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766-81-4

Basic Information
CAS No.: 766-81-4
Name: 1-BROMO-3-ETHYNYL-BENZENE
Article Data: 27
Molecular Structure:
Molecular Structure of 766-81-4 (1-BROMO-3-ETHYNYL-BENZENE)
Formula: C8H5Br
Molecular Weight: 181.032
Synonyms: 3'-Bromophenylacetylene;1-Bromo-3-ethynylbenzene;Benzene, 1-bromo-3-ethynyl-;
Density: 1.5 g/cm3
Boiling Point: 211.8 °C at 760 mmHg
Flash Point: 85.7 °C
Hazard Symbols: Xn
Risk Codes: 36/37/38
Safety: 26-36/37/39
PSA: 0.00000
LogP: 2.43040
Synthetic route
3989-13-7

2-(3-bromophenyl)ethynyltrimethylsilane

766-81-4

3-bromophenylacetylene

Conditions
ConditionsYield
With methanol; potassium carbonate for 0.5h;98%
With ethanol; caesium carbonate In dichloromethane at 20℃; for 4h; Inert atmosphere;93.9%
With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 2h;92%
3132-99-8

m-bromobenzoic aldehyde

90965-06-3

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate

766-81-4

3-bromophenylacetylene

Conditions
ConditionsYield
With potassium carbonate In methanol at 20℃; for 12h;95%
With potassium carbonate In methanol at 20℃;84%

1-bromo-3-(2',2'-dibromovinyl)benzene

766-81-4

3-bromophenylacetylene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; water; triphenylphosphine In tetrahydrofuran at 80℃; for 2.5h; Corey-Fuchs Alkyne Synthesis; Sealed tube;91%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25 - 30℃; for 16h;83%
With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 3h; Inert atmosphere;
Stage #1: 1-bromo-3-(2',2'-dibromovinyl)benzene With n-butyllithium In tetrahydrofuran at -78℃; for 2h;
Stage #2: With methanol In tetrahydrofuran for 1h;

C9H7Br3O2

766-81-4

3-bromophenylacetylene

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 115℃; for 12h;90%
2142-63-4

1-(3-Bromophenyl)ethanone

A

766-81-4

3-bromophenylacetylene

B

138857-35-9

1-Brom-3-(1-chlorethenyl)benzol

Conditions
ConditionsYield
With pyridine; phosphorus pentachloride at 110℃; for 0.0583333h; microwave irradiation;A 54%
B 33 % Chromat.
2142-63-4

1-(3-Bromophenyl)ethanone

766-81-4

3-bromophenylacetylene

Conditions
ConditionsYield
With phosphorus pentachloride; sodium ethanolate 1) 35 deg C, 15 min, 2) 3 h, 110 deg C; Yield given. Multistep reaction;
67-56-1

methanol

3989-13-7

2-(3-bromophenyl)ethynyltrimethylsilane

A

766-81-4

3-bromophenylacetylene

B

1-bromo-3-(2-methoxy-vinyl)benzene

Conditions
ConditionsYield
With potassium carbonate at 120 - 130℃; for 0.25h; microwave irradiation;
591-18-4

1-Bromo-3-iodobenzene

1066-54-2

trimethylsilylacetylene

766-81-4

3-bromophenylacetylene

Conditions
ConditionsYield
Stage #1: 1-Bromo-3-iodobenzene; trimethylsilylacetylene With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃;
Stage #2: With methanol; water; potassium carbonate In tetrahydrofuran at 20℃;
With potassium carbonate In methanol; acetonitrile at 40℃; Sonogashira Cross-Coupling; chemoselective reaction;
591-18-4

1-Bromo-3-iodobenzene

766-81-4

3-bromophenylacetylene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Pd(PPh3)2Cl2; CuI; Et3N / 3 h / 20 °C
2: Pd(PPh3)2Cl2TBAF / tetrahydrofuran / 1 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
2: sodium methylate; potassium carbonate / dichloromethane / 1 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: palladium on copper / Inert atmosphere
2: potassium carbonate; methanol / Inert atmosphere
View Scheme
14473-91-7

3-Bromocinnamic acid

766-81-4

3-bromophenylacetylene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chloroform / 20 - 60 °C / Irradiation; Bromination
2: potassium carbonate / dimethyl sulfoxide / 12 h / 115 °C
View Scheme
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    1-BROMO-3-ETHYNYL-BENZENE

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  • 766-81-4  CAS NO.766-81-4

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    766-81-4 CAS NO.766-81-4

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  • 1-(4-Nitrobenzyl)-1h-imidazole CAS NO.766-81-4

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    1-(4-Nitrobenzyl)-1h-imidazole CAS NO.766-81-4

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  • 1-Bromo-3-ethynylbenzene cas no. 766-81-4 98%

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    1-BROMO-3-ETHYNYL-BENZENE

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  • 1-(4-Nitrobenzyl)-1h-imidazole CAS NO.766-81-4

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Specification

The systematic name of 3'-Bromophenyl acetylene is 1-bromo-3-ethynylbenzene. With the CAS registry number 766-81-4, it is also named as Benzene, 1-bromo-3-ethynyl-. The product's category is Aromatic Halides (substituted). In addition, its molecular formula is C8H5Br and molecular weight is 181.03.

The other characteristics of 3'-Bromophenyl acetylene can be summarized as: (1)ACD/LogP: 3.17; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.17; (4)ACD/LogD (pH 7.4): 3.17; (5)ACD/BCF (pH 5.5): 151.53; (6)ACD/BCF (pH 7.4): 151.53; (7)ACD/KOC (pH 5.5): 1265.94; (8)ACD/KOC (pH 7.4): 1265.94; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.604; (13)Molar Refractivity: 41.53 cm3; (14)Molar Volume: 120.6 cm3; (15)Polarizability: 16.46×10-24cm3; (16)Surface Tension: 46 dyne/cm; (17)Density: 1.5 g/cm3; (18)Flash Point: 85.7 °C; (19)Enthalpy of Vaporization: 42.98 kJ/mol; (20)Boiling Point: 211.8 °C at 760 mmHg; (21)Vapour Pressure: 0.261 mmHg at 25 °C.

Uses of 3'-Bromophenyl acetylene: it can be used to produce 1-bromo-3-(1-bromo-vinyl)-benzene.



This reaction needs NEt4Br and CH2Cl2. The yield is 73 %.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
(1)SMILES: Brc1cc(C#C)ccc1
(2)InChI: InChI=1/C8H5Br/c1-2-7-4-3-5-8(9)6-7/h1,3-6H
(3)InChIKey: TZDXNFAAJNEYIO-UHFFFAOYAF
(4)Std. InChI: InChI=1S/C8H5Br/c1-2-7-4-3-5-8(9)6-7/h1,3-6H
(5)Std. InChIKey: TZDXNFAAJNEYIO-UHFFFAOYSA-N