| Identification | More | [Name]
3-Bromothiophene-2-carbaldehyde | [CAS]
930-96-1 | [Synonyms]
3-BROMO-2-FORMYLTHIOPHENE
3-BROMO-2-THIOPHENECARBALDEHYDE
3-BROMOTHIOPHENE-2-CARBALDEHYDE
3-BROMOTHIOPHENE-2-CARBOXALDEHYDE
BUTTPARK 43\57-52
3-Bromothiophene-2-carboxaldehyde, 95%+
3-Bromo-2-Formylthophene
3-Bromothiophene-2-carboxaldehyde, GC 97%
3-BROMOTHIOPHENE-2-CARBOXALDEHYDE 98%
3-Bromo-2-thiophenecarboxaldehyde | [EINECS(EC#)]
672-838-0 | [Molecular Formula]
C5H3BrOS | [MDL Number]
MFCD00126680 | [Molecular Weight]
191.05 | [MOL File]
930-96-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
25 °C | [Boiling point ]
77-79°C 0,2mm | [density ]
1,8 g/cm3 | [refractive index ]
1.6377 | [Fp ]
110-113°C/10mm | [storage temp. ]
Refrigerator | [form ]
clear liquid | [color ]
Light yellow to Amber to Dark green | [Water Solubility ]
Not miscible in water. | [Sensitive ]
Air Sensitive | [BRN ]
109757 | [InChI]
InChI=1S/C5H3BrOS/c6-4-1-2-8-5(4)3-7/h1-3H | [InChIKey]
BCZHCWCOQDRYGS-UHFFFAOYSA-N | [SMILES]
C1(C=O)SC=CC=1Br | [CAS DataBase Reference]
930-96-1(CAS DataBase Reference) | [Storage Precautions]
Store under inert gas |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/38:Irritating to eyes and skin .
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 ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless to yellow liquid | [Uses]
3-Bromothiophene-2-carboxaldehyde is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff. | [Synthesis Reference(s)]
Journal of Medicinal Chemistry, 34, p. 1805, 1991 DOI: 10.1021/jm00110a008 | [Synthesis]
Diisopropylamine (51.6 kg, 509.9 mol, 1.0 eq.) and anhydrous tetrahydrofuran (THF) (385.0 kg) were added to a 1000 L autoclave under nitrogen protection. After cooling the system to 0-5 °C, n-butyllithium (BuLi) (131.4 kg, 463.8 mol, 1.0 eq.) was slowly added. After addition, stirring was continued at 0-5 °C for 30 min. Subsequently, a solution of 3-bromothiophene (75.0 kg, 460.0 mol, 1.0 eq.) in THF (20.0 kg) was added dropwise. After dropwise addition, stirring was continued at 0-5 °C for 30 min. Next, a solution of N,N-dimethylformamide (DMF) (35.3 kg, 473.3 mol, 1.0 eq.) in THF (10.0 kg) was slowly added dropwise. After completion of dropwise addition, stirring was maintained at 0-5 °C for 3 hours. Upon completion of the reaction, a 14% aqueous ammonium chloride (NH4Cl) solution (700.0 g) was slowly added dropwise at 0-5 °C. After addition, the reaction was stirred at 0-5 °C for 15 min and allowed to stand for 15 min. The organic phase was separated and stored temporarily in a clean PTFE drum. The aqueous phase was re-pumped into the reactor, methyl tertiary butyl ether (MTBE) (150.0 kg) was added, stirred for 15 min, and allowed to stand for 15 min before separating the phase and collecting the upper organic phase. All organic phases were combined and dried with anhydrous sodium sulfate (85.0 kg) for several hours until the moisture content was <1%. Filtration, the filter cake was washed with methyl tert-butyl ether (20 mL x 2), the filtrates were combined and concentrated under reduced pressure to remove the solvent to give 3-bromothiophene-2-carbaldehyde (93.8 kg, 100% yield). | [References]
[1] Patent: CN103172646, 2016, B. Location in patent: Paragraph 0101-0104
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 31, p. 5263 - 5273
[3] Macromolecules, 2013, vol. 46, # 6, p. 2078 - 2091
[4] Tetrahedron Letters, 2012, vol. 53, # 2, p. 166 - 169
[5] Journal of the American Chemical Society, 2014, vol. 136, # 19, p. 7132 - 7139 |
|
|