2623-87-2

Basic information

• Product Name: 4-Bromobutyric acid
• Synonyms: 4-BROMOBUTANOIC ACID;4-BROMOBUTYRIC ACID;4-BROMO-N-BUTYRIC ACID;RARECHEM AL BO 0176;4-bromo-butanoicaci;Butanoic acid, 4-bromo-;Butyric acid, 4-bromo-;Carboxypropyl bromide
• CAS NO: 2623-87-2
• Molecular Formula: C₄H₇BrO₂
• Molecular Weight: 167
• EINECS: 220-083-9
• Product Categories: Acids & Esters;Bromine Compounds;omega-Bromocarboxylic Acids;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;Bifunctional CrosslinkersCarbonyl Compounds;C1 to C5;Carboxylic Acids;Linkers;Peptide Synthesis;Piperidines
• Mol File: 2623-87-2.mol
• Article Data: 19

Chemical Properties

• Melting Point: 30-31 °C(lit.)
• Boiling Point: 128-131 °C11 mm Hg(lit.)
• Flash Point: 115 °C
• Appearance: Light brown/Low Melting Crystals
• Density: 1.4397 (rough estimate)
• Vapor Pressure: 0.00763mmHg at 25°C
• Refractive Index: 1.4730 (estimate)
• Storage Temp.: 2-8°C
• PKA: 4.51±0.10(Predicted)
• Water Solubility: Soluble in water and dilute alkali.
• Sensitive: Light Sensitive
• BRN: 1743056
• CAS DataBase Reference: 4-Bromobutyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromobutyric acid(2623-87-2)
• EPA Substance Registry System: 4-Bromobutyric acid(2623-87-2)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-28A
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• F: 13
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 2623-87-2(Hazardous Substances Data)

Usage

Chemical Properties

light brown low melting crystals

Uses

4-Bromobutyric acid is used as a bifunctional cross-linker and as a pharmaceutical intermediate. It is also used to synthesize 4-Bromobutyryl chloride.

Synthesis

4-Bromobutyric acid may be produced by a reaction of Y-butyrolactone with hydrogen bromide. The hydrogen bromide to be used may be gas or an aqueous Solution thereof. The reaction temperature is usually about 10 to 100°C., and the amount of hydrogen bromide to be used is usually about 1 to 10 moles per mole of Y-butyrolactone.

InChI:InChI=1/C4H7BrO2/c5-3-1-2-4(6)7/h1-3H2,(H,6,7)/p-1

Synthetic route

bromopentene (1119-51-3) → bromobutyric acid (2623-87-2)

Conditions	Yield
With jones reagent; osmium(VIII) oxide In water; acetone for 20h; Ambient temperature;	89%

4-butanolide (96-48-0) → bromobutyric acid (2623-87-2)

Conditions	Yield
With tetrabutylammomium bromide; hydrogen bromide In water for 0.166667h; Microwave irradiation;	87%
With trimethylsilyl bromide; iodine(I) bromide for 12h; Ambient temperature;	73%
With sulfuric acid; hydrogen bromide In water for 12h; Inert atmosphere; Reflux;	65%

cyclopropanecarboxylic acid (1759-53-1) → bromobutyric acid (2623-87-2)

Conditions	Yield
With water; boron tribromide In dichloromethane at 23℃; for 46h; regioselective reaction;	67%
With hydrogen bromide at 175℃;

4-phenyloxybutanoic acid (6303-58-8) → bromobutyric acid (2623-87-2)

Conditions	Yield
With hydrogen bromide at 120℃;

but-3-enoic acid (625-38-7) → bromobutyric acid (2623-87-2)

Conditions	Yield
With hydrogen bromide; toluene
With hydrogen bromide; Petroleum ether
With hexane; hydrogen bromide; dibenzoyl peroxide

4-ethoxybutanoic acid (10374-37-5) → bromobutyric acid (2623-87-2)

Conditions	Yield
With hydrogen bromide; acetic acid

4-(4-nitrophenoxy)butanoic acid (28341-54-0) → bromobutyric acid (2623-87-2)

Conditions	Yield
With hydrogen bromide at 100℃;

4-bromobutanenitrile (5332-06-9) → bromobutyric acid (2623-87-2)

