2-[(1-Naphthylmethyl)thio]acetic acid

Base Information

• Chemical Name: 2-[(1-Naphthylmethyl)thio]acetic acid
• CAS No.: 5254-92-2
• Molecular Formula: C₁₃H₁₂O₂S
• Molecular Weight: 232.303
• Hs Code.: 2930909090
• NSC Number: 112702
• DSSTox Substance ID: DTXSID80296924
• Wikidata: Q82037747
• ChEMBL ID: CHEMBL1741925
• Mol file: 5254-92-2.mol

Synonyms:5254-92-2;2-[(1-naphthylmethyl)thio]acetic acid;NSC112702;2-(Naphth-1-ylmethylthio)acetic acid;2-(naphthalen-1-ylmethylsulfanyl)acetic acid;NSC-112702;2-((Naphthalen-1-ylmethyl)thio)acetic acid;Maybridge1_006523;NCIStruc1_000843;NCIStruc2_000645;SCHEMBL5638078;CHEMBL1741925;HMS560A11;DTXSID80296924;(R)-2-METHOXYISOPROPYLAMINE;((1-naphthylmethyl)thio)acetic acid;CCG-38043;MFCD01314232;NCGC00014124;NCI112702;AKOS000151428;NCGC00014124-02;NCGC00097233-01;2-(naphthalen-1-ylmethylthio)acetic acid;NCI60_000278;FT-0610780;2-[(naphthalen-1-ylmethyl)sulfanyl]acetic acid;2-{[(naphthalen-1-yl)methyl]sulfanyl}acetic acid;SR-01000644986-1

Chemical Property of 2-[(1-Naphthylmethyl)thio]acetic acid

Chemical Property:

• Vapor Pressure: 4.58E-08mmHg at 25°C
• Melting Point: 111-113 °C
• Refractive Index: 1.67
• Boiling Point: 427.4 °C at 760 mmHg
• Flash Point: 212.3 °C
• PSA: 62.60000
• Density: 1.28 g/cm³
• LogP: 3.15760
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 232.05580079
• Heavy Atom Count: 16
• Complexity: 242

Purity/Quality:

98% ^*data from raw suppliers

2-(Naphth-1-ylmethylthio)acetic acid 95.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2CSCC(=O)O

Technology Process of 2-[(1-Naphthylmethyl)thio]acetic acid

There total 8 articles about 2-[(1-Naphthylmethyl)thio]acetic acid 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: 81.0%

methyl 2-(naphthalen-1-ylmethylthio)acetate → α-Naphthylmethylenthioessigsaeure (5254-92-2)

Guidance literature:

With acetic acid; In water; for 20h; Reflux;

DOI:10.1021/acs.joc.7b00172

Reference yield: 80.0%

mercaptoacetic acid (68-11-1) + 1-Chloromethylnaphthalene (86-52-2) → α-Naphthylmethylenthioessigsaeure (5254-92-2)

Guidance literature:

With sodium hydroxide; In acetone; at 0 - 5 ℃; for 15h;

DOI:10.1016/0039-128X(81)90038-6

Reference yield:

1-Chloromethylnaphthalene (86-52-2) → α-Naphthylmethylenthioessigsaeure (5254-92-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / acetone / 0.08 h / 0 °C

1.2: 14 h / Reflux

2.1: acetic acid / water / 20 h / Reflux

With potassium carbonate; acetic acid; In water; acetone;

DOI:10.1021/acs.joc.7b00172

upstream raw materials:

sodium monochloroacetic acid

mercaptoacetic acid

1-Chloromethylnaphthalene

α-Naphthylmethylenthioessigsaeureethylester

Downstream raw materials:

α-Naphthylmethylensulfinylacetohydroxamsaeure

12,15-bisthia-1,3,5(10),6,8,13(14)-gonahexaen-17-one

1-oxo-3-thia-1,2,3,4-tetrahydrophenanthrene

Refernces

• 1、 Ramadas,Chenchaiah Ch.. "Heterocyclic steroids - part X: Total synthesis of 12,15-bisthia-1,3,5(10),6,8,13(14)-gonahexaen-17-one". . p. 353 - 359. Retrieved 2007/10/02.