584-93-0

Basic information

• Product Name: 2-Bromovaleric acid
• Synonyms: (S)-2-Bromovaleric Acid;2-Bromovalericacid,98%;2-bromopentanoic (valeric) acid;2-bromo-3-methyl butanoic acid，2-bromo-valeric acid;2-BroMovaleric acid, 98% 25GR;A-BROMO-N-VALERIC ACID;ALPHA-BROMO-N-VALERIC ACID;2-BROMOVALERIC ACID
• CAS NO: 584-93-0
• Molecular Formula: C₅H₉BrO₂
• Molecular Weight: 181.03
• EINECS: 209-546-6
• Product Categories: Organic acids;C1 to C5;Carbonyl Compounds;Carboxylic Acids
• Mol File: 584-93-0.mol
• Article Data: 17

Chemical Properties

• Melting Point: 252 °C (sublm)
• Boiling Point: 132-136 °C25 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear pale yellow/Liquid
• Density: 1.381 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.021mmHg at 25°C
• Refractive Index: n20/D 1.4709(lit.)
• PKA: 2.97±0.20(Predicted)
• BRN: 1721172
• CAS DataBase Reference: 2-Bromovaleric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromovaleric acid(584-93-0)
• EPA Substance Registry System: 2-Bromovaleric acid(584-93-0)

Safety Data

• Hazard Codes: T,C
• Statements: 23/24/25-34-22
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• RTECS: YV6191500
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 584-93-0(Hazardous Substances Data)

Usage

Chemical Properties

Clear pale yellow liquid

Uses

2-Bromovaleric acid was used in the solid-phase synthesis of 2,4,5-trisubstituted thiomorpholine-3-ones.

InChI:InChI=1/C5H9BrO2/c1-2-3-4(6)5(7)8/h4H,2-3H2,1H3,(H,7,8)/p-1/t4-/m0/s1

Synthetic route

valeric acid (109-52-4) → 2-Bromovaleric acid (584-93-0)

Conditions	Yield
With bromine; phosphorus trichloride for 4.5h; Heating;	91%
With N-Bromosuccinimide; sulfuric acid In trifluoroacetic acid at 85℃; for 16h;	86%
With bromine; trichlorophosphate at 80 - 105℃; for 17h;	72.6%

n-propylmalonic acid (616-62-6) → 2-Bromovaleric acid (584-93-0)

Conditions	Yield
With diethyl ether; bromine in direktem Sonnenlicht einwirken und erhitzt die hierbei erhaltene Brompropylmalonsaeure auf 145;

2-hydroperoxy-butan-2-ol (19393-67-0) + acrylonitrile (107-13-1) → 2-Bromovaleric acid (584-93-0)

Conditions	Yield
With hydrogen bromide; iron(II) sulfate

n-valeryl chloride (638-29-9) → 2-Bromovaleric acid (584-93-0)

Conditions	Yield
With bromine at 90℃; for 16h; 2) 100 deg C, 0.5 h; Yield given;

2-aminopentanoic acid (760-78-1) → 2-Bromovaleric acid (584-93-0)

Conditions	Yield
With hydrogen bromide; sodium nitrite In water

2-Bromovaleric acid (584-93-0) + diallylamine (124-02-7) → N,N-diallyl-2-bromopentanamide

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane at 15℃; for 2h;	90%

2-Bromovaleric acid (584-93-0) → 3-[4-[4-(3-Chlorophenyl)-1-piperazinyl[butyl]-5-propyl-2,4-thiazolidinedione Dihydrochloride + 5-(propyl)-2,4-thiazolidinedione sodium salt

Conditions	Yield
With thiourea	A n/a B 87%

propan-1-ol (71-23-8) + 2-Bromovaleric acid (584-93-0) → propyl 2-bromopentanoate

