(S)-(+)-3-Bromo-2-methyl-1-propanol

Base Information

• Chemical Name: (S)-(+)-3-Bromo-2-methyl-1-propanol
• CAS No.: 98244-48-5
• Molecular Formula: C₄H₉BrO
• Molecular Weight: 153.019
• European Community (EC) Number: 628-633-3
• DSSTox Substance ID: DTXSID30450756
• Nikkaji Number: J1.317.139D
• Wikidata: Q82270571
• Mol file: 98244-48-5.mol

Synonyms:98244-48-5;(S)-3-Bromo-2-methylpropan-1-ol;(S)-(+)-3-Bromo-2-methyl-1-propanol;(2S)-3-bromo-2-methylpropan-1-ol;(2S)-3-Bromo-2-methyl-propan-1-ol;(S)-3-bromo-2-methyl-1-propanol;1-Propanol, 3-bromo-2-methyl-, (2S)-;(S)-3-bromo-2-methylpropanol;MFCD00064575;3-Bromo-2-methyl-1-propanol #;SCHEMBL240970;(S)-2-methyl-3-bromopropanol;BDBM36058;DTXSID30450756;3-bromo-2-(S)-methyl-1-propanol;AMY14347;YDA24448;(S)-2-Methyl-3-bromo-1-propanol;(2s)-3-bromo-2-methyl-1-propanol;(S)-3-Bromo-2-methyl-propan-1-ol;AKOS015909897;1-Propanol,3-bromo-2-methyl-,(2S)-;AS-60622;CS-0101486;D76160;(S)-(+)-3-Bromo-2-methyl-1-propanol, 97%;(S)-(+)-3-Bromo-2-methyl-1-propanol, purum, >=96.0% (sum of enantiomers, GC)

Chemical Property of (S)-(+)-3-Bromo-2-methyl-1-propanol

Chemical Property:

• Vapor Pressure: 0.313mmHg at 25°C
• Refractive Index: n20/D 1.483(lit.)
• Boiling Point: 177.548 °C at 760 mmHg
• PKA: 14?+-.0.10(Predicted)
• Flash Point: 86.111 °C
• PSA: 20.23000
• Density: 1.449 g/cm³
• LogP: 1.00970
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 151.98368
• Heavy Atom Count: 6
• Complexity: 30.7

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-(+)-3-Bromo-2-methyl-1-propanol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

Useful:

• Canonical SMILES: CC(CO)CBr
• Isomeric SMILES: C[C@@H](CO)CBr
• Uses: (2S)-3-Bromo-2-methyl-1-propanol is used as a reagent in the preparation of of pyrazolopyrimidinamine derivatives and their tyrosine and phosphinositide kinase inhibitory activity. (S)-(+)-3-Bromo-2-methyl-1-propanol is a precursor to synthesize the phase II mexiletine metabolite, (R)-mexiletine N-carbonyloxy-β-D-glucuronide. It can be used in the synthesis of (R)-(+)-muscopyridine, polycavernoside A and (+)-allopumiliotoxin 323B′. It can also be employed in building homochiral porous molecular networks.

Technology Process of (S)-(+)-3-Bromo-2-methyl-1-propanol

There total 4 articles about (S)-(+)-3-Bromo-2-methyl-1-propanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

1'-(3'-hydroxy-2'-methylpropyl) (1S)-10-camphorsulfonate → (R)-3-bromo-2-methyl-1-propanol (93381-28-3) + (S)-3-bromo-2-methyl-1-propanol (40145-08-2,88523-22-2,93381-28-3,98244-48-5)

Guidance literature:

With tetrabutylammomium bromide; Inert atmosphere; Schlenk technique; Heating;

DOI:10.1021/jo5025392

Reference yield:

1,3-dibromo-2-methylpropane (28148-04-1) → (R)-3-bromo-2-methyl-1-propanol (93381-28-3) + (S)-3-bromo-2-methyl-1-propanol (40145-08-2,88523-22-2,93381-28-3,98244-48-5)

Guidance literature:

With Bradyrhizobium japonicum USDA₁₁₀ haloalkane dehalogenase; water; In dimethyl sulfoxide; at 30 ℃; for 0.5h; pH=8.2; optical yield given as %ee; enantioselective reaction; Tris-SO₄ buffer; Enzymatic reaction;

DOI:10.1016/j.tet.2012.06.059

Reference yield:

(-)-(S)-4-bromo-3-methylbut-1-ene (156714-06-6) → (R)-3-bromo-2-methyl-1-propanol (93381-28-3) + (S)-3-bromo-2-methyl-1-propanol (40145-08-2,88523-22-2,93381-28-3,98244-48-5)

Guidance literature:

(-)-(S)-4-bromo-3-methylbut-1-ene; With ozone; In hexane; dichloromethane; at -80 ℃; for 0.333333h; Inert atmosphere; Schlenk technique;

With sodium tetrahydroborate; In hexane; dichloromethane; water; at -80 - 20 ℃; Overall yield = 30 %; Overall yield = 22.5 mg; Inert atmosphere; Schlenk technique;

DOI:10.1021/jo401536u

upstream raw materials:

Toluene-4-sulfonic acid (S)-3-hydroxy-2-methyl-propyl ester

1,3-dibromo-2-methylpropane

(-)-(S)-4-bromo-3-methylbut-1-ene

Downstream raw materials:

(2S)-1-bromo-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropane

[(S)-(-)-3-hydroxy-2-methylpropyl]triphenylphosphonium bromide

2-[3-(3-chlorophenyl)-7-((S)-3-hydroxy-2-methylpropoxy)-1-oxo-1H-isoquinolin-2-yl]-N-isopropylacetamide

(S)-(+)-2-[6-(3-hydroxy-2-methylpropoxy)-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide

Refernces

• 1、 Guduguntla, Sureshbabu,Fananas-Mastral, Martin,Feringa, Ben L.. "Synthesis of optically active β- Or γ-alkyl-substituted alcohols through copper-catalyzed asymmetric allylic alkylation with organolithium reagents". . p. 8274 - 8280. Retrieved 2013/09/24.
• 2、 Allmendinger, Thomas. "Ethyl phenylsulfinyl fluoroacetate, a new and versatile reagent for the preparation of α-fluoro-α,β-unsaturated carboxylic acid esters". . p. 4905 - 4914. Retrieved 2007/10/02.