701-99-5

Basic information

• Product Name: Phenoxyacetyl chloride
• Synonyms: LABOTEST-BB LT00643586;AKOS BBS-00003927;PHENOXYACETYL CHLORIDE;phenoxy-acetylchlorid;Phenyloxyacetyl chloride;Acyl chloride kind;Acetylchloride,phenoxy-;Phenoxyacetic acid chloride
• CAS NO: 701-99-5
• Molecular Formula: C₈H₇ClO₂
• Molecular Weight: 170.59
• EINECS: 211-862-4
• Product Categories: Biochemistry;Nucleosides, Nucleotides & Related Reagents;Protecting Agents for Hydroxyl and Amino Groups;Protecting Agents, Phosphorylating Agents & Condensing Agents;Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 701-99-5.mol
• Article Data: 81

Chemical Properties

• Melting Point: 100-100.5 °C
• Boiling Point: 225-226 °C(lit.)
• Flash Point: 227 °F
• Appearance: Clear slightly yellow to brown/Liquid
• Density: 1.235 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0823mmHg at 25°C
• Refractive Index: n20/D 1.534(lit.)
• Storage Temp.: Store at RT.
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 607585
• CAS DataBase Reference: Phenoxyacetyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Phenoxyacetyl chloride(701-99-5)
• EPA Substance Registry System: Phenoxyacetyl chloride(701-99-5)

Safety Data

• Hazard Codes: C
• Statements: 14-34-36/37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 10-19
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 701-99-5(Hazardous Substances Data)

Usage

Description

Phenoxyacetyl chloride is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals and chemical compounds. It is known for its reactivity and ability to form esters, amides, and other derivatives, making it a versatile building block in organic chemistry.

Uses

Phenoxyacetyl chloride is used in the synthesis of:
1. Series of macrocyclic bis-β-lactams: These complex ring structures have potential applications in the development of new antibiotics and other medicinal compounds.
2. 5-phenyl-6-epiphenoxymethylpenicillin benzyl ester: Phenoxyacetyl chloride is a derivative of penicillin, a widely used antibiotic, and may have potential applications in medicine.
3. N-protected guanosine derivatives: These compounds are useful in RNA synthesis, which is an important area of research in molecular biology and drug development.
4. Phenyloxyketene: Phenoxyacetyl chloride is used for cycloaddition to imines, leading to the formation of β-lactams, which are a class of compounds with potential applications in medicine and as catalysts in organic synthesis.
In addition to these specific applications, Phenoxyacetyl chloride is also used in various chemical reactions to form esters, amides, and other functional groups, making it a valuable reagent in organic chemistry and pharmaceutical research.

Purification Methods

If it has no OH band in the IR then distil it in a vacuum, taking precautions for the moisture-sensitive compound. If it contains free acid (due to hydrolysis, OH bands in the IR), then add an equal volume of redistilled SOCl2, reflux for 2-3hours, evaporate and distil the residue in a vacuum as before. The amide has m 101o. [McElvain & Carney J Am Chem Soc 68 2592 1946, Beilstein 6 III 613.]

InChI:InChI=1/C8H7ClO2/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 122-59-8 2-phenoxyacetic acid 
• 3598-16-1 2-phenoxyacetic acid sodium salt 
• 10026-13-8 phosphorus pentachloride 
• 2065-23-8 methyl 2-phenoxyacetate 
• 79-11-8 chloroacetic acid 
• 108-95-2 phenol 
• 2555-49-9 phenoxyacetic acid ethyl ester 
• 139-02-6 sodium phenoxide 

