62595-74-8

Basic information

• Product Name: 3-broMopiperidine-2,6-dione
• Synonyms: 3-broMopiperidine-2,6-dione
• CAS NO: 62595-74-8
• Molecular Formula: C₅H₆BrNO₂
• Molecular Weight: 192.01064
• Mol File: 62595-74-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 107 °C(Solv: chloroform (67-66-3))
• Boiling Point: 336.42°C at 760 mmHg
• Flash Point: 157.261°C
• Appearance: /
• Density: 1.748g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: 2-8°C
• PKA: 10.08±0.40(Predicted)
• CAS DataBase Reference: 3-broMopiperidine-2,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-broMopiperidine-2,6-dione(62595-74-8)
• EPA Substance Registry System: 3-broMopiperidine-2,6-dione(62595-74-8)

Safety Data

• Hazardous Substances Data: 62595-74-8(Hazardous Substances Data)

Usage

General Description

3-Bromopiperidine-2,6-dione is a chemical compound with the molecular formula C5H7BrO2. It is a derivative of piperidine and is used in organic synthesis. 3-broMopiperidine-2,6-dione has a cyclic structure with a piperidine ring and a bromine atom attached to the carbon at position 3. The presence of the bromine atom makes this compound useful in various chemical reactions, such as nucleophilic substitution and palladium-catalyzed cross-coupling reactions. 3-Bromopiperidine-2,6-dione has potential applications in the pharmaceutical industry and in the development of new materials. However, it is important to handle this compound with caution due to its potential hazards, including its toxic and irritant properties.

InChI:InChI=1/C5H6BrNO2/c6-3-1-2-4(8)7-5(3)9/h3H,1-2H2,(H,7,8,9)

Synthetic route

piperidine-2,6-dione (1121-89-7) → 3-bromopiperidine-2,6-dione (62595-74-8)

Conditions	Yield
With bromine In chloroform at 110℃; for 1.5h;	99%
With bromine In chloroform at 20 - 110℃; for 1.5h; Inert atmosphere; Sealed tube;	55%
With bromine In chloroform at 113℃; for 1.5h; Sealed tube;	54.5%

4-nitroisoindoline + 3-bromopiperidine-2,6-dione (62595-74-8) → 3-(4-nitro-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione

Conditions	Yield
With copper(l) iodide; potassium carbonate In tetrahydrofuran at 60℃; for 6h; Reagent/catalyst; Solvent; Temperature;	90.4%
In N,N-dimethyl-formamide at 100℃; for 20h; Solvent; Temperature;	73.1%

3-bromopiperidine-2,6-dione (62595-74-8) + (3-aminophenyl)carbamic acid tert-butyl ester (68621-88-5) → tert-butyl N-[3-[(2,6-dioxo-3-piperidyl)amino]phenyl]carbamate

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 80℃; for 16h;	84.2%
In N,N-dimethyl-formamide at 80℃; for 12h;

3-bromopiperidine-2,6-dione (62595-74-8) + benzyl-methyl-amine (103-67-3) → 3-(benzyl-methyl-amino)-piperidine-2,6-dione

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 16h;	83%
In tetrahydrofuran at 72℃; for 16h;

1-methyl-piperazine (109-01-3) + 3-bromopiperidine-2,6-dione (62595-74-8) → 3-(4-methylpiperazin-1-yl)piperidine-2,6-dione

Conditions	Yield
at 20℃; for 2h;	82%

3-bromopiperidine-2,6-dione (62595-74-8) → 3-azidopiperidine-2,6-dione

Conditions	Yield
With sodium azide In water; acetone at 20℃; for 24h; Inert atmosphere;	80%
With sodium azide In acetone at 20℃; for 48h;	1.44g

3-bromopiperidine-2,6-dione (62595-74-8) + C25H26F2N4O3 → C30H31F2N5O5

Conditions	Yield
Stage #1: C25H26F2N4O3 With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.25h; Stage #2: 3-bromopiperidine-2,6-dione In tetrahydrofuran; mineral oil for 1h;	78.41%

