38771-21-0

Usage

Uses

Used in Pharmaceutical Industry:
4-BROMO-1-BUTYNE is used as a pharmaceutical intermediate for the synthesis of various drugs and medicinal compounds. Its unique structure allows for the development of new and innovative pharmaceuticals.
Used in Chemical Synthesis:
4-BROMO-1-BUTYNE is used as a reactant in the synthesis of various complex organic molecules. Some of its applications include:
Macrocycles: It is used in the cobalt-mediated [2+2+2] co-cyclotrimerization process to form macrocyclic compounds.
2,4,5-trisubstituted oxazoles: It is used in a gold-catalyzed formal [3+2] cycloaddition to synthesize 2,4,5-trisubstituted oxazoles.
1,3,4-oxadiazoles: It is used in intramolecular 1,3-dipolar cycloaddition reactions to form 1,3,4-oxadiazoles.
Azulene derivatives: It is used in the reductive cyclization of lactones bearing alkynes to prepare azulene derivatives.
Substituted α-pyrones: It is used in gold-catalyzed coupling reactions to synthesize substituted α-pyrones.
Overall, 4-BROMO-1-BUTYNE is a valuable compound in the fields of pharmaceuticals and organic synthesis, offering a wide range of applications and opportunities for the development of new and innovative products.

InChI:InChI=1/C4H5Br/c1-2-3-4-5/h1H,3-4H2

Synthetic route

1-butyn-4-ol (927-74-2) → 4-bromobut-1-yne (38771-21-0)

Conditions	Yield
With phosphorus tribromide	27%
With pyridine; diethyl ether; phosphorus tribromide
With pyridine; phosphorus tribromide
In phosphorus tribromide; diethyl ether	11 g (59%)
With phosphorus tribromide

3-butyn-1-yl p-toluenesulfonate (23418-85-1) → 4-bromobut-1-yne (38771-21-0)

Conditions	Yield
With ethoxyethoxyethanol; calcium bromide
With lithium bromide In acetone Yield given;
With sodium bromide In acetonitrile

4-bromobut-1-yne (38771-21-0) + 1-(azidomethyl)-4-methoxybenzene (70978-37-9) → 1-(4-methoxybenzyl)-4-vinyl-1H-1,2,3-triazole

Conditions	Yield
Stage #1: 4-bromobut-1-yne; 1-(azidomethyl)-4-methoxybenzene With copper(ll) sulfate pentahydrate; sodium L-ascorbate In ethanol; water at 25℃; for 12h; Green chemistry; Stage #2: With sodium hydroxide In ethanol; water at 45℃; for 8h; Reagent/catalyst; Temperature; Concentration; Green chemistry;	99%

4-bromobut-1-yne (38771-21-0) + 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (1214264-88-6) → 2-(4-bromobut-1-en-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (1620061-24-6)

Conditions	Yield
With (1,3-bis(2,6-di-iso-propylphenyl)-4,5-dihydroimidazol-2-ylidene) copper chloride; potassium tert-butylate In tetrahydrofuran; methanol at 50℃; for 3h; Schlenk technique; Inert atmosphere; regioselective reaction;	99%

4-bromobut-1-yne (38771-21-0) + tert-butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride → tert-butyl 2-(but-3-ynyl)-2,9-diazaspiro[5.5]undecane-9-carboxylate

Conditions	Yield
Stage #1: tert-butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride With caesium carbonate In acetonitrile at 20℃; for 0.166667h; Stage #2: 4-bromobut-1-yne In acetonitrile for 18h; Reflux;	98%
With caesium carbonate In acetonitrile for 18h; Reflux;	98%
With caesium carbonate In acetonitrile at 60℃;	72%
With caesium carbonate In acetonitrile Reflux;	13.6 g

4-bromobut-1-yne (38771-21-0) + 3,5-bis(pentafluorosulfanyl)phenyl azide → 1-(3,5-bis(pentafluorosulfanyl)phenyl)-4-(2-bromoethyl)-1H-1,2,3-triazole

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate; benzoic acid In water; tert-butyl alcohol at 20℃; for 0.333333h; Inert atmosphere;	98%

4-bromobut-1-yne (38771-21-0) + 4-fluorobenzyl azide (159979-96-1) → C11H11BrFN3 (1251392-43-4)

Conditions	Yield
With copper(II) loaded mesoporous SBA-15 In dichloromethane at 20℃; Huisgen Cycloaddition; regioselective reaction;	98%

4-bromobut-1-yne (38771-21-0) + (2-methylallyl)zinc bromide*LiCl + (E)-6-chloro-1-iodo-hex-1-ene (807329-90-4) → (E)-1-(6-chlorohex-1-en-1-yl)-2-(2-methylallyl)cyclobut-1-ene

Conditions	Yield
Stage #1: 4-bromobut-1-yne With n-butyllithium In tetrahydrofuran at -78 - -30℃; for 0.333333h; Inert atmosphere; Stage #2: (2-methylallyl)zinc bromide*LiCl In tetrahydrofuran at -30 - 20℃; for 1h; Inert atmosphere; Stage #3: (E)-6-chloro-1-iodo-hex-1-ene With trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	98%

