3355-28-0

Basic information

• Product Name: 1-BROMO-2-BUTYNE
• Synonyms: 1-BROMO-2-BUTYNE;2-BUTYNYL BROMIDE;1-BROMO-2-BUTYNE 98%;1-Bromo-2-butyne,98%;1-Bromobut-2-yne;But-2-yn-1-yl bromide;1-broMo -2-Ding Que;1-BroMo-2-butyne, 96.0%(GC)
• CAS NO: 3355-28-0
• Molecular Formula: C₄H₅Br
• Molecular Weight: 132.99
• EINECS: -0
• Product Categories: Acetylenes;Functionalized Acetylenes;Alkynyl;Halogenated Hydrocarbons;Organic Building Blocks;Intermediates
• Mol File: 3355-28-0.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 40-41 °C20 mm Hg(lit.)
• Flash Point: 97 °F
• Appearance: Clear pale yellow-greenish/Liquid
• Density: 1.519 g/mL at 25 °C(lit.)
• Vapor Pressure: 15.2mmHg at 25°C
• Refractive Index: n20/D 1.508(lit.)
• Storage Temp.: Flammables area
• Solubility: Miscible with acetonitrile.
• BRN: 605306
• CAS DataBase Reference: 1-BROMO-2-BUTYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2-BUTYNE(3355-28-0)
• EPA Substance Registry System: 1-BROMO-2-BUTYNE(3355-28-0)

Safety Data

• Statements: 10
• Safety Statements: 16-24/25
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10-23
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 3355-28-0(Hazardous Substances Data)

Usage

Uses

1-Bromo-2-butyne is used in the preparation of six to eight annulated ring compounds in reaction with indoles and pseudopterane (+/-)-Kallolide B, which is a marine natural product. Further, it acts as a precursor in the preparation of axially chiral teranyl compounds, alkylation of L-tryptophan methyl ester, 4-butynyloxybenzene sulfonyl chloride and mono-propargylated diene derivative. In addition to this, it is also used in the synthesis of isopropylbut-2-ynylamine, allenylcyclobutanol derivatives, allyl-[4-(but-2-ynyloxy)phenyl]sulfane, allenylindium and axially chiral teranyl compounds.

General Description

1-Bromo-2-butyne is a propargyl bromide derivative. It is one of the constitutional isomer of bromo butyne. Its Br-loss threshold photoionization breakdown diagram has been analyzed to derive dissociative photoionization thresholds to C4H5+ production. It participates in the preparation of linagliptin.

InChI:InChI=1/C4H5Br/c1-2-3-4-5/h4H2,1H3

Synthetic route

methyl propargyl alcohol (764-01-2) → 1-Bromo-2-butyne (3355-28-0)

Conditions	Yield
With bromine; triphenylphosphine In dichloromethane at 0℃; for 1h;	100%
With phosphorus tribromide	89%
With bromine; triphenylphosphine In dichloromethane at 0℃; for 1h;	89%

2-But-2-ynyl-1,3-diisopropyl-isourea (113984-38-6) → 1,3-diisopropylurea (4128-37-4) + 1-Bromo-2-butyne (3355-28-0)

Conditions	Yield
With trifluorormethanesulfonic acid; tetrabutylammomium bromide In dichloromethane at 40℃; for 15h;	A n/a B 58%

4-methoxy-but-2-yne (2768-41-4) → 1-Bromo-2-butyne (3355-28-0)

Conditions	Yield
With Acetyl bromide; zinc dibromide at 60 - 65℃;

tetra-N-methyl-phosphorodiamidic acid but-2-ynyl ester (53799-88-5) → 1-Bromo-2-butyne (3355-28-0)

Conditions	Yield
With phosphorus tribromide In diethyl ether for 4h; Heating;

tetra-N-methyl-phosphorodiamidic acid prop-2-ynyl ester (53799-85-2) + methyl iodide (74-88-4) → 1-Bromo-2-butyne (3355-28-0)

Conditions	Yield
(i) NaH, (ii) PBr3; Multistep reaction;

methyl propargyl alcohol (764-01-2) + phosphorus tribromide (7789-60-8) → 1-Bromo-2-butyne (3355-28-0)

Conditions	Yield
With pyridine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; pentane	11.0 g (58%)
With pyridine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; pentane	11.0 g (58%)

1-Bromo-2-butyne (3355-28-0) + 8,9-anhydroerythromycin A 6,9-hemiacetal (33396-29-1) → N-2-butynyl-8,9-anhydroerythromycin A 6,9-hemiacetal bromide (127955-28-6)

