8-Iodo-1-tetralone

Base Information

• Chemical Name: 8-Iodo-1-tetralone
• CAS No.: 651735-61-4
• Molecular Formula: C₁₀H₉IO
• Molecular Weight: 272.085
• DSSTox Substance ID: DTXSID70460273
• Nikkaji Number: J1.989.924A
• Wikidata: Q82284270
• Mol file: 651735-61-4.mol

Synonyms:651735-61-4;8-iodo-1-tetralone;8-Iodo-3,4-dihydronaphthalen-1(2H)-one;8-iodo-3,4-dihydro-2H-naphthalen-1-one;8-iodo-1,2,3,4-tetrahydronaphthalen-1-one;8-Iodotetralin-1-one;8-iodotetralone;1(2H)-Naphthalenone,3,4-dihydro-8-iodo-;SCHEMBL19899072;DTXSID70460273;BBB73561;AKOS015915218;FT-0654266;A834993

Chemical Property of 8-Iodo-1-tetralone

Chemical Property:

• Vapor Pressure: 6.07E-05mmHg at 25°C
• Refractive Index: 1.644
• Boiling Point: 345.7 °C at 760 mmHg
• Flash Point: 162.8 °C
• PSA: 17.07000
• Density: 1.757 g/cm³
• LogP: 2.81020
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 271.96981
• Heavy Atom Count: 12
• Complexity: 190

Purity/Quality:

97% ^*data from raw suppliers

8-Iodo-3,4-dihydronaphthalen-1(2H)-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C(=O)C1)C(=CC=C2)I

Technology Process of 8-Iodo-1-tetralone

There total 4 articles about 8-Iodo-1-tetralone 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: 60.0%

8-aminotetralone (210346-49-9) → 8-iodo-3,4-dihydronaphthalen-1(2H)-one (651735-61-4)

Guidance literature:

8-aminotetralone; With hydrogenchloride; sodium nitrite; In water; acetic acid; at 0 ℃; for 0.0833333h;

With potassium iodide; In water; acetic acid; at 60 ℃; for 1h;

DOI:10.1021/jo035289s

Reference yield:

N-(5,6,7,8-tetrahydronaphthalen-1-yl)acetamide (6272-18-0) → 8-iodo-3,4-dihydronaphthalen-1(2H)-one (651735-61-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium permanganate; MgSO₄ / acetone; H₂O / 2.25 h / 20 °C

2.1: 9.11 g / aq. HCl / 3 h / 90 °C

3.1: HCl; NaNO₂ / H₂O; acetic acid / 0.08 h / 0 °C

3.2: 60 percent / KI / H₂O; acetic acid / 1 h / 60 °C

With hydrogenchloride; potassium permanganate; magnesium sulfate; sodium nitrite; In water; acetic acid; acetone;

DOI:10.1021/jo035289s

Reference yield:

N-(8-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)acetamide (110139-15-6) → 8-iodo-3,4-dihydronaphthalen-1(2H)-one (651735-61-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 9.11 g / aq. HCl / 3 h / 90 °C

2.1: HCl; NaNO₂ / H₂O; acetic acid / 0.08 h / 0 °C

2.2: 60 percent / KI / H₂O; acetic acid / 1 h / 60 °C

With hydrogenchloride; sodium nitrite; In water; acetic acid;

DOI:10.1021/jo035289s

upstream raw materials:

8-aminotetralone

N-(5,6,7,8-tetrahydronaphthalen-1-yl)acetamide

N-(8-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)acetamide

1-amino-5,6,7,8-tetrahydronaphthalene

Downstream raw materials:

(S)-methyl 2-[(R)-[(tert-butoxycarbonyl)amino](phenyl)methyl]-8-iodo-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Refernces

• 1、 Gelat, Fabien,Richard, Vincent,Berger, Olivier,Montchamp, Jean-Luc. "Development of a new family of chiral auxiliaries". supporting information. p. 1819 - 1821. Retrieved 2015/04/27.