(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.: 132747-20-7
• Molecular Formula: 2BrH*C₅H₁₀N₂
• Molecular Weight: 259.972
• Hs Code.: 29335990
• European Community (EC) Number: 679-970-8
• DSSTox Substance ID: DTXSID101347438
• Mol file: 132747-20-7.mol

Synonyms:132747-20-7;(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane Dihydrobromide;(1S,4S)-2,5-diazabicyclo[2.2.1]heptane;dihydrobromide;2,5-Diazabicyclo[2.2.1]heptane, hydrobromide (1:2), (1S,4S)-;SCHEMBL1013822;DTXSID101347438;MFCD08272741;AKOS022179951;CS-W010152;AC-29213;AS-71099;D2658;D90097;(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane 2HBr;A888261;2,5-Diazabicyclo[2.2.1]heptane,hydrobromide(1:2);(1s,2s)-2,5-diazabicyclo[2.2.1]heptane dihydrobromide;(1S,4S)-2,5-Diazabicylo[2.2.1]heptane dihydrobromide;(1S,4S)-2,5-diaza-bicyclo[2.2.1]heptane dihydrobromide;(1S,4S)-(+)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide, 97%;(1S,4S)-2,5-Diazabicyclo(2.2.1)heptane.2HBr;(1S,2S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide;(1S,4S)-(+)-2,5-diazabicyclo [2,2,1]heptane dihydrobromide

Chemical Property of (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane Dihydrobromide

Chemical Property:

• Vapor Pressure: 0.00765mmHg at 25°C
• Melting Point: 300 °C
• Boiling Point: 261.8 °C at 760 mmHg
• Flash Point: 112.1 °C
• PSA: 24.06000
• LogP: 1.89390
• Storage Temp.: Sealed in dry,Room Temperature
• Sensitive.: Hygroscopic
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 259.93467
• Heavy Atom Count: 9
• Complexity: 72.1

Purity/Quality:

97% ^*data from raw suppliers

(1S,4S)-(+)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CNC1CN2.Br.Br
• Isomeric SMILES: C1[C@H]2CN[C@@H]1CN2.Br.Br
• Uses: (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane Dihydrobromide acts as a reagent for the synthesis and characterization of new piperazine-type inhibitors for mitochondrial ubiquinone reductase, preparation of heterocyclic compounds as chemokine receptor inhibitors useful in treatment of CXCR4-mediated diseases. (1S,4S)-(+)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide can be used as:A starting material for the synthesis of chiral diazabicyclic ligands, applicable in the preparation of dicopper(II) complexes.A precursor in the preparation of diazabicyclo[2.2.1]heptane derivatives as catalysts, which are applicable in the asymmetric catalysis reactions.An organocatalyst in Biginelli reaction of aromatic aldehydes with ethyl acetoacetate and urea.

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