98244-48-5

Basic information

• Product Name: (S)-(+)-3-BROMO-2-METHYL-1-PROPANOL
• Synonyms: (S)-3-broMo-2-Methylpropan-1-ol;(S)-(+)-3-BroMo-2-Methyl-1-propanol 97%;(2S)-3-Bromo-2-methyl-propan-1-ol;(S)-(+)-3-BROMO-2-METHYL-1-PROPANOL;(S)-3-BROMO-2-METHYL-PROPANOL;3-Bromo-2-Methyl-1-Propanol;3-Bromo-2-methyl-1-propanolS-form
• CAS NO: 98244-48-5
• Molecular Formula: C₄H₉BrO
• Molecular Weight: 153.02
• Product Categories: Chiral Building Blocks;Organic Building Blocks;Small molecule;Heterocyclic Compounds;Alcohols
• Mol File: 98244-48-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 177.548 °C at 760 mmHg
• Flash Point: 198 °F
• Appearance: /
• Density: 1.461 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.313mmHg at 25°C
• Refractive Index: n20/D 1.483(lit.)
• Storage Temp.: 2-8°C
• PKA: 14?+-.0.10(Predicted)
• BRN: 4738280
• CAS DataBase Reference: (S)-(+)-3-BROMO-2-METHYL-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-3-BROMO-2-METHYL-1-PROPANOL(98244-48-5)
• EPA Substance Registry System: (S)-(+)-3-BROMO-2-METHYL-1-PROPANOL(98244-48-5)

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: 98244-48-5(Hazardous Substances Data)

Usage

Description

(S)-(+)-3-BROMO-2-METHYL-1-PROPANOL is a chiral organic compound with the molecular formula C4H9BrO. It is characterized by its specific stereochemistry, with the (S) configuration indicating that the hydroxyl group is on the left side of the molecule when viewed from the bromine atom. (S)-(+)-3-BROMO-2-METHYL-1-PROPANOL is a versatile building block in organic synthesis and has various applications in different industries.

Uses

Used in Pharmaceutical Industry:
(S)-(+)-3-BROMO-2-METHYL-1-PROPANOL is used as a reagent in the preparation of pyrazolopyrimidinamine derivatives, which exhibit tyrosine and phosphinositide kinase inhibitory activity. These derivatives have potential applications in the development of drugs targeting various diseases, including cancer and inflammatory conditions.
Used in Synthesis of Metabolites:
(S)-(+)-3-BROMO-2-METHYL-1-PROPANOL serves as a precursor to synthesize the phase II mexiletine metabolite, (R)-mexiletine N-carbonyloxy-β-D-glucuronide. This metabolite is important for understanding the pharmacokinetics and pharmacodynamics of mexiletine, a drug used to treat certain types of abnormal heart rhythms.
Used in Natural Product Synthesis:
(S)-(+)-3-BROMO-2-METHYL-1-PROPANOL can be used in the synthesis of various natural products, such as (R)-(+)-muscopyridine, polycavernoside A, and (+)-allopumiliotoxin 323B′. These compounds have diverse biological activities and are of interest in the fields of medicinal chemistry and drug discovery.
Used in Materials Science:
(S)-(+)-3-BROMO-2-METHYL-1-PROPANOL can also be employed in building homochiral porous molecular networks. These networks have potential applications in various fields, including gas storage, separation, and catalysis, due to their unique structural and functional properties.

InChI:InChI=1/C4H9BrO/c1-4(2-5)3-6/h4,6H,2-3H2,1H3/t4-/m1/s1

Upstream product

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

Downstream Products

• 143088-61-3 (2S)-1-bromo-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropane 
• 148144-56-3 (+)-(S)-3-(4-chlorophenoxy)-2-methyl-1-propanol 
• 81658-46-0 [(S)-(-)-3-hydroxy-2-methylpropyl]triphenylphosphonium bromide 
• 639010-91-6 (-)-(S)-2-methyl-3-phenoxy-1-propanol 
• 1011029-62-1 2-[3-(3-chlorophenyl)-7-((S)-3-hydroxy-2-methylpropoxy)-1-oxo-1H-isoquinolin-2-yl]-N-isopropylacetamide 
• 610318-97-3 (S)-[3-(2-methyl-3-bromopropoxy)phenyl]acetic acid methyl ester 
• 470454-12-7 2-(S)-methyl-3-(2-hydroxy-3-methoxy-phenylthio)propan-1-ol 
• 470453-88-4 (2S)-3-[(2-methoxyphenyl)thio]-2-methyl-propan-1-ol 
• 909392-34-3 (S)-(+)-2-[6-(3-hydroxy-2-methylpropoxy)-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide 
• 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 
• 1169759-98-1 (S)-2-methyl 3-(2-hydroxy-3-ethylbenzenethio)-propanol 
• 1169760-00-2 (S)-2-methyl 3-(2-hydroxy-3-i-propylbenzenethio)-propanol 

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.