Conditions	Yield
With hydrogen bromide Heating;
With hydrogen bromide Hydrolysis;

4-butanolide (96-48-0) + hydrogen bromide (10035-10-6, 12258-64-9) → bromobutyric acid (2623-87-2)

Conditions	Yield
at 100℃; im Druckrohr;

hydrogen bromide (10035-10-6, 12258-64-9) + cyclopropanecarboxylic acid (1759-53-1) → bromobutyric acid (2623-87-2)

Conditions	Yield
at 175℃;

4-phenyloxybutanoic acid (6303-58-8) + hydrogen bromide (10035-10-6, 12258-64-9) → bromobutyric acid (2623-87-2)

Conditions	Yield
at 120℃;

but-3-enoic acid (625-38-7) + hydrogen bromide (10035-10-6, 12258-64-9) + toluene (108-88-3) → bromobutyric acid (2623-87-2)

but-3-enoic acid (625-38-7) + hydrogen bromide (10035-10-6, 12258-64-9) + petroleum ether → bromobutyric acid (2623-87-2)

acetyl chloride (75-36-5) + 2-bromoethanol (540-51-2) → bromobutyric acid (2623-87-2)

Conditions	Yield
With triethylamine In dichloromethane	0.241 g (72%)

methanol (67-56-1) + bromobutyric acid (2623-87-2) → Methyl 4-bromobutyrate (4897-84-1)

Conditions	Yield
With acetyl chloride at 0 - 20℃; for 18h; Inert atmosphere;	100%
With thionyl chloride at 0 - 20℃;	89%
With thionyl chloride at 0 - 20℃; Inert atmosphere;	85%

bromobutyric acid (2623-87-2) → 4-bromobutyroyl chloride (927-58-2)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 4h;	100%
With thionyl chloride at 70℃; for 3h; Heating;	79%
With thionyl chloride

bromobutyric acid (2623-87-2) → 4-iodobutanoic acid (7425-27-6)

Conditions	Yield
With potassium iodide In acetone for 6h; Heating;	100%
With sodium iodide In acetone for 16h;	85%
With sodium iodide In acetone for 5h; Ambient temperature;

tris(methylthio)methane (5418-86-0) + bromobutyric acid (2623-87-2) → 5,5,5-tris(methylsulfanyl)pentanoic acid

Conditions	Yield
With n-butyllithium at 20℃; for 3h; Substitution;	100%

4-(trimethylsilyl)morpholine (13368-42-8) + bromobutyric acid (2623-87-2) → Methoxytrimethylsilane (1825-61-2) + morpholinium hydrobromide (6377-82-8) + trimethylsilyl 4-morpholinobutyrate

Conditions	Yield
With methanol at 20℃; for 24h;	A n/a B 99.1% C 71%

bromobutyric acid (2623-87-2) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 4-trimethylsiloxybutyramide (100446-67-1)

Conditions	Yield
With methanol In dimethyl sulfoxide at 20℃;	99%

bromobutyric acid (2623-87-2) → 4-Bromo-1-butanol (33036-62-3)

Conditions	Yield
Stage #1: bromobutyric acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: With sodium tetrahydroborate; water In tetrahydrofuran at 0℃; for 0.5h;	99%
Stage #1: bromobutyric acid With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 0℃; for 0.166667h; Stage #2: With sodium tetrahydroborate In water; ethyl acetate at 0℃; for 0.366667h;	92%
With dimethylsulfide borane complex	86%

bromobutyric acid (2623-87-2) + n-octylmagnesium chloride (38841-98-4) → lauric acid (143-07-7)

Conditions	Yield
Stage #1: bromobutyric 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;	99%

bromobutyric acid (2623-87-2) + benzyl alcohol (100-51-6) → benzyl 4-bromobutanoate (126430-46-4)

