Propionyl chloride

Base Information

• Chemical Name: Propionyl chloride
• CAS No.: 79-03-8
• Molecular Formula: C3H5ClO
• Molecular Weight: 92.5251
• Hs Code.: 2915.90
• European Community (EC) Number: 201-170-0
• NSC Number: 83547
• UN Number: 1815
• UNII: MB6VL5OMB9
• DSSTox Substance ID: DTXSID4058819
• Nikkaji Number: J4.227G
• Wikipedia: Propionyl_chloride
• Wikidata: Q13534584
• Mol file: 79-03-8.mol

Synonyms:propanoyl chloride;propionyl chloride

Chemical Property of Propionyl chloride

Chemical Property:

• Appearance/Colour: colorless liquid with a pungent odor
• Vapor Pressure: 105mmHg at 25°C
• Melting Point: -94 °C
• Refractive Index: 1.4302
• Boiling Point: 75.5 °C at 760 mmHg
• Flash Point: 11.7 °C
• PSA: 17.07000
• Density: 1.068 g/cm³
• LogP: 1.16180
• Storage Temp.: Flammables area
• Sensitive.: Moisture Sensitive
• Water Solubility.: REACTS
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 92.0028925
• Heavy Atom Count: 5
• Complexity: 42.2
• Transport DOT Label: Flammable Liquid Corrosive

Purity/Quality:

Propionyl Chloride >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, C
• Hazard Codes: F,C
• Statements: 11-14-34-20/22
• Safety Statements: 9-16-26-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: CCC(=O)Cl
• General Description: Propionyl chloride is a reactive acyl chloride used as a reagent in organic synthesis, particularly in the formation of enolates and asymmetric alkylations when combined with chiral auxiliaries like SuperQuat derivatives. It serves as a key intermediate in reactions involving nucleophilic substitution or acylation, contributing to the synthesis of complex molecules with high diastereoselectivity. Its reactivity makes it valuable for large-scale applications, such as in the preparation of chiral building blocks for pharmaceuticals.

Technology Process of Propionyl chloride

There total 20 articles about Propionyl 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: 97.0%

propionic acid (802294-64-0,79-09-4) → propionyl chloride (79-03-8)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; at 70 - 75 ℃;

Reference yield: 89.0%

→ propionyl chloride (79-03-8)

Guidance literature:

Reference yield: 57.9%

propionic acid (802294-64-0,79-09-4) → propionyl chloride (79-03-8) + propionic acid anhydride (123-62-6)

Guidance literature:

With phosphorus trichloride; at 40 - 50 ℃; 4-5h;

DOI:10.1007/BF00960670

upstream raw materials:

benzoyl chloride

propionic acid

3,4-dichloro-(E)-3-hexene

trimethylsilyl propionate

Downstream raw materials:

1-(5-methylthiophen-2-yl)propan-1-one

1-(1H-imidazol-1-yl)propan-1-one

1-(5-chloro-thiophen-2-yl)-propan-1-one

1-(5-bromothiophen-2-yl)propan-1-one

Refernces

A novel and practical synthesis of ramelteon

10.1021/op500386g

The study outlines an efficient and practical synthesis process for ramelteon, a sedative-hypnotic drug used for treating insomnia. The novel synthesis involves the use of acetonitrile as a nucleophilic reagent to add to 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4b]furan-8-one, followed by a catalytic hydrogenation step that合并了debromination, dehydration, olefin reduction, and cyano reduction into one operation, resulting in the ethylamine compound. The process utilizes dibenzoyl-L-tartaric acid for salt formation and as a resolution agent, leading to the target compound ramelteon with an overall yield nearly double that of existing methods. The study emphasizes the avoidance of the traditional Wittig-Horner reaction, simplifying the synthesis with cost-effective reagents and reduced reaction steps.

Asymmetric alkylations using SuperQuat auxiliaries - An investigation into the synthesis and stability of enolates derived from 5,5-disubstituted oxazolidin-2-ones

10.1039/a809715a

The researchers synthesized various SuperQuat auxiliaries, including 5,5-dimethyl and 5,5-diphenyl derivatives, and compared their performance in enolate alkylation reactions. They found that the 4-isopropyl-5,5-dimethyl SuperQuat provided superior results, achieving high yields and excellent diastereoselectivities. This was attributed to the geminal dimethyl groups at the 5-C position, which suppressed endocyclic cleavage pathways and improved the stability and reactivity of the enolates. The study concluded that the 5,5-dimethyl-4-isopropyloxazolidin-2-one is an effective chiral auxiliary for asymmetric enolate alkylations, offering a robust alternative to the Evans' auxiliary for large-scale synthesis. Key chemicals used in the process included n-butyllithium, propionyl chloride, benzyl bromide, and various α-amino acids for the synthesis of the SuperQuat auxiliaries.