2-Phenyl-4,5,6,7-tetrahydro-4,7-dithia-1,3-indandion (7747-10-6) + 3-bromopiperidine-2,6-dione (62595-74-8) → 3-<2-(1,3-Dioxo-2-phenyl-4,5,6,7-tetrahydro-4,7-dithiaindanyl)>glutarimid (76059-14-8)

Conditions	Yield
With sodium 1.) EtOH, 2.) THF, reflux, 1 h;	78%

3-bromopiperidine-2,6-dione (62595-74-8) + C27H30N4O3 → tert-butyl 7-[4-[[1-(2,6-dioxo-3-piperidyl)-2-oxobenzo[cd]indol-6-yl]methyl]pyrazol-1-yl]-4-azaspiro[2.5]octane-4-carboxylate

Conditions	Yield
Stage #1: C27H30N4O3 With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.25h; Stage #2: 3-bromopiperidine-2,6-dione In tetrahydrofuran; mineral oil	75.67%

3-bromopiperidine-2,6-dione (62595-74-8) + 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (1745-07-9) → 3-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)piperidine-2,6-dione

Conditions	Yield
at 20℃; for 18h;	75%

3-bromopiperidine-2,6-dione (62595-74-8) + tert-butyl 4-[4-[1-(2-oxo-1H-benzo[cd]indol-6-yl)cyclopropyl]pyrazol-1-yl]piperidine-1-carboxylate → tert-butyl 4-[4-[1-[1-(2,6-dioxo-3-piperidyl)-2-oxobenzo[cd]indol-6-yl]cyclopropyl]pyrazol-1-yl]piperidine-1-carboxylate

Conditions	Yield
Stage #1: tert-butyl 4-[4-[1-(2-oxo-1H-benzo[cd]indol-6-yl)cyclopropyl]pyrazol-1-yl]piperidine-1-carboxylate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.166667h; Stage #2: 3-bromopiperidine-2,6-dione In tetrahydrofuran; mineral oil	74.71%

3-bromopiperidine-2,6-dione (62595-74-8) + C26H31N3O → 3-(6-((1-((1r,4r)-4-neopentylcyclohexyl)-1H-pyrazol-4-yl)methyl)-2-oxobenzo[cd]indol-1(2H)-yl)piperidine-2,6-dione

Conditions	Yield
Stage #1: C26H31N3O With sodium hydride In tetrahydrofuran; mineral oil at 25℃; for 3.5h; Stage #2: 3-bromopiperidine-2,6-dione In mineral oil	71.98%

3-bromopiperidine-2,6-dione (62595-74-8) + tert-butyl 4-[4-[(2-oxo-1H-benzo[cd]indol-6-yl)methyl]phenyl]piperazine-1-carboxylate → tert-butyl 4-[4-[[1-(2,6-dioxo-3-piperidyl)-2-oxobenzo[cd]indol-6-yl]methyl]phenyl]piperazine-1-carboxylate

Conditions	Yield
Stage #1: tert-butyl 4-[4-[(2-oxo-1H-benzo[cd]indol-6-yl)methyl]phenyl]piperazine-1-carboxylate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Stage #2: 3-bromopiperidine-2,6-dione In tetrahydrofuran; mineral oil at 60℃; for 0.5h;	70.37%

3-bromopiperidine-2,6-dione (62595-74-8) + 2,2'-disulfanediyldiisonicotinamide → 2-((2,6-dioxopiperidin-3-yl)thio)isonicotinamide

Conditions	Yield
Stage #1: 2,2'-disulfanediyldiisonicotinamide With potassium carbonate; sodium thiosulfate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 3-bromopiperidine-2,6-dione In N,N-dimethyl-formamide at 20℃; for 2h;	69.2%

3-bromopiperidine-2,6-dione (62595-74-8) + 3-Bromothiophenol (6320-01-0) → 3-((3-bromophenyl)thio)piperidine-2,6-dione