Conditions	Yield
With sulfuric acid Reflux;	87%

2-Bromovaleric acid (584-93-0) + triethylammonium-2-N-morpholino-dithiocarbamate (23336-68-7) → 2-N-morpholino-dithiocarbamoyl-pentanoic acid (181036-27-1)

Conditions	Yield
In benzene at 20℃; for 16h;	85%
In Petroleum ether for 6h; Ambient temperature; Yield given;

2-Bromovaleric acid (584-93-0) + 2-methyl-4-nitro-benzenamine (99-52-5) → 2-Bromo-pentanoic acid (2-methyl-4-nitro-phenyl)-amide (83473-12-5)

Conditions	Yield
With phosphorus trichloride In benzene for 3h; Heating;	84%

2-Bromovaleric acid (584-93-0) + 2-(4-chloro-5-methyl-2-mercaptobenzenesulfonylimino)hexahydropyrimidine (188717-79-5) → 2-[5-Chloro-4-methyl-2-(tetrahydro-pyrimidin-2-ylidenesulfamoyl)-phenylsulfanyl]-pentanoic acid (188718-92-5)

Conditions	Yield
With sodium hydroxide; sodium carbonate In water at 80 - 85℃; for 2h;	78%

2-Bromovaleric acid (584-93-0) + 1-(4-chloro-5-cyano-2-mercaptobenzenesulphonyl)-2-imidazolidinone (160985-01-3) → 2-[5-Chloro-4-cyano-2-(2-oxo-imidazolidine-1-sulfonyl)-phenylsulfanyl]-pentanoic acid

Conditions	Yield
With sodium hydroxide; sodium carbonate In water at 40 - 80℃; for 6.5h;	76%

2-Bromovaleric acid (584-93-0) + 2,6-dimethyl-4-nitroaniline (16947-63-0) → 2-Chloro-pentanoic acid (2,6-dimethyl-4-nitro-phenyl)-amide

Conditions	Yield
With phosphorus trichloride In benzene for 3h; Heating;	73%

2-Bromovaleric acid (584-93-0) + 1-(5-cyano-2-mercaptobenzenesulphonyl)-2-imidazolidinone (160985-00-2) → 2-[4-Cyano-2-(2-oxo-imidazolidine-1-sulfonyl)-phenylsulfanyl]-pentanoic acid

Conditions	Yield
With sodium hydroxide; sodium carbonate In water at 40 - 80℃; for 6.5h;	73%

2-Bromovaleric acid (584-93-0) + dibenzylamine (103-49-1) → N,N-dibenzyl-2-bromopentanamide

Conditions	Yield
Stage #1: 2-Bromovaleric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #2: dibenzylamine With lithium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	71%

piperidine (110-89-4) + 2-Bromovaleric acid (584-93-0) → 2-bromo-1-(piperidin-1-yl)pentan-1-one

Conditions	Yield
Stage #1: 2-Bromovaleric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #2: piperidine With lithium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	69%

5-bromo-2-pyridylamine (1072-97-5) + 2-Bromovaleric acid (584-93-0) → 2-Bromo-pentanoic acid (5-bromo-pyridin-2-yl)-amide

Conditions	Yield
Stage #1: 2-Bromovaleric acid With oxalyl dichloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane at 0 - 20℃; for 5h; Stage #2: 5-bromo-2-pyridylamine With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 1.16667h;	65%

2-Bromovaleric acid (584-93-0) + diethylamine (109-89-7) → 2-bromo-N, N-diethylpentanamide

Conditions	Yield
Stage #1: 2-Bromovaleric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #2: diethylamine With lithium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	64%

2-Bromovaleric acid (584-93-0) + 2-(4-chloro-5-methyl-2-mercaptobenzenesulfonylimino)-5,5-dimethylhexahydropyrimidine (188717-81-9) → 2-[5-Chloro-2-(5,5-dimethyl-tetrahydro-pyrimidin-2-ylidenesulfamoyl)-4-methyl-phenylsulfanyl]-pentanoic acid (188718-95-8)

