626-87-9

Basic information

• Product Name: 1,4-Dibromopentane
• Synonyms: (RS)-1,4-Dibromopentane;1,4-dibromo-pentan;pentane,1,4-dibromo-;1,4-Dibromopentane,97%;1,4-Dibrompentan;1,4-DibromopentaneDISC 05/09/02;1,4-DibroMopentane, 97% 25GR;1,4-DIBROMOPENTANE
• CAS NO: 626-87-9
• Molecular Formula: C₅H₁₀Br₂
• Molecular Weight: 229.94
• EINECS: 210-967-2
• Product Categories: Alkyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 626-87-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: −34.4 °C(lit.)
• Boiling Point: 98-99 °C25 mm Hg(lit.)
• Flash Point: >110°C
• Appearance: clear, colorless to pale yellow liquid.
• Density: 1.687 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.502mmHg at 25°C
• Refractive Index: n20/D 1.508
• Storage Temp.: 2-8°C
• Water Solubility: Insoluble in water.
• BRN: 605295
• CAS DataBase Reference: 1,4-Dibromopentane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dibromopentane(626-87-9)
• EPA Substance Registry System: 1,4-Dibromopentane(626-87-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 626-87-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow-brown liquid with a wine smell.

Uses

1,4-Dibromopentane is used in the preparation of pharaoh ant trail pheromone stereoisomer, indolizidine alkaloid. It is also involved in the preparation 1,2-dimethyl-1-phenylcyclopentane and boc-L-2-amino-6-bromoheptanoic acid.

Preparation

1,4-Dibromopentane is synthesized by ring-opening bromination of 2-methyltetrahydrofuran with hydrobromic acid and sulfuric acid. First, add hydrobromic acid into the reaction pot for cooling, slowly add 2-methyltetrahydrofuran and sulfuric acid in turn under stirring, and finish the addition when the temperature does not exceed 40°C. The temperature was raised to 60°C, reacted for 2h, and then reacted at 80-85°C for 4h. After cooling, the bromide was separated and washed with water until neutral to obtain 1,4-dibromopentane as an oily substance. Yield 92.5%.

Synthesis Reference(s)

Journal of the American Chemical Society, 74, p. 917, 1952 DOI: 10.1021/ja01124a016

InChI:InChI=1/C5H10Br2/c1-5(7)3-2-4-6/h5H,2-4H2,1H3/t5-/m1/s1

Synthetic route

2-methyltetrahydrofuran (96-47-9) → 1,4-dibromopentane (626-87-9) + C5H12BrO3P

Conditions	Yield
With hydrogen bromide; phosphorus tribromide at 30℃; for 0.666667h;	A 34% B 43%

2-methyltetrahydrofuran (96-47-9) → 1,4-dibromopentane (626-87-9)

Conditions	Yield
With sulfuric acid; hydrogen bromide
With aluminum tri-bromide
With phosphorus tribromide
With hydrogen bromide

1,4-Pentanediol (626-95-9) → 1,4-dibromopentane (626-87-9)

Conditions	Yield
With hydrogen bromide
With hydrogen bromide; calcium chloride
With hydrogen bromide Heating;

n-Pent-4-enyl alcohol (821-09-0) → 1,4-dibromopentane (626-87-9)

Conditions	Yield
With hydrogen bromide at 100 - 110℃;

methyl-cyclobutane (598-61-8) → 1,4-dibromopentane (626-87-9)

Conditions	Yield
With bromine im direkten Sonnenlicht;

2-methylfuran (534-22-5) → 1,4-dibromopentane (626-87-9)

Conditions	Yield
(i) H2, (ii) aq. HBr; Multistep reaction;

ethylcyclopropane (1191-96-4) → 1,4-dibromopentane (626-87-9)

Conditions	Yield
With bromine In dichloromethane

5-methoxy-2-pentanol (18423-18-2) → 1,4-dibromopentane (626-87-9)

Conditions	Yield
With hydrogen bromide

2-methyltetrahydrofuran (96-47-9) + hydrogen bromide (10035-10-6, 12258-64-9) → 1,4-dibromopentane (626-87-9)

γ-pentylene oxide → 1,4-dibromopentane (626-87-9)

