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3355-28-0

Basic Information
CAS No.: 3355-28-0
Name: 1-Bromo-2-butyne
Molecular Structure:
Molecular Structure of 3355-28-0 (1-Bromo-2-butyne)
Formula: C4H5Br
Molecular Weight: 132.99
Synonyms: 2-Butyne,bromo- (6CI,7CI);1-Bromo-2-butyne;1-Bromo-3-methyl-2-butyne;2-Butyn-1-ylbromide;2-Butynyl bromide;4-Bromobut-2-yne;
EINECS: -0
Density: 1.46 g/cm3
Melting Point:
Boiling Point: 124.7 °C at 760 mmHg
Flash Point: 36.3 °C
Solubility:
Appearance: Clear pale yellow-greenish liquid
Hazard Symbols: R10:;
Risk Codes: 10
Safety: 16
Transport Information: UN 1993 3/PG 3
PSA: 0.00000
LogP: 1.40460
Synthetic route
764-01-2

methyl propargyl alcohol

3355-28-0

1-Bromo-2-butyne

Conditions
ConditionsYield
With bromine; triphenylphosphine In dichloromethane at 0℃; for 1h;100%
With phosphorus tribromide89%
With bromine; triphenylphosphine In dichloromethane at 0℃; for 1h;89%
113984-38-6

2-But-2-ynyl-1,3-diisopropyl-isourea

A

4128-37-4

1,3-diisopropylurea

B

3355-28-0

1-Bromo-2-butyne

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; tetrabutylammomium bromide In dichloromethane at 40℃; for 15h;A n/a
B 58%
2768-41-4

4-methoxy-but-2-yne

3355-28-0

1-Bromo-2-butyne

Conditions
ConditionsYield
With Acetyl bromide; zinc dibromide at 60 - 65℃;
53799-88-5

tetra-N-methyl-phosphorodiamidic acid but-2-ynyl ester

3355-28-0

1-Bromo-2-butyne

Conditions
ConditionsYield
With phosphorus tribromide In diethyl ether for 4h; Heating;
53799-85-2

tetra-N-methyl-phosphorodiamidic acid prop-2-ynyl ester

74-88-4

methyl iodide

3355-28-0

1-Bromo-2-butyne

Conditions
ConditionsYield
(i) NaH, (ii) PBr3; Multistep reaction;
764-01-2

methyl propargyl alcohol

7789-60-8

phosphorus tribromide

3355-28-0

1-Bromo-2-butyne

Conditions
ConditionsYield
With pyridine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; pentane11.0 g (58%)
With pyridine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; pentane11.0 g (58%)
3355-28-0

1-Bromo-2-butyne

33396-29-1

8,9-anhydroerythromycin A 6,9-hemiacetal

127955-28-6

N-2-butynyl-8,9-anhydroerythromycin A 6,9-hemiacetal bromide

Conditions
ConditionsYield
In chloroform for 2h; Ambient temperature;100%
3355-28-0

1-Bromo-2-butyne

609-08-5

Diethyl methylmalonate

182809-41-2

diethyl 2-(but-2-yn-1-yl)-2-methylmalonate

Conditions
ConditionsYield
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%
825-90-1

sodium p-hydroxybenzenesulfonate

3355-28-0

1-Bromo-2-butyne

4-but-2-ynyloxy-benzenesulfonic acid sodium salt

Conditions
ConditionsYield
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%
2141-99-3

2-tert-butylisoindole-1,3-dione

3355-28-0

1-Bromo-2-butyne

N-tert-butyl-2-(2-methyl-buta-2,3-dienoyl)benzamide

Conditions
ConditionsYield
With magnesium; mercury dichloride In tetrahydrofuran at 0℃; for 2h;100%
4410-99-5

2-mercaptophenylethane

3355-28-0

1-Bromo-2-butyne

(2-but-2-ynylsulfanylethyl)benzene

Conditions
ConditionsYield
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℃;
3355-28-0

1-Bromo-2-butyne

105-53-3

diethyl malonate

117500-14-8

diethyl 2-(but-2-yn-1-yl)malonate

Conditions
ConditionsYield
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%
3355-28-0