Conditions	Yield
In chloroform for 2h; Ambient temperature;	100%

1-Bromo-2-butyne (3355-28-0) + Diethyl methylmalonate (609-08-5) → diethyl 2-(but-2-yn-1-yl)-2-methylmalonate (182809-41-2)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	100%
Stage #1: Diethyl methylmalonate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 1-Bromo-2-butyne In tetrahydrofuran at -78℃; for 1h;	97.6%
Stage #1: Diethyl methylmalonate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 1-Bromo-2-butyne In tetrahydrofuran at -78 - 20℃;	97.6%

sodium p-hydroxybenzenesulfonate (825-90-1) + 1-Bromo-2-butyne (3355-28-0) → 4-but-2-ynyloxy-benzenesulfonic acid sodium salt

Conditions	Yield
With sodium hydroxide In water; isopropyl alcohol at 70℃; for 15h;	100%
With sodium hydroxide In water; isopropyl alcohol at 70℃; for 15h;	100%
With sodium hydroxide In water; isopropyl alcohol at 70℃; for 15h;	100%

2-tert-butylisoindole-1,3-dione (2141-99-3) + 1-Bromo-2-butyne (3355-28-0) → N-tert-butyl-2-(2-methyl-buta-2,3-dienoyl)benzamide

Conditions	Yield
With magnesium; mercury dichloride In tetrahydrofuran at 0℃; for 2h;	100%

2-mercaptophenylethane (4410-99-5) + 1-Bromo-2-butyne (3355-28-0) → (2-but-2-ynylsulfanylethyl)benzene

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; for 1.5h;	100%
Stage #1: 2-mercaptophenylethane With sodium hydride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 1-Bromo-2-butyne In tetrahydrofuran at 20℃;

1-Bromo-2-butyne (3355-28-0) + diethyl malonate (105-53-3) → diethyl 2-(but-2-yn-1-yl)malonate (117500-14-8)

Conditions	Yield
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran; mineral oil for 0.833333h; Stage #2: 1-Bromo-2-butyne In tetrahydrofuran; mineral oil for 2h;	100%
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran; mineral oil for 0.833333h; Stage #2: 1-Bromo-2-butyne In tetrahydrofuran; mineral oil for 2h;	100%
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran for 0.833333h; Stage #2: 1-Bromo-2-butyne In tetrahydrofuran for 2h;	97.6%

1-Bromo-2-butyne (3355-28-0) + ethyl cyclohexyl [4-(hydroxyphenyl)sulfanyl]acetate (287393-00-4) → ethyl-{[4-(2-butynyloxy)phenyl]sulfanyl}(cyclohexyl)acetate (287393-01-5)

Conditions	Yield
	100%
With potassium carbonate In acetone Heating;

dimethyl 2-(3,3-dimethoxypropyl)-1,3-propanedioate (53744-52-8) + 1-Bromo-2-butyne (3355-28-0) → 4,4-bis(methoxycarbonyl)-6-octynal dimethyl acetal (828913-58-2)

Conditions	Yield
Stage #1: dimethyl 2-(3,3-dimethoxypropyl)-1,3-propanedioate With sodium hydride In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: 1-Bromo-2-butyne In tetrahydrofuran at 20℃; for 5h;	100%

dimethyl 2-(2,2-dimethoxyethyl)-1,3-propanedioate (51534-81-7) + 1-Bromo-2-butyne (3355-28-0) → 3,3-bis(methoxycarbonyl)-5-heptynal dimethyl acetal (828913-50-4)

Conditions	Yield
Stage #1: dimethyl 2-(2,2-dimethoxyethyl)-1,3-propanedioate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 1-Bromo-2-butyne In tetrahydrofuran at 20℃; for 4h;	100%
Stage #1: dimethyl 2-(2,2-dimethoxyethyl)-1,3-propanedioate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 1-Bromo-2-butyne With sodium iodide In N,N-dimethyl-formamide at 20℃; for 1h;	96%

2-pyrrolidinon (616-45-5) + 1-Bromo-2-butyne (3355-28-0) → 1-but-2-ynyl-pyrrolidin-2-one

Conditions	Yield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In tetrahydrofuran for 4h; Heating;	100%

piperidin-2-one (675-20-7) + 1-Bromo-2-butyne (3355-28-0) → 1-but-2-ynyl-piperidin-2-one

Conditions	Yield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In tetrahydrofuran for 4h; Heating;	100%

2-(4-fluoro-benzenesulfonyl)-3-pyridin-3-ylpropionic acid tert-butyl ester + 1-Bromo-2-butyne (3355-28-0) → 2-(4-fluoro-benzenesulfonyl)-2-pyridin-3-ylmethyl-hex-4-ynoic acid tert-butyl ester

