1,2,3,4-Tetrahydro-4,4-dimethylnaphthalene-1-carbonitrile

Base Information

• Chemical Name: 1,2,3,4-Tetrahydro-4,4-dimethylnaphthalene-1-carbonitrile
• CAS No.: 78103-84-1
• Molecular Formula: C13H15 N
• Molecular Weight: 185.269
• Hs Code.: 2926909090
• European Community (EC) Number: 278-837-8
• DSSTox Substance ID: DTXSID10888533
• Nikkaji Number: J319.723I
• Mol file: 78103-84-1.mol

Synonyms:78103-84-1;1,2,3,4-Tetrahydro-4,4-dimethylnaphthalene-1-carbonitrile;4,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-carbonitrile;4,4-dimethyl-2,3-dihydro-1H-naphthalene-1-carbonitrile;EINECS 278-837-8;1-Naphthalenecarbonitrile, 1,2,3,4-tetrahydro-4,4-dimethyl-;SCHEMBL7947851;1,1-dimethyl-4-cyano-tetralin;DTXSID10888533;4,4-Dimethyltetralin-1-carbonitrile;CS-0242499;EN300-250442

Chemical Property of 1,2,3,4-Tetrahydro-4,4-dimethylnaphthalene-1-carbonitrile

Chemical Property:

• Vapor Pressure: 0.000414mmHg at 25°C
• Boiling Point: 316.3°C at 760 mmHg
• Flash Point: 117.2°C
• PSA: 23.79000
• Density: 1.02g/cm³
• LogP: 3.36518
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 185.120449483
• Heavy Atom Count: 14
• Complexity: 258

Purity/Quality:

99% ^*data from raw suppliers

1,2,3,4-Tetrahydro-4,4-dimethylnaphthalene-1-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC(C2=CC=CC=C21)C#N)C

Technology Process of 1,2,3,4-Tetrahydro-4,4-dimethylnaphthalene-1-carbonitrile

There total 5 articles about 1,2,3,4-Tetrahydro-4,4-dimethylnaphthalene-1-carbonitrile 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: 92.0%

5-methyl-2-phenylhex-4-enenitrile (38179-48-5) → ethyl 1-cyano-1,2,3,4-tetrahydro-4,4-dimethylnaphthalene-1-carboxylate (78103-84-1)

Guidance literature:

With PPA; phosphoric acid; In toluene;

Reference yield:

C16H19NO2 (1323928-41-1) → ethyl 1-cyano-1,2,3,4-tetrahydro-4,4-dimethylnaphthalene-1-carboxylate (78103-84-1)

Guidance literature:

Multi-step reaction with 2 steps

1: water / dimethyl sulfoxide / 2 h / Reflux

2: bismuth(lll) trifluoromethanesulfonate / nitromethane / 2 h / Reflux; Inert atmosphere

With bismuth(lll) trifluoromethanesulfonate; water; In nitromethane; dimethyl sulfoxide; 2: Friedel Crafts alkylation;

DOI:10.1002/ejoc.201100213

Reference yield:

ethyl phenylcyanoacetate (4553-07-5) → ethyl 1-cyano-1,2,3,4-tetrahydro-4,4-dimethylnaphthalene-1-carboxylate (78103-84-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: water / dimethyl sulfoxide / 2 h / Reflux

3.1: bismuth(lll) trifluoromethanesulfonate / nitromethane / 2 h / Reflux; Inert atmosphere

With bismuth(lll) trifluoromethanesulfonate; water; sodium hydride; In tetrahydrofuran; nitromethane; dimethyl sulfoxide; 3.1: Friedel Crafts alkylation;

DOI:10.1002/ejoc.201100213

upstream raw materials:

5-methyl-2-phenylhex-4-enenitrile

C₁₆H₁₉NO₂

ethyl phenylcyanoacetate

prenyl bromide

Downstream raw materials:

1,1-dimethyl-4-propionyl-tetralin