1-Hydroxypyrrolidine

Base Information

• Chemical Name: 1-Hydroxypyrrolidine
• CAS No.: 5904-62-1
• Molecular Formula: C4H9 N O
• Molecular Weight: 87.1216
• European Community (EC) Number: 227-600-7
• NSC Number: 71874
• UNII: H3ED8F4KUG
• DSSTox Substance ID: DTXSID40207793
• Nikkaji Number: J388.271C
• Wikidata: Q83081790
• Mol file: 5904-62-1.mol

Synonyms:1-Hydroxypyrrolidine;pyrrolidin-1-ol;5904-62-1;hydroxypyrrolidine;H3ED8F4KUG;EINECS 227-600-7;NSC-71874;n-hydroxypyrrolidine;NSC71874;1-PYRROLIDINOL;Pyrrolidine, 1-hydroxy-;UNII-H3ED8F4KUG;DTXSID40207793;NSC 71874;AKOS006275746;EN300-2232849

Chemical Property of 1-Hydroxypyrrolidine

Chemical Property:

• Vapor Pressure: 1.8mmHg at 25°C
• Boiling Point: 153.3°Cat760mmHg
• Flash Point: 78.4°C
• PSA: 23.47000
• Density: 1.134g/cm³
• LogP: 0.40930
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 87.068413911
• Heavy Atom Count: 6
• Complexity: 40.8

Purity/Quality:

99% ^*data from raw suppliers

PYRROLIDIN-1-OL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(C1)O

Technology Process of 1-Hydroxypyrrolidine

There total 10 articles about 1-Hydroxypyrrolidine 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: 100.0%

1,4-dibromo-butane (110-52-1) → pyrrolidin-1-ol (5904-62-1)

Guidance literature:

With hydroxylamine hydrochloride; triethylamine; for 1.5h; Heating;

DOI:10.1016/j.bmcl.2004.11.048

Reference yield: 84.0%

→ pyrrolidin-1-ol (5904-62-1)

Guidance literature:

Reference yield: 72.0%

pyrrolidine (123-75-1) → pyrrolidin-1-ol (5904-62-1)

Guidance literature:

With 2-hydroxy-N,N,N-trimethyl ethanaminium peroxydisulfate; at 60 ℃; for 1h; chemoselective reaction; Inert atmosphere; Green chemistry;

DOI:10.1055/s-0036-1589089

upstream raw materials:

pyrrolidine

1-pyrroline N-oxide

1-ethyl-pyrrolidine-1-oxide

1-hydroxy-pyrrolidine-2,5-dione

Downstream raw materials:

1-pyrroline N-oxide

2(β)-phenylhexahydropyrrolo(1,2-b)isoxazole

2,2-tetramethylene-5-oxo-4-phenyl-2,5-dihydroisoxazol-2-ium-3-olate

1-pyrrolidinecarboxaldehyde

Refernces

Facile synthesis of α,α′ disubstituted N-hydroxypyrrolidines and N-hydroxypiperidines via double 1,4-addition of hydroxylamine

10.1016/j.tetlet.2006.03.064

The research presents a versatile and efficient method for synthesizing α,α'-disubstituted N-hydroxypiperidines and N-hydroxypyrrolidines through a double 1,4-addition of hydroxylamine to bis α,β-unsaturated diesters. The synthesis occurs in an environmentally friendly ethanol/water system at room temperature. Key chemicals involved include octa-2,6-dienedioic acid diethyl ester and nona-2,6-dienedioic acid diethyl ester, which are synthesized from succinaldehyde or glutaraldehyde. Hydroxylamine is used for the double 1,4-addition, yielding N-hydroxypyrrolidines and N-hydroxypiperidines with good selectivity for the cis isomers. The study also explores the behavior of the double 1,4-addition in systems containing a ketone, revealing that the keto group can be selectively converted to either an oxime or an N-hydroxy compound by adjusting the amount of hydroxylamine.

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