Conditions	Yield
	100%
	100%

C18H16N2O2S + 1-Bromo-2-butyne (3355-28-0) → C22H20N2O2S (1147480-13-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h;	100%

dansylamide (1431-39-6) + 1-Bromo-2-butyne (3355-28-0) → N,N-bis(2-butynyl)-5-(dimethylamino)naphthalene-1-sulfonamide (1264264-16-5)

Conditions	Yield
With potassium carbonate In acetonitrile for 2h; Reflux;	100%

methyl 4-hydroxylbenzoate (99-76-3) + 1-Bromo-2-butyne (3355-28-0) → methyl 4-(but-2-yn-1-yloxy)benzoate (362705-52-0)

Conditions	Yield
With potassium carbonate In butanone at 20℃; for 23h; Reflux;	100%
With potassium carbonate In butanone at 20℃; for 23h; Reflux;	100%
Stage #1: methyl 4-hydroxylbenzoate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: 1-Bromo-2-butyne In N,N-dimethyl-formamide; mineral oil at 19℃; for 20h; Inert atmosphere;	79%

5-hydroxy-1-(pyrrolidin-1-yl)pentan-1-one (73200-35-8) + 1-Bromo-2-butyne (3355-28-0) → 5-(but-2-ynyloxy)-1-(pyrrolidin-1-yl)pentan-1-one (1221896-11-2)

Conditions	Yield
Stage #1: 5-hydroxy-1-(pyrrolidin-1-yl)pentan-1-one With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Stage #2: 1-Bromo-2-butyne In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	100%

N-{4-[1-(benzenesulfonyl)-1H-indol-2-yl]-4-oxobutyl}benzenesulfonamide (1271726-25-0) + 1-Bromo-2-butyne (3355-28-0) → 4-((N-but-2-ynyl)phenylsulfonylamido)-1-(1-phenylsulfonylindol-2-yl)butan-1-one (1271726-28-3)

Conditions	Yield
Stage #1: N-{4-[1-(benzenesulfonyl)-1H-indol-2-yl]-4-oxobutyl}benzenesulfonamide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Inert atmosphere; Stage #2: 1-Bromo-2-butyne In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Inert atmosphere;	100%

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester (4326-36-7) + 1-Bromo-2-butyne (3355-28-0) → methyl (S)-2-tert-butoxycarbonylamino-3-(4-but-2-ynyloxy-phenyl)-propionate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 19h; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	30%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 19h;

2-Iodophenol (533-58-4) + 1-Bromo-2-butyne (3355-28-0) → 1-(but-2-yn-1-yloxy)-2-iodobenzene (1188474-17-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	100%
With potassium carbonate In acetonitrile at 60℃; for 2h;	85%

N-allyl-2-bromo-4,5-dimethoxybenzenesulfonamide (1378317-35-1) + 1-Bromo-2-butyne (3355-28-0) → N-allyl-2-bromo-N-(but-2-yn-1-yl)-4,5-dimethoxybenzenesulfonamide

Conditions	Yield
Stage #1: N-allyl-2-bromo-4,5-dimethoxybenzenesulfonamide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Stage #2: 1-Bromo-2-butyne In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h;	100%
Stage #1: N-allyl-2-bromo-4,5-dimethoxybenzenesulfonamide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 1-Bromo-2-butyne In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h;	94%

N-methyl-4-bromobenzylamine (699-03-6) + 1-Bromo-2-butyne (3355-28-0) → N-(4-bromobenzyl)-N-methylbut-2-yn-1-amine hydrochloride

Conditions	Yield
Stage #1: N-methyl-4-bromobenzylamine; 1-Bromo-2-butyne With potassium carbonate; potassium iodide In toluene; acetonitrile at 40℃; Sealed tube; Stage #2: With hydrogenchloride In diethyl ether Sealed tube;	100%

C10H11NO3 + 1-Bromo-2-butyne (3355-28-0) → C14H17NO3

Conditions	Yield
With indium; ammonium chloride In tetrahydrofuran at 0 - 20℃;	100%

1-Bromo-2-butyne (3355-28-0) + 3,5-dichlorosalicyclaldehyde (90-60-8) → 2-(but-2-yn-1-yloxy)-3,5-dichlorobenzaldehyde

Conditions	Yield
Stage #1: 3,5-dichlorosalicyclaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: 1-Bromo-2-butyne In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	99.6%
Stage #1: 3,5-dichlorosalicyclaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: 1-Bromo-2-butyne In N,N-dimethyl-formamide at 20℃; Inert atmosphere;

benzaldehyde (100-52-7) + 1-Bromo-2-butyne (3355-28-0) → 2-methyl-1-phenylbuta-2,3-dien-1-ol (78808-42-1)

