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Thermo Scientific Chemicals
Phenyl chloroformate, 99%
CAS: 1885-14-9 | C7H5ClO2 | 156.57 g/mol
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Catalog number A12618.30
also known as A12618-30
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Quantity:
250 g
Price (USD)
75.65
Online Exclusive
84.20Save 8.55 (10%)
Each
Chemical Identifiers
CAS1885-14-9
IUPAC Namephenyl carbonochloridate
Molecular FormulaC7H5ClO2
InChI KeyAHWALFGBDFAJAI-UHFFFAOYSA-N
SMILESClC(=O)OC1=CC=CC=C1
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Specifications
Specification Sheet
Specification SheetAppearance (Color)Clear colorless
FormLiquid
Assay (GC)≥98.5% (UK-sourced material)
Assay from Supplier's CofA≥98.5% (US-sourced material)
CommentMaterial sourced in UK and US
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Phenyl chloroformate is used in the synthesis of poly(2-(phenoxycarbonyloxy)ethyl methacrylate) and phenyl-(4-vinylphenyl) carbonate. It acts as a precursor of phenyl mixed anhydrides which are used in peptide coupling reactions. It serves as a dehydrating reagent for the conversion of primary amides to nitriles and an intermediate in the synthesis of pharmaceuticals and carbamates.
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
Phenyl chloroformate is used in the synthesis of poly(2-(phenoxycarbonyloxy)ethyl methacrylate) and phenyl-(4-vinylphenyl) carbonate. It acts as a precursor of phenyl mixed anhydrides which are used in peptide coupling reactions. It serves as a dehydrating reagent for the conversion of primary amides to nitriles and an intermediate in the synthesis of pharmaceuticals and carbamates.
Solubility
Miscible with N,N-dimethylformamide.
Notes
Store in cool place. Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with bases, alcohols and amines. Hydrolyses in water.
Phenyl chloroformate is used in the synthesis of poly(2-(phenoxycarbonyloxy)ethyl methacrylate) and phenyl-(4-vinylphenyl) carbonate. It acts as a precursor of phenyl mixed anhydrides which are used in peptide coupling reactions. It serves as a dehydrating reagent for the conversion of primary amides to nitriles and an intermediate in the synthesis of pharmaceuticals and carbamates.
Solubility
Miscible with N,N-dimethylformamide.
Notes
Store in cool place. Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with bases, alcohols and amines. Hydrolyses in water.
RUO – Research Use Only
General References:
- Precursor of phenyl mixed anhydrides, which can be used, e.g. in peptide coupling reactions.
- Also used in the cleavage of tertiary amines: J. Chem. Soc. (C), 2015 (1967); cf Ethyl chloroformate, L06311, and 1-Chloroethyl chloroformate, L14197. Review: Synthesis, 1 (1989).
- Reagent for dehydration of primary amides to nitriles under mild conditions: Indian J. Chem., 40B, 722 (2001).
- Wieting, J. M.; Fisher, T. J.; Schafer, A. G.; Visco, M. D.; Gallucci, J. C.; Mattson, A. E. Preparation and Catalytic Activity of BINOL-Derived Silanediols. Eur. J. Org. Chem. 2015, 2015 (3), 525-533.
- Kevill, D. N.; Ryu, Z. H. Correlation of the rates of solvolysis of 2, 1-benzoxathiol-3-one-1, 1-dioxide (2-sulfobenzoic acid cyclic anhydride). J. Chem. Res. 2015, 39 (10), 561-566.