(R)-tebuconazole

Base Information

• Chemical Name: (R)-tebuconazole
• CAS No.: 120786-56-3
• Molecular Formula: C₁₆H₂₂ClN₃O
• Molecular Weight: 307.823
• DSSTox Substance ID: DTXSID001033397
• Nikkaji Number: J407.334G
• Wikidata: Q27157209
• Mol file: 120786-56-3.mol

Synonyms:(R)-tebuconazole;120786-56-3;(3R)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-ylmethyl)pentan-3-ol;SCHEMBL5595539;CHEBI:83781;DTXSID001033397;Q27157209;(3R)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol;(alphaR)-alpha-[2-(4-Chlorophenyl)ethyl]-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol;1H-1,2,4-Triazole-1-ethanol, .alpha.-[2-(4-chlorophenyl)ethyl]-.alpha.-(1,1-dimethylethyl)-, (.alpha.R)-

Chemical Property of (R)-tebuconazole

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 307.1451400
• Heavy Atom Count: 21
• Complexity: 326

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)C(CCC1=CC=C(C=C1)Cl)(CN2C=NC=N2)O
• Isomeric SMILES: CC(C)(C)[C@](CCC1=CC=C(C=C1)Cl)(CN2C=NC=N2)O

Technology Process of (R)-tebuconazole

There total 12 articles about (R)-tebuconazole 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: 49.0%

sodium triazole (41253-21-8) + Methanesulfonic acid (S)-2-[2-(4-chloro-phenyl)-ethyl]-2-hydroxy-3,3-dimethyl-butyl ester (119298-84-9) → (R)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (80443-41-0,107534-96-3,119364-85-1,120786-56-3) + (S)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (119364-85-1)

Guidance literature:

In N,N-dimethyl-formamide; at 120 ℃; for 6h; Yields of byproduct given. Title compound not separated from byproducts;

Reference yield:

tebuconazole (107534-96-3) → (R)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (80443-41-0,107534-96-3,119364-85-1,120786-56-3) + (S)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (119364-85-1)

Guidance literature:

With Chiralpak ID; In hexane; isopropyl alcohol; Resolution of racemate;

DOI:10.1002/chir.22390

Reference yield:

1-(2-bromoethyl)-4-chlorobenzene (6529-53-9) → (R)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (80443-41-0,107534-96-3,119364-85-1,120786-56-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) Mg / 1) ether, 2) 3 h, refluxe

2: NCS, AgNO₃ / acetonitrile / 15 h / 40 - 50 °C

3: LiAlH₄ / diethyl ether / 3 h / 35 °C

4: NEt₃ / CH₂Cl₂ / 4 h / 25 °C

5: dimethylformamide / 6 h / 120 °C

With N-chloro-succinimide; lithium aluminium tetrahydride; silver nitrate; magnesium; triethylamine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

sodium triazole

Methanesulfonic acid (R)-2-[2-(4-chloro-phenyl)-ethyl]-2-hydroxy-3,3-dimethyl-butyl ester

Methanesulfonic acid (S)-2-[2-(4-chloro-phenyl)-ethyl]-2-hydroxy-3,3-dimethyl-butyl ester

1-(2-bromoethyl)-4-chlorobenzene