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1499-17-8

1499-17-8 Structure

1499-17-8 Structure
IdentificationBack Directory
[Name]

1,2-PHENYLENE PHOSPHOROCHLORIDATE
[CAS]

1499-17-8
[Synonyms]

o-Phenylene chlorophosphate
1,2-PHENYLENE CHLOROPHOSPHATE
o-Phenylenephosphorochloridate
1,2-PHENYLENE PHOSPHOROCHLORIDATE
Catechol cyclophosphorochloridate
O,O-(o-Phenylene) chlorophosphate
2-Chloro-2-oxo-1,3,2-benzodioxaphosphole
3,2-benzodioxaphosphole,2-chloro-2-oxide
1,2-PHENYLENE PHOSPHOROCHLORIDATE, TECH.
2-Chloro-1,3-dioxa-2-phosphaindan 2-oxide
2-CHLORO-1,3,2-BENZODIOXAPHOSPHOLE 2-OXIDE
1,3,2-Benzodioxaphosphole, 2-chloro-, 2-oxide
2-Chlorobenzo[d][1,3,2]dioxaphosphole 2-oxide
o-Phenylene phosphorochloridate technical grade
8-chloro-7,9-dioxa-8$l^{5}-phosphabicyclo[4.3.0]nona-1,3,5-triene 8-oxide
2-Chloro-1,3,2-benzodioxaphosphole 2-oxide, o-Phenylene chlorophosphate
[EINECS(EC#)]

216-106-7
[Molecular Formula]

C6H4ClO3P
[MDL Number]

MFCD00005854
[MOL File]

1499-17-8.mol
[Molecular Weight]

190.52
Chemical PropertiesBack Directory
[Melting point ]

56-62 °C
[Boiling point ]

120 °C9 mm Hg(lit.)
[density ]

1.57±0.1 g/cm3(Predicted)
[storage temp. ]

2-8°C
[form ]

solid
[BRN ]

142368
[EPA Substance Registry System]

1,3,2-Benzodioxaphosphole, 2-chloro-, 2-oxide (1499-17-8)
Safety DataBack Directory
[Hazard Codes ]

C
[Risk Statements ]

14-34
[Safety Statements ]

26-36/37/39-45
[RIDADR ]

UN 3261 8/PG 2
[WGK Germany ]

3
[F ]

10
[HazardClass ]

8
[PackingGroup ]

III
Hazard InformationBack Directory
[Uses]

Reactant for preparation of:
  • Uridine diphosphate-glucose derivatives as potential chain terminators of β-glucan biosynthesis with antifungal activity
  • Vinyloxy phosphorus monomers

  • Phosphorylation agent
[Application]

1,2-Phenylene phosphorochloridate can be used for the phosphorylation of alcohols; peptide synthesis, β-lactam synthesis.
[Preparation]

1,2-Phenylene phosphorochloridate is prepared by heating 2,2,2-trichloro-1,3,2-benzodioxaphosphole with a slight excess of  acetic anhydride.
[reaction suitability]

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
[Purification Methods]

After distilling it in a vacuum, it sets to a colourless solid. It is soluble in pet ether, *benzene and slightly soluble in Et2O. [Khwaja et al. J Chem Soc (C) 2092 1970, Anschütz & Broeker Justus Liebigs Ann Chem 454 109 1927, Beilstein 6 IV 5602.]
Spectrum DetailBack Directory
[Spectrum Detail]

1,2-PHENYLENE PHOSPHOROCHLORIDATE(1499-17-8)1HNMