| Identification | More | [Name]
2-Acetyl-5-bromothiophene | [CAS]
5370-25-2 | [Synonyms]
1-(5-BROMO-2-THIENYL)ETHAN-1-ONE
2-ACETYL-5-BROMOTHIOPHENE
5-BROMO-2-THIENYL METHYL KETONE
AKOS 93373
BUTTPARK 52\12-17
LABOTEST-BB LT01138486
1-(5-Bromo-2-thienyl)ethanone
1-(5-Bromo-thiophen-2-yl)-ethanone
2-Acetyl-5-bromthiophen
5-Bromo 2-acetylthiophene
Ethanone, 1-(5-bromo-2-thienyl)-
Ethanone,1-(5-bromo-2-thienyl)-
Ketone, 5-bromo-2-thienyl methyl
2-Acetyl-5-Bromo Thiophenone
2-ACETYL-5-BROMOTHIOPHENE ,98%
1-(5-Bromothiophene-2-yl)ethanone
2-Bromo-5-acetylthiophene
5-Acetyl-2-bromothiophene
Methyl(5-bromo-2-thienyl) ketone | [EINECS(EC#)]
226-363-7 | [Molecular Formula]
C6H5BrOS | [MDL Number]
MFCD00014528 | [Molecular Weight]
205.07 | [MOL File]
5370-25-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
94-96 °C (lit.) | [Boiling point ]
103 °C/4 mmHg (lit.) | [density ]
1.649 (estimate) | [Fp ]
103°C/4mm | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [solubility ]
soluble in Methanol | [form ]
Crystalline Flakes or Powder | [color ]
Yellow | [Sensitive ]
Light Sensitive | [BRN ]
113949 | [InChI]
InChI=1S/C6H5BrOS/c1-4(8)5-2-3-6(7)9-5/h2-3H,1H3 | [InChIKey]
IGBZCOWXSCWSHO-UHFFFAOYSA-N | [SMILES]
C(=O)(C1SC(Br)=CC=1)C | [CAS DataBase Reference]
5370-25-2(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Acetyl-5-bromothiophene(5370-25-2) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S22:Do not breathe dust . | [RIDADR ]
UN2811 | [WGK Germany ]
3
| [HazardClass ]
LIGHT SENSITIVE | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
2-Acetyl-5-bromothiophene was used as a starting reagent in the synthesis of bithiophene bis-imidazo[1,2-a]pyridine derivatives. It was also used in the preparation of phosphorus-containing fused bicyclic 5,6-membered compounds. | [Synthesis Reference(s)]
Journal of Heterocyclic Chemistry, 18, p. 1345, 1981 DOI: 10.1002/jhet.5570180714
Synthetic Communications, 11, p. 29, 1981 DOI: 10.1080/00397918108064279 | [Synthesis]
The general procedure for the synthesis of 2-acetyl-5-bromothiophene from 2-acetylthiophene was as follows: 2-acetylthiophene (1.08 mL, 10 mmol), N-bromosuccinimide (NBS) (1.78 g, 30 mmol), and acetic anhydride (3.78 mL, 40 mmol) were added sequentially to a dry, 25 mL round-bottomed flask, which was equipped with a protective tube. Acetic acid (0.40 mL) was subsequently added to the mixture. The reaction mixture was stirred at 50 °C for 1 h protected from light and the color of the solution was observed to change from colorless to light yellow. Upon completion of the reaction, the mixture was cooled to room temperature and poured into 100 mL of water with continuous stirring until the acetic anhydride was completely hydrolyzed. At this point, 2-acetyl-5-bromothiophene precipitated as white crystals. The product was collected by filtration and washed in batches with 50 mL of water to give a final yield of 82%. The melting point of the product was 92-94 °C (acetone).1H NMR (300 MHz, CDCl3) data were as follows: δ 7.40 (d, J=3.9 Hz, 1H), 7.08 (d, J=3.9 Hz, 1H), 2.48 (s, 3H). | [References]
[1] Tetrahedron Letters, 2010, vol. 51, # 1, p. 205 - 208
[2] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9180 - 9187
[3] Tetrahedron Letters, 2014, vol. 55, # 5, p. 996 - 1001
[4] Tetrahedron Letters, 2014, vol. 55, # 5, p. 996 - 1001
[5] Organic Letters, 2013, vol. 15, # 9, p. 2108 - 2111 |
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