1,2,3,4-Tetrahydronaphthalene-1-carbonitrile

Base Information

• Chemical Name: 1,2,3,4-Tetrahydronaphthalene-1-carbonitrile
• CAS No.: 56536-96-0
• Molecular Formula: C₁₁H₁₁N
• Molecular Weight: 157.215
• Hs Code.: 2926909090
• European Community (EC) Number: 611-399-1
• UNII: 27327TPP91
• DSSTox Substance ID: DTXSID101286230
• Nikkaji Number: J3.119.104A
• Wikidata: Q27254157
• Mol file: 56536-96-0.mol

Synonyms:56536-96-0;1-Cyanotetraline;1,2,3,4-tetrahydronaphthalene-1-carbonitrile;1-Cyanotetralin;1-Cyano-1,2,3,4-tetrahydronaphthalene;1-Naphthalenecarbonitrile, 1,2,3,4-tetrahydro-;1,2,3,4-tetrahydro-1-naphthalenecarbonitrile;alpha-Cyanotetraline;UNII-27327TPP91;1-Cyano tetralin;MFCD08703294;(1RS)-1,2,3,4-Tetrahydronaphthalene-1-carbonitrile;27327TPP91;Tetryzoline hydrochloride specified impurity A [EP];1-Cyano Tetrahydronaphathalene;tetralin-1-carbonitrile;cyanotetralin;cyanotetrahydronaphthalene;1-Cyanotetrahydronaphathalene;.ALPHA.-CYANOTETRALINE;SCHEMBL779498;HMRIXHRQNXHLSL-UHFFFAOYSA-N;DTXSID101286230;AKOS009156517;1,2,3,4-Tetrahydro-1-naphthonitrile;CS-W021269;AS-15754;SY104383;.ALPHA.-CYANOTETRALINE [EP IMPURITY];FT-0756989;T3492;.ALPHA.-CYANOTETRALINE [USP IMPURITY];EN300-29902;1,2,3,4-tetrahydro-naphthalene-1-carbonitrile;A831083;Q27254157;Z295443708;TETRYZOLINE HYDROCHLORIDE IMPURITY A [EP IMPURITY];(1RS)-1,2,3,4-Tetrahydronaphthalene-1-carbonitrile (alpha-Cyanotetraline);Tetryzoline Hydrochloride Imp. A (EP);Tetryzoline Imp. A (EP);Tetryzoline Hydrochloride Impurity A;Tetryzoline Impurity A

Chemical Property of 1,2,3,4-Tetrahydronaphthalene-1-carbonitrile

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 48-50 °C
• Refractive Index: 1.55
• Boiling Point: 309 ºC
• Flash Point: 114 ºC
• PSA: 23.79000
• Density: 1.06
• LogP: 2.63008
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Sparingly), DMSO (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 157.089149355
• Heavy Atom Count: 12
• Complexity: 200

Purity/Quality:

98%, ^*data from raw suppliers

1-Cyanotetraline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C2=CC=CC=C2C1)C#N
• Uses: 1-Cyanotetraline is used in the synthesis of aldose reductase inhibitors. Also reductase enzymes are believed to catalyze the formation of sorbitol from glucose leading to the chronic complications of diabetes mellitus. It is also used in the synthesis of baclofen analogs, potent GABAB agonists. 1-Cyanotetraline is used in the synthesis of aldose reductase inhibitors. Also reductase enzymes are believed to catalyze the formation of sorbitol from glucose leading to the chronic complications of diabetes mellitus. It is also used in the synthesis of baclofen analogs, potent GABAB agonists.

Technology Process of 1,2,3,4-Tetrahydronaphthalene-1-carbonitrile

There total 22 articles about 1,2,3,4-Tetrahydronaphthalene-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: 87.0%

acrylonitrile (107-13-1,25014-41-9) + 3-Phenylpropionic acid (501-52-0) → 1-cyanotetraline (132205-64-2,56536-96-0)

Guidance literature:

With sodium persulfate; silver nitrate; ferric nitrate; In water; 1,2-dichloro-ethane; acetonitrile; for 4h; Heating;

DOI:10.1016/0040-4039(95)00746-Y

Reference yield: 80.0%

1-tetralone tosylhydrazone (17336-59-3) + potassium thioacyanate (333-20-0) → 1-cyanotetraline (132205-64-2,56536-96-0)

Guidance literature:

With copper(l) iodide; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene; toluene-4-sulfonic acid hydrazide; In 1-methyl-pyrrolidin-2-one; acetonitrile; at 80 ℃; for 7h; under 760.051 Torr; Molecular sieve; Green chemistry;

DOI:10.1021/acs.joc.7b00836

Reference yield: 79.0%

1-chlorotetralin (58485-68-0) + potassium cyanide (151-50-8) → 1-cyanotetraline (132205-64-2,56536-96-0)

Guidance literature:

With 18-crown-6 ether; In acetonitrile; for 5h; Heating;

DOI:10.1002/ardp.19893221210

upstream raw materials:

[(p-methylphenyl)sulfonylmethyl]isonitrile

3,4-dihydronaphthalene-1(2H)-one

1-chlorotetralin

potassium cyanide

Downstream raw materials:

tetrahydrozoline

1,2,3,4-tetrahydronaphthalene-1-carboxamide

tetralin-1-carboxylic acid

Δ-3,4-naphthalene-1-carbonitrile

Refernces

• 1、 Sun, Ming-Xue,Wang, Yao-Feng,Xu, Bao-Hua,Ma, Xin-Qi,Zhang, Suo-Jiang. "A metal-free direct C (sp3)-H cyanation reaction with cyanobenziodoxolones". supporting information. p. 1971 - 1975. Retrieved 2018/03/23.
• 2、 Falk, Anna,Goederz, Anna-Lena,Schmalz, Hans-Guenther. "Enantioselective nickel-catalyzed hydrocyanation of vinylarenes using chiral phosphine-phosphite ligands and TMS-CN as a source of HCN". supporting information. p. 1576 - 1580. Retrieved 2013/03/13.