4-Bromophenylacetylene Chemical Properties

Melting point:

64-67 °C(lit.)

Boiling point:

88-90°C 16mm

Density 

1.4255 (rough estimate)

refractive index 

1.6411 (estimate)

Flash point:

88-90°C/16mm

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Soluble in chloroform, diethyl ether and ethanol.

form 

Powder, Crystalline Powder or Solid

color 

White to yellow

BRN 

1209726

InChI

InChI=1S/C8H5Br/c1-2-7-3-5-8(9)6-4-7/h1,3-6H

InChIKey

LTLVZQZDXQWLHU-UHFFFAOYSA-N

SMILES

C1(Br)=CC=C(C#C)C=C1

CAS DataBase Reference

766-96-1(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-bromo-4-ethynyl-(766-96-1)

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-51/53

Safety Statements 

61

RIDADR 

UN 3077 9/PG 3

WGK Germany 

2

HazardClass 

9

PackingGroup 

III

HS Code 

29039990

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Aquatic Chronic 2

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Bromophenylacetylene Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

Starting material for heterocyclotriynes, second-order nonlinear optical materials, and unsymmetrical 1,4-diarylbutadiynes

Uses

4-Bromophenylacetylene, is used as the starting material for second-order nonlinear optical materials, heterocyclotriynes, and unsymmetrical 1,4-diarylbutadiynes.

Uses

1-Bromo-4-ethynylbenzene was used in the synthesis of 1-bromo-4-(4′-tetrahydropyranyloxy-1′-ethynylphenyl)benzene.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 3224, 1989 DOI: 10.1021/jo00274a055
Tetrahedron, 62, p. 6673, 2006 DOI: 10.1016/j.tet.2005.12.077

Synthesis

Under nitrogen protection, 25 mL of triethylamine, 1.415 g (5.0 mmol) of 4-bromoiodobenzene, 420 mg (5.0 mmol) of 2-methyl-3-butyn-2-ol, and 70 mg (0.1 mmol) of bis(triphenylphosphine)palladium dichloride (Pd(PPh3)2Cl2), triphenylphosphine ( PPh3) 105 mg (0.4 mmol), copper iodide (CuI) 38 mg (0.2 mmol), 35 ?? reaction until thin layer chromatography monitoring raw materials on the disappearance of bromoiodobenzene spots as the end point. Reaction solution evaporated solvent under reduced pressure, CH2Cl2 dissolved, washed sequentially with 5% dilute hydrochloric acid, saturated NaCl solution, anhydrous MgSO4 drying, filtration. After the filtrate was evaporated the solvent under reduced pressure, the crude product was purified by column chromatography (eluent: petroleum ether:ethyl acetate=10:1) to obtain 4-(4-bromophenyl)-2-methyl-3-butynyl-2-ol as white solid 1.052 g (4.4 mmol) in 90% yield.
. Under the protection of nitrogen, 30 mL of toluene, 4-(4-bromophenyl)-2-methyl-3-butynyl-2-alcohol 478 mg (2.0 mmol), NaOH 480 mg (12 mmol) and diethylene glycol monoethyl ether 8.6 mL were added to the Schlenk reaction flask, and the reaction was carried out at 75 ?? until the disappearance of spots of raw materials was monitored by thin-layer chromatography as the end point. Cooled to room temperature, washed sequentially with 5% dilute hydrochloric acid, saturated NaCl solution, anhydrous MgSO4 drying, filtration. After the filtrate was evaporated to dry the solvent under reduced pressure, the crude product was purified by column chromatography (eluent petroleum ether) to give a white solid 319 mg (1.76 mmol). NMR spectra proved that the product was (4-bromophenyl)acetylene in 80% yield.

4-Bromophenylacetylene(766-96-1)Related Product Information

• Triphenylphosphine
• 3-Bromoanisole
• Triphenylmethyl Chloride
• Phenylacetylene
• (FORMYLMETHYLENE)TRIPHENYLPHOSPHORANE
• 2-Phenylphenol
• Phenylacetone
• Bis(4-bromophenyl)acetylene
• (4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE
• 3-BROMOPHENYLACETYLENE
• Bromine
• 1-[2-(4-BROMOPHENYL)ETHYNYL]-2-FLUORO-4-PENTYLBENZENE
• 4-BROMO-1-ETHYNYL-2-FLUOROBENZENE 96
• 2-[(4-BROMOPHENYL)ETHYNYL] THIOPHENE
• 3-(4-BROMO-PHENYL)-PROP-2-YN-1-OL
• 2-BROMOPHENYLACETYLENE
• 4-Bromophenylacetylene
• acetylene