Conditions	Yield
With hydrogen bromide at 100℃;

<α-bromo-ethyl>-cyclopropane → 1,4-dibromopentane (626-87-9)

Conditions	Yield
With hydrogen bromide

1,4-Pentanediol (626-95-9) + hydrogen bromide (10035-10-6, 12258-64-9) → 1,4-dibromopentane (626-87-9)

Conditions	Yield
at 100℃;

1,4-Pentanediol (626-95-9) + water (7732-18-5) + hydrogen bromide (10035-10-6, 12258-64-9) → 1,4-dibromopentane (626-87-9)

methyl-cyclobutane (598-61-8) + bromine (7726-95-6) → 1,4-dibromopentane (626-87-9)

Conditions	Yield
im direkten Sonnenlicht;

5-methoxy-2-pentanone (17429-04-8) → 1,4-dibromopentane (626-87-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Na, H2O / diethyl ether 2: HBr View Scheme

n-Amyl nitrite (463-04-7) → 1,4-dibromopentane (626-87-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) benzene, (ii) aq. HCl 2: NaBH4, aq. NaOH / methanol 3: HBr, CaCl2 View Scheme

5-Hydroxy-2-pentanone (1071-73-4) → 1,4-dibromopentane (626-87-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4, aq. NaOH / methanol 2: HBr, CaCl2 View Scheme

ethyl 2-acetyl-4-methoxybutanoate (90647-46-4) → 1,4-dibromopentane (626-87-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) NaOH, (ii) H2SO4 2: Na, H2O / diethyl ether 3: HBr View Scheme

tert-butyl (4-hydroxyphenyl)(methyl)carbamate (180593-41-3) → [4-(5-Bromo-pentyloxy)-phenyl]-methyl-carbamic acid tert-butyl ester + 1,4-dibromopentane (626-87-9)

potassium phtalimide (1074-82-4) + 1,4-dibromopentane (626-87-9) → 4-bromo-1-phthalimidopentane (59353-62-7)

Conditions	Yield
In 1,1,1-trichloroethane at 60℃; for 24h;	100%
In acetone for 24h; Reflux;	99%
In acetone for 72h; Reflux;	91%

diethyl phenylsulfonylmethylphosphonate (56069-39-7) + 1,4-dibromopentane (626-87-9) → (1-Benzenesulfonyl-2-methyl-cyclopentyl)-phosphonic acid diethyl ester

Conditions	Yield
With sodium hydroxide; trimethyldodecylammonium chloride In water for 20h; Ambient temperature;	95%

1,4-dibromopentane (626-87-9) → 2-methylthiolane (1795-09-1)

Conditions	Yield
With sodium sulfide In dimethyl sulfoxide at 150℃; for 0.25h;	94.1%
With sodium sulfide; ethanol
With sodium sulfide; ethanol
With sodium sulfide; water

1,4-dibromopentane (626-87-9) → 1,4-bis(azido)pentane (99595-69-4)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 60℃; for 24h;	93%
With sodium azide In water at 120℃; for 0.5h; microwave irradiation;	82%
With methanol; sodium azide

1,4-dibromopentane (626-87-9) → 1-Iodo-4-bromopentane (141884-09-5)

Conditions	Yield
With sodium iodide In acetone Ambient temperature;	93%

2-(3-aminophenyl)acetonitrile (4623-24-9) + 1,4-dibromopentane (626-87-9) → 2-(3-(2-methylpyrrolidin-1-yl)phenyl)acetonitrile

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene for 20h; Reflux;	93%

NH-pyrazole (288-13-1) + 1,4-dibromopentane (626-87-9) → (+/-)-5-methyl-5,6,7,8-tetrahydropyrazolo[1,2-a]pyridazin-4-ium bromide

Conditions	Yield
With sodium hydride In 1,4-dioxane for 16h; Heating;	92%

p-aminophenylacetonitrile (3544-25-0) + 1,4-dibromopentane (626-87-9) → (x)BrH*C13H16N2

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene for 20h; Reflux;	92%

p-aminophenylacetonitrile (3544-25-0) + 1,4-dibromopentane (626-87-9) → 2-(4-(2-methylpyrrolidin-1-yl)phenyl)acetonitrile