Conditions	Yield
With sodium hydroxide; sodium carbonate In water at 80 - 85℃; for 2h;	60%

2-Bromovaleric acid (584-93-0) + p-Chlorothiophenol (106-54-7) → 2-((4-chlorophenyl)thio)pentanoic acid

Conditions	Yield
With sodium hydroxide In water at 140℃; for 0.333333h; Microwave irradiation;	58%

2-Bromovaleric acid (584-93-0) + diisopropylamine (108-18-9) → 2-bromo-N, N-diisopropylpentanamide

Conditions	Yield
Stage #1: 2-Bromovaleric acid With oxalyl dichloride In dichloromethane at 40℃; for 2h; Inert atmosphere; Stage #2: diisopropylamine With lithium chloride In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;	57%

2-Bromovaleric acid (584-93-0) + 1-(4-chloro-2-mercapto-5-methylbenzenesulfonyl)imidazolidin-2-one → 2-[5-Chloro-4-methyl-2-(2-oxo-imidazolidine-1-sulfonyl)-phenylsulfanyl]-pentanoic acid (168698-63-3)

Conditions	Yield
With sodium hydroxide; sodium carbonate In water at 40 - 80℃; for 6.5h;	55%

2-Bromovaleric acid (584-93-0) + isopropylamine (75-31-0) → 2-bromo-N-isopropylpentanamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 10h;	54%

2-Bromovaleric acid (584-93-0) + 4-Chloro-N-[4-ethyl-tetrahydro-pyrimidin-(2E)-ylidene]-2-mercapto-5-methyl-benzenesulfonamide (188717-83-1) → 2-{5-Chloro-2-[4-ethyl-tetrahydro-pyrimidin-(2E)-ylidenesulfamoyl]-4-methyl-phenylsulfanyl}-pentanoic acid (188718-97-0)

Conditions	Yield
With sodium hydroxide; sodium carbonate In water at 80 - 85℃; for 2h;	53%

2-Bromovaleric acid (584-93-0) + N-Benzylaniline (758640-21-0) → N-benzyl-2-bromo-N-phenylpentanamide

Conditions	Yield
Stage #1: 2-Bromovaleric acid With oxalyl dichloride In dichloromethane at 40℃; for 2h; Inert atmosphere; Stage #2: N-Benzylaniline With lithium chloride In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;	53%

p-cresol (106-44-5) + 2-Bromovaleric acid (584-93-0) → 2-(p-tolyloxy)pentanoic acid

Conditions	Yield
With sodium hydroxide In water at 0 - 100℃; for 20h;	51.9%

morpholine (110-91-8) + 2-Bromovaleric acid (584-93-0) → 2-bromo-1-morpholinopentan-1-one

Conditions	Yield
Stage #1: 2-Bromovaleric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #2: morpholine With lithium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	46%

2-Bromovaleric acid (584-93-0) → valeric acid (109-52-4)

Conditions	Yield
With phosphate buffer; tris[3-(2-methoxyethoxy)propyl]stannane In water Irradiation; or with ACVA initiation;	37%

2-Bromovaleric acid (584-93-0) + para-thiocresol (106-45-6) → 2-(p-tolylthio)pentanoic acid

Conditions	Yield
With sodium hydroxide In water at 140℃; for 0.333333h; Microwave irradiation;	37%

2-Bromovaleric acid (584-93-0) + thiophenol (108-98-5) → 2-(phenylthio)pentanoic acid

Conditions	Yield
With sodium hydroxide In water at 140℃; for 0.333333h; Microwave irradiation;	36%

2-Bromovaleric acid (584-93-0) + 2.6-dimethylpiperidine (504-03-0) → 2-bromo-1-(2,6-dimethylpiperidin-1-yl)pentan-1-one

Conditions	Yield
Stage #1: 2-Bromovaleric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #2: 2.6-dimethylpiperidine With lithium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	32%

