o-Toluoyl chloride

Base Information

• Chemical Name: o-Toluoyl chloride
• CAS No.: 933-88-0
• Molecular Formula: C8H7ClO
• Molecular Weight: 154.596
• Hs Code.: 29163900
• European Community (EC) Number: 213-273-8,253-674-5
• UNII: J9YKN18E7R
• DSSTox Substance ID: DTXSID1061314
• Nikkaji Number: J60.353H
• Wikidata: Q27281395
• Mol file: 933-88-0.mol

Synonyms:o-Toluoyl chloride;933-88-0;2-Methylbenzoyl chloride;Benzoyl chloride, 2-methyl-;Methylbenzoyl chloride;o-Methylbenzoyl chloride;2-Toluoyl chloride;o-Toluic acid chloride;2-methylbenzoic acid chloride;2-Methyl-Benzoyl Chloride;37808-28-9;2-methylbenzoylchloride;EINECS 213-273-8;UNII-J9YKN18E7R;J9YKN18E7R;CCRIS 8618;EINECS 253-674-5;2-methyl benzoyl chloride;Benzoyl chloride,2-methyl-;Toluoylchloride;o-toloyl chloride;o-toluic chloride;orthotoluoyl chloride;o-methylbenzoylchloride;ortho-toluoyl chloride;Benzoyl chloride, methyl-;o-Toluoyl chloride, 99%;SCHEMBL93382;2-methyl-benzoic acid chloride;DTXSID1061314;STR00279;MFCD00000668;STL141092;AKOS005256976;LS-188215;FT-0633137;T0310;EN300-56164;Q-200304;Q27281395;F2190-0039

Chemical Property of o-Toluoyl chloride

Chemical Property:

• Appearance/Colour: clear pale yellow to yellow to faintly pink liquid
• Melting Point: -18oC
• Refractive Index: n20/D 1.5549(lit.)
• Boiling Point: 213.5 °C at 760 mmHg
• Flash Point: 84.1 °C
• PSA: 17.07000
• Density: 1.17 g/cm³
• LogP: 2.37400
• Storage Temp.: Room Temperature, Under Inert Atmosphere
• Sensitive.: Moisture Sensitive
• Water Solubility.: Reacts with water.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.0185425
• Heavy Atom Count: 10
• Complexity: 133

Purity/Quality:

99% ^*data from raw suppliers

o-Toluoyl Chloride >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 23-26-27-36/37/39-45-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=CC=C1C(=O)Cl
• Uses: O-Toluoyl Chloride is used in the synthesis if quinolinone compounds as SARS CoV 3CLpro inhibitors. Also used in the synthesis of benzooxaboroles as orally active anti-inflammatory agents.

Technology Process of o-Toluoyl chloride

There total 15 articles about o-Toluoyl 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%

ortho-methylbenzoic acid (118-90-1) → ortho-toluoyl chloride (933-88-0)

Guidance literature:

With oxalyl dichloride; In benzene; at 20 ℃; for 14h;

DOI:10.1016/j.tet.2005.06.093

Reference yield: 93.0%

ortho-methylphenyl iodide (615-37-2) + carbon monoxide (201230-82-2) → ortho-toluoyl chloride (933-88-0)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; benzyltriphenylphosphonium chloride; In toluene; at 110 ℃; for 24h; under 38002.6 Torr; Glovebox; Autoclave; Inert atmosphere;

DOI:10.1021/ja4098093

Reference yield: 70.0%

2-methyl-benzyl alcohol (89-95-2) → ortho-toluoyl chloride (933-88-0)

Guidance literature:

With o-chlorobenzoyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1002/anie.201604921

upstream raw materials:

ortho-methylbenzoic acid

2-methylbenzoic anhydride

ortho-tolylmagnesium bromide

oxalyl dichloride

Downstream raw materials:

ethyl (2-methylbenzoyl)acetate

(4-methoxyphenyl)(2-methylphenyl)methanone

5-chloro-2-hydroxy-2'-methylbenzophenone

6β-(2-methyl-benzoylamino)-penicillanic acid

Refernces

• 1、 Kalsi, Deepti,Barsu, Nagaraju,Sundararaju, Basker. "CoIII-Catalyzed Isonitrile Insertion/Acyl Group Migration Between C?H and N?H bonds of Arylamides". supporting information. p. 2360 - 2364. Retrieved 2018/02/22.
• 2、 De La Higuera Macias, Maximiliano,Arndtsen, Bruce A.. "Functional Group Transposition: A Palladium-Catalyzed Metathesis of Ar-X σ-Bonds and Acid Chloride Synthesis". supporting information. p. 10140 - 10144. Retrieved 2018/08/23.