(R)-5-Bromomethyl-2-pyrrolidinone

Base Information

• Chemical Name: (R)-5-Bromomethyl-2-pyrrolidinone
• CAS No.: 98612-60-3
• Molecular Formula: C5H8BrNO
• Molecular Weight: 178.03
• Hs Code.: 29339900
• European Community (EC) Number: 686-905-7
• DSSTox Substance ID: DTXSID60503704
• Nikkaji Number: J181.387K
• Wikidata: Q72447991
• Mol file: 98612-60-3.mol

Synonyms:98612-60-3;(R)-5-Bromomethyl-2-pyrrolidinone;(R)-5-(Bromomethyl)pyrrolidin-2-one;(5R)-5-(bromomethyl)pyrrolidin-2-one;(R)-(-)-5-Bromomethyl-2-pyrrolidinone;2-Pyrrolidinone, 5-(bromomethyl)-, (R)-;MFCD06799465;SCHEMBL1748821;DTXSID60503704;QFOSFXPTXNRRMF-SCSAIBSYSA-N;(r)-5-bromomethylpyrrolidin-2-one;FD1199;AKOS005146087;AKOS015833848;CS-W020693;GS-3936;(5R)-5-(bromomethyl)-2-pyrrolidinone;(R)-5-(Bromomethyl)-2-pyrrolidinone, 96%;A845883

Chemical Property of (R)-5-Bromomethyl-2-pyrrolidinone

Chemical Property:

• Vapor Pressure: 0.000115mmHg at 25°C
• Melting Point: 76-80°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

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

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (R)-5-Bromomethyl-2-pyrrolidinone

There total 5 articles about (R)-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: 90.0%

<(2R)-5-oxopyrrolidin-2-yl>methyl 4-methylbenzenesulfonate (128899-31-0) → (5R)-5-(bromomethyl)pyrrolidin-2-one (98612-60-3)

Guidance literature:

With lithium bromide; In acetone; at 80 ℃;

Reference yield: 77.0%

(R)-5-hydroxymethylpyrrolidin-2-one (66673-40-3) → (5R)-5-(bromomethyl)pyrrolidin-2-one (98612-60-3)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1002/hlca.19900730113

Reference yield:

D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (5R)-5-(bromomethyl)pyrrolidin-2-one (98612-60-3)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂O / 63 h / Heating

2: SOCl₂ / 48 h / Ambient temperature; pH=0

3: 58 percent / NaBH₄ / propan-2-ol / 20 h / Ambient temperature

4: 77 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1.5 h / Ambient temperature

With sodium tetrahydroborate; thionyl chloride; carbon tetrabromide; water; triphenylphosphine; In dichloromethane; isopropyl alcohol;

DOI:10.1002/hlca.19900730113

upstream raw materials:

(R)-5-hydroxymethylpyrrolidin-2-one

D-Glutamic acid

methyl (2R)-pyroglutamate

D-pyrrolidone-5-carboxylic acid

Downstream raw materials:

(5R)-5-benzylpyrrolidin-2-one

majusculamide D

(-)-AKS 19

Refernces

• 1、 -. "MUSCARINIC AGONISTS". . . Retrieved 2017/02/28.
• 2、 -. "HEPATITIS C VIRUS INHIBITORS". Page/Page column 125-126. . Retrieved 2012/12/13.