Conditions | Yield |
---|---|
With N-hydroxyphthalimide; oxygen In acetonitrile at 30℃; for 3h; Schlenk technique; | 95% |
With N-hydroxyphthalimide; oxygen In acetonitrile at 30℃; under 760.051 Torr; for 3h; Catalytic behavior; Solvent; Schlenk technique; | 95% |
5-bromopentanoic acid
Conditions | Yield |
---|---|
With sulfuric acid; sodium bromide In water at 90 - 95℃; for 8h; Temperature; Concentration; | 88.9% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; hydrogen bromide In water for 0.166667h; Microwave irradiation; | 85% |
With sulfuric acid; water; hydrogen bromide | |
With hydrogen bromide |
1,4-dioxane
3,4,5,6-tetrahydro-2H-pyran-2-one
A
5-bromopentanoic acid
B
β-(β'-bromoethoxy)ethyl 4-bromovalerate
Conditions | Yield |
---|---|
With hydrogen bromide In water 1) room temp. 1h; 2) 80 degC, 1,5h; 3) room temp. 12h; | A 64.12% B 20.24% |
3,4,5,6-tetrahydro-2H-pyran-2-one
A
5-bromopentanoic acid
B
β-(β'-bromoethoxy)ethyl 4-bromovalerate
Conditions | Yield |
---|---|
With hydrogen bromide In 1,4-dioxane; water 1) room temp. 1 h; 2) 80 deg C, 1,5 h; 3) room temp. 12 h; | A 64.12% B 20.24% |
Conditions | Yield |
---|---|
With hydrogen bromide for 17h; Heating; | 38% |
With hydrogen bromide | |
With hydrogen bromide | |
Multi-step reaction with 2 steps 1: potassium hydroxide 2: water; hydrobromic acid View Scheme | |
Multi-step reaction with 2 steps 2: water; hydrobromic acid View Scheme |
Conditions | Yield |
---|---|
With hydrogen bromide; dibenzoyl peroxide | |
With ascaridole; hexane; hydrogen bromide |
valeric acid
5-bromopentanoic acid
Conditions | Yield |
---|---|
With sulfuric acid; hydrogen bromide | |
With sulfuric acid; hydrogen bromide Cooling with ice; Heating; |
Conditions | Yield |
---|---|
With water; hydrogen bromide |
Conditions | Yield |
---|---|
With water; hydrogen bromide |
Conditions | Yield |
---|---|
With hydrogen bromide | |
(hydrolysis); |
ethyl 2-hydroxyethylpropionate
5-bromopentanoic acid
Conditions | Yield |
---|---|
With sulfuric acid; hydrogen bromide zuletzt auf dem Wasserbad; |
(4-cyano)butyl acetate
5-bromopentanoic acid
Conditions | Yield |
---|---|
With water; hydrogen bromide |
diethyl 2-(3-bromopropane)malonate
5-bromopentanoic acid
Conditions | Yield |
---|---|
With hydrogen bromide |
Conditions | Yield |
---|---|
With hydrogen bromide |
Conditions | Yield |
---|---|
With hydrogen bromide |
Conditions | Yield |
---|---|
With dihydrogen peroxide Behandeln des Reaktionsprodukts in Aether mit einer aus Kupfer(I)-chlorid (oder Eisen(II)-sulfat) und wss.Bromwasserstoffsaeure bereiteten Loesung; | |
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / chloroform / Reflux 2: hydrogen bromide; sodium bromide; sulfuric acid / 85 - 90 °C View Scheme |
ethyl 5-bromovalerate
5-bromopentanoic acid
Conditions | Yield |
---|---|
(hydrolysis); | |
With water; lithium hydroxide In methanol at 20℃; for 0.5h; |
cyclopentanone hydroperoxide
A
5-bromopentanoic acid
C
2-bromocyclopentanone
Conditions | Yield |
---|---|
With hydrogen bromide; sodium bromide; copper(ll) bromide In water at 25℃; | A 15.0 g B 0.4 g C 0.6 g |
C17H34O2Sn
5-bromopentanoic acid
Conditions | Yield |
---|---|
