(R)-2-Amino-3-(1H-imidazol-4-yl)propan-1-ol dihydrochloride

Base Information

• Chemical Name: (R)-2-Amino-3-(1H-imidazol-4-yl)propan-1-ol dihydrochloride
• CAS No.: 75614-84-5
• Molecular Formula: C₆H₁₁N₃O*2ClH
• Molecular Weight: 214.095
• Hs Code.: 29331190
• DSSTox Substance ID: DTXSID00487231
• Mol file: 75614-84-5.mol

Synonyms:75614-84-5;D-Histidinol dihydrochloride;(R)-2-Amino-3-(1H-imidazol-4-yl)propan-1-ol dihydrochloride;(2R)-2-amino-3-(1H-imidazol-5-yl)propan-1-ol;dihydrochloride;(R)-2-Amino-3-(1H-imidazol-4-yl)-propan-1-ol dihydrochloride;D-Histidinol 2HCl;D(+)-Histidinol dihydrochloride;DTXSID00487231;D-Histidinol dihydrochloride, 98%;(+)-beta-Aminoimidazole-4-propanol dihydrochloride;A838464;H-D-His-ol inverted exclamation mark currency2HCl;(r)-2-amino-3-(1h-imidazol-4-yl)propan-1-ol 2hcl

Chemical Property of (R)-2-Amino-3-(1H-imidazol-4-yl)propan-1-ol dihydrochloride

Chemical Property:

• Melting Point: 193-195 °C(lit.)
• PSA: 74.93000
• LogP: 1.57610
• Storage Temp.: 0-6°C
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 213.0435674
• Heavy Atom Count: 12
• Complexity: 99

Purity/Quality:

97% ^*data from raw suppliers

D-Histidinol dihydrochloride 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26-36/37-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(NC=N1)CC(CO)N.Cl.Cl
• Isomeric SMILES: C1=C(NC=N1)C[C@H](CO)N.Cl.Cl

Technology Process of (R)-2-Amino-3-(1H-imidazol-4-yl)propan-1-ol dihydrochloride

There total 5 articles about (R)-2-Amino-3-(1H-imidazol-4-yl)propan-1-ol dihydrochloride 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: 84.0%

2-(R)-(triphenylmethylamino)-3-<1-(triphenylmethyl)imidazol-4(5)-yl>propanol ditrityl-D-histidinol (223910-40-5) → 2-(R)-amino-3-(1H-imidazol-4(5)-yl)propanol dihydrochloride (1596-64-1,75614-84-5,120612-44-4)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 70 - 80 ℃; for 2h;

DOI:10.1021/jm980408v

Reference yield:

(+/-)-2-amino-3-(1(3)H-imidazol-4-yl)-propan-1-ol; dihydrochloride (1596-64-1,75614-84-5,120612-44-4) → 2-(S)-amino-3-(1H-imidazol-4(5)-yl)propanol dihydrochloride (1596-64-1) + 2-(R)-amino-3-(1H-imidazol-4(5)-yl)propanol dihydrochloride (1596-64-1,75614-84-5,120612-44-4)

Guidance literature:

With chiral stationary phase including isopropyl-functionalized CF₆; In methanol; acetic acid; triethylamine; acetonitrile; at 0 ℃; Purification / work up;

Reference yield:

(R)-histidine methyl ester dihydrochloride (4467-54-3,5619-10-3,7389-87-9,18684-16-7,22888-60-4,32381-17-2,92742-29-5,100009-20-9) → 2-(R)-amino-3-(1H-imidazol-4(5)-yl)propanol dihydrochloride (1596-64-1,75614-84-5,120612-44-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / Et₃N / acetonitrile / Ambient temperature

2: 1.) LiAlH₄, 2.) aq. NaOH / 1.) THF, 2.) THF, RT, 15 min

3: 84 percent / 3 M HCl / tetrahydrofuran / 2 h / 70 - 80 °C

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jm980408v

upstream raw materials:

histidine methyl ester

2-(R)-(triphenylmethylamino)-3-<1-(triphenylmethyl)imidazol-4(5)-yl>propanol ditrityl-D-histidinol

(R)-histidine methyl ester dihydrochloride

(+/-)-2-amino-3-(1⁽³⁾H-imidazol-4-yl)-propan-1-ol; dihydrochloride

Downstream raw materials:

2-(S)-amino-3-(1H-imidazol-4⁽⁵⁾-yl)propanol dihydrochloride

2-(R)-amino-3-(1H-imidazol-4⁽⁵⁾-yl)propanol dihydrochloride