| Identification | More | [Name]
5-Bromothiophene-2-carbaldehyde | [CAS]
4701-17-1 | [Synonyms]
5-BROMO-2-FORMYLTHIOPHENE
5-BROMO-2-THIOPHENECARBALDEHYDE
5-BROMO-2-THIOPHENECARBOXALDEHYDE
5-BROMOTHIOPHENE-2-ALDEHYDE
5-BROMO-THIOPHENE-2-CARBALDEHYDE
5-BROMOTHIOPHENE-2-CARBOXALDEHYDE
AKOS BBS-00003268
LABOTEST-BB LT00112291
TIMTEC-BB SBB000294
2-Thiophenecarboxaldehyde, 5-bromo-
5-BROMOTHIOPHENE-2-CARBALDEHYDE 98%
2-BROMO-5-THIOPHENECARBOXALDEHYDE
5-Bromothiophene-2-Aldehyde98%
5-Bromothiophene-2-Aldehyde 98%
2-BROMOTHIOPHENE-5-CARBOXALDEHYDE
5-bromothenaldehyde
5-BROMO-2-THIIOPHENE CARBOXALDEHYDE | [EINECS(EC#)]
225-176-8 | [Molecular Formula]
C5H3BrOS | [MDL Number]
MFCD00005432 | [Molecular Weight]
191.05 | [MOL File]
4701-17-1.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow to brown liquid after melting | [Melting point ]
55°C | [Boiling point ]
105-107 °C11 mm Hg(lit.)
| [density ]
1.607 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.637(lit.)
| [Fp ]
210 °F
| [storage temp. ]
0-6°C | [solubility ]
Soluble in chloroform and methanol. | [form ]
Liquid After Melting | [color ]
Clear yellow to brown | [Sensitive ]
Air Sensitive | [BRN ]
108404 | [InChI]
1S/C5H3BrOS/c6-5-2-1-4(3-7)8-5/h1-3H | [InChIKey]
GFBVUFQNHLUCPX-UHFFFAOYSA-N | [SMILES]
[H]C(=O)c1ccc(Br)s1 | [LogP]
2.566 (est) | [CAS DataBase Reference]
4701-17-1(CAS DataBase Reference) | [NIST Chemistry Reference]
5-Bromo-2-thiophenecarboxaldehyde(4701-17-1) | [Storage Precautions]
Store under inert gas |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P280a-P304+P340-P305+P351+P338-P405-P501a | [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 ]
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 .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant/Air Sensitive | [TSCA ]
N | [HS Code ]
29349990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
clear yellow to brown liquid after melting | [Uses]
5-Bromo-2-thiophenecarboxaldehyde was used to prepare 5-[18F]fluoro-2-2-thiophene carboxaldehyde. Also is used in biological studies as anti-inflammatory and anti-tumor activity of the marine mangrove Rhizophora apiculata. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 72, p. 1422, 1950 DOI: 10.1021/ja01159a527 | [Synthesis]
2.1.1 Synthesis of 5-bromo-2-thiophenecarboxaldehyde
Under nitrogen protection, 2-thiophenecarboxaldehyde (6.0 g, 53.5 mmol) was dissolved in anhydrous chloroform (125 mL). Subsequently, N-bromosuccinimide (10.4 g, 58.9 mmol) was slowly added and the reaction mixture was stirred for 12 h at room temperature. After completion of the reaction, the mixture was extracted with chloroform (3 × 50 mL), and the organic phases were combined and washed with deionized water (2 × 50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using chloroform as eluent to afford 5-bromo-2-thiophenecarboxaldehyde as a colorless oil (10.0 g, 98% yield).
1H NMR (400 MHz, CDCl3): δ 7.20 (d, 1H, J = 4.0 Hz), 7.53 (d, 1H, J = 8.0 Hz), 9.79 (s, 1H). | [References]
[1] Physica B: Condensed Matter, 2017, vol. 519, p. 53 - 58
[2] Tetrahedron, 2007, vol. 63, # 37, p. 9188 - 9194
[3] Tetrahedron Letters, 2005, vol. 46, # 12, p. 1989 - 1992
[4] Patent: WO2018/67786, 2018, A1. Location in patent: Page/Page column 134; 135
[5] Journal of the Chemical Society, 1958, p. 1721 |
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