(e)-3-o-Tolylacryloyl chloride

Base Information

• Chemical Name: (e)-3-o-Tolylacryloyl chloride
• CAS No.: 83612-52-6
• Molecular Formula: C10H9ClO
• Molecular Weight: 180.634
• Hs Code.: 2916399090
• European Community (EC) Number: 673-215-6
• DSSTox Substance ID: DTXSID40420708
• Wikidata: Q76310613
• Mol file: 83612-52-6.mol

Synonyms:83612-52-6;(e)-3-o-tolylacryloyl chloride;(2E)-3-(2-METHYLPHENYL)ACRYLOYL CHLORIDE;15873-40-2;(E)-3-o-Tolyl-acryloyl chloride;(E)-3-(2-methylphenyl)prop-2-enoyl chloride;(E)-3-(o-Tolyl)acryloyl chloride;(2E)-3-(2-methylphenyl)prop-2-enoyl chloride;3-o-tolyl-acryloyl chloride;3-(o-Tolyl)acryloylchloride;3-(o-Tolyl)acryloyl chloride;SCHEMBL6421785;SCHEMBL6421789;(E)-2-methylcinnamoyl chloride;DTXSID40420708;ISMYAVWQKWXKOM-VOTSOKGWSA-N;3-(2-Methylphenyl)acryloyl chloride;BBL015052;MFCD03424736;STL197461;AKOS005173543;VS-04823

Chemical Property of (e)-3-o-Tolylacryloyl chloride

Chemical Property:

• PSA: 17.07000
• LogP: 2.77360
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 180.0341926
• Heavy Atom Count: 12
• Complexity: 186

Purity/Quality:

98%min ^*data from raw suppliers

(2E)-3-(2-Methylphenyl)acryloyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1C=CC(=O)Cl
• Isomeric SMILES: CC1=CC=CC=C1/C=C/C(=O)Cl

Technology Process of (e)-3-o-Tolylacryloyl chloride

There total 5 articles about (e)-3-o-Tolylacryloyl 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-(2-methylphenyl)acrylic acid (939-57-1,2373-76-4,41397-71-1) → (E)‐3‐(o‐tolyl)acryloyl chloride (83612-52-6)

Guidance literature:

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

DOI:10.1021/jacs.0c10832

Reference yield:

2-methylcinnamic acid (2373-76-4) → (E)‐3‐(o‐tolyl)acryloyl chloride (83612-52-6)

Guidance literature:

With thionyl chloride; for 5h; Reflux;

DOI:10.1016/j.ejmech.2011.03.067

Reference yield:

2-methylphenyl aldehyde (529-20-4) → (E)‐3‐(o‐tolyl)acryloyl chloride (83612-52-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / Na / 3 h / 0 °C

2: 69 percent / 2 M aq. NaOH / 2.5 h / Heating

3: 89 percent / SOCl₂ / 2 h / Heating

With sodium hydroxide; thionyl chloride; sodium;

upstream raw materials:

(E)-3-(2-methylphenyl)acrylic acid

ethyl trans-2-methylcinnamate

2-methylphenyl aldehyde

2-(Diethoxymethyl)methylbenzene

Downstream raw materials:

5-bromo-2-{[(2E)-3-(2-methylphenyl)prop-2-enoyl]amino}benzamide

5-chloro-2-{[(2E)-3-(2-methylphenyl)prop-2-enoyl]amino}benzamide

O-methylcinnamoyl azide

<1-(2-Methylcinnamoyl)prop-1-ylidene>triphenylphosphorane

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、 Gunia-Krzy?ak, Agnieszka,?elaszczyk, Dorota,Waszkielewicz, Anna M.,Pańczyk, Katarzyna,Marona, Henryk,Rapacz, Anna,Filipek, Barbara,?es?awska, Ewa,S?oczyńska, Karolina,P?kala, El?bieta,Nitek, Wojciech. "Structure-anticonvulsant activity studies in the group of (E)-N-cinnamoyl aminoalkanols derivatives monosubstituted in phenyl ring with 4-Cl, 4-CH3or 2-CH3". . p. 471 - 482. Retrieved 2016/12/30.