Phenoxyacetic anhydride

CAS

14316-61-1

Catalog Number

ACM14316611

Category

Main Products

Molecular Weight

286.28

Molecular Formula

C₁₆H₁₄O₅

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Specification

Synonyms

PHENOXYACETIC ANHYDRIDE;Bis(phenoxyacetic)anhydride;2-Phenoxyacetic anhydride

IUPAC Name

(2-phenoxyacetyl)2-phenoxyacetate

Canonical SMILES

C1=CC=C(C=C1)OCC(=O)OC(=O)COC2=CC=CC=C2

InChI Key

CCSBNBKMACZDGN-UHFFFAOYSA-N

Boiling Point

427.8ºC at 760mmHg

Melting Point

70-74°C

Flash Point

190ºC

Density

1.234g/cm³

Exact Mass

286.08400

Hazard Statements

Safety Description

26-36

Supplemental Hazard Statements

H315-H319-H335

Symbol

GHS07

Side Reactions of Phenoxyacetic Anhydride in the Synthesis of cmG-Incorporated ODNs

Sasami, Takeshi, et al. Bioorganic & medicinal chemistry, 2009, 17(3), 1398-1403.

A protocol for the synthesis of 2-N-carbamoylguanine (cmG)-incorporated oligodeoxynucleotides (ODNs) is reported. The 6-O-unprotected 2-N-carbamoyldeoxyguanosine 3'-phosphoramidite derivatives were synthesized from 2'-deoxyguanosine in only three separate steps. However, the 6-O-unprotected cmG residue was found to react with the phenoxyacetic anhydride used in the capping reaction. Here, the use of the 6-O-protected phosphoramidite derivative could inhibit the reaction with phenoxyacetic anhydride, while more chemical steps are required.
· Synthesis of ODN using phosphoramidite 2
We successfully synthesized ODN1, 5'-d(TACTA[cmG]CTCAT)-3', by employing 2-N-carbamoyl guanine phosphoramidite (2) on an automated DNA synthesizer. The chain elongation process included the following steps: (i) detritylation, (ii) coupling, (iii) capping with phenoxyacetic anhydride (Pac2O), and (iv) iodine oxidation. After completing the final chain elongation, the ODN, which retained the terminal DMTr group, was released from the solid support by treatment with aqueous ammonia, and the base- and phosphate-protecting groups were also removed in this solution.
· Side reaction of the 2-N-carbmoyl guanine moiety resulting from acylated regents
Next, the reactivity of Pac2O with the carbamoyl group was explored at the nucleoside level. The 3',5'-O-disilylated 2-N-carbamoyl guanine derivative 6 was subjected to treatment with 4.0 equivalents of phenoxyacetic anhydride in pyridine.

Phenoxyacetic Anhydride for End-Capping in Oligonucleotide Synthesis

Vrantza, Despoina, et al. Helvetica chimica acta, 2006, 89(10), 2371-2386.

They designed and characterised two new photolabile natural nucleosides: 6-[(1-oxidopyridin-2-yl)sulfanyl]- (1a) and 6-[(pyridin-2-yl)sulfanyl]-2',6-dideoxyguanosine (2a). End-capping in the solid phase oligonucleotide synthesis was accomplished by phenoxyacetic anhydride ((Pac)2O).
Solid-Phase Synthesis of Oligonucleotides
· Oligonucleotides of 3-, 5-, 9- and 15-mers were synthesized to 1-mmol scale using phosphoramidite chemistry in an automated nucleic acid synthesis machine. Because the modifying nucleosides are very unstable in alkaline deprotection, an amino functional of the nucleobases was replaced by a Pac-protection system.
· Following standard protocols, the synthesis was performed on controlled-pore-glass (CPG) support, with three key modifications: First, the coupling time for the modified nucleoside phosphoramidite was increased to 5 minutes, as opposed to the usual 30 seconds for regular nucleosides. Furthermore, a phenoxyacetic anhydride ((Pac)2O) solution in THF was utilized for the capping step to avoid potential transacylation reactions. The oxidation step followed, using a 20-mM iodine (I2) solution to mitigate any oxidative degradation of the modified nucleosides during solid-phase assembly.
· After the synthesis was completed, the base-labile protective groups from the oligodeoxyribonucleotides were removed by treating them with concentrated aqueous ammonia (32%) at room temperature for 4 hours. Solvents were subsequently evaporated under vacuum, and the resulting crude oligomers were purified using reverse-phase HPLC.

What is the molecular formula of Phenoxyacetic anhydride?

The molecular formula of Phenoxyacetic anhydride is C16H14O5.

What are the synonyms of Phenoxyacetic anhydride?

The synonyms of Phenoxyacetic anhydride include 2-Phenoxyacetic anhydride, Acetic acid, phenoxy-, anhydride, (2-phenoxyacetyl) 2-phenoxyacetate, NSC 259934, PHENOXYACETICANHYDRIDE, Phenoxyacetc anhydrde, SCHEMBL264346, 2-phenoxyacetyl 2-phenoxyacetate, DTXSID30312648, MFCD00059681, NSC259934, AKOS016009546, NSC-259934, AS-58486, Phenoxyacetic anhydride, >=97.0% (T), CS-0020049, FT-0742969, P0111, D91899, A855328, J-007754, J-523929.

What is the CAS number of Phenoxyacetic anhydride?

The CAS number of Phenoxyacetic anhydride is 14316-61-1.

What is the IUPAC Name of Phenoxyacetic anhydride?

The IUPAC Name of Phenoxyacetic anhydride is (2-phenoxyacetyl) 2-phenoxyacetate.

What is the InChI of Phenoxyacetic anhydride?

The InChI of Phenoxyacetic anhydride is InChI=1S/C16H14O5/c17-15(11-19-13-7-3-1-4-8-13)21-16(18)12-20-14-9-5-2-6-10-14/h1-10H,11-12H2.

What is the InChIKey of Phenoxyacetic anhydride?

The InChIKey of Phenoxyacetic anhydride is CCSBNBKMACZDGN-UHFFFAOYSA-N.

What is the molecular weight of Phenoxyacetic anhydride?

The molecular weight of Phenoxyacetic anhydride is 286.28g/mol.

How many hydrogen bond donor counts does Phenoxyacetic anhydride have?

Phenoxyacetic anhydride has 0 hydrogen bond donor counts.