(1S,4S)-2,5-DIAZABICYCLO[2.2.1]HEPTANE DIHYDROBROMIDE

Base Information

• Chemical Name: (1S,4S)-2,5-DIAZABICYCLO[2.2.1]HEPTANE DIHYDROBROMIDE
• CAS No.: 100944-14-7
• Molecular Formula: 2BrH*C₅H₁₀N₂
• Molecular Weight: 259.972
• Mol file: 100944-14-7.mol

Synonyms:2,5-Diazabicyclo[2.2.1]heptane,dihydrobromide (9CI);2,5-Diazabicyclo[2.2.1]heptane dihydrobromide;

Chemical Property of (1S,4S)-2,5-DIAZABICYCLO[2.2.1]HEPTANE DIHYDROBROMIDE

Chemical Property:

• Boiling Point: 261.8 °C at 760 mmHg
• Flash Point: 112.1 °C
• PSA: 24.06000
• LogP: 1.89390

Purity/Quality:

99% ^*data from raw suppliers

2,5-Diazabicyclo[2.2.1]heptane,hydrobromide(1:2) 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,4S)-2,5-DIAZABICYCLO[2.2.1]HEPTANE DIHYDROBROMIDE

There total 2 articles about (1S,4S)-2,5-DIAZABICYCLO[2.2.1]HEPTANE DIHYDROBROMIDE 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: 94.0%

(1S,4S)-2-Benzyl-2,5-diazabicyclo<2.2.1>heptane dihydrobromide (100944-15-8,134003-82-0,116258-17-4) → (1S,4S)-2,5-Diazabicyclo<2.2.1>heptane dihydrobromide (100944-14-7,116258-16-3,132747-20-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; water; for 1h; under 3361.55 Torr;

DOI:10.1002/ejoc.200700785

Reference yield:

(1S,4S)-5-Benzyl-2-tosyl-2,5-diazabicyclo<2.2.1>heptane (5234-72-0,59436-75-8) → (1S,4S)-2,5-Diazabicyclo<2.2.1>heptane dihydrobromide (100944-14-7,116258-16-3,132747-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / red phosphorus, 48 percent aq. hydrobromic acid / H₂O / 24 h / Heating

2: 90 percent / hydrogen / 10 percent Pd-C / methanol; H₂O / 24 h / 3620.04 Torr

With phosphorus; hydrogen bromide; hydrogen; palladium on activated charcoal; In methanol; water;

DOI:10.1055/s-1990-27056

Reference yield: 86.0%

benzofuran-2(3H)-one (553-86-6) + (1S,4S)-2,5-Diazabicyclo<2.2.1>heptane dihydrobromide (100944-14-7,116258-16-3,132747-20-7) → (1S,4S)-2,5-bis[2-(2-hydroxyphenyl)acetyl]diazabicyclo[2.2.1]heptane (1032278-89-9)

Guidance literature:

(1S,4S)-2,5-Diazabicyclo<2.2.1>heptane dihydrobromide; With potassium hydroxide; In methanol; at 5 - 10 ℃; for 1h;

benzofuran-2(3H)-one; In toluene; at 20 ℃; for 0.0833333h; Further stages.;

DOI:10.1002/ejoc.200700785

upstream raw materials:

(1S,4S)-2-Benzyl-2,5-diazabicyclo<2.2.1>heptane dihydrobromide

(1S,4S)-5-Benzyl-2-tosyl-2,5-diazabicyclo<2.2.1>heptane

Downstream raw materials:

(1S,4S)-2,5-bis[2-(2-hydroxyphenyl)acetyl]diazabicyclo[2.2.1]heptane

Refernces

• 1、 Jordis,Sauter,Siddiqi,Kuenburg,Bhattacharya. "Synthesis of (1R,4R)- and (1S,4S)-2,5-diazabicyclo[2.2.1]heptanes and their N-substituted derivatives". . p. 925 - 930. Retrieved 2007/10/02.