Methyl 5-cyanonaphthalene-2-carboxylate

Base Information

• Chemical Name: Methyl 5-cyanonaphthalene-2-carboxylate
• CAS No.: 91804-23-8
• Molecular Formula: C₁₃H₉NO₂
• Molecular Weight: 211.22
• DSSTox Substance ID: DTXSID60700973
• Wikidata: Q82632512
• Mol file: 91804-23-8.mol

Synonyms:91804-23-8;METHYL 5-CYANO-2-NAPHTHOATE;METHYL 5-CYANONAPHTHALENE-2-CARBOXYLATE;METHYL5-CYANO-2-NAPHTHOATE;2-Naphthalenecarboxylicacid, 5-cyano-, methyl ester;DTXSID60700973;AB44561;2-Naphthalenecarboxylicacid,5-cyano-,methyl ester;A860224

Chemical Property of Methyl 5-cyanonaphthalene-2-carboxylate

Chemical Property:

• PSA: 50.09000
• LogP: 2.49808
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 211.063328530
• Heavy Atom Count: 16
• Complexity: 317

Purity/Quality:

97% ^*data from raw suppliers

methyl5-cyano-2-naphthoate 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC2=C(C=C1)C(=CC=C2)C#N

Technology Process of Methyl 5-cyanonaphthalene-2-carboxylate

There total 2 articles about Methyl 5-cyanonaphthalene-2-carboxylate 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:

5-bromo-2-naphthalenecarboxylic acid methyl ester (67878-76-6) + copper(I) cyanide (544-92-3) → 5-cyanonaphthalene-2-carboxylic acid methyl ester (91804-23-8)

Guidance literature:

Reference yield:

5-bromonaphthalene-2-carboxylic acid (1013-83-8) → 5-cyanonaphthalene-2-carboxylic acid methyl ester (91804-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.82 g / HCl(g) / 5 h / Heating

2: pyridine / dimethylformamide / 6 h / 160 °C

With pyridine; hydrogenchloride; In N,N-dimethyl-formamide;

DOI:10.1021/jm030540h

Reference yield:

5-cyanonaphthalene-2-carboxylic acid methyl ester (91804-23-8) → 5-(3-chloro-phenoxymethyl)-naphthalen-2-ylamine

Guidance literature:

Multi-step reaction with 6 steps

1.1: aq. NaOH / methanol / 20 °C

2.1: 4.2 g / Et₃N; phosphorazidic acid diphenyl ester / 72 h

3.1: pyridine / acetic acid / 0.5 h

3.2: 2.71 g / Raney Ni; pyridine / acetic acid / 1.5 h / 46 °C

4.1: NaBH₄ / ethanol / 2 h / 20 °C

5.1: Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 6 h / 20 °C

6.1: TFA / CH₂Cl₂ / 6 h / 20 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; diphenyl phosphoryl azide; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid;

DOI:10.1021/jm030540h

upstream raw materials:

5-bromo-2-naphthalenecarboxylic acid methyl ester

copper(I) cyanide

5-bromonaphthalene-2-carboxylic acid

Downstream raw materials:

(5-formylnaphthalen-2-yl)carbamic acid tert-butyl ester

(5-hydroxymethylnaphthalen-2-yl)carbamic acid tert-butyl ester

(5-cyanonaphthalen-2-yl)carbamic acid tert-butyl ester

(5-styryl-naphthalen-2-yl)-carbamic acid tert-butyl ester