Downstream Products

• 7497-89-4 methyl 3-phenoxypropanoate 
• 66902-58-7 phenoxy-acetic acid-[3-(2-methyl-piperidino)-propylester]; hydrochloride 
• 101939-11-1 3,3-dimethyl-4-phenoxyacetyl-piperazine-2,6-dione 
• 101721-20-4 phenoxy-acetic acid-(4-amino-2-methyl-[6]quinolylamide) 
• 94576-80-4 phenoxy-acetic acid-(1-phenyl-2-pyrrolidino-ethyl ester); hydrochloride 
• 114276-15-2 phenoxy-acetic acid-[β-(2-methyl-pyrrolidino)-β'-p-tolyloxy-isopropyl ester] 
• 112375-80-1 phenoxy-acetic acid-[β-(4-bromo-phenoxy)-β'-(2-methyl-pyrrolidino)-isopropyl ester] 
• 102955-54-4 phenoxy-acetic acid-(2,2-dimethyl-1-phenyl-3-piperidino-propylester); hydrochloride 
• 102946-91-8 phenoxy-acetic acid-(1-ethyl-2,2-dimethyl-1-phenyl-3-piperidino-propylester); hydrochloride 
• 102706-69-4 (+/-)-phenoxyacetic acid-(4-ethyl-1-but-2t-enyl-2t,5c-dimethyl-[4r]piperidyl ester) 
• 19513-78-1 1-(4-methoxy-phenyl)-2-phenoxy-ethanone 
• 107855-45-8 phenoxyketene 
• 19054-87-6 1-(2,4-dimethyl-phenyl)-2-phenoxy-ethanone 
• 74717-60-5 N^α-Phenoxyacetyl-L-tryptophan 

Relevant articles and documents

Novel 4-(3-phenylpropionamido), 4-(2-phenoxyacetamido) and 4-(cinnamamido) substituted benzamides bearing the pyrazole or indazole nucleus: synthesis, biological evaluation and mechanism of action

Based on some common structural features of known compounds interfering with p53 pathways and our previously synthesized benzamides, we synthesized new ethyl 5-(4-substituted benzamido)-1-phenyl-1H-pyrazole-4-carboxylates 26a-c, ethyl 5-(4-substituted benzamido)-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylates 27a-c and N-(1H-indazol-6-yl)-4-substituted benzamides 31a,b bearing in the 4 position of the benzamido moiety the 2-phenylpropanamido or 2-phenoxyacetamido or cinnamamido groups. A preliminary test to evaluate the antiproliferative activity against human lung carcinoma H292 cells highlighted how compound 26c showed the best activity. This last was therefore selected for further studies with the aim to find the mechanism of action. Compound 26c induces intrinsic apoptotic pathway by activating p53 and is also able to activate TRAIL-inducing death pathway by promoting increase of DR4 and DR5 death receptors, downregulation of c-FLIPL and caspase-8 activation.

Synthesis of N-trifluoromethyl amides from carboxylic acids

Found in biomolecules, pharmaceuticals, and agrochemicals, amide-containing molecules are ubiquitous in nature, and their derivatization represents a significant methodological goal in fluorine chemistry. Trifluoromethyl amides have emerged as important functional groups frequently found in pharmaceutical compounds. To date, there is no strategy for synthesizing N-trifluoromethyl amides from abundant organic carboxylic acid derivatives, which are ideal starting materials in amide synthesis. Here, we report the synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature. Through this strategy, isothiocyanates are desulfurized with AgF, and then the formed derivative is acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method shows broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners, and should find application in the modification of advanced intermediates.

Toward Soluble 5,10-Diheterotruxenes: Synthesis and Reactivity of 5,10-Dioxatruxenes, 5,10-Dithiatruxenes, and 5,10-Diazatruxenes

The following work presents three general approaches allowing, for the first time, the synthesis of 5,10-diheterotruxene derivatives containing two identical heteroatoms, namely, oxygen OOC, nitrogen NNC, or sulfur SSC. Two of described pathways involve the photocyclization of the corresponding triene 2 as a key step leading to a heptacyclic aromatic system. The third approach is based on the acidic condensation between ninhydrin 14 and benzo[b]heteroole 15. Typical functionalizations of the 5,10-diheterotruxene core have also been presented. In addition, the article discusses the advantages and limitations of the three suggested paths for receiving specific 5,10-diheterotruxene derivatives because the universal method suitable for obtaining molecules with any type of heteroatoms is not known so far.