Conditions	Yield
With toluene-4-sulfonic acid In cyclohexane Reflux;	98%
With sulfuric acid; magnesium sulfate In dichloromethane at 20℃; for 48h;	95%
With toluene-4-sulfonic acid In cyclohexane at 85℃; for 16h; Inert atmosphere;	83%

bromobutyric acid (2623-87-2) + C66H94CoN16O15P → C69H101CoN15O17P

Conditions	Yield
Stage #1: C66H94CoN16O15P With methanol; ammonium bromide for 0.333333h; Inert atmosphere; Stage #2: With zinc for 0.333333h; Inert atmosphere; Stage #3: bromobutyric acid for 0.5h; Inert atmosphere;	98%

endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide (21715-90-2) + bromobutyric acid (2623-87-2) → N-hydroxy-5-norbornene-2,3-dicarboximide bromobutanoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide	97%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h;

bromobutyric acid (2623-87-2) + 2-[2-(2-azidoethoxy)ethoxy]ethanol (86520-52-7) → 2-[2-(2-azidoethoxy)ethoxy]ethyl 4-bromobutanoate

Conditions	Yield
Stage #1: bromobutyric acid; 2-[2-(2-azidoethoxy)ethoxy]ethanol With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Stage #2: With triethylamine In dichloromethane for 1h;	97%

4-butanolide (96-48-0) + bromobutyric acid (2623-87-2) + N-benzyl-N,N-bis(trimethylsilyl)amine (18406-59-2) → N-benzyl-4-hydroxybutanamide (19340-88-6) + N-benzyl-4-(trimethylsiloxy)butanamide (100446-71-7)

Conditions	Yield
With methanol for 1h;	A 6.7 g B 96%

bromobutyric acid (2623-87-2) → 4-mercaptobutyric acid (13095-73-3)

Conditions	Yield
With thiourea; sodium hydroxide In ethanol; water for 5h; Reflux;	96%
Stage #1: bromobutyric acid With thiourea In ethanol for 3h; Reflux; Stage #2: With sodium hydroxide	87%
Stage #1: bromobutyric acid With thiourea In ethanol for 3h; Reflux; Stage #2: With sodium hydroxide In ethanol; water for 2h; Reflux;	87%

bromobutyric acid (2623-87-2) + tert-butyl alcohol (75-65-0) → tert-butyl 4-bromobutyrate (110661-91-1)

Conditions	Yield
Stage #1: bromobutyric acid With trifluoroacetic anhydride In tetrahydrofuran at -40℃; for 0.5h; Stage #2: tert-butyl alcohol In tetrahydrofuran at 20℃;	95%
With trifluoroacetic anhydride In tetrahydrofuran at -40 - 20℃;	90%
With sulfuric acid; magnesium sulfate In dichloromethane at 20℃; for 72h;	79%

decylthiol (143-10-2) + bromobutyric acid (2623-87-2) → 6-(decylthio)hexanoic Acid (287194-91-6)

Conditions	Yield
With potassium hydroxide In ethanol for 3h; Heating / reflux;	95%
Stage #1: decylthiol; bromobutyric acid Neat (no solvent); Stage #2: With potassium hydroxide In ethanol Stage #3: With water Acidic aqueous solution;	95%

bromobutyric acid (2623-87-2) + 3-Phenyl-1-propanol (122-97-4) → (3-Phenylpropyl)4-bromobutanoate (156390-14-6)

Conditions	Yield
	95%

bromobutyric acid (2623-87-2) + betulin (473-98-3) → 3β-hydroxylup-20(29)-en-28-yl 4-bromobutanoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Steglich Esterification;	95%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;	80%

bromobutyric acid (2623-87-2) + meta-hydroxybenzaldehyde (100-83-4) → 3-formylphenyl 4-bromobutanoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	93%

bromobutyric acid (2623-87-2) + hexadecanoic acid, 2-hydroxy-1,3-propanediyl ester (502-52-3) → 2-((4-bromobutanoyl)oxy)propane-1,3-diyl dipalmitate (185672-31-5)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 19h;	93%

1-(2-hydroxy-4-methoxyphenyl)ethanone (552-41-0) + bromobutyric acid (2623-87-2) → C13H15BrO4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;	93%

bromobutyric acid (2623-87-2) + triphenylphosphine (603-35-0) → (3-carboxypropyl)(triphenyl)phosphonium bromide (17857-14-6)

Conditions	Yield
In toluene for 48h; Inert atmosphere; Reflux;	92%
at 80℃; for 24h; Inert atmosphere;	90%
at 120℃; for 16h; Inert atmosphere;	89%

bromobutyric acid (2623-87-2) + N-(3-trimethylsiloxypropyl)trimethyl(amino)silane (38033-39-5) → N-(3-trimethylsiloxypropyl)-4-trimethylsiloxybutyramide