1-Bromo-2-butyne

287393-00-4

ethyl cyclohexyl [4-(hydroxyphenyl)sulfanyl]acetate

287393-01-5

ethyl-{[4-(2-butynyloxy)phenyl]sulfanyl}(cyclohexyl)acetate

Conditions
ConditionsYield
100%
With potassium carbonate In acetone Heating;
53744-52-8

dimethyl 2-(3,3-dimethoxypropyl)-1,3-propanedioate

3355-28-0

1-Bromo-2-butyne

828913-58-2

4,4-bis(methoxycarbonyl)-6-octynal dimethyl acetal

Conditions
ConditionsYield
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%
51534-81-7

dimethyl 2-(2,2-dimethoxyethyl)-1,3-propanedioate

3355-28-0

1-Bromo-2-butyne

828913-50-4

3,3-bis(methoxycarbonyl)-5-heptynal dimethyl acetal

Conditions
ConditionsYield
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%
616-45-5

2-pyrrolidinon

3355-28-0

1-Bromo-2-butyne

1-but-2-ynyl-pyrrolidin-2-one

Conditions
ConditionsYield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In tetrahydrofuran for 4h; Heating;100%
675-20-7

piperidin-2-one

3355-28-0

1-Bromo-2-butyne

1-but-2-ynyl-piperidin-2-one

Conditions
ConditionsYield
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

3355-28-0

1-Bromo-2-butyne

2-(4-fluoro-benzenesulfonyl)-2-pyridin-3-ylmethyl-hex-4-ynoic acid tert-butyl ester

Conditions
ConditionsYield
100%
100%

C18H16N2O2S

3355-28-0

1-Bromo-2-butyne

1147480-13-4

C22H20N2O2S

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h;100%
1431-39-6

dansylamide

3355-28-0

1-Bromo-2-butyne

1264264-16-5

N,N-bis(2-butynyl)-5-(dimethylamino)naphthalene-1-sulfonamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 2h; Reflux;100%
99-76-3

methyl 4-hydroxylbenzoate

3355-28-0

1-Bromo-2-butyne

362705-52-0

methyl 4-(but-2-yn-1-yloxy)benzoate

Conditions
ConditionsYield
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%
73200-35-8

5-hydroxy-1-(pyrrolidin-1-yl)pentan-1-one

3355-28-0

1-Bromo-2-butyne

1221896-11-2

5-(but-2-ynyloxy)-1-(pyrrolidin-1-yl)pentan-1-one

Conditions
ConditionsYield
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%
1271726-25-0

N-{4-[1-(benzenesulfonyl)-1H-indol-2-yl]-4-oxobutyl}benzenesulfonamide

3355-28-0

1-Bromo-2-butyne

1271726-28-3

4-((N-but-2-ynyl)phenylsulfonylamido)-1-(1-phenylsulfonylindol-2-yl)butan-1-one

Conditions
ConditionsYield
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%
4326-36-7

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

3355-28-0

1-Bromo-2-butyne

methyl (S)-2-tert-butoxycarbonylamino-3-(4-but-2-ynyloxy-phenyl)-propionate

Conditions
ConditionsYield
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;
533-58-4

2-Iodophenol

3355-28-0

1-Bromo-2-butyne

1188474-17-0

1-(but-2-yn-1-yloxy)-2-iodobenzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Inert atmosphere;100%
With potassium carbonate In acetonitrile at 60℃; for 2h;85%
1378317-35-1

N-allyl-2-bromo-4,5-dimethoxybenzenesulfonamide

3355-28-0

1-Bromo-2-butyne

N-allyl-2-bromo-N-(but-2-yn-1-yl)-4,5-dimethoxybenzenesulfonamide

Conditions
ConditionsYield
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%
699-03-6

N-methyl-4-bromobenzylamine

3355-28-0

1-Bromo-2-butyne

N-(4-bromobenzyl)-N-methylbut-2-yn-1-amine hydrochloride

Conditions
ConditionsYield
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

3355-28-0

1-Bromo-2-butyne

C14H17NO3

Conditions
ConditionsYield
With indium; ammonium chloride In tetrahydrofuran at 0 - 20℃;100%
3355-28-0

