1-methyl-4-(3-methylbut-3-enoxysulfonyl)benzene

Base Information

• Chemical Name: 1-methyl-4-(3-methylbut-3-enoxysulfonyl)benzene
• CAS No.: 781-03-3
• Molecular Formula: C12H16 O3 S
• Molecular Weight: 240.323
• Mol file: 781-03-3.mol

Synonyms:3-Buten-1-ol,3-methyl-, 4-methylbenzenesulfonate (9CI); 3-Buten-1-ol, 3-methyl-,p-toluenesulfonate (8CI); 3-Methyl-3-buten-1-ol tosylate; 3-Methyl-3-butenyltosylate; Isopentenyl tosylate; NSC 250986

Chemical Property of 1-methyl-4-(3-methylbut-3-enoxysulfonyl)benzene

Chemical Property:

• Vapor Pressure: 9.03E-05mmHg at 25°C
• Boiling Point: 350.2°C at 760 mmHg
• Flash Point: 165.6°C
• PSA: 51.75000
• Density: 1.118g/cm³
• LogP: 3.74730

Purity/Quality:

99%min ^*data from raw suppliers

IsopentenylTosylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Isopentenyl Tosylate is an intermediate in the synthesis of Isopentenyl Pyrophosphate Triammonium Salt (I821850) which is used for the preparation of antitumor agents phosphohalohydrins.

Technology Process of 1-methyl-4-(3-methylbut-3-enoxysulfonyl)benzene

There total 4 articles about 1-methyl-4-(3-methylbut-3-enoxysulfonyl)benzene 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: 100.0%

2-methyl-1-buten-4-ol (763-32-6) + p-toluenesulfonyl chloride (98-59-9) → isopentenyl tosylate (781-03-3)

Guidance literature:

With pyridine; at 0 ℃; for 2.5h;

Reference yield:

1-(tert-butyldimethylsiloxy)-3-methyl-3-butene (74915-94-9) → isopentenyl tosylate (781-03-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

2: 1.09 g / calcium hydride; N,N-dimethyl-4-aminopyridine / CH₂Cl₂ / 20 °C

With dmap; calcium hydride; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0524050

Reference yield:

methyl 3-methyl-3-butenoate (25859-52-3) → isopentenyl tosylate (781-03-3)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium hydride

2: pyridine

With lithium aluminium tetrahydride; In pyridine;

DOI:10.1016/S0040-4039(00)85264-8

upstream raw materials:

2-methyl-1-buten-4-ol

p-toluenesulfonyl chloride

1-(tert-butyldimethylsiloxy)-3-methyl-3-butene

methyl 3-methyl-3-butenoate

Downstream raw materials:

4-bromo-2-methylbut-1-ene

2-[benzyl(3-methylbut-3-en-1-yl)amino]benzonitrile

(2-(3-methylbut-3-enylthio)phenyl)methanol

4-methyl-N-(3-methylbut-3-en-1-yl)benzenesulfonamide

Refernces

• 1、 Chen, Chen,Ding, Jie,Huang, Yujie,Liu, Liying,Zhu, Bolin. "Palladium-Catalyzed Carbamoyl-Carbamoylation/ Carboxylation/Thioesterification of Alkene-Tethered Carbamoyl Chlorides Using Mo(CO)6 as the Carbonyl Source". supporting information. . Retrieved 2022/01/04.
• 2、 Berlin, K. Darrell,Bryant, Daniel J.,Bunce, Richard A.. "1,3,3-Trimethylindolin-5-amine and 4-Formylphenyl 4,4-Dimethylchroman-6-carboxylate Thiosemicarbazone (OHet72)". . p. 68 - 77. Retrieved 2021/01/05.