ert-butyl 4-(bromomethylene)piperidine-1-carboxylate

Base Information

• Chemical Name: ert-butyl 4-(bromomethylene)piperidine-1-carboxylate
• CAS No.: 1020329-80-9
• Molecular Formula: C11H18BrNO2
• Molecular Weight: 276.173
• Mol file: 1020329-80-9.mol

Synonyms:1-(tert-Butoxycarbonyl)-4-bromomethylenepiperidine;1-N-Boc-4-(bromomethylene)piperidine;

Chemical Property of ert-butyl 4-(bromomethylene)piperidine-1-carboxylate

Chemical Property:

• Boiling Point: 317.686 °C at 760 mmHg
• PKA: -1.51±0.20(Predicted)
• Flash Point: 145.932 °C
• PSA: 29.54000
• Density: 1.391 g/cm³
• LogP: 3.23400
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

1-Boc-4-(bromomethylene)piperidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ert-butyl 4-(bromomethylene)piperidine-1-carboxylate

There total 4 articles about ert-butyl 4-(bromomethylene)piperidine-1-carboxylate 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: 96.0%

tert-butyl 4-(dibromomethylidene)piperidine-1-carboxylate (305794-65-4) → tert-butyl 4-(bromomethylidene)piperidine-1-carboxylate (1020329-80-9)

Guidance literature:

tert-butyl 4-(dibromomethylidene)piperidine-1-carboxylate; With ammonium chloride; In tetrahydrofuran; methanol; at 0 ℃; for 0.5h; Inert atmosphere;

With zinc; In tetrahydrofuran; methanol; at 20 ℃; for 4h; Inert atmosphere;

Reference yield: 36.0%

(bromomethyl)triphenyl phosphonium bromide (1034-49-7) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → tert-butyl 4-(bromomethylidene)piperidine-1-carboxylate (1020329-80-9)

Guidance literature:

(bromomethyl)triphenyl phosphonium bromide; With lithium hexamethyldisilazane; In tetrahydrofuran; at -20 ℃; for 1h;

N-tert-butyloxycarbonylpiperidin-4-one; In tetrahydrofuran; at -20 ℃; for 16h;

Reference yield:

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → tert-butyl 4-(bromomethylidene)piperidine-1-carboxylate (1020329-80-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triphenylphosphine; carbon tetrabromide / acetonitrile / 2.25 h / 0 - 20 °C / Inert atmosphere

2.1: ammonium chloride / tetrahydrofuran; methanol / 0.5 h / 0 °C / Inert atmosphere

2.2: 20 °C

With carbon tetrabromide; ammonium chloride; triphenylphosphine; In tetrahydrofuran; methanol; acetonitrile;

upstream raw materials:

tert-butyl 4-(dibromomethylidene)piperidine-1-carboxylate

(bromomethyl)triphenyl phosphonium bromide

N-tert-butyloxycarbonylpiperidin-4-one

di-tert-butyl dicarbonate

Downstream raw materials:

tert-butyl 4-(3-hydroxybenzylidene)piperidine-1-carboxylate

tert-butyl 4-[4-(tetrahydro-2H-pyran-4-ylsulfonyl)benzylidene]piperidine-1-carboxylate

tert-butyl 4-[2-chloro-4-(methoxycarbonyl)benzylidene]piperidine-1-carboxylate

N-pyridazin-3-yl-4-[3-(tetrahydro-2H-pyran-2-ylmethoxy)benzylidene]piperidine-1-carboxamide

Refernces

• 1、 -. "C10-ALKYLENE SUBSTITUTED 13-MEMBERED MACROLIDES AND USES THEREOF". Paragraph 00300. . Retrieved 2020/06/10.
• 2、 -. "MITOCHONDRIAL INHIBITORS FOR THE TREATMENT OF PROLIFERATION DISORDERS". Page/Page column 24; 29. . Retrieved 2019/07/19.