| Identification | More | [Name]
4-Bromothiophene-2-carboxaldehyde | [CAS]
18791-75-8 | [Synonyms]
4-BROMO-2-FORMYLTHIOPHENE
4-BROMO-2-THIOPHENECARBALDEHYDE
4-BROMO-2-THIOPHENECARBOXALDEHYDE
4-BROMOTHIOPHENE-2-ALDEHYDE
4-BROMOTHIOPHENE-2-CARBALDEHYDE
4-BROMOTHIOPHENE-2-CARBOXALDEHYDE
LABOTEST-BB LT00112358
TIMTEC-BB SBB000293
Bromothiophene-2-carboxaldehyde
4-Bromo-2-thiophene
2-THIOPHENE-4-BROMOCARBOXALDEHYDE
4-BROMO-2-THIOPHENECARBOXALDEHYDE 90%
2-Thiophenecarboxaldehyde, 4-bromo- | [EINECS(EC#)]
242-577-3 | [Molecular Formula]
C5H3BrOS | [MDL Number]
MFCD00005431 | [Molecular Weight]
191.05 | [MOL File]
18791-75-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
44-46 °C (lit.) | [Boiling point ]
114-115 °C/11 mmHg (lit.) | [density ]
1.770 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
soluble in Methanol | [form ]
Powder or Granules | [color ]
White to beige | [Sensitive ]
Air Sensitive | [BRN ]
108455 | [InChI]
InChI=1S/C5H3BrOS/c6-4-1-5(2-7)8-3-4/h1-3H | [InChIKey]
PDONIKHDXYHTLS-UHFFFAOYSA-N | [SMILES]
C1(C=O)SC=C(Br)C=1 | [CAS DataBase Reference]
18791-75-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [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 ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
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 .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
10-23 | [Hazard Note ]
Irritant | [TSCA ]
N | [HazardClass ]
IRRITANT | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
4-Bromo-2-thiophenecarboxaldehyde has been used:
- as building block for the synthesis of tetrahydroisoquinolinones
- in the synthesis of 3-[(4-bromo-2-thienyl)methylenehydrazinocarbonyl]-1H-1,2,4-triazole
| [Synthesis]
General procedure: a THF solution of 1 M NaHMDS (8.8 mL, 8.8 mmol) was slowly added dropwise to the substrate (6.8 mmol) at 0°C. The reaction mixture was stirred for 30 min at 0 °C, then a solution of anhydrous THF (2 mL) with electrophilic reagent (8.3 mmol) was slowly added and stirring was continued for 3 h at 0 °C. Upon completion of the reaction, the reaction was quenched with saturated NH4Cl solution (5 mL) and diluted with hexane (20 mL). The organic layer was separated and washed with 15 wt% NaCl aqueous solution (10 mL) and subsequently concentrated to give the crude product. The product was purified by fast chromatography using a silica gel column pretreated with Et3N and 0.1% Et3N/4.9% EtOAc/95% hexane as eluent. | [References]
[1] Tetrahedron Letters, 2012, vol. 53, # 2, p. 166 - 169
[2] Tetrahedron Letters, 2012, vol. 53, # 2, p. 166 - 169 |
|
|