(R)-2-Amino-2-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol

Base Information

• Chemical Name: (R)-2-Amino-2-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol
• CAS No.: 250249-03-7
• Molecular Formula: C₁₂H₁₆Br₂N₄O
• Molecular Weight: 392.093
• Mol file: 250249-03-7.mol

Synonyms:(R)-2-Amino-2-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol

Chemical Property of (R)-2-Amino-2-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-Amino-2-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol

There total 11 articles about (R)-2-Amino-2-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol 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: 92.0%

2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethylamine (218912-14-2) → (R)-2-Amino-2-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol (250249-03-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

Reference yield:

methyl 3,5-dibromo-4-aminobenzoate (3282-10-8) → (R)-2-Amino-2-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol (250249-03-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

2.1: NaNO₂; aq. HCl / acetic acid / 0.5 h / 0 °C

2.2: 75 percent / KOH; H₂O / 0.5 h / 0 °C

3.1: 88 percent / PCC / CH₂Cl₂ / 2 h / 25 °C

4.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

5.1: AD-α; H2O / 2-methyl-propan-2-ol / 6 h / 25 °C

6.1: 88 percent / imidazole / dimethylformamide / 5 h / 0 °C

7.1: 79 percent / Ph₃P; DEAD; diphenylphosphoryl azide / tetrahydrofuran / 2 h / 0 °C

8.1: 78 percent / Ph₃P; H₂O / tetrahydrofuran / 3 h / 60 °C

9.1: 92 percent / (n-Bu)4NF / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; AD-α; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; water; triphenylphosphine; pyridinium chlorochromate; sodium nitrite; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Reduction / 2.1: Diazotization / 2.2: Substitution / 3.1: Oxidation / 4.1: Condensation / 5.1: Addition / 6.1: Etherification / 7.1: Substitution / 8.1: Reduction / 9.1: Substitution;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

Reference yield:

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → (R)-2-Amino-2-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol (250249-03-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 100 percent / SOCl₂ / 2 h / Heating

2.1: 98 percent / Br₂; AcOH / 0.5 h / 25 °C

3.1: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

4.1: NaNO₂; aq. HCl / acetic acid / 0.5 h / 0 °C

4.2: 75 percent / KOH; H₂O / 0.5 h / 0 °C

5.1: 88 percent / PCC / CH₂Cl₂ / 2 h / 25 °C

6.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

7.1: AD-α; H2O / 2-methyl-propan-2-ol / 6 h / 25 °C

8.1: 88 percent / imidazole / dimethylformamide / 5 h / 0 °C

9.1: 79 percent / Ph₃P; DEAD; diphenylphosphoryl azide / tetrahydrofuran / 2 h / 0 °C

10.1: 78 percent / Ph₃P; H₂O / tetrahydrofuran / 3 h / 60 °C

11.1: 92 percent / (n-Bu)4NF / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; AD-α; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; water; bromine; acetic acid; triphenylphosphine; pyridinium chlorochromate; sodium nitrite; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Esterification / 2.1: Bromination / 3.1: Reduction / 4.1: Diazotization / 4.2: Substitution / 5.1: Oxidation / 6.1: Condensation / 7.1: Addition / 8.1: Etherification / 9.1: Substitution / 10.1: Reduction / 11.1: Substitution;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

upstream raw materials:

2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethylamine

methyl 3,5-dibromo-4-aminobenzoate

4-amino-benzoic acid

4-methoxycarbonyl aniline

Downstream raw materials:

C₅₈H₇₉Br₂ClN₈O₁₁Si