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene for 20h; Reflux;	92%
With N-ethyl-N,N-diisopropylamine In toluene for 20h; Reflux;

1,4-dibromopentane (626-87-9) + p-aminoethylbenzoate (94-09-7) → 4-(2-methylpyrrolidin-1-yl)benzoic acid ethyl ester

Conditions	Yield
With potassium carbonate In water at 120℃; for 0.333333h; microwave irradiation;	89%

1,4-dibromopentane (626-87-9) + trimethylamine (75-50-3) → (+/-)-(4-bromopentyl)trimethylammonium bromide

Conditions	Yield
In diethyl ether; ethanol 1) 0 deg C, 1 h; 2) r.t., 3 days;	88%

1,4-dibromopentane (626-87-9) + potassium thioacetate (10387-40-3) → 4-bromopentyl thioacetate (221218-83-3)

Conditions	Yield
In acetone for 21h; Ambient temperature;	88%

thiophenol (108-98-5) + 1,4-dibromopentane (626-87-9) → C17H20S2

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium bromide In dichloromethane; water 0 deg C, 1 h, RT, 0.5 h;	87%

4,4,5,5‐tetramethyl‐2‐[5‐phenyl‐1‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)propyl]‐1,3,2‐dioxaborolane (1379610-52-2) + 1,4-dibromopentane (626-87-9) → 2,2'-(7-bromo-1-phenyloctane-3,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions	Yield
Stage #1: 4,4,5,5‐tetramethyl‐2‐[5‐phenyl‐1‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)propyl]‐1,3,2‐dioxaborolane With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at 0℃; for 0.166667h; Sealed tube; Inert atmosphere; Stage #2: 1,4-dibromopentane In tetrahydrofuran at 0℃; for 0.25h; Sealed tube; Inert atmosphere;	86%

1,4-dibromopentane (626-87-9) + aniline (62-53-3) → (+/-)-2-methyl-1-phenylpyrrolidine (33342-99-3, 160751-58-6, 160751-59-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	85%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere;	80%
With potassium carbonate In water at 120℃; for 0.333333h; microwave irradiation;	68%

phosphan (7803-51-2) + 1,4-dibromopentane (626-87-9) → 1,4-Bis-phosphanyl-pentane (128503-78-6) + methyl-2 phospholanne (262593-97-5)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 3h;	A 5% B 80%
With potassium hydroxide In dimethyl sulfoxide at 30℃; for 3h;	A 5% B 80%

1,4-dibromopentane (626-87-9) + bis(pinacol)diborane (73183-34-3) → 2-(4-bromopentyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1382358-46-4)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt In water; tert-butyl alcohol at 60℃; Inert atmosphere;	79%
With tris-(dibenzylideneacetone)dipalladium(0); P(t-Bu)2Me*HBF4; sodium methylate In 1,4-dioxane at 25℃; for 24h; Inert atmosphere;	62%

1-lithio-1-methylseleno-1-phenylethane (109289-60-3) + 1,4-dibromopentane (626-87-9) → 2,7-(dimethylseleno)-2,7-diphenyl-3-methyloctane

Conditions	Yield
	78%

1,4-dibromopentane (626-87-9) + 3-chloroprop-1-ene (107-05-1) → 7-bromo-3-chloro-1-octene (76599-62-7)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 15h;	78%

1,4-dibromopentane (626-87-9) → 2-methylselenolan (145065-96-9)

Conditions	Yield
With selenium; sodium tetrahydroborate In ethanol for 3h; Heating;	78%

2-amino-3-cyanobenzofuran-5-carboxylic acid methyl ester + 1,4-dibromopentane (626-87-9) → methyl 3-cyano-2-(2-methylpyrrolidin-1-yl)benzofuran-5-carboxylate

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 120℃; for 0.0833333h;	78%

1,4-dibromopentane (626-87-9) + diethyl malonate (105-53-3) → methyl-2 cyclopentanedicarboxylate-1,1 de diethyle (5222-64-0)

Conditions	Yield
With sodium hydride In 1,2-dimethoxyethane	77%
With ethanol; sodium
With sodium ethanolate

