110556-33-7

Basic information

• Product Name: METHYL (R)-(+)-3-BROMO-2-METHYLPROPIONATE
• Synonyms: (R)-(+)-3-Bromoisobutyric Acid Methyl Ester (R)-(+)-3-Bromo-2-Methylpropionic Acid Methyl Ester Methyl (R)-(+)-3-Bromo-2-methylpropionate;Methyl (R)-(+)-3-bromo-2-methylpropionate 97%;(R)-Methyl 3-bromo-2-methylpropanoate;Methyl (R)-(+)-3-Bromoisobutyrate;(+)-METHYL (R)-3-BROMO-2-METHYLPROPIONATE;METHYL (R)-(+)-3-BROMO-2-METHYLPROPIONATE;METHYL (R)-(+)-3-BROMOISOBUTYRATE;(+)-METHYL (R)-BETA-BROMOISOBUTYRATE
• CAS NO: 110556-33-7
• Molecular Formula: C₅H₉BrO₂
• Molecular Weight: 181.03
• Product Categories: Carboxylic Acids (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry
• Mol File: 110556-33-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 85 °C37 mm Hg(lit.)
• Flash Point: 165 °F
• Appearance: /
• Density: 1.422 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.25mmHg at 25°C
• Refractive Index: n20/D 1.455
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1720833
• CAS DataBase Reference: METHYL (R)-(+)-3-BROMO-2-METHYLPROPIONATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (R)-(+)-3-BROMO-2-METHYLPROPIONATE(110556-33-7)
• EPA Substance Registry System: METHYL (R)-(+)-3-BROMO-2-METHYLPROPIONATE(110556-33-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 110556-33-7(Hazardous Substances Data)

Usage

Uses

Methyl (R)-(+)-3-bromo-2-methylpropionate can be used as a reactant to prepare: (S)-3-(6-Methoxy-pyridin-3-yl)-2-methylpropionic acid methylester by reacting with 5-bromo-2-methoxy pyridine via nucleophilic displacement reaction. Decahydroisoquinoline derivative (NVP-ACQ090) as a potent antagonist of somatostatin sst3 receptor.It can also be used as a reference compound in the enantioselective alkylation reaction of hydrophobic vitamin B12 derivatives.

InChI:InChI=1/C5H9BrO2/c1-4(3-6)5(7)8-2/h4H,3H2,1-2H3/t4-/m0/s1

Upstream product

• 72657-23-9 methyl (R)-3-hydroxy-2-methylpropionate 
• 73295-10-0 (S)-3-acetoxy-2-methyl-propionic acid methyl ester 
• 80657-57-4 3-hydroxy-(2S)-methylpropionate 
• 186581-53-3 diazomethane 
• 110595-22-7 (R)-4-acetoxy-3-methyl-1-butene 
• 20609-71-6 3-bromo-2-methyl-propionic acid methyl ester 
• 142402-78-6 methyl (2S)-3-hydroxy-2-methyl-3-(methylsulfonyloxy)propanoate 

Downstream Products

• 38574-62-8 methyl (S)-(+)-2-benzylpropionate 
• 123154-31-4 (R)-2-methoxycarbonylpropyltriphenylphosphonium bromide 
• 123154-32-5 (Z),(S)-3-(3-methoxycarbonyl-1-butenyl)-1-tosylindole 
• 126522-30-3 (S)-3-(3-methoxycarbonylbutyl)-1-tosylindole 
• 1353161-22-4 methyl N-benzyl-2-(2-methoxycarbonyl-(S)-2-methylethyl)azetidine-2-carboxylate 

Relevant articles and documents

Efficient procedures to prepare primary and secondary alkyl halides from alkanols via the corresponding sulfonates under mild conditions

The study presented herein shows that sulfonate/halide exchange can be advantageously performed in THF to avoid several side reactions such as elimination and epimerization when the reaction is performed from a chiral alkyl sulfonate or a substrate having a C-H acidic chiral center. The main limitation of this procedure was found to be the conversion of secondary alkyl sulfonates to alkyl chlorides. In this case, the addition of a catalytic amount of manganese chloride clearly accelerates the rate and the efficiency of the reaction. Copyright

Asymmetric synthesis of 2-alkyl-3-phosphonopropanoic acids via P - C bond formation and hydrogenation

Allylic acetates, formed by the acetylation of Baylis Hillman adducts, undergo addition of phosphorus nucleophiles to give stereoselectively the Z-unsaturated esters. TFA cleavage of the fert-butyl ester and asymmetric hydrogenation of the unsaturated aci

SYNTHESIS OF THE (S)-ENANTIOMER OF PANICULIDINE A. ABSOLUTE CONFIGURATION OF NATURAL PANICULIDINES

The (S)-enantiomer of paniculidine A (an indole alkaloid from the plant Murraya paniculata) was synthesized from (R)-5-acetoxy-4-methylpentanoic acid by its oxidative transformation into (S)-methyl 2-methyl-3-acetoxypropionate, substitution of the acetoxy group by bromine, Wittig reaction of (R)-2-methoxycarbonylpropyltriphenylphosphonium bromide with 1-tosyl-3-formylindole, hydrogenation of the side chain of (Z,S)-3-(3-methoxycarbonyl-1-butenyl)-tosylindole and reductive desulfonylation of (S)-3-(3-methoxycarbonylbutyl)-1-tosylindole.Comparison of the D values of the synthesized (S)-paniculidine A with published data for the natural product showed that the latter has the (R) configuration.Condensation of the (R)-4-(2-tetrahydropyranyloxy)-3-methylbromobutane obtained from (R)-5-acetoxy-4-methylpentanoic acid with β-indolylmagnesium iodide followed by removal of the tetrahydropyranyl protecting group gave the (R)-enantiomer of paniculidinol .Its (S)-enantiomer was prepared by hydride reduction of (S)-paniculidine A.