With hydrogen bromide Irradiation; |
5-bromopentanoic acid
Conditions | Yield |
---|---|
With silver(I) bromide; hydrogen bromide |
5-bromopentanoic acid
Conditions | Yield |
---|---|
With hydrogen bromide at 145℃; im geschlossenen Rohr; |
pent-4-enoic acid
hexane
hydrogen bromide
5-bromopentanoic acid
ascaridole
pent-4-enoic acid
hexane
hydrogen bromide
5-bromopentanoic acid
pent-4-enoic acid
hydrogen bromide
diphenylamine
5-bromopentanoic acid
5-bromopentanoic acid
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid |
pent-4-enoic acid
hydrogen bromide
hydroquinone
5-bromopentanoic acid
pent-4-enoic acid
hydrogen bromide
toluene
5-bromopentanoic acid
pent-4-enoic acid
hydrogen bromide
dibenzoyl peroxide
5-bromopentanoic acid
5-bromopentanoic acid
5-iodopentanoic acid
Conditions | Yield |
---|---|
With potassium iodide In acetone for 6h; Heating; | 100% |
With acetone; sodium iodide | |
Multi-step reaction with 2 steps 1: KHS 2: hydriodic acid View Scheme |
Conditions | Yield |
---|---|
With thionyl chloride | 100% |
With oxalyl dichloride In benzene at 20 - 50℃; Inert atmosphere; | 98% |
With oxalyl dichloride In benzene at 50℃; for 3h; | 97% |
1-[5-(aminomethyl)-2-nitrophenyl]ethanol
5-bromopentanoic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; | 100% |
Conditions | Yield |
---|---|
With acetyl chloride for 5h; Reflux; | 99% |
With hydroxy-substituted sulfonic acid-functionalized silica (HO-SAS) at 110℃; Fischer-Speier Esterification; Flow reactor; | 99% |
With acetyl chloride for 5h; Reflux; | 99% |
5-bromopentanoic acid
(3R,5R)-1-benzyl-5-(hydroxydiphenylmethyl)pyrrolidin-3-yl 5-bromopentanoate
Conditions | Yield |
---|---|
Stage #1: 5-bromopentanoic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.166667h; Stage #2: (3R,5R)-1-benzyl-5-(hydroxydiphenylmethyl)pyrrolidin-3-ol In dichloromethane at 0℃; for 1.5h; Reflux; | 99% |
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; for 5h; Addition; | 98% |
With sulfuric acid In dichloromethane for 48h; Ambient temperature; | 96% |
With sulfuric acid at 20℃; for 120h; autoclave; | 72% |
5-bromopentanoic acid
5-bromopentanamide
Conditions | Yield |
---|---|
Stage #1: 5-bromopentanoic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 40℃; for 2h; Stage #2: With ammonium hydroxide In tetrahydrofuran at 20℃; for 2h; | 98% |
Multi-step reaction with 2 steps 1: SOCl2 / 4 h / Heating 2: 28percent NH4OH / H2O / 0.75 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Stage #1: 5-bromopentanoic acid; (3Z,13Z)-7-[(3Z)-hex-3-en-1-yl]-10-[(3Z)-non-3-en-1-yl]nonadeca-3,13-dien-9-ol With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 30℃; for 18h; Stage #2: 2-(N,N-dimethylamino)ethanol In dichloromethane at 80℃; for 5h; Sealed tube; | 98% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Schlenk technique; Inert atmosphere; | 98% |
5-bromopentanoic acid
(3R,5S)-1-benzyl-5-[bis(3,5-dimethylphenyl)(hydroxy)methyl]pyrrolidin-3-ol
{(3R,5S)-1-benzyl-5-[bis(3,5-dimethylphenyl)(hydroxy)methyl]pyrrolidin-3-yl} 5-bromopentanoate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 1.66667h; Reflux; | 97% |
5-bromopentanoic acid
5-(nitrooxy)pentanoic acid
Conditions | Yield |