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃; for 2h;	67.1%

3-bromopiperidine-2,6-dione (62595-74-8) + tert-butyl 4-(5-chloro-6-oxo-1,6-dihydropyridazin-4-yl)piperazine-1-carboxylate → tert-butyl 4-(5-chloro-1-(2,6-dioxopiperidin-3-yl)-6-oxo-1,6-dihydropyridazin-4-yl)piperazine-1-carboxylate

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide for 48h;	67%

1,2,3,4-tetrahydroisoquinoline (91-21-4) + 3-bromopiperidine-2,6-dione (62595-74-8) → 3-(3,4-dihydroisoquinolin-2(1H)-yl)piperidine-2,6-dione

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 72℃; for 1.5h;	66%

1,2,3,4-tetrahydroisoquinoline (91-21-4) + 3-bromopiperidine-2,6-dione (62595-74-8) → 3-(isoindolin-2-yl)piperidine-2,6-dione

Conditions	Yield
In tetrahydrofuran at 72℃; for 14h;	66%

3-bromopiperidine-2,6-dione (62595-74-8) + thiophenol (108-98-5) → 3-(phenylthio)piperidine-2,6-dione

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;	66%

3-bromopiperidine-2,6-dione (62595-74-8) + 1-cyclopropyl-1H-benzo[d]imidazole-2-thiol → 3-((1-cyclopropyl-1H-benzo[d]imidazol-2-yl)thio)piperidine-2,6-dione

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;	65.6%

3-bromopiperidine-2,6-dione (62595-74-8) + 3-fluoro-4-(4-(4-((2-oxo-1,2-dihydrobenzo[cd]indol-6-yl)methyl)benzyl)piperazin-1-yl)benzonitrile → 4-(4-(4-((1-(2,6-dioxopiperidin-3-yl)-2-oxo-1,2-dihydrobenzo[cd]indol-6-yl)methyl)benzyl)piperazin-1-yl)-3-fluorobenzonitrile

Conditions	Yield
Stage #1: 3-fluoro-4-(4-(4-((2-oxo-1,2-dihydrobenzo[cd]indol-6-yl)methyl)benzyl)piperazin-1-yl)benzonitrile With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.25h; Stage #2: 3-bromopiperidine-2,6-dione In tetrahydrofuran; mineral oil	63%

3-bromopiperidine-2,6-dione (62595-74-8) + 7-chloro-1,2,3,4-tetrahydro-isoquinoline (82771-60-6) → 3-(7-chloro-3,4-dihydroisoquinolin-2(1H)-yl)piperidine-2,6-dione

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 16h;	62%

3-bromopiperidine-2,6-dione (62595-74-8) + C27H30N4O3 → C32H35N5O5

Conditions	Yield
Stage #1: C27H30N4O3 With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.25h; Stage #2: 3-bromopiperidine-2,6-dione In tetrahydrofuran; mineral oil	61%

3-bromopiperidine-2,6-dione (62595-74-8) + di-tert-butyl dicarbonate (24424-99-5) + 6-fluoro-3-nitroaniline (369-36-8) → 3-((3-amino-4-fluorophenyl)amino)piperidine-2,6-dione

Conditions	Yield
Stage #1: di-tert-butyl dicarbonate; 6-fluoro-3-nitroaniline With dmap In tetrahydrofuran at 50℃; for 12h; Inert atmosphere; Stage #2: With palladium/alumina; hydrogen In methanol at 15℃; under 2585.81 Torr; for 2h; Stage #3: 3-bromopiperidine-2,6-dione Further stages;	60.6%

3-bromopiperidine-2,6-dione (62595-74-8) + C27H23FN6O → 4-[4-[[1-[[1-(2,6-dioxo-3-piperidyl)-2-oxobenzo[cd]indol-6-yl]methyl]pyrazol-4-yl]methyl]piperazin-1-yl]-3-fluorobenzonitrile

