(S)-(+)-5-Bromomethyl-2-pyrrolidinone

Base Information

• Chemical Name: (S)-(+)-5-Bromomethyl-2-pyrrolidinone
• CAS No.: 72479-05-1
• Molecular Formula: C5H8BrNO
• Molecular Weight: 178.029
• Hs Code.: 29339900
• European Community (EC) Number: 686-904-1
• DSSTox Substance ID: DTXSID30459385
• Nikkaji Number: J1.499.084D
• Wikidata: Q72447989
• Mol file: 72479-05-1.mol

Synonyms:72479-05-1;(S)-(+)-5-Bromomethyl-2-pyrrolidinone;(S)-5-(Bromomethyl)-2-pyrrolidinone;(S)-5-(bromomethyl)pyrrolidin-2-one;(5S)-5-(bromomethyl)pyrrolidin-2-one;(S)-5-Bromomethyl-2-pyrrolidinone;(S)-5-Bromomethyl-2-oxopyrrolidine;(5S)-5-(bromomethyl)-2-pyrrolidinone;MFCD01632456;(S)-5-(BROMOMETHYL)-2-PYRROLIDONE;SCHEMBL378495;DTXSID30459385;QFOSFXPTXNRRMF-BYPYZUCNSA-N;AMY25044;CS-B0460;5beta-(Bromomethyl)pyrrolidine-2-one;AKOS015833846;(2-pyrrolidon-5-(S)-yl)methylbromide;DS-13486;(S)-5-(Bromomethyl)-2-pyrrolidinone, 96%;EN300-264301;A837537

Chemical Property of (S)-(+)-5-Bromomethyl-2-pyrrolidinone

Chemical Property:

• Vapor Pressure: 0.000115mmHg at 25°C
• Melting Point: 75-79°C
• Refractive Index: 1.506
• Boiling Point: 336.1 °C at 760 mmHg
• PKA: 15.39±0.40(Predicted)
• Flash Point: 157.1 °C
• PSA: 29.10000
• Density: 1.541 g/cm³
• LogP: 0.98870
• Storage Temp.: 2-8°C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 176.97893
• Heavy Atom Count: 8
• Complexity: 105

Purity/Quality:

99% ^*data from raw suppliers

(S)-5-(Bromomethyl)-2-pyrrolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-43-36-22
• Safety Statements: 26-36/37/39-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)NC1CBr
• Isomeric SMILES: C1CC(=O)N[C@@H]1CBr

Technology Process of (S)-(+)-5-Bromomethyl-2-pyrrolidinone

There total 6 articles about (S)-(+)-5-Bromomethyl-2-pyrrolidinone 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: 95.0%

(S)-Pyroglutaminol (17342-08-4) → (S)-(-)-5-(Bromomethyl)-2-pyrrolidinone (72479-05-1)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 25 ℃; for 70h;

DOI:10.1002/hlca.19960790404

Reference yield: 86.0%

(S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester (51693-17-5) → (S)-(-)-5-(Bromomethyl)-2-pyrrolidinone (72479-05-1)

Guidance literature:

With lithium bromide; In acetone; Reflux; Inert atmosphere;

Reference yield:

methyl (S)-pyroglutamate (4931-66-2) → (S)-(-)-5-(Bromomethyl)-2-pyrrolidinone (72479-05-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / NaBH₄ / ethanol / 2 h / Ambient temperature

2: 72.8 percent / CBr₄, Ph₃P / acetonitrile / Ambient temperature

With sodium tetrahydroborate; carbon tetrabromide; triphenylphosphine; In ethanol; acetonitrile;

DOI:10.1021/ja00158a052

upstream raw materials:

(S)-Pyroglutaminol

L-glutamic acid

ethyl (S)-pyroglutamate

methyl (S)-pyroglutamate

Downstream raw materials:

(S)-5-biphenyl-4-ylmethylpyrrolidin-2-one

(S)-2-{3,5-dimethyl-4-[(5-oxopyrrolidin-2-yl)methoxy]phenyl}-5,7-dimethoxyquinazolin-4(3H)-one

(S)-3,5-dimethyl-4-[(5-oxopyrrolidin-2-yl)methoxy]benzaldehyde

(4S)-4-amino-5-(propylthio)pentanal O-benzyloxime

Refernces

• 1、 -. "BICYCLIC AZA COMPOUNDS AS MUSCARINIC M1 RECEPTOR AGONISTS.". . . Retrieved 2015/09/22.
• 2、 -. "TREATMENT OF DISEASES BY EPIGENETIC REGULATION". Paragraph 0708. . Retrieved 2013/11/05.