| Identification | More | [Name]
3-(4-BROMOBENZOYL)PROPIONIC ACID | [CAS]
6340-79-0 | [Synonyms]
3-(4-BROMOBENZOYL)PROPIONIC ACID
3-(P-BROMOBENZOYL)PROPIONIC ACID
4-(4-BROMOPHENYL)-4-OXOBUTANOIC ACID
4-(4-BROMOPHENYL)-4-OXOBUTYRIC ACID
BETA-(P-BROMOBENZOYL)PROPIONIC ACID
TIMTEC-BB SBB000956
Benzenebutanoic acid, 4-bromo-gamma-oxo-
3-(4-BROMOBENZOYL)PROPIONIC ACID, 98+%
3-(4-Bromobenzoyl)propanoic acid
4-Bromo-γ-oxobenzenebutanoic acid
4-Oxo-4-(4-bromophenyl)butanoic acid
γ-Oxo-4-bromobenzenebutyric acid | [EINECS(EC#)]
228-732-8 | [Molecular Formula]
C10H9BrO3 | [MDL Number]
MFCD00016563 | [Molecular Weight]
257.08 | [MOL File]
6340-79-0.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light beige shiny crystalline flakes | [Melting point ]
148-152 °C (lit.) | [Boiling point ]
147-150 °C | [density ]
1.5943 (rough estimate) | [refractive index ]
1.4620 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Shiny Crystalline Flakes or Powder | [pka]
4.44±0.17(Predicted) | [color ]
White to light beige | [BRN ]
2104410 | [InChI]
InChI=1S/C10H9BrO3/c11-8-3-1-7(2-4-8)9(12)5-6-10(13)14/h1-4H,5-6H2,(H,13,14) | [InChIKey]
ZODFRCZNTXLDDW-UHFFFAOYSA-N | [SMILES]
C1(C=CC(Br)=CC=1)C(=O)CCC(=O)O | [CAS DataBase Reference]
6340-79-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
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
| [HS Code ]
29183000 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light beige shiny crystalline flakes | [Synthesis]
The general procedure for the synthesis of 3-(4-bromobenzoyl)propionic acid from butanedioic anhydride and bromobenzene was as follows: butanedioic anhydride (5.0 g, 50 mmol) and bromobenzene (48 g, 300 mmol) were cooled to 0 °C. Anhydrous aluminum chloride (13.3 g, 100 mmol) was added to the reaction mixture under nitrogen protection and stirred at 0 °C for 4 hours. Subsequently, the reaction mixture was slowly warmed to room temperature and stirring was continued for 96 hours under nitrogen protection. Upon completion of the reaction, the mixture was cooled again to 0 °C, concentrated hydrochloric acid (125 mL) was slowly added and stirred under nitrogen protection for 1 hour. The reaction mixture was filtered and washed with water (1 L) to give a light yellow solid. The solid was purified by recrystallization from toluene to give 4-(4-bromophenyl)-4-oxobutanoic acid (12 g, 46.68 mmol, 93.4% yield). Mass spectrometry (ESI-quadrupole) m/z: calculated values of C10H9BrO3 were 255.97, 257.97; measured values: 258.0 (11), 257.0 (98), 256.0 (12), 255.0 (100), 213.0 (18), 211.0 (17) (in negative ion mode). High performance liquid chromatography (HPLC) retention time: 24.4 min. 1H NMR (500 MHz, DMSO-d6) δ: 2.59 (2H, triple peaks, J=6.5 Hz, CH2), 3.21 (2H, triple peaks, J=6.5 Hz, CH2), 7.88 (2H, double peaks, J=8.8 Hz, ArH), 7.96 (2H. double peak, J=8.8Hz, ArH), 12.19 (1H, broad single peak, OH). | [References]
[1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 365, p. 181 - 188
[2] Journal of Organic Chemistry, 2001, vol. 66, # 22, p. 7283 - 7286
[3] Organic Syntheses, 2002, vol. 79, p. 204 - 204
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4345 - 4359
[5] Organic Process Research and Development, 2014, vol. 18, # 1, p. 215 - 227 |
|
|