Conditions	Yield
Stage #1: C27H23FN6O With sodium hydride In tetrahydrofuran; mineral oil at 5 - 20℃; for 0.25h; Stage #2: 3-bromopiperidine-2,6-dione In tetrahydrofuran; mineral oil	60.5%

4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (149377-19-5) + 3-bromopiperidine-2,6-dione (62595-74-8) → tert-butyl 4-[4-[(2,6-dioxo-3-piperidyl)oxy]phenyl]piperidine-1-carboxylate

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 90℃; for 12h; Inert atmosphere;	60%

3-bromopiperidine-2,6-dione (62595-74-8) + 6-[[4-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)phenyl]methyl]-1H-benzo[cd]indol-2-one → 3-[6-[[4-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)phenyl]methyl]-2-oxobenzo[cd]indol-1-yl]piperidine-2,6-dione

Conditions	Yield
Stage #1: 6-[[4-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)phenyl]methyl]-1H-benzo[cd]indol-2-one With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Stage #2: 3-bromopiperidine-2,6-dione In tetrahydrofuran; mineral oil at 20 - 70℃;	59.59%

3-bromopiperidine-2,6-dione (62595-74-8) + monothiophthalimide (18138-18-6) → 3-(3-oxo-2,3-dihydroisoindol-1-ylidene)piperidine-2,6-dione

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 7h; Eschenmoser coupling reaction; Heating;	58%
With sodium carbonate In tetrahydrofuran for 7h; Eschenmoser coupling; Heating / reflux;	58%

3-bromopiperidine-2,6-dione (62595-74-8) + C26H31N3O → 3-(6-((1-((1s,4s)-4-neopentylcyclohexyl)-1H-pyrazol-4-yl)methyl)-2-oxobenzo[cd]indol-1(2H)-yl)piperidine-2,6-dione

Conditions	Yield
Stage #1: C26H31N3O With sodium hydride In tetrahydrofuran; mineral oil at 25℃; for 0.166667h; Stage #2: 3-bromopiperidine-2,6-dione In mineral oil	57.48%

3-bromopiperidine-2,6-dione (62595-74-8) + 1-ethyl-1H-benzo[d]imidazole-2-thiol (39573-31-4) → 3-((1-ethyl-1H-benzo[d]imidazol-2-yl)thio)piperidine-2,6-dione

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;	57.3%

Upstream product

• 1121-89-7 piperidine-2,6-dione 

Downstream Products

• 16477-31-9 3-(2,3-Dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-2,6-dioxopiperidine 
• 76059-14-8 3-<2-(1,3-Dioxo-2-phenyl-4,5,6,7-tetrahydro-4,7-dithiaindanyl)>glutarimid 
• 74972-59-1 3-(2-methyl-1,3-dioxo-1H-inden-2-yl)piperidine-2,6-dione 
• 76059-13-7 3-<2-(1,3-Dioxo-2-phenylindanyl)>glutarimid 
• 477728-23-7 C₁₈H₁₇NO₂S 
• 870806-30-7 3-(2-aminobenzylamino)piperidine-2,6-dione 
• 730240-80-9 3-(2-chlorobenzylamino)-piperidine-2,6-dione 
• 1174737-83-7 2-(4-hydroxyphenyl)-6,7-dihydro[1,3]thiazolo[4,5-b]pyridin-5(4H)-one 
• 1004763-36-3 2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-4,5,6,7-tetrahydro[1,3]thiazolo[4,5-b]pyridine 
• 351432-17-2 3-(benzylamino)piperidine-2,6-dione 
• 1426940-60-4 2-(4-fluorophenyl)-5-(6-methoxy-5-(4,5,6,7-tetrahydrothiazolo[4,5-b]pyridin-2-yl)pyridin-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide 
• 1426940-57-9 2-(4-fluorophenyl)-5-(6-methoxy-5-(5-oxo-4,5,6,7-tetrahydrothiazolo[4,5-b]pyridin-2-yl)pyridin-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide 

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