Conditions	Yield
With indium; ammonium chloride In tetrahydrofuran at 0 - 20℃;	99%
Stage #1: 1-Bromo-2-butyne With sodium iodide; tin(ll) chloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: benzaldehyde In N,N-dimethyl-formamide at 0 - 20℃;	86%
Stage #1: 1-Bromo-2-butyne With sodium iodide; tin(ll) chloride In N,N-dimethyl-formamide at 0℃; for 1.5h; Stage #2: benzaldehyde In N,N-dimethyl-formamide	80%

nonan-1-al (124-19-6) + 1-Bromo-2-butyne (3355-28-0) → 3-Methyl-dodeca-1,2-dien-4-ol (78808-47-6)

Conditions	Yield
indium In water Ambient temperature;	99%
With gallium; indium In tetrahydrofuran at 25℃; for 1h;	75%

1-Bromo-2-butyne (3355-28-0) + Ethyl isobutyrate (97-62-1) → ethyl 2,2-dimethylhex-4-ynoate (116252-14-3)

Conditions	Yield
Stage #1: Ethyl isobutyrate With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: 1-Bromo-2-butyne In tetrahydrofuran; hexane at -78℃; for 0.75h;	99%
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide In tetrahydrofuran at -10℃;	95%
With lithium diisopropyl amide	76%
Stage #1: Ethyl isobutyrate With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.75h; Inert atmosphere; Stage #2: 1-Bromo-2-butyne In tetrahydrofuran; hexane at -78 - 20℃; for 0.4h; Inert atmosphere;	61%

4-methoxy-phenol (150-76-5) + 1-Bromo-2-butyne (3355-28-0) → 1-(but-2-yn-1-yloxy)-4-methoxybenzene (41580-74-9)

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 6h;	99%
With caesium carbonate In N,N-dimethyl-formamide at 20℃;
Stage #1: 4-methoxy-phenol With caesium carbonate In N,N-dimethyl-formamide for 0.333333h; Stage #2: 1-Bromo-2-butyne In N,N-dimethyl-formamide at 20℃;

1-Bromo-2-butyne (3355-28-0) + ethyl isopropyl [4-(hydroxyphenyl)sulfanyl]acetate (287393-36-6) → ethyl-{[4-(2-butynyloxy)phenyl]sulfanyl}(isopropyl)acetate (287393-37-7)

Conditions	Yield
	99%
With potassium carbonate In acetone Heating;

3-(1-{6-[4-(2-ethoxycarbonyl-ethyl)-2,5-dioxo-imidazolidin-1-yl]-hexyl}-2,5-dioxoimidazolidin-4-yl)-propionic acid ethyl ester (892495-95-3) + 1-Bromo-2-butyne (3355-28-0) → 3-(3-but-2-ynyl-1-{6-[3-but-2-ynyl-4-(2-ethoxycarbonyl-ethyl)-2,5-dioxo-imidazolidin-1-yl]hexyl}-2,5-dioxo-imidazolidin-4-yl)propionic acid ethyl ester

Conditions	Yield
With potassium carbonate In acetone Heating;	99%

Upstream product

• 764-01-2 methyl propargyl alcohol 
• 7789-60-8 phosphorus tribromide 
• 113984-38-6 2-But-2-ynyl-1,3-diisopropyl-isourea 
• 53799-85-2 tetra-N-methyl-phosphorodiamidic acid prop-2-ynyl ester 
• 74-88-4 methyl iodide 
• 53799-88-5 tetra-N-methyl-phosphorodiamidic acid but-2-ynyl ester 
• 2768-41-4 4-methoxy-but-2-yne 

Downstream Products

• 18476-67-0 2-(4-methoxyphenyl)-5-methylbenzofuran 
• 287201-52-9 (4-but-2-ynyloxyphenylsulfanyl)acetic acid ethyl ester 
• 287393-37-7 ethyl-{[4-(2-butynyloxy)phenyl]sulfanyl}(isopropyl)acetate 
• 287393-40-2 ethyl-{[4-(2-butynyloxy)phenyl]sulfanyl}(phenyl)acetate 
• 287393-04-8 ethyl-{[4-(2-butynyloxy)phenyl]sulfanyl}(4-methoxyphenyl)acetate 
• 287392-79-4 2-(4-but-2-ynyloxyphenylsulfanyl)octanoic acid ethyl ester 
• 287393-01-5 ethyl-{[4-(2-butynyloxy)phenyl]sulfanyl}(cyclohexyl)acetate 
• 507989-55-1 4,4-bis(benzyloxycarbonyl)-1,7-dimethylhepta-1,6-diyne 
• 501328-47-8 2-(but-2-ynyloxymethyl)benzothiazole 

Relevant articles and documents

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