Thermo Scientific Chemicals

Phenoxyacetyl chloride, 98%, Thermo Scientific Chemicals

Catalog number: A13761.30
250 g, Each
Thermo Scientific Chemicals

Phenoxyacetyl chloride, 98%, Thermo Scientific Chemicals

Catalog number: A13761.30
250 g, Each
Quantity
Catalog number: A13761.30
also known as A13761-30
Price (EUR)
Quantity
-

Chemical Identifiers

CAS
701-99-5
IUPAC Name
2-phenoxyacetyl chloride
Molecular Formula
C8H7ClO2
InChI Key
PKUPAJQAJXVUEK-UHFFFAOYSA-N
SMILES
ClC(=O)COC1=CC=CC=C1
Assay (Titration ex Chloride)
≥97.5%
Refractive Index
1.5320-1.5360 @ 20?C
Form
Liquid
Identification (FTIR)
Conforms
Appearance (Color)
Clear colorless to yellow to brown

Description

Acylation of D- and DL-WV with phenoxyacetyl chloride, followed by cleavage of the t-butyl ester,afforded the penultimate penicilloic acids. Phenoxyacetyl chloride was used in the synthesis of series of macrocyclic bis-β-lactams, 5-phenyl-6-epiphenoxymethylpenicillin benzyl ester, N-protected guanosine derivatives, useful in RNA synthesis, phenyloxyketene, for cycloaddition to imines leading to β-lactams. Treatment of iminophosphoranes with phenoxyacetyl chloride afforded respectively the trans- and cis-3-(acylamino)-p-lactams. By the oxidative addition of stannous fluoride to allyliodide, with 1, 2-O-isopropylidene-D-glyceraldehyde and phenoxyacetyl chloride results in the predominant formation of erythro homoallylester, which is in turn converted into 2-deoxy-D-ribose. The 4-disubstituted P-lactams (4a-c and 6a-b) were prepared through the reaction of N,N-diphenylhydrazones and N-methyl-N-phenylhydrazones of ketones with phenoxyacetyl chloride/Et3N in dichloromethane.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Acylation of D- and DL-WV with phenoxyacetyl chloride, followed by cleavage of the t-butyl ester,afforded the penultimate penicilloic acids. Phenoxyacetyl chloride was used in the synthesis of series of macrocyclic bis-β-lactams, 5-phenyl-6-epiphenoxymethylpenicillin benzyl ester, N-protected guanosine derivatives, useful in RNA synthesis, phenyloxyketene, for cycloaddition to imines leading to β-lactams. Treatment of iminophosphoranes with phenoxyacetyl chloride afforded respectively the trans- and cis-3-(acylamino)-p-lactams. By the oxidative addition of stannous fluoride to allyliodide, with 1, 2-O-isopropylidene-D-glyceraldehyde and phenoxyacetyl chloride results in the predominant formation of erythro homoallylester, which is in turn converted into 2-deoxy-D-ribose. The 4-disubstituted P-lactams (4a-c and 6a-b) were prepared through the reaction of N,N-diphenylhydrazones and N-methyl-N-phenylhydrazones of ketones with phenoxyacetyl chloride/Et3N in dichloromethane.

Notes
Moisture Sensitive. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents, moisture.
RUO – Research Use Only

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    Safety and Handling


    Classification of the substance or mixture
    CLP classification - Regulation(EC) No 1272/2008
    Skin Corrosion/Irritation
    Category 1
    Serious Eye Damage/Eye Irritation
    Category 1
    Specific target organ toxicity - (single exposure)
    Category 3
    Label Elements
    Signal Word

    Danger

    Hazard Statements

    H314 - Causes severe skin burns and eye damage

    H335 - May cause respiratory irritation

    EU Specific Hazard Statements

    EUH014 - Reacts violently with water

    Precautionary Statements

    P280 - Wear protective gloves/protective clothing/eye protection/face protection

    P301 + P330 + P331 - IF SWALLOWED: Rinse mouth. Do NOT induce vomiting

    P303 + P361 + P353 - IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water or shower

    P304 + P340 - IF INHALED: Remove person to fresh air and keep comfortable for breathing

    P305 + P351 + P338 - IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing

    P310 - Immediately call a POISON CENTER or doctor/physician