---|---|
With silver nitrate In acetonitrile at 70℃; for 16h; | 96.18% |
With silver nitrate In acetonitrile at 20℃; for 48h; | 89% |
With silver nitrate In acetonitrile at 70℃; for 2h; Darkness; Inert atmosphere; | 77% |
Conditions | Yield |
---|---|
With potassium fluoride; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20℃; for 5h; | 96% |
With Amberlyst A26 (hydrogen carbonate form) 1.) aq. MeOH, 20 deg C, 18 h, 2.) THF, reflux, 18 h; Yield given. Multistep reaction; | |
With potassium carbonate In water; dimethyl sulfoxide at 50℃; Rate constant; | |
With 2,3,3-trimethylbenzo[e]indole; potassium iodide In acetonitrile at 80 - 85℃; for 96h; |
5-bromopentanoic acid
triphenylphosphine
(4-carboxybutyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
In acetonitrile at 80℃; for 24h; | 96% |
In acetonitrile for 24h; Heating; | 92% |
In toluene for 48h; Inert atmosphere; Reflux; | 88% |
diazomethane
5-bromopentanoic acid
5-bromovaleric acid methyl ester
Conditions | Yield |
---|---|
In diethyl ether for 3h; | 96% |
In diethyl ether |
5-bromopentanoic acid
5-bromopentan-1-ol
Conditions | Yield |
---|---|
With dimethylsulfide borane complex | 96% |
With lithium aluminium tetrahydride; sulfuric acid In tetrahydrofuran for 0.25h; T < 2 deg C; Yield given; | |
With dimethylsulfide; borane | |
With diphenylsilane; triphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer In tetrahydrofuran at 20℃; for 48h; | 63 % Spectr. |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene Reflux; Dean-Stark; | 96% |
With 4-(dimethylamino)pyridinium tosylate; diisopropyl-carbodiimide | 95% |
Stage #1: 5-bromopentanoic acid With 4-(dimethylamino)pyridinium tosylate; diisopropyl-carbodiimide In dichloromethane at 20℃; for 2h; Stage #2: benzyl alcohol In dichloromethane | 95% |
5-bromopentanoic acid
(2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 1.5h; Reflux; | 96% |
5-bromopentanoic acid
Conditions | Yield |
---|---|
With dmap; copper diacetate In acetonitrile at 80℃; for 0.416667h; Schlenk technique; Sealed tube; | 96% |
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 20 - 22℃; for 45h; | 95% |
sulfuric acid In toluene for 1.5h; Heating; | 88.5% |
With sulfuric acid | 87% |
endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide
5-bromopentanoic acid
N-hydroxy-5-norbornene-2,3-dicarboximide bromopentanoate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide | 95% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; |
5-bromopentanoic acid
(3R,5S)-1-benzyl-5-[bis(3,5-bis(trifluoromethyl)phenyl)(hydroxy)methyl]pyrrolidin-3-ol
{(3R,5S)-1-benzyl-5-[bis(3,5-bis(trifluoromethyl)phenyl)(hydroxy)methyl]pyrrolidin-3-yl} 5-bromopentanoate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 1.66667h; Reflux; | 95% |
Conditions | Yield |
---|---|
Stage #1: 5-bromopentanoic acid With 1-methyl-pyrrolidin-2-one; tert-butylmagnesium chloride In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: n-octylmagnesium chloride With buta-1,3-diene; nickel dichloride In tetrahydrofuran under 760.051 Torr; for 1h; Inert atmosphere; Cooling with ice; | 95% |
Conditions | Yield |
---|---|