Conditions	Yield
With methanol In various solvent(s)	92%

bromobutyric acid (2623-87-2) + 1-(2-Nitrobenzenesulfonyloxy)-6-nitrobenzotriazole (85310-49-2) → 4-Bromo-butyric acid 6-nitro-benzotriazol-1-yl ester (121335-12-4)

Conditions	Yield
With triethylamine In dichloromethane for 2h; Ambient temperature;	92%

2,3,3-trimethylbenzo[e]indole (41532-84-7) + bromobutyric acid (2623-87-2) → C19H23NO2

Conditions	Yield
In toluene Inert atmosphere; Reflux;	92%

bromobutyric acid (2623-87-2) → 1-Bromo-3-fluoropropane (352-91-0)

Conditions	Yield
With xenon difluoride In dichloromethane at 22℃; for 10h;	91%
With xenon difluoride; [18F]fluoride ion, cyclotron produced, NCA for 0.5h; Mechanism; Ambient temperature;

bromobutyric acid (2623-87-2) + triphenylmethanethiol (3695-77-0) → 4-[(triphenylmethyl)thio]butanoic acid (377733-71-6)

Conditions	Yield
Stage #1: triphenylmethanethiol With sodium hydride In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Stage #2: bromobutyric acid In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	91%
Stage #1: triphenylmethanethiol With sodium methylate In methanol; toluene Stage #2: bromobutyric acid In methanol; toluene at 5 - 20℃;	76%
With sodium methylate In methanol; water; toluene at 0 - 40℃; for 30h;	50%
With sodium methylate
With sodium methylate

bromobutyric acid (2623-87-2) + camptothecin (7689-03-4) → camptothecin 20-(4-bromo)-n-butyrate (935761-80-1)

Conditions	Yield
Stage #1: bromobutyric acid; camptothecin With sodium hydroxide; sulfuric acid; phosphorus pentoxide Heating / reflux; Stage #2: With sodium hydroxide In water	91%

bromobutyric acid (2623-87-2) + butan-1-ol (71-36-3) → butyl 4-bromobutanoate (3540-75-8)

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide	91%

bromobutyric acid (2623-87-2) + Methyl 4-hydroxyphenylacetate (14199-15-6) → methyl 2-(4'-(4"-bromobutanoyloxy)phenyl)acetate

Conditions	Yield
With trichlorophosphate In benzene at 80℃; for 5.5h;	91%

Upstream product

• 6303-58-8 4-phenyloxybutanoic acid 
• 625-38-7 but-3-enoic acid 
• 5332-06-9 4-bromobutanenitrile 
• 96-48-0 4-butanolide 
• 10035-10-6 hydrogen bromide 
• 1759-53-1 cyclopropanecarboxylic acid 
• 75-36-5 acetyl chloride 
• 540-51-2 2-bromoethanol 
• 108-88-3 toluene 
• 1119-51-3 bromopentene 
• 28341-54-0 4-(4-nitrophenoxy)butanoic acid 
• 10374-37-5 4-ethoxybutanoic acid 

Downstream Products

• 2969-81-5 Ethyl 4-bromobutyrate 
• 30845-11-5 S-(3-Carboxypropyl)-cystein 
• 96-48-0 4-butanolide 
• 591-81-1 4-hydroxybutanoic acid 
• 927-58-2 4-bromobutyroyl chloride 
• 28341-54-0 4-(4-nitrophenoxy)butanoic acid 
• 56-12-2 4-amino-n-butyric acid 
• 19340-88-6 N-benzyl-4-hydroxybutanamide 
• 100446-71-7 N-benzyl-4-(trimethylsiloxy)butanamide 
• 24157-02-6 4-bromo-1,1-dimethoxybutane 
• 93523-31-0 4-(trimethylsiloxy)-N-(trimethylsilyl)butyramide 
• 106627-43-4 diphenylmethyl 4-bromobutyrate 
• 3884-71-7 bromo-5-pentanone-2 
• 53293-00-8 hex-5-ynoic acid 

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