36854-57-6

Basic information

• Product Name: 2-Phenylbutyryl chloride
• Synonyms: 2-PHENYLBUTYRYL CHLORIDE;2-PHENYLBUTYRIC CHLORIDE;2-ETHYL-2-PHENYLACETYL CHLORIDE;2-phenylbutyril chloride;2-Phenyl Butyric acid Chloride;2-Phenylbutyryl hloride;2PhenylButylrylChloride;2-Phenylbutyrylchloride,98%
• CAS NO: 36854-57-6
• Molecular Formula: C₁₀H₁₁ClO
• Molecular Weight: 182.65
• EINECS: 253-241-0
• Product Categories: Miscellaneous;Acid Halides;Carbonyl Compounds;Organic Building Blocks;Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 36854-57-6.mol
• Article Data: 33

Chemical Properties

• Melting Point: 178-180 °C
• Boiling Point: 122-125 °C20 mm Hg(lit.)
• Flash Point: 209 °F
• Appearance: Clear pale yellow to yellow liquid
• Density: 1.093 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0343mmHg at 25°C
• Refractive Index: n20/D 1.516(lit.)
• Storage Temp.: 0-6°C
• Solubility: Chloroform, Hexanes
• Sensitive: Moisture Sensitive
• BRN: 2045209
• CAS DataBase Reference: 2-Phenylbutyryl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenylbutyryl chloride(36854-57-6)
• EPA Substance Registry System: 2-Phenylbutyryl chloride(36854-57-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 22-26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• RTECS: ET5957500
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 36854-57-6(Hazardous Substances Data)

Usage

Chemical Properties

Clear pale yellow to yellow liquid

Uses

Different sources of media describe the Uses of 36854-57-6 differently. You can refer to the following data:
1. α-Ethyl-benzeneacetyl Chloride is used in the synthesis of mild and neutral system for selective reduction of organic functional groups. Also used in the preparation of phenothiazine derivatives for the reversible inhibition of human butyrylcholinesterase.
2. (R)-(-)-2-phenylbutyryl chloride may be employed as chiral reagent for the determination of dopamine and dopamine-derived salsolinol and norsalsolinol in human brain by GC-MS method. Chiral (S)-(+)-2-phenylbutyryl chloride may be used as derivatization reagent for the hydroxyl groups during the GC-MS assay for the enantiomers of 1,2-propanediol, 1,3-butanediol, 1,3-pentanediol and their corresponding hydroxyacids in biological fluids.

General Description

The kinetic resolution of racemic 2-phenylbutyryl chloride by sterically hindered chiral secondary alcohols has been evaluated. 2-Phenylbutyryl chloride reacts with 4-methoxybenzoyl chloride catalyzed by PdBr(Ph)(PPh3)2 to yield 1-(4-methoxyphenyl)-2-phenyl-2-buten-1-one.

InChI:InChI=1/C10H11ClO/c1-2-9(10(11)12)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3/t9-/m0/s1

Upstream product

• 103-82-2 phenylacetic acid 
• 769-68-6 2-phenylbutanenitrile 
• 90-27-7 2-Phenylbutyric acid 

Downstream Products

• 113861-62-4 2-phenyl-butyric acid-(3-diethylamino-2,2-dimethyl-propyl ester) 
• 92702-71-1 optically inactive N-(2-phenyl-butyryl)-methionine 
• 359828-75-4 3-oxo-4-phenyl-hexanoic acid ethyl ester 
• 30544-14-0 N-(2-phenyl-butyryl)-glycine ethyl ester 
• 102667-02-7 1,4-bis-(2-phenyl-butyryl)-piperazine 
• 6957-17-1 (+/-)-4-phenylhexan-3-one 
• 40893-04-7 2-methoxyphenyl 2-phenylbutanoate 
• 98964-26-2 2-((Ξ)-2-phenyl-butyrylamino)-2-deoxy-D-glucose 
• 90-26-6 2-phenylbutyramide 
• 122514-23-2 2-bromo-2-phenyl-butyryl bromide 
• 92321-53-4 2-Phenyl-buttersaeure-diethylamid 
• 28623-70-3 2-ethyl-2-phenyl-N-phenylacetamide 
• 63868-18-8 17-((Ξ)-2-phenyl-butyl)-morphinan-3-ol 
• 4378-36-3 fenbutrazate 

Relevant articles and documents

Palladium-Catalyzed 2-(Neopentylsulfinyl)aniline Directed C–H Acetoxylation and Alkenylation of Arylacetamides

The 2-(neopentylsulfinyl)aniline directing group that promotes rapid palladium-catalyzed C–H acetoxylation and alkenylation of arylacetamides has been developed. The acetoxylation reaches completion within only 40 min at 100 °C and leads to the bis-functionalized products. Alternatively, the reaction can be carried out at room temperature, which is beneficial for sensitive substrates. For the alkenylation, we have developed a protocol in which easily available 1-substituted cyclopropanols were employed as equivalents of vinyl ketones.

Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters

A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.