29585-01-1

Basic information

• Product Name: 2-Pentanone, 3-bromo-4-methyl-
• Synonyms: 3-bromo-4-methyl-pentan-2-one;3-bromo-4-methyl-2-pentanone;3-Brom-4-methyl-pentan-2-on;3-bromo-4-methylpentane-2-one;2-Pentanone,3-bromo-4-methyl
• CAS NO: 29585-01-1
• Molecular Formula: C6H11BrO
• Molecular Weight: 179.05500
• Mol File: 29585-01-1.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 2-Pentanone, 3-bromo-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pentanone, 3-bromo-4-methyl-(29585-01-1)
• EPA Substance Registry System: 2-Pentanone, 3-bromo-4-methyl-(29585-01-1)

Safety Data

• Hazardous Substances Data: 29585-01-1(Hazardous Substances Data)

Usage

Preparation

Synthesis of 3-bromo-4-methyl-pentan-2-one: Br2 (16.14 g, 101.0 mmol) dissolved in acetic acid (10 mL) was added dropwise to a solution of isobuthylmethylketone (10.01 g, 100.0 mmol) dissolved in acetic acid (200 mL) at r.t. The solution was stirred overnight at r.t. Water (400 mL) was added and the solution was extracted with DCM (4 x 80 mL). The organic phase was washed with NaHCO3 (aq) (2 x 50 mL) and water (2 x 50 mL). The solvent was removed under reduced pressure giving the crude product (18.0 g) brown oil. Distillation gave 4.3 g (24 %) of the bromoketone 23(b.p. 60 – 62°C, 12mmHg). Rf 0.48 in 15% EtOAc in Hexanes. IR (neat) ν 2967, 2874, 1721, 1467, 1389, 1370, 1289, 1190, 1148, 1041, 948, 827 cm-1 . 1H NMR (300 MHz, CDCl3)a 0.96 (d, J = 6.3 Hz, 3 H), 1.11 (d, J = 6.6 Hz, 3 H), 2.14 - 2.30 (m, 1 H), 2.35 (s, 3 H), 4.03 (d, J = 8 Hz, 2 H). C 13 NMR (75 MHz, CDCl3) a 20.1, 26.3, 31.1, 63.0, 202.1.

Upstream product

• 7732-18-5 water 
• 7726-95-6 bromine 
• 108-10-1 4-methyl-2-pentanone 

Downstream Products

• 128277-85-0 cis-1,5-dimethyl-2-isopropyl-3-piperidol (a-epimer) 
• 128277-85-0 trans-1,5-dimethyl-2-isopropyl-3-piperidol (e-epimer) 
• 128277-85-0 cis-1,5-dimethyl-2-isopropyl-3-piperidol (e-epimer) 
• 128277-85-0 trans-1,5-dimethyl-2-isopropyl-3-piperidol (a-epimer) 
• 804482-39-1 N-(5-isopropyl-4-methyl-1,3-thiazol-2-yl)-3-nitrobenzenesulfonamide 
• 27872-69-1 4-methyl-3-phenylthio-2-pentanone 
• 98432-10-1 5-isopropyl-4-methyl-3H-thiazole-2-thione 
• 19410-17-4 2-(4-dimethylamino-phenyl)-5-isopropyl-3,4-dimethyl-thiazolium; iodide 
• 408507-19-7 3-(N-methylamino)-4-methyl-2-pentanone 

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