2-(6-Methoxynaphthalen-2-yl)acetonitrile

Base Information

• Chemical Name: 2-(6-Methoxynaphthalen-2-yl)acetonitrile
• CAS No.: 71056-96-7
• Molecular Formula: C13H11NO
• Molecular Weight: 197.236
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID40433757
• Nikkaji Number: J2.255.502B
• Wikidata: Q82247972
• Mol file: 71056-96-7.mol

Synonyms:2-(6-methoxynaphthalen-2-yl)acetonitrile;71056-96-7;2-(6-METHOXY-2-NAPHTHYL)ACETONITRILE;2-(6-Methoxy-2-naphthyl)ethanenitrile;SCHEMBL1448749;DTXSID40433757;NLQWCQWHTQUUNU-UHFFFAOYSA-N;(6-Methoxy-2-naphthyl)acetonitrile;2-cyanomethyl-6-methoxy-naphthalene;6-Methoxynaphthalene-2-acetonitrile;AKOS006327512;(6-Methoxynaphthalen-2-yl)acetonitrile;CS-0303041;FT-0671285;EN300-1837289

Chemical Property of 2-(6-Methoxynaphthalen-2-yl)acetonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.61
• Boiling Point: 374.348°C at 760 mmHg
• Flash Point: 157.742°C
• PSA: 33.02000
• Density: 1.135g/cm³
• LogP: 2.91448
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 197.084063974
• Heavy Atom Count: 15
• Complexity: 255

Purity/Quality:

99% ^*data from raw suppliers

2-(6-Methoxy-2-naphthyl)acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)C=C(C=C2)CC#N
• Uses: 2-(6-Methoxy-2-naphthyl)acetonitrile (cas# 71056-96-7) is a compound useful in organic synthesis.

Technology Process of 2-(6-Methoxynaphthalen-2-yl)acetonitrile

There total 10 articles about 2-(6-Methoxynaphthalen-2-yl)acetonitrile 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%

2-trimethylsilylacetonitrile (18293-53-3) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → 2-(6-methoxynaphthalen-2-yl)acetonitrile (71056-96-7)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; zinc(II) fluoride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 90 ℃; for 18h;

DOI:10.1021/ja053027x

Reference yield: 77.0%

zinc(II) cyanide (557-21-1) + (6-methoxynaphthalen-2-yl)methyl pivalate → 2-(6-methoxynaphthalen-2-yl)acetonitrile (71056-96-7)

Guidance literature:

zinc(II) cyanide; (6-methoxynaphthalen-2-yl)methyl pivalate; With potassium phosphate; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; In N,N-dimethyl-formamide; for 0.0166667h; Inert atmosphere; Sealed tube;

With diethylzinc; In hexane; N,N-dimethyl-formamide; at 110 ℃; for 16h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.8b01763

Reference yield: 76.0%

2-(Bromomethyl)-6-methoxynaphthalene (73022-40-9) + sodium cyanide (143-33-9,25596-52-5) → 2-(6-methoxynaphthalen-2-yl)acetonitrile (71056-96-7)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; In dichloromethane; water; for 20h; Heating;

DOI:10.1021/jo00199a048

upstream raw materials:

2-(Bromomethyl)-6-methoxynaphthalene

sodium cyanide

2-(chloromethyl)-6-methoxynaphthalene

2-trimethylsilylacetonitrile

Downstream raw materials:

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

6-methoxy-2-naphthylacetic acid

N-[2-(6-Methoxynaphthyl)ethyl]-4-methoxybenzamide

methyl 6-methoxy-2-naphthylacetate

Refernces

• 1、 Velcicky, Juraj,Soicke, Arne,Steiner, Roland,Schmalz, Hans-Guenther. "Palladium-catalyzed cyanomethylation of aryl halides through domino Suzuki coupling-isoxazole fragmentation". supporting information; experimental part. p. 6948 - 6951. Retrieved 2011/06/19.
• 2、 -. "NAPTHTHALENE DERIVATIVES WHICH INHIBIT THE CYTOKINE OR BIOLOGICAL ACTIVITY OF MACROPHAGE MIGRATION INHIBITORY FACTOR (MIF)". Page 88. . Retrieved 2010/02/04.