626-87-9

Usage

Uses

Used in Pharmaceutical Industry:
1,4-Dibromopentane is used as an intermediate in the synthesis of various pharmaceutical compounds. It is particularly employed in the preparation of pharaoh ant trail pheromone stereoisomer, an indolizidine alkaloid. This alkaloid has potential applications in the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
1,4-Dibromopentane is used as a versatile building block in the synthesis of various organic compounds. It is involved in the preparation of 1,2-dimethyl-1-phenylcyclopentane, a compound with potential applications in the chemical and pharmaceutical industries. 1,4-Dibromopentane can also be used as a starting material for the synthesis of other complex organic molecules.
Used in Peptide Synthesis:
1,4-Dibromopentane is used as a protecting group in the synthesis of peptides. It is involved in the preparation of Boc-L-2-amino-6-bromoheptanoic acid, a protected amino acid derivative. The use of 1,4-dibromopentane in this process helps to prevent unwanted side reactions and ensures the selective formation of the desired peptide product.

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 
• 626-95-9 1,4-Pentanediol 
• 821-09-0 n-Pent-4-enyl alcohol 
• 598-61-8 methyl-cyclobutane 
• 534-22-5 2-methylfuran 
• 1191-96-4 ethylcyclopropane 
• 18423-18-2 5-methoxy-2-pentanol 
• 10035-10-6 hydrogen bromide 
• 7732-18-5 water 
• 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 

Downstream Products

• 105973-52-2 1-(2-methoxy-phenyl)-2-methyl-pyrrolidine 
• 105971-45-7 N-(4-methylphenyl)-2-methyltetrahydropyrrole 
• 105972-02-9 1-(4-methoxyphenyl)-2-methylpyrrolidine 
• 16525-39-6 1-methyl-adiponitrile 
• 59353-62-7 4-bromo-1-phthalimidopentane 
• 21693-55-0 1,2,3,4-tetrahydro-1,5,7-trimethyl-naphthalene 
• 30316-36-0 1,2,3,4-tetrahydro-1,6,8-trimethylnaphthalene 
• 33342-99-3 (+/-)-2-methyl-1-phenylpyrrolidine 
• 105971-44-6 2-methyl-1-(o-tolyl)pyrrolidine 
• 110194-65-5 1-methyl-N¹,N⁴-di-o-tolyl-butanediyldiamine 
• 96-47-9 2-methyltetrahydrofuran 
• 1795-09-1 2-methylthiolane 
• 504-60-9 penta-1,3-diene 
• 1119-51-3 bromopentene 

Relevant academic research and scientific papers

Analine derivatives as OSC inhibitors

The present invention relates to compounds of formula (I) wherein U, Y, V, W, L, X, A1, A2, A3, A4, A5 and A6 are as defined in the description and claims and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with 2,3-oxidosqualene-lanosterol cyclase such as hypercholesterolemia, hyperlipemia, arteriosclerosis, vascular diseases, mycoses, parasite infections, gallstones, tumors and/or hyperproliferative disorders, and/or treatment and/or prophylaxis of impaired glucose tolerance and diabetes.