a-Tosyl-(4-fluorobenzyl) isocyanide

Base Information

• Chemical Name: a-Tosyl-(4-fluorobenzyl) isocyanide
• CAS No.: 165806-95-1
• Molecular Formula: C15H12FNO2S
• Molecular Weight: 289.33
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID90445502
• Nikkaji Number: J980.437D
• Mol file: 165806-95-1.mol

Synonyms:165806-95-1;a-Tosyl-(4-fluorobenzyl) isocyanide;alpha-(p-Toluenesulfonyl)-4-fluorobenzylisonitrile;1-fluoro-4-(isocyano(tosyl)methyl)benzene;a-Tosyl-(4-fluorobenzyl)isocyanide;A-(P-TOLUENESULFONYL)-4-FLUOROBENZYLISONITRILE;1-[(4-fluorophenyl)-isocyanomethyl]sulfonyl-4-methylbenzene;alpha-[(4-Methylphenyl)sulphonyl]-4-fluorobenzylisonitrile;MFCD03787932;alpha-Tosyl-4-fluorobenzyl isocyanide;1-((4-fluorophenyl)(isocyano)methylsulfonyl)-4-methylbenzene;1-Fluoro-4-[isocyano(tosyl)methyl]benzene;1-fluoro-4-{isocyano[(4-methylphenyl)sulfonyl]methyl}benzene;(4-Fluorophenyl)(isocyano)methyl 4-methylphenyl sulphone;1-FLUORO-4-[ISOCYANO[(4-METHYLPHENYL)SULFONYL]METHYL]BENZENE;[1-(4-FLUOROPHENYL)-1-TOSYL]METHYL ISOCYANIDE;LEVAMISOLEPHOSPHATE;SCHEMBL992209;AMY1891;DTXSID90445502;AKOS015909340;AB15903;AS-30573;SY109724;a-(p-Tolylsulfonyl)-4-fluorobenzylisocyanide;A3676;FT-0604151;alpha-(p-Toluenesulfonyl)4fluorobenzylisonitrile;ALPHA-TOSYL-(4-FLUOROBENZYL) ISOCYANIDE;alpha-(p-toluenesulfonyl)-4-fluorobenzylisonitile;alpha-(p-Toluenesulfonyl)-4-fluorobenzylisocyanide;alpha-(p-toluene-sulfonyl)-4-fluorobenzyl isocyanide;alpha-(p-toluenesulfonyl)-4-fluoro-benzylisonitrile;alpha-(p-toluenesulfonyl)-4-fluorobenzyl isocyanide;J-519603;4-Fluoro-alpha-(toluene-4-sulphonyl)benzyl isocyanide;1-[(4-fluorophenyl)-isocyano-methyl]sulfonyl-4-methyl-benzene;1-[1-Isocyano-1-(toluene-4-sulfonyl)-methyl]-4-fluorobenzene;Benzene, 1-fluoro-4-[isocyano[(4-methylphenyl)sulfonyl]methyl]-;BENZENE,1-FLUORO-4-[ISOCYANO[(4-METHYLPHENYL)SULFONYL]METHYL]-

Chemical Property of a-Tosyl-(4-fluorobenzyl) isocyanide

Chemical Property:

• Boiling Point: 164.5oC at 760mmHg
• Flash Point: 73.3oC
• PSA: 42.52000
• Density: 1.46g/cm3
• LogP: 3.83740
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 289.05727796
• Heavy Atom Count: 20
• Complexity: 460

Purity/Quality:

99% ^*data from raw suppliers

α-(p-Toluenesulfonyl)-4-fluorobenzylisonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)C(C2=CC=C(C=C2)F)[N+]#[C-]
• Uses: Alpha-(p-toluenesulfonyl)-4-fluorobenzylisonitrile is a useful reagent for the development of DNA-compatible method for novel functionalized imidazoles.

Technology Process of a-Tosyl-(4-fluorobenzyl) isocyanide

There total 7 articles about a-Tosyl-(4-fluorobenzyl) isocyanide 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: 90.0%

N-[(4-fluorophenyl)[(4-methylphenyl)sulfonyl]methyl]formamide (165806-94-0) → 1-((4-fluorophenyl)(isocyano)methylsulfonyl)-4-methylbenzene (165806-95-1)

Guidance literature:

With triethylamine; trichlorophosphate; In 1,2-dimethoxyethane;

Reference yield: 90.0%

→ 1-((4-fluorophenyl)(isocyano)methylsulfonyl)-4-methylbenzene (165806-95-1)

Guidance literature:

Reference yield:

p-toluene sulfinic acid (536-57-2) → 1-((4-fluorophenyl)(isocyano)methylsulfonyl)-4-methylbenzene (165806-95-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / TMSCl / toluene; acetonitrile / 5 h / 50 °C

2: 78 percent / POCl₃, Et₃N / tetrahydrofuran / 0 °C

With chloro-trimethyl-silane; triethylamine; trichlorophosphate; In tetrahydrofuran; toluene; acetonitrile;

DOI:10.1016/0040-4039(96)01886-2

upstream raw materials:

N-[(4-fluorophenyl)[(4-methylphenyl)sulfonyl]methyl]formamide

p-toluene sulfinic acid

4-fluorobenzaldehyde

N-[(4-Fluoro-phenyl)-formylamino-methyl]-formamide

Downstream raw materials:

4-(4-Fluorophenyl)-5-(pyridin-4-yl)-1H-imidazole

5-(2-Aminopyrimidin-4-yl)-4-(4-fluorophenyl)-1-(2,2,6,6-tetramethylpiperidin-4-yl)imidazole

1-(2,2,6,6-tetramethyl-4-piperidinyl)-4-(4-fluorophenyl)-5-acetylimidazole

5-(2-Aminopyrimidin-4-yl)-4-(4-fluorophenyl)-1-[3-(4-Morpholinyl)propyl]imidazole

Refernces

• 1、 Divakaran, Anand,Talluri, Siva K.,Ayoub, Alex M.,Mishra, Neeraj K.,Cui, Huarui,Widen, John C.,Berndt, Norbert,Zhu, Jin-Yi,Carlson, Angela S.,Topczewski, Joseph J.,Schonbrunn, Ernst K.,Harki, Daniel A.,Pomerantz, William C. K.. "Molecular Basis for the N-Terminal Bromodomain-and-Extra-Terminal-Family Selectivity of a Dual Kinase-Bromodomain Inhibitor". supporting information. p. 9316 - 9334. Retrieved 2018/10/24.
• 2、 -. "4-SUBSTITUTED-6-ISOPROPYL-BENZENE-1,3-DIOL COMPOUNDS AND THEIR USE". Page/Page column 137. . Retrieved 2009/06/27.