With trifluoroacetic anhydride; Duolite ES 467 H+ phosphonic resin In nitromethane at 25℃; for 0.5h; | 94% |
5-bromopentanoic acid
5-mercaptopentanoic acid
Conditions | Yield |
---|---|
Stage #1: 5-bromopentanoic acid With thiourea In ethanol at 80℃; for 20h; Stage #2: With sodium hydroxide at 90℃; for 16h; | 94% |
Stage #1: 5-bromopentanoic acid With thiourea In ethanol for 20h; Reflux; Stage #2: With sodium hydroxide In water at 90℃; for 16h; Inert atmosphere; Stage #3: With sulfuric acid In water Cooling with ice; Inert atmosphere; | 87% |
Stage #1: 5-bromopentanoic acid With thiourea In ethanol for 16h; Heating; Stage #2: With sodium hydroxide for 6h; Heating; | 82% |
5-bromopentanoic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 1.16667h; | 94% |
5-bromopentanoic acid
(2R)-(-)-2-phenyl-2-(piperidin-1-yl)ethanol
Conditions | Yield |
---|---|
Stage #1: (2R)-(-)-2-phenyl-2-(piperidin-1-yl)ethanol With methanesulfonyl chloride; triethylamine In chloroform at 0 - 5℃; for 0.5h; Stage #2: 5-bromopentanoic acid With triethylamine In chloroform at 5 - 20℃; for 16h; enantiospecific reaction; | 94% |
5-bromopentanoic acid
dibenzyl 5,5'-((1,4-phenylenebis(azanediyl))bis(carbonyl))bis(3-hydroxypyrrolidine-1-carboxylate)
dibenzyl 5,5'-((1,4-phenylenebis(azanediyl))bis(carbonyl))bis(3-((5-bromopentanoyl)oxy)-pyrrolidine-1-carboxylate)
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 4h; | 93% |
5-bromopentanoic acid
N,0-dimethylhydroxylamine
5-bromo-N-methoxy-N-methylpentanamide
Conditions | Yield |
---|---|
Stage #1: 5-bromopentanoic acid; N,0-dimethylhydroxylamine In toluene at 0℃; for 0.166667h; Stage #2: With phosphorus trichloride In toluene at 20 - 60℃; for 0.5h; | 93% |
5-bromopentanoic acid
dibenzyl 5,5'-((ethane-1,2-diylbis(azanediyl))bis(carbonyl))bis(3-hydroxypyrrolidine-1-carboxylate)
dibenzyl 5,5'-((ethane-1,2-diylbis(azanediyl))bis(carbonyl))bis(3-((5-bromopentanoyl)oxy)pyrrolidine-1-carboxylate)
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 4h; | 92% |
IUPAC Name: 5-Bromopentanoic acid
Molecular Formula: C5H9BrO2
Molecular Weight: 181.03 g/mol
SMILES: C(CCCBr)C(O)=O
InChI: InChI=1/C5H9BrO2/c6-4-2-1-3-5(7)8/h1-4H2,(H,7,8)
EINECS: 218-185-3
Product Categories: Organic acids;Acids & Esters; Bromine Compounds; omega-Bromocarboxylic Acids; omega-Functional Alkanols, Carboxylic Acids, Amines & Halides; C1 to C5; Carbonyl Compounds; Carboxylic Acids
Index of Refraction: 1.492
Molar Refractivity: 34.5 cm3
Molar Volume: 118.8 cm3
Polarizability: 13.68×10-24 cm3
Surface Tension: 43.3 dyne/cm
Density: 1.522 g/cm3
Flash Point: 114.4 °C
Enthalpy of Vaporization: 55.42 kJ/mol
Boiling Point: 265.5 °C at 760 mmHg
Melting Point: 38-40 °C(lit.)
Vapour Pressure of 5-Bromovaleric acid (CAS NO.2067-33-6): 0.00264 mmHg at 25 °C
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
RIDADR: UN3261
WGK Germany: 3
HazardClass: 8
PackingGroup of 5-Bromovaleric acid (CAS NO.2067-33-6): III
5-Bromovaleric acid (CAS NO.2067-33-6), its Synonyms are 5-Bromopentanoic acid ; Valeric acid, 5-bromo- ; delta-Bromovaleric acid ; Pentanoic acid, 5-bromo- . It is yellowish to light brown crystals or cryst. powder.
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