1-Bromo-2-butyne

90-60-8

3,5-dichlorosalicyclaldehyde

2-(but-2-yn-1-yloxy)-3,5-dichlorobenzaldehyde

Conditions
ConditionsYield
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;
100-52-7

benzaldehyde

3355-28-0

1-Bromo-2-butyne

78808-42-1

2-methyl-1-phenylbuta-2,3-dien-1-ol

Conditions
ConditionsYield
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%
124-19-6

nonan-1-al

3355-28-0

1-Bromo-2-butyne

78808-47-6

3-Methyl-dodeca-1,2-dien-4-ol

Conditions
ConditionsYield
indium In water Ambient temperature;99%
With gallium; indium In tetrahydrofuran at 25℃; for 1h;75%
3355-28-0

1-Bromo-2-butyne

97-62-1

Ethyl isobutyrate

116252-14-3

ethyl 2,2-dimethylhex-4-ynoate

Conditions
ConditionsYield
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 amide76%
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%
150-76-5

4-methoxy-phenol

3355-28-0

1-Bromo-2-butyne

41580-74-9

1-(but-2-yn-1-yloxy)-4-methoxybenzene

Conditions
ConditionsYield
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℃;
3355-28-0

1-Bromo-2-butyne

287393-36-6

ethyl isopropyl [4-(hydroxyphenyl)sulfanyl]acetate

287393-37-7

ethyl-{[4-(2-butynyloxy)phenyl]sulfanyl}(isopropyl)acetate

Conditions
ConditionsYield
99%
With potassium carbonate In acetone Heating;
892495-95-3

3-(1-{6-[4-(2-ethoxycarbonyl-ethyl)-2,5-dioxo-imidazolidin-1-yl]-hexyl}-2,5-dioxoimidazolidin-4-yl)-propionic acid ethyl ester

3355-28-0

1-Bromo-2-butyne

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
ConditionsYield
With potassium carbonate In acetone Heating;99%
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    A1-Bromo-2-butyne

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Specification

The IUPAC name of this chemical is 1-bromobut-2-yne. With the CAS registry number 3355-28-0, it is also named as 2-Butyne, 1-bromo-. The product's categories are Acetylenes; Functionalized Acetylenes; Alkynyl; Halogenated Hydrocarbons; Organic Building Blocks. It is clear pale yellow-greenish liquid which is flammable, so keep it away from sources of ignition. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.79; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.78; (4)ACD/LogD (pH 7.4): 1.78; (5)ACD/BCF (pH 5.5): 13.38; (6)ACD/BCF (pH 7.4): 13.38; (7)ACD/KOC (pH 5.5): 222.82; (8)ACD/KOC (pH 7.4): 222.82; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.489; (13)Molar Refractivity: 26.31 cm3; (14)Molar Volume: 91 cm3; (15)Polarizability: 10.43×10-24 cm3; (16)Surface Tension: 35 dyne/cm; (17)Enthalpy of Vaporization: 34.76 kJ/mol; (18)Vapour Pressure: 15.2 mmHg at 25°C; (19)Exact Mass: 131.957463; (20)MonoIsotopic Mass: 131.957463; (21)Heavy Atom Count: 5; (22)Complexity: 62.2.

Preparation of 1-Bromo-2-butyne: It can be obtained by but-2-yn-1-ol. This reaction needs reagent PBr3. The yield is 89 %. 

Uses of 1-Bromo-2-butyne: It can react with 4-thioxo-3,4-dihydro-1H-pyrimidin-2-one to get 4-but-2-ynylsulfanyl-1H-pyrimidin-2-one. This reaction needs reagent NaOMe and solvent methanol at ambient temperature. The reaction time is 3 days. The yield is 62.2 %.

People can use the following data to convert to the molecule structure. 
1. SMILES:BrCC#CC
2. InChI:InChI=1/C4H5Br/c1-2-3-4-5/h4H2,1H3 
3. InChIKey:LNNXOEHOXSYWLD-UHFFFAOYAL