1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-3,5-difluoro- (9CI)

Base Information

• Chemical Name: 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-3,5-difluoro- (9CI)
• CAS No.: 152434-75-8
• Molecular Formula: C₈H₉F₂NO₃
• Molecular Weight: 205.161
• Mol file: 152434-75-8.mol

Synonyms:1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-3,5-difluoro- (9CI)

Chemical Property of 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-3,5-difluoro- (9CI)

Chemical Property:

• Boiling Point: 425.2±40.0 °C(Predicted)
• PKA: 7.88±0.41(Predicted)
• PSA: 86.71000
• Density: 1.584±0.06 g/cm3(Predicted)
• LogP: 1.06840

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-3,5-difluoro- (9CI)

There total 12 articles about 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-3,5-difluoro- (9CI) 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:

2,6-difluoro-3,4-dimethoxyphenethanolamine (152435-00-2) → 2,6-difluoronorepinephrine (152434-75-8)

Guidance literature:

With boron tribromide; In dichloromethane; Ambient temperature;

DOI:10.1021/jm00076a024

Reference yield:

2,4-difluorophenol (367-27-1) → 2,6-difluoronorepinephrine (152434-75-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 95 percent / K₂CO₃ / acetone / 48 h / Heating

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) -78 deg C, 15 min, b) from -78 deg C to RT, 1 h

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 3 h, 2.) THF, hexane, a) -78 deg C, 15 min, b) from -78 deg C to RT, 1 h

4: 2,2,2-trifluoroethanol, tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / -78 - 20 °C

5: 1.) m-chloroperbenzoic acid, 2.) 10percent aq. KOH / 1.) CH₂Cl₂, reflux, 4 d, 2.) MeOH, 1 h

6: 96 percent / imidazole / dimethylformamide

7: 1.) sec-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, RT, 1 h

8: 10percent aq. HCl

9: 95 percent / K₂CO₃ / acetone / Ambient temperature

10: ZnI₂ / CHCl₃ / Ambient temperature

11: 73 percent / LiAlH₄ / diethyl ether / a) reflux, 2 h, b) RT, overnight

12: BBr₃ / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; 2,2,2-trifluoroethanol; tetrabutyl ammonium fluoride; sec.-butyllithium; boron tribromide; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00076a024

Reference yield:

2,4-difluoro-1-methoxybenzene (452-10-8) → 2,6-difluoronorepinephrine (152434-75-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) -78 deg C, 15 min, b) from -78 deg C to RT, 1 h

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 3 h, 2.) THF, hexane, a) -78 deg C, 15 min, b) from -78 deg C to RT, 1 h

3: 2,2,2-trifluoroethanol, tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / -78 - 20 °C

4: 1.) m-chloroperbenzoic acid, 2.) 10percent aq. KOH / 1.) CH₂Cl₂, reflux, 4 d, 2.) MeOH, 1 h

5: 96 percent / imidazole / dimethylformamide

6: 1.) sec-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, RT, 1 h

7: 10percent aq. HCl

8: 95 percent / K₂CO₃ / acetone / Ambient temperature

9: ZnI₂ / CHCl₃ / Ambient temperature

10: 73 percent / LiAlH₄ / diethyl ether / a) reflux, 2 h, b) RT, overnight

11: BBr₃ / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; 2,2,2-trifluoroethanol; tetrabutyl ammonium fluoride; sec.-butyllithium; boron tribromide; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00076a024

upstream raw materials:

2,6-difluoro-3,4-dimethoxyphenethanolamine

2,4-difluorophenol

2,4-difluoro-1-methoxybenzene

3,5-difluoro-2-methoxybenzaldehyde