2873-18-9

Basic information

• Product Name: 2-BROMO-5-CHLOROTHIOPHENE
• Synonyms: 2-Bromo-5-chlorothiophene 98%;Thiophene, 2-bromo-5-chloro-;Thiophene,2-bromo-5-chloro-;α-Bromo-α-chlorothiophene;2-BROMO-5-CHLOROTHIOPHENE;2-CHLORO-5-BROMO THIOPHENE;2-CHLORO-5-BROMO THIOPHENE 98.0%MIN;2-Bromo-5-chlorothiophene,95%
• CAS NO: 2873-18-9
• Molecular Formula: C₄H₂BrClS
• Molecular Weight: 197.48
• EINECS: 220-708-5
• Product Categories: Thiophene&Benzothiophene;Miscellaneous;Thiophens;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiophenes;ThiophenesBuilding Blocks;Heterocycle-oher series
• Mol File: 2873-18-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: -20°C
• Boiling Point: 69-70 °C18 mm Hg(lit.)
• Flash Point: 185 °F
• Appearance: /liquid
• Density: 1.803 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.46mmHg at 25°C
• Refractive Index: n20/D 1.596(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• BRN: 109897
• CAS DataBase Reference: 2-BROMO-5-CHLOROTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-5-CHLOROTHIOPHENE(2873-18-9)
• EPA Substance Registry System: 2-BROMO-5-CHLOROTHIOPHENE(2873-18-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-24/25
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2873-18-9(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR LIGHT YELLOW TO PINK-ORANGE LIQUID

Uses

2-Bromo-5-chlorothiophene was used in the synthesis of monomer of 1,4-bis(5-chlorothiophene)-buta-1,3-diyne and 5-chloro-2-[(trimethylsilyl)-ethynyl]thiophene.

General Description

2-Bromo-5-chlorothiophene is a halogen-substituted thiophene and its photodissociation dynamics was studied by resonance enhanced multiphoton ionization time-of-flight technique. Electrochemical reduction of 2-bromo-5-chlorothiophene at carbon cathode in dimethylformamide containing tetramethylammonium perchlorate was reported.

InChI:InChI=1/C4H2BrClS/c5-3-1-2-4(6)7-3/h1-2H

Upstream product

• 1003-09-4 2-bromothiophene 
• 96-43-5 2-thienyl chloride 

Downstream Products

• 406232-85-7 4-(2-chloro-thien-3-yl)-benzoic acid 
• 36155-88-1 3-bromo-4-chlorothiophene 
• 32431-92-8 5-Brom-3-chlorthiophen 
• 32431-93-9 4-bromo-2-chlorothiophene 
• 35717-20-5 2-chloro-5-phenylthiophene 
• 117175-12-9 2-benzyl-5-chlorothiophene 
• 1431042-84-0 2-chloro-5-((4-((5-methylthiophen-2-yl)ethynyl)phenyl)ethynyl)thiophene 
• 1349847-26-2 C₁₂H₈ClFO₂S 
• 1240285-17-9 {4-chloro-2-[(5-chloro-2-thienyl)ethynyl]phenoxy}acetic acid 
• 1334497-46-9 2-chloro-5-N-methylaniline-thiophene 

Relevant articles and documents

Synthesis and structural characterization of 2,5-dihalo-3,4- dinitrothiophenes

Using new nitration protocols, we have been able to efficiently dinitrate 2,5-dihalothiophenes with yields of ～80-95%. The resulting products 2,5-dibromo-3,4-dinitrothiophene (1), 2,5-dichloro-3,4-dinitrothiophene (2), 2-bromo-5-chloro-3,4-dinitrothiophene (3), as well as the analogous 2-bromo-3,4-dinitrothiophene (4), all crystallize easily allowing their characterization via X-ray crystallography. Crystallization of 1 occurs in the monoclinic space group C2/c with a=14.547(3)A, b=7.3534(15)A, c=10.775(2)A, β=128.89(3)°, and Z=4. Crystallization of 2 occurs in the tetragonal space group I-42d with a=9.9398(14)A, b=9.9398(14)A, c=16.866(3)A, and Z=8. Crystallization of 3 occurs as a pseudo-merohedral twin in the triclinic space group P-1 with a=7.340(5)A, b=8.094(5)A, c=9.112(5)A, α=82.059(5)°, β=66.232(5)°, γ=63.021(5)°, and Z=2. Crystallization of 4 occurs in the triclinic space group P-1 with a=7.1787(14)A, b=7.4092(15)A, c=8.3151(17)A, α=101.67(3)°, β=96.00(3)°, γ=116.13(3)°, and Z=2. The structures of all compounds exhibit the formation of interesting solid-state assemblies due to halogen-bonding interactions between the halogen and nitro groups. Springer Science+Business Media, LLC 2007.

Charge Density - Activation Energy Correlations in Electrophilic Bromination of Thiophenes

Charge density calculations are made on eleven thiophenes by Hueckel LCAO MO and Del Re methods and correlated with experimental activation energies(Ea) obtained for the molecular bromination of these compounds.The need for the inclusion of ?-charges in any correlation of charge density with kinetic data is stressed. - Keywords: Charge density/ Activation energy / Bromination of thiophenes