acid; sulfur tetrafluoride; boron trifluoride diethyl etherate; water; sodium methylate; hydrazine hydrate; In methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetone; diethylene glycol; benzene;

DOI:10.1021/jo00136a028

Reference yield:

1,5-di-tert-butyl 3-ethyl 3-acetylpentane-1,3,5-tricarboxylate (72653-14-6) → amino-4-fluorobicyclo[2.2.2]octane (78385-91-8)

Guidance literature:

Multi-step reaction with 14 steps

1: KOAc/Ac₂O / 2 h / Heating

2: 250 - 260 °C / 10 Torr

3: methanol

4: H₂O/KOH / ethanol / 16 h / Ambient temperature

5: hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 10 h / Heating

6: 91 percent / concn H₂SO₄ / 1,2-dichloro-ethane / 20 h / Heating

7: 92 percent / BF₃*OEt₂ / Ambient temperature

8: 94 percent / NaOMe / methanol / 2 h / Heating

9: 92 percent / SF₄ / 24 h / Ambient temperature

10: 96 percent / H₂O/KOH / ethanol / 16 h / Ambient temperature

11: thionyl chloride

12: NaN₃ / acetone; H₂O / 1 h / 0 - 5 °C

13: CH₂Cl₂; benzene / 2 h / Heating

14: concn HCl / CH₂Cl₂; benzene / 3 h / Heating

With hydrogenchloride; potassium hydroxide; thionyl chloride; sodium azide; sulfuric acid; sulfur tetrafluoride; boron trifluoride diethyl etherate; water; sodium methylate; potassium acetate; acetic anhydride; hydrazine hydrate; In methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetone; diethylene glycol; benzene;

DOI:10.1021/jo00136a028

Reference yield:

5-Acetyl-2,8-dioxo-oxocane-5-carboxylic acid ethyl ester → amino-4-fluorobicyclo[2.2.2]octane (78385-91-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 250 - 260 °C / 10 Torr

2: methanol

3: H₂O/KOH / ethanol / 16 h / Ambient temperature

4: hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 10 h / Heating

5: 91 percent / concn H₂SO₄ / 1,2-dichloro-ethane / 20 h / Heating

6: 92 percent / BF₃*OEt₂ / Ambient temperature

7: 94 percent / NaOMe / methanol / 2 h / Heating

8: 92 percent / SF₄ / 24 h / Ambient temperature

9: 96 percent / H₂O/KOH / ethanol / 16 h / Ambient temperature

10: thionyl chloride

11: NaN₃ / acetone; H₂O / 1 h / 0 - 5 °C

12: CH₂Cl₂; benzene / 2 h / Heating

13: concn HCl / CH₂Cl₂; benzene / 3 h / Heating

With hydrogenchloride; potassium hydroxide; thionyl chloride; sodium azide; sulfuric acid; sulfur tetrafluoride; boron trifluoride diethyl etherate; water; sodium methylate; hydrazine hydrate; In methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetone; diethylene glycol; benzene;

DOI:10.1021/jo00136a028

upstream raw materials:

1-Fluoro-4-isocyanato-bicyclo[2.2.2]octane

ethyl 1-acetyl-4-oxocyclohexane-1-carboxylate

1,5-di-tert-butyl 3-ethyl 3-acetylpentane-1,3,5-tricarboxylate

4-methoxybicyclo<2.2.2>octane-1-carboxylic acid

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