2-Bromovaleric acid (584-93-0) + N-cyclohexyl-cyclohexanamine (101-83-7) → 2-bromo-N,N-dicyclohexylpentanamide

Conditions	Yield
Stage #1: 2-Bromovaleric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #2: N-cyclohexyl-cyclohexanamine With lithium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	28%

2-Bromovaleric acid (584-93-0) + benzylamine (100-46-9) → N-benzyl-2-bromopentanamide

Conditions	Yield
Stage #1: 2-Bromovaleric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #2: benzylamine With lithium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	19%

morpholine (110-91-8) + 2-Bromovaleric acid (584-93-0) → 2-morpholino-valeric acid ethyl ester (100050-35-9)

Upstream product

• 565-74-2 2-Bromo-3-methylbutyric acid 
• 109-52-4 Valeric acid 
• 7719-12-2 Phosphorus trichloride 

Downstream Products

• 5849-30-9 3-methyl-1-(4-methylpiperazin-1-yl)pyrido[1,2-a]benzimidazole-4-carbonitrile 
• 5849-31-0 1-[4-(5,5-dimethyl-4,5-dihydro-1,3-thiazol-2-yl)piperazin-1-yl]-3-methylpyrido[1,2-a]benzimidazole-4-carbonitrile 
• 58493-17-7 2-{4-[3-(4-hydroxy-3,5-dimethoxyphenyl)propanoyl]piperazin-1-yl}-N-methylacetamide ethanedioate (1:1) 
• 58493-18-8 2-{4-[3-(4-hydroxy-3,5-dimethoxyphenyl)propanoyl]piperazin-1-yl}-N-propylacetamide ethanedioate (1:1) 
• 58493-19-9 2-{4-[3-(4-hydroxy-3,5-dimethoxyphenyl)propanoyl]piperazin-1-yl}-N,N-dimethylacetamide ethanedioate (1:1) 
• 58493-20-2 3-(4-hydroxy-3,5-dimethoxyphenyl)-1-{4-[2-oxo-2-(pyrrolidin-1-yl)ethyl]piperazin-1-yl}propan-1-one ethanedioate (1:1) 
• 58493-21-3 2,6-dimethoxy-4-{3-[4-(2-morpholin-4-yl-2-oxoethyl)piperazin-1-yl]-3-oxopropyl}phenol (2Z)-but-2-enedioate (salt) 
• 58493-22-4 1-{4-[2-(azepan-1-yl)-2-oxoethyl]piperazin-1-yl}-3-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one ethanedioate (1:1) 
• 58493-47-3 N-VANILLYLOCTANAMIDE 
• 58493-48-4 (7E)-N-(4-hydroxy-3-methoxybenzyl)-9-methyldec-7-enamide 
• 58493-49-5 OLVANIL 
• 58493-50-8 Octadecanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)- 
• 58493-54-2 threo-Glycopyrronium bromide 
• 5849-36-5 DIPHENYLPHOSPHINIC ANHYDRIDE 

Recommend Products

• 119-61-9  benzophenone 
• 5445-27-2  2,3-epoxy-3-methyl-2-propyl-butyric acid ethyl ester 
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• 109-52-4  valeric acid 
• 91721-30-1  2-(2-chloro-anilino)-5-propyl-thiazol-4-one 
• 5344-82-1  o-chlorophenylthiourea 
• 92108-57-1  2-(2-methoxy-anilino)-5-propyl-thiazol-4-one 
• 1516-37-6  1-(2-methoxyphenyl)thiourea 
• 77124-15-3  (E)-3-phenyl-2-propyl-prop-2-enoic acid 
• 100-52-7  benzaldehyde 
• 19128-88-2  L-2-phenoxy-valeric acid 
• 19222-52-7  D-2-phenoxy-valeric acid 
• 83119-84-0  α-(2,3-dichloro-4-methoxy)phenylthio-n-valeric acid 
• 83119-51-1  2,3-dichloro-4-methoxythiophenol