4-bromobut-1-yne (38771-21-0) + 1-(azidomethyl)-4-methoxybenzene (70978-37-9) → 1-methoxybenzyl-5-vinyl-(1H)-1,2,3-triazole (1431946-51-8)

Conditions	Yield
Stage #1: 4-bromobut-1-yne; 1-(azidomethyl)-4-methoxybenzene With pentamethylcyclopentadienyl bis(triphenylphosphine)ruthenium(II) chloride In 1,4-dioxane at 60℃; for 12h; Inert atmosphere; Green chemistry; Stage #2: With sodium hydroxide In 1,4-dioxane; ethanol; water at 45℃; for 8h; Reagent/catalyst; Inert atmosphere; Green chemistry;	97%

4-bromobut-1-yne (38771-21-0) + cyclohexane carbonitrile (766-05-2) → 1-(but-3-yn-1-yl)cyclohexane-1-carbonitrile

Conditions	Yield
Stage #1: cyclohexane carbonitrile With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 4-bromobut-1-yne In tetrahydrofuran; hexane at -78 - 24℃; for 14h; Inert atmosphere;	97%

4-bromobut-1-yne (38771-21-0) + C18H21NO (115-46-8) → azacyclonol hydrobromide + C22H25NO (476468-82-3)

Conditions	Yield
In tetrahydrofuran at 68℃; for 20h; Heating / reflux;	A n/a B 96.1%

4-bromobut-1-yne (38771-21-0) + 1-azidooctane (7438-05-3) → 4-(2-bromoethyl)-1-octyl-1H-1,2,3-triazole (1248633-72-8)

Conditions	Yield
With copper(II) acetate monohydrate In water at 20℃; regioselective reaction;	96%

4-bromobut-1-yne (38771-21-0) + C12H15NO2 → C16H19NO2

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile Inert atmosphere; Reflux;	96%

4-bromobut-1-yne (38771-21-0) + methyl 2-fluoro-5-nitro-benzoate (2965-22-2) → methyl 2-(2-cyanoethylamino)-5-nitrobenzoate

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 0 - 70℃; for 5h;	96%

chloro-trimethyl-silane (75-77-4) + 4-bromobut-1-yne (38771-21-0) → 4-bromo-1-trimethylsilylbut-1-yne (69361-41-7)

Conditions	Yield
Stage #1: 4-bromobut-1-yne With n-butyllithium In diethyl ether; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In diethyl ether; hexane at -78 - 20℃; Inert atmosphere;	95%
With n-butyllithium Multistep reaction;
With n-butyllithium 1) THF, n-hexane, -70 deg C, 4 h, 2) room temperature, 20 h; Yield given. Multistep reaction;

4-bromobut-1-yne (38771-21-0) + 4-(2-azidoethyl)-1-[2-(1-octyl-1H-1,2,3-triazol-4-yl)ethyl]-1H-1,2,3-triazole (1314581-66-2) → 4-{2-[4-(2-bromoethyl)-1H-1,2,3-triazol-1-yl]ethyl}-1-[2-(1-octyl-1H-1,2,3-triazol-4-yl)ethyl]-1H-1,2,3-triazole (1314581-68-4)

Conditions	Yield
With copper(II) acetate monohydrate In water at 20℃; regioselective reaction;	95%

4-bromobut-1-yne (38771-21-0) + 1-(azidomethyl)-4-methoxybenzene (70978-37-9) → 1-methoxybenzyl-4-bromoethyl-(1H)-1,2,3-triazole (1270874-89-9)

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In ethanol; water at 25℃; for 12h; Reagent/catalyst; Temperature; Concentration; Green chemistry;	95%

4-bromobut-1-yne (38771-21-0) + 3-methylbenzo[g]pteridine-2,4(1H,3H)-dione (2891-59-0) → 1-(but-3-ynyl)-3-methylalloxazine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 24h; Inert atmosphere;	95%

4-bromobut-1-yne (38771-21-0) + imino({[3-({4-[2-methoxy-4-(piperazin-1-yl)phenyl]-1,3,5-triazin-2-yl}amino)phenyl]methyl})methyl-λ6-sulfanone → C26H31N7O2S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 78℃; for 4h;	95%

4-bromobut-1-yne (38771-21-0) + benzyl azide (622-79-7) → 1-benzyl-4-(2-bromoethyl)-1H-1,2,3-triazole (1250525-60-0)

Conditions	Yield
With [5-(3-butylimidazol-2-yliden-1-yl)-25,26,27,28-tetrapropyloxycalix[4]arene]copper bromide In neat (no solvent) at 20℃; for 4h; Inert atmosphere;	94%
With copper(l) iodide In glycerol at 20℃; for 7h; Green chemistry;	93%
With copper(II) acetate monohydrate In water at 20℃; regioselective reaction;	89%

