1-Naphthaleneacetonitrile, 5,6,7,8-tetrahydro-

Base Information

• Chemical Name: 1-Naphthaleneacetonitrile, 5,6,7,8-tetrahydro-
• CAS No.: 3160-17-6
• Molecular Formula: C₁₂H₁₃N
• Molecular Weight: 171.242
• Hs Code.: 2926909090
• Mol file: 3160-17-6.mol

Synonyms:1-Cyanmethyl-5,6,7,8-tetrahydro-naphthalin;5-cyanomethyl-1,2,3,4-tetrahydronaphthalene;5-Cyanmethyl-tetralin;(5,6,7,8-Tetrahydro-[1]naphthyl)-acetonitril;(5,6,7,8-tetrahydro-[1]naphthyl)-acetonitrile;1-NAPHTHALENEACETONITRILE, 5,6,7,8-TETRAHYDRO;

Chemical Property of 1-Naphthaleneacetonitrile, 5,6,7,8-tetrahydro-

Chemical Property:

• PSA: 23.79000
• LogP: 2.63148

Purity/Quality:

95% ^*data from raw suppliers

1-NAPHTHALENEACETONITRILE,5,6,7,8-TETRAHYDRO 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Naphthaleneacetonitrile, 5,6,7,8-tetrahydro-

There total 12 articles about 1-Naphthaleneacetonitrile, 5,6,7,8-tetrahydro- 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: 69.0%

tricarbonyl{(4a,5,6,7,8,8a-η)-1,2,3,4-tetrahydronaphthalene}chromium(0) (12154-63-1) + lithioacetonitrile (99749-00-5) → 2-(5,6,7,8-tetrahydronaphthalene-1-yl)acetonitrile (3160-17-6)

Guidance literature:

With I₂; HMPT; In tetrahydrofuran; Lithioacetonitrile, prepd. in THF from BuLi, diisopropylamine, and acetonitrile at -78°C, was treated with HMPT. The mixt. was stirred at -78°C for 1 h, a soln. of iodine in THF was added, and the mixt. was warmed to room temp.; Recrystd. from hexane; elem.anal.;

DOI:10.1016/0022-328X(88)83005-5

Reference yield:

sodium cyanide (773837-37-9) + (5,6,7,8-tetrahydronaphthalene-1-yl)methanol (41790-30-1) → 2-(5,6,7,8-tetrahydronaphthalene-1-yl)acetonitrile (3160-17-6)

Guidance literature:

(5,6,7,8-tetrahydronaphthalene-1-yl)methanol; With thionyl chloride; In dichloromethane; at 0 - 20 ℃; for 17h;

sodium cyanide; In dimethyl sulfoxide; at 20 ℃; for 1.5h;

Reference yield:

tetralin (119-64-2) → 2-(5,6,7,8-tetrahydronaphthalene-1-yl)acetonitrile (3160-17-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) conc. HCl, conc. H₂SO₄, 2.) glacial AcOH, AcONa*3H₂O, 3.) 4M NaOH, 4.) pyridinium dichromate, silica gel

2: 79 percent / sodium borohydride / ethanol / 1.5 h

3: 100 percent / SOCl₂ / toluene / 2 h

4: dimethylsulfoxide / 3 h

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; dipyridinium dichromate; thionyl chloride; sulfuric acid; sodium acetate; silica gel; acetic acid; In ethanol; dimethyl sulfoxide; toluene;

upstream raw materials:

ethanol

5-(chloromethyl)-1,2,3,4-tetrahydronaphthalene

potassium cyanide

tetralin

Downstream raw materials:

(1,2,3,4-tetrahydro-5-naphthyl)acetic acid

Refernces

• 1、 Horn Jensen, Eva,Nielsen, Per Halfdan. "SYNTHESIS OF TRICYCLIC BENZAZEPINES AND THEIR DOPAMINE D1- AND D2-AFFINITY". . p. 2441 - 2458. Retrieved 2007/10/03.