2,5-Dibromothiophene
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2,5-Dibromothiophene
structure -
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CAS No:
3141-27-3
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Formula:
C4H2Br2S
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Chemical Name:
2,5-Dibromothiophene
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Synonyms:
Thiophene,2,5-dibromo-;2,5-Dibromothiophene;NSC 4488
- Categories:
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CAS No:
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
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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