4,4'-bipyridine (553-26-4) + 4-bromobut-1-yne (38771-21-0) → C18H18N2(2+)*2Br(1-)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 48h;	94%

4-bromobut-1-yne (38771-21-0) + thioxo-1,2,4-triazino (18α)-19β,28-epoxyoleanane → 3-(but-1-ynesulfanyl)-1,2,4-triazino (18α)-19β,28-epoxyoleanane

Conditions	Yield
With triethylamine In tetrahydrofuran for 18h;	94%

N-allyl-p-toluidine (15258-46-5) + 4-bromobut-1-yne (38771-21-0) → C14H17N

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile Inert atmosphere; Reflux;	94%

4-bromobut-1-yne (38771-21-0) + 3-nitrophenyl azide (1516-59-2) → C10H9BrN4O2

Conditions	Yield
With copper(l) iodide In acetonitrile	94%

4-bromobut-1-yne (38771-21-0) + 1-bromo-4-(diazomethyl)benzene (73900-14-8) → 1-bromo-4-(5-bromopenta-1,2-dien-1-yl)benzene

Conditions	Yield
Stage #1: 4-bromobut-1-yne With copper(l) iodide; triethylamine In 1,4-dioxane for 0.166667h; Flow reactor; Stage #2: 1-bromo-4-(diazomethyl)benzene In 1,4-dioxane; dichloromethane at 20℃; for 0.166667h; Flow reactor;	93%

4-bromobut-1-yne (38771-21-0) + 4-(2-azidoethyl)-1-octyl-1H-1,2,3-triazole (1314581-62-8) → 4-(2-bromoethyl)-1-[2-(1-octyl-1H-1,2,3-triazol-4-yl)ethyl]-1H-1,2,3-triazole (1314581-64-0)

Conditions	Yield
With copper(II) acetate monohydrate In water at 20℃; regioselective reaction;	92%

4-bromobut-1-yne (38771-21-0) + C17H18N4O4 (1426338-65-9) → C16H17BrN4O2 (1426338-67-1)

Conditions	Yield
With copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 30℃; for 0.5h; Sonication;	92%

4-bromobut-1-yne (38771-21-0) + 2-(3-azidopropyl)-1H-isoindolone-1,3(2H)-dione (88192-21-6) → C15H15BrN4O2 (1426338-63-7)

Conditions	Yield
With copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 30℃; for 0.5h; Sonication;	92%

4-bromobut-1-yne (38771-21-0) + para-thiocresol (106-45-6) → 4-methylphenyl 3-butyn-1-yl sulfide (36832-63-0)

Conditions	Yield
With potassium carbonate In acetone for 6h; Reflux; Inert atmosphere;	92%

4-bromobut-1-yne (38771-21-0) + 6C16H36N(1+)*C6H9N4O63P2V3W15(6-) → 6C16H36N(1+)*C10H14BrN4O63P2V3W15(6-)

Conditions	Yield
With tetrakis(actonitrile)copper(I) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 70℃; for 4h; Inert atmosphere; Darkness;	92%

4-bromobut-1-yne (38771-21-0) + (Z)-2-(8-azidooctyl)-1-vinyldiazene 1-oxide → (Z)-2-{8-[4-(2-bromoethyl)-1H-1,2,3-triazol-1-yl]octyl}-1-vinyldiazene 1-oxide

Conditions	Yield
With tetrakis(actonitrile)copper(I) hexafluorophosphate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In methanol at 20℃;	91%

4-bromobut-1-yne (38771-21-0) + Undecane-1-thiol (5332-52-5) → 3-butynyl-1-(undecyl)sulfane

Conditions	Yield
With potassium hydroxide In ethanol for 24h; Reflux;	91%

Upstream product

• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 
• 927-74-2 3-Butyn-1-ol 

Downstream Products

• 117500-15-9 ethyl 2-(ethoxycarbonyl)-5-hexynoate 
• 98891-36-2 (S)-2-amino-5-hexynoic acid 
• 622382-82-5 4-bromo-2-[(dimethylphenylsilyl)methylene]butanal 
• 266683-40-3 [Ni(C₆H₅)CH₂NH((CH₂)3CH)CON(C₆H₄)C(C₆H₅)NCH(CH₂CH₂CCH)COO] 
• 1206796-08-8 (E)-2-(4-(4-(but-3-ynylamino)styryl)-3-cyano-5,5-dimethylfuran-2(5H)-ylidene)malononitrile 
• 1300750-66-6 6-(2-bromoethyl)-4-phenyl-2H-pyran-2-one 
• 36832-63-0 4-methylphenyl 3-butyn-1-yl sulfide 
• 1613266-90-2 4-(4-(2-bromoethyl)-1H-1,2,3-triazol-1-yl)benzenesulfonamide 
• 1613266-99-1 4-(4-(2-bromoethyl)-1H-1,2,3-triazol-1-yl)-2,3,5,6-tetrafluorobenzenesulfonamide 

Relevant academic research and scientific papers

HYBRID NECROPTOSIS INHIBITORS

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