3-(Naphthalen-1-yl)prop-2-enoyl chloride

Base Information

• Chemical Name: 3-(Naphthalen-1-yl)prop-2-enoyl chloride
• CAS No.: 52031-69-3
• Molecular Formula: C13H9ClO
• Molecular Weight: 216.66300
• DSSTox Substance ID: DTXSID60696448
• Mol file: 52031-69-3.mol

Synonyms:DTXSID60696448;OPIGLBSXOOGSLX-UHFFFAOYSA-N;3-(1-naphthalenyl)-2-propenoyl chloride;3-(Naphthalen-1-yl)prop-2-enoyl chloride

Chemical Property of 3-(Naphthalen-1-yl)prop-2-enoyl chloride

Chemical Property:

• PSA: 17.07000
• LogP: 3.61840
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 216.0341926
• Heavy Atom Count: 15
• Complexity: 259

Purity/Quality:

(2E)-3-(1-naphthyl)acryloylchloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-(Naphthalen-1-yl)prop-2-enoyl chloride

There total 7 articles about 3-(Naphthalen-1-yl)prop-2-enoyl chloride 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: 100.0%

(E)-3-(naphthalen-1-yl)acrylic acid (13026-12-5,116659-84-8,2006-14-6) → (E)‐3‐(naphthalen‐1‐yl)acryloyl chloride (120681-10-9,52031-69-3)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jacs.0c10832

Reference yield:

3-(1-naphthyl)propenoic acid (13026-12-5) → 3-(1-Naphthyl)acryloylchlorid (52031-69-3)

Guidance literature:

With pyridine; oxalyl dichloride; In dichloromethane; at 0 ℃;

Reference yield:

1-naphthaldehyde (66-77-3) → (E)‐3‐(naphthalen‐1‐yl)acryloyl chloride (120681-10-9,52031-69-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / KOH / acetonitrile; H₂O / 3 h / 60 °C

2: 76 percent / SOCl₂, pyridine / CH₂Cl₂ / 0.08 h

With pyridine; potassium hydroxide; thionyl chloride; In dichloromethane; water; acetonitrile;

DOI:10.1002/ardp.19943271004

upstream raw materials:

3-(1-naphthyl)propenoic acid

1-naphthaldehyde

(E)-3-(naphthalen-1-yl)acrylic acid

(E)-ethyl 3-(naphthalen-1-yl)acrylate

Downstream raw materials:

C₂₇H₂₉NO₄

(E)-N-[4-(4-Benzhydryl-piperazin-1-yl)-butyl]-3-naphthalen-1-yl-acrylamide

1-(2-hydroxyphenyl)-3-(naphthalen-1-yl) prop-2-en-1-one

1-chloronaphtho<2,1-b>thiophene-2-carboxoyl chloride

Refernces

• 1、 Lee, Yong Ho,Denton, Elliott H.,Morandi, Bill. "Modular Cyclopentenone Synthesis through the Catalytic Molecular Shuffling of Unsaturated Acid Chlorides and Alkynes". supporting information. p. 20948 - 20955. Retrieved 2020/12/21.
• 2、 Zhao, Tingxing,Qin, Dekun,Han, Weiguo,Yang, Shiping,Feng, Boya,Gao, Ge,You, Jingsong. "Co(iii)-catalyzed: Z -selective oxidative C-H/C-H cross-coupling of alkenes with triisopropylsilylacetylene". supporting information. p. 6118 - 6121. Retrieved 2019/06/03.