(2S)-1-chloro-3-(1H-imidazol-5-yl)propan-2-amine

Base Information

• Chemical Name: (2S)-1-chloro-3-(1H-imidazol-5-yl)propan-2-amine
• CAS No.: 75614-86-7
• Molecular Formula: C₆H₁₀ClN₃*2ClH
• Molecular Weight: 232.54
• DSSTox Substance ID: DTXSID10415949
• Wikidata: Q82225039
• Mol file: 75614-86-7.mol

Synonyms:s-a-chloromethylhistamine;(2S)-1-chloro-3-(1H-imidazol-5-yl)propan-2-amine;r(-)-alpha-Chloromethyl histamine dihydrochloride;75614-86-7;SCHEMBL6336321;DTXSID10415949

Chemical Property of (2S)-1-chloro-3-(1H-imidazol-5-yl)propan-2-amine

Chemical Property:

• PSA: 54.70000
• LogP: 2.82260
• Solubility.: Dimethyl Sulfoxide, Methanol, Water
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 159.0563250
• Heavy Atom Count: 10
• Complexity: 99

Purity/Quality:

98% ^*data from raw suppliers

R(-)-α-ChloromethylHistamineDihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(NC=N1)CC(CCl)N
• Isomeric SMILES: C1=C(NC=N1)C[C@@H](CCl)N
• Uses: Histamine analog, with histamine-like activity.

Technology Process of (2S)-1-chloro-3-(1H-imidazol-5-yl)propan-2-amine

There total 6 articles about (2S)-1-chloro-3-(1H-imidazol-5-yl)propan-2-amine 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: 90.0%

(S)-histidinol (4836-52-6) → (S)-(+)-4-(2-amino-3-chloropropyl)-imidazole dihydrochloride (75614-85-6,75614-86-7)

Guidance literature:

With thionyl chloride; In sulfolane; at 55 ℃; for 7h;

DOI:10.1002/ardp.19803130810

Reference yield:

R-(+)-4-(2-Amino-3-hydroxypropyl)-imidazol (70142-15-3) → R-(-)-4-(2-Amino-3-chlorpropyl)-imidazol-dihydrochlorid (75614-85-6,75614-86-7)

Guidance literature:

With thionyl chloride; In sulfolane;

DOI:10.1002/ardp.19803130810

Reference yield:

L-histidine monohydrochloride (645-35-2) → (S)-(+)-4-(2-amino-3-chloropropyl)-imidazole dihydrochloride (75614-85-6,75614-86-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / HCl / 3 h / Heating

2: LiAlH₄ / tetrahydrofuran / 3 h / Heating

3: 90 percent / SOCl₂ / tetrahydrothiophene 1,1-dioxide / 7 h / 55 °C

With hydrogenchloride; lithium aluminium tetrahydride; thionyl chloride; In tetrahydrofuran; sulfolane;

DOI:10.1002/ardp.19803130810

upstream raw materials:

(S)-histidinol

L-histidine monohydrochloride

L-Histidine methyl ester

R-(+)-4-(2-Amino-3-hydroxypropyl)-imidazol

Downstream raw materials:

(R)(?)-α-methyl-1H-imidazole-4-ethanamine dihydrochloride

[3H]-(R)α-methylhistamine

(R)-2-(1H-Imidazol-4-yl)-1-methyl-ethylamine

Refernces