93381-28-3

Basic information

• Product Name: (R)-(-)-3-BROMO-2-METHYL-1-PROPANOL
• Synonyms: (R)-(-)-3-BROMO-2-METHYL-1-PROPANOL;(R)-3-BroMo-2-Methylpropan-1-ol;(R)-(-)-3-BroMo-2-Methyl-1-propanol 97%;>=96.0% (suM of enantioMers, GC);(2R)-3-bromo-2-methylpropan-1-ol
• CAS NO: 93381-28-3
• Molecular Formula: C₄H₉BrO
• Molecular Weight: 153.02
• Product Categories: Chiral Building Blocks;Organic Building Blocks;Alcohols
• Mol File: 93381-28-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 73-74 °C9 mm Hg(lit.)
• Flash Point: 187 °F
• Appearance: /
• Density: 1.461 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.313mmHg at 25°C
• Refractive Index: n20/D 1.4840(lit.)
• Storage Temp.: 2-8°C
• BRN: 3600269
• CAS DataBase Reference: (R)-(-)-3-BROMO-2-METHYL-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-3-BROMO-2-METHYL-1-PROPANOL(93381-28-3)
• EPA Substance Registry System: (R)-(-)-3-BROMO-2-METHYL-1-PROPANOL(93381-28-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• F: 9
• Hazardous Substances Data: 93381-28-3(Hazardous Substances Data)

Usage

Description

(R)-(-)-3-BROMO-2-METHYL-1-PROPANOL is a chiral organic compound characterized by its unique molecular structure, featuring a bromo and a methyl group attached to a propane backbone. (R)-(-)-3-BROMO-2-METHYL-1-PROPANOL is known for its specific stereochemistry, with the R-configuration indicating the arrangement of atoms in three-dimensional space.

Uses

Used in Pharmaceutical Industry:
(R)-(-)-3-BROMO-2-METHYL-1-PROPANOL is used as a starting material for the total syntheses of complex bioactive molecules such as epothilone C and bistramide A. These molecules have significant therapeutic potential, with epothilone C being a potent microtubule-stabilizing agent used in cancer treatment and bistramide A possessing antimicrobial properties.
Used in Materials Science:
(R)-(-)-3-BROMO-2-METHYL-1-PROPANOL is utilized as a structural modifier in the development of homochiral porous molecular networks. These networks are of interest for their potential applications in gas storage, separation processes, and as catalysts, where the chiral nature of the compound can influence the selectivity and efficiency of these materials.

InChI:InChI=1/C4H9BrO/c1-4(2-5)3-6/h4,6H,2-3H2,1H3/t4-/m0/s1

Upstream product

• 28148-04-1 1,3-dibromo-2-methylpropane 
• 93290-77-8 (R)-(-)-3-bromo-2-methylpropyl-trifluoroacetate 
• 121749-23-3 Toluene-4-sulfonic acid (S)-3-hydroxy-2-methyl-propyl ester 
• 156714-06-6 (-)-(S)-4-bromo-3-methylbut-1-ene 

Downstream Products

• 148144-59-6 (-)-(R)-3-(4-chlorophenoxy)-2-methyl-1-propanol 
• 639010-91-6 (-)-(S)-2-methyl-3-phenoxy-1-propanol 
• 143088-61-3 (2S)-1-bromo-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropane 
• 218451-11-7 4-cyano-1-(3-hydroxy-2(S)-methylpropyl)-4-phenylpiperidine 
• 1112170-79-2 N-(4-fluoro-3-methoxy-benzyl)-6-(2-((R)-3-hydroxy-2-methyl-propyl)-2H-tetrazol-5-yl)-2-methyl-pyrimidine-4-carboxamide 
• 1174675-07-0 (S)-2-methyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-propan-1-ol 
• 1033226-04-8 1-((2S)-3-bromo-2-methylpropyl)-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide 
• 1458653-42-3 (S)-3-(4-bromo-3,5-dimethyl-phenoxy)-2-methyl-propan-1-ol 
• 1450841-70-9 C₁₁H₁₃BrO₂ 
• 1622091-26-2 (R)-tert-butyl 4-((4-((4-(3-bromo-2-methylpropoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoate 
• 1033226-05-9 1-((2R)-3-bromo-2-methylpropyl)-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide 
• 1112170-78-1 N-(4-fluoro-3-methoxy-benzyl)-6-(2-((S)-3-hydroxy-2-methyl-propyl)-2H-tetrazol-5-yl)-2-methyl-pyrimidine-4-carboxamide 

Relevant articles and documents

A scalable, Nonenzymatic synthesis of highly stereopure difunctional C4 secondary methyl linchpin synthons

In response to the continuing widespread use of heterodifunctional C4 secondary methyl building blocks in asymmetric synthesis, we have developed a mole-scale, two-step synthesis of a 1:1 mixture of the diastereomers of 3-bromo-2-methyl-1-propyl camphorsulfonate (casylate). One isomer (2S) has been crystallized to >99:1 dr in ～25% yield. Equilibration of the mother liquor (enriched in 2R) to a 1:1 mixture and recrystallization significantly raises the overall yield of 2S. Applications of 2S include chemoselective Grignard coupling, enabling the very short synthesis of highly stereopure long-chain natural products containing remote, methyl-bearing stereogenic centers [e.g., (R)-tuberculostearic acid], with complete control of configuration. Also, Ag-mediated, completely chemoselective Br displacement from 2S leads to a range of >99:1 er difunctional synthons. Both applications incorporate concurrent recovery of CasO. The enantiomer of 2S can be made from commercial (1R)-10-CasOH.

Haloalkane dehalogenase catalysed desymmetrisation and tandem kinetic resolution for the preparation of chiral haloalcohols

Six different bacterial haloalkane dehalogenases were recombinantly produced in Escherichia coli, purified, and used to catalyse the conversion of prochiral short-chain dihaloalkanes and a meso dihaloalkane, yielding enantioenriched haloalcohols. A two-reaction one-enzyme process was established in which the desymmetrisation of a dihaloalkane is followed by kinetic resolution of the chiral haloalcohol that is produced in the first step. In case of 1,3-dibromo-2-methylpropane and 1,3-dibromo-2-phenylpropane, an increase of the enantiomeric excess of the respective haloalcohol was observed in time, leading to ee values of >97%, with analytical yields of 24 and 52%, respectively. The results show that haloalkane dehalogenases can be used for the production of highly enantioenriched haloalcohols and that in some cases product enantiopurity can be improved by allowing a two-step one-enzyme tandem reaction.

Ethyl phenylsulfinyl fluoroacetate, a new and versatile reagent for the preparation of α-fluoro-α,β-unsaturated carboxylic acid esters

The title compound 2 can be alkylated with a wide range of alkyl halides and Michael acceptors. Subsequent thermal elimination of phenyl sulfinic acid 3 leads to α-fluoro-α,β-unsaturated ethyl carboxylates 5 and 10, an important class of intermediates for fluorine containing biologically active compounds.