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Home > Encyclopedia > 2,5-Dibromothiophene

2,5-Dibromothiophene

2,5-Dibromothiophene structure

2,5-Dibromothiophene 

structure

Description

Light Yellow Liquid

2,5-Dibromothiophene Basic Attributes

241.928

241.93

221-547-3

F0033K8CXM

4488

DTXSID3062863

2934999090

Characteristics

28.2

3.7

Light Yellow Liquid

2.148 g/cm3 @ Temp: 21 °C

-6 °C

210.3 °C

99.4±0.0 °C

1.638

Practically insoluble in water

0-6ºC

Safety Information

II

6.1

UN2810

3

R20/21;R28;R36/37/38;R43;R68

S45-S36/37/39-S28A-S26-S36

T+:Verytoxic;

Stable at room temperature in closed containers under normal storage and handling conditions.

P261-P305 + P351 + P338

H315-H319-H335

|Danger|H300 (12.77%): Fatal if swallowed [Danger Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P272, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

2,5-Dibromothiophene Use and Manufacturing

Methods of Manufacturing

Compound 4 was prepared according to the reported process (Kellogag RM, Schaap AP, Harper ET, wynberg NDH. Acid-catalyzed brominations, deuterations, rearrangements, and debrominations of thiophenes under mild conditions. J Org Chem 1968; 33: 2902-9) .N-Bromosuccinimide (60 g, 0.33 mol) was added to a solution of thiophene (14.0 g, 0.16 mol) in 250 mL of a 50: 50 (v / v) mixture of acetic acid and chloroform. The mixture, Refluxed for 15 minutes.After cooling to room temperature, Water was added, and the mixture was extracted with chloroform.The organic phase was extracted with sodium sulfate and concentrated by evaporation under reduced pressure.The crude composition was purified by column chromatography with hexane to give the desired compound as a liquid (31.5 g, 84percent).Compound II-1 (2.42 g, 10 mmol), Compound III (1.08 g, 10 mmol), Pd(OAc) 2 (0.22 g, 1 mmol), BINAP (2, 2'-bisdiphenylphosphino-1, 1'-binaphthyl, 0.62 g, 1 mmol) and t-BuOK (2.24 g, 20 mmol) plusInto 50 mL of dry 1, 2-dimethoxyethane (DME), the reaction mixture was stirred under a nitrogen atmosphere overnight, TLC detectionThe reaction is now complete.The reaction mixture was carefully poured into 200 mL of ice water, stirred, extracted with 50 mL×3 CH 2 Cl 2 , and the combined phases were combined.It was washed with 1percent diluted hydrochloric acid and brine and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, and the filtrate was evaporated to dryness on a rotary evaporator.The residue was purified using silica gel column chromatography.Compound IV-I, 1.88 g (yield 70percent) was obtained.

Thiophene, 2,5-dibromo-: ACTIVE

Computed Properties

Molecular Weight:241.93
XLogP3:3.7
Hydrogen Bond Acceptor Count:1
Exact Mass:241.82235
Monoisotopic Mass:239.82440
Topological Polar Surface Area:28.2
Heavy Atom Count:7
Complexity:58.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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