1,4-dibromopentane (626-87-9) + hydroxy-phenyl-acetic acid ethyl ester (774-40-3, 4358-88-7) → 6-Bromo-2-hydroxy-2-phenyl-heptanoic acid ethyl ester

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran 1.) -78 deg C, 15 min; 2.) warm up to RT, 1 h;	77%

1,4-dibromopentane (626-87-9) → 1,4-dichloropentane (626-92-6)

Conditions	Yield
With lithium chloride In N,N-dimethyl-formamide at 90℃; Inert atmosphere;	77%

(diphenylthiophosphinoyl)acetonitrile (69039-10-7) + 1,4-dibromopentane (626-87-9) → (1R,2R)-1-(Diphenyl-phosphinothioyl)-2-methyl-cyclopentanecarbonitrile

Conditions	Yield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In acetonitrile at 20℃; for 7.5h;	76%

3-pentylmagnesium bromide (4852-26-0) + 1,4-dibromopentane (626-87-9) → 2-bromo-6-ethyloctane (1402161-14-1)

Conditions	Yield
With copper(l) chloride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	76%

1,4-dibromopentane (626-87-9) + potassium thioacetate (10387-40-3) → 4-bromopentyl thioacetate (221218-83-3) + thioacetic acid S-(4-acetylsulfanyl-1-methyl-butyl) ester

Conditions	Yield
With silica gel In benzene at 60℃; for 7h;	A 75% B 11%

Isobutyronitrile (78-82-0) + 1,4-dibromopentane (626-87-9) → 6-bromo-2,2-dimethylheptanenitrile

Conditions	Yield
Stage #1: Isobutyronitrile With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 1h; Stage #2: 1,4-dibromopentane In tetrahydrofuran at -78 - 20℃;	74%

Methyl pivalate (598-98-1) + 1,4-dibromopentane (626-87-9) → 2-methyl-1-tert-butylcyclopentan-1-ol

Conditions	Yield
Stage #1: 1,4-dibromopentane With magnesium In tetrahydrofuran at 20℃; for 4h; Stage #2: Methyl pivalate In tetrahydrofuran at 0 - 20℃;	72%

tert-butylmagnesium chloride (677-22-5) + 1,4-dibromopentane (626-87-9) → 6-bromo-2,2-dimethylheptane (1282059-68-0)

Conditions	Yield
With cobalt(II) chloride; lithium iodide; isoprene In tetrahydrofuran at -78 - 50℃; for 12h; Inert atmosphere;	71%
With cobalt(II) chloride; lithium iodide; isoprene In tetrahydrofuran at -78 - 50℃; for 12h; Inert atmosphere;	71%

Upstream product

• 96-47-9 2-methyltetrahydrofuran 
• 821-09-0 n-Pent-4-enyl alcohol 
• 626-95-9 1,4-Pentanediol 
• 10035-10-6 hydrogen bromide 
• 7732-18-5 water 
• 598-61-8 methyl-cyclobutane 
• 7726-95-6 bromine 
• 17429-04-8 5-methoxy-2-pentanone 
• 463-04-7 n-Amyl nitrite 
• 1071-73-4 5-Hydroxy-2-pentanone 
• 90647-46-4 ethyl 2-acetyl-4-methoxybutanoate 
• 180593-41-3 tert-butyl (4-hydroxyphenyl)(methyl)carbamate 
• 18423-18-2 5-methoxy-2-pentanol 
• 1191-96-4 ethylcyclopropane 

Downstream Products

• 56399-58-7 rel(1R,2S)-1,2-dimethyl-1-phenyl cyclopentane 
• 56399-58-7 rel(1R,2S)-1,2-dimethyl-1-phenyl cyclopentane 
• 107-81-3 2-bromopentane 
• 74-85-1 ethene 
• 109-67-1 1-penten 
• 187737-37-7 propene 
• 598-61-8 methyl-cyclobutane 
• 109-66-0 pentane 
• 123-75-1 pyrrolidine 
• 1795-09-1 2-methylthiolane 
• 626-95-9 1,4-Pentanediol 
• 504-60-9 penta-1,3-diene 
• 2004-70-8 1-methylbuta-1,3-diene 
• 591-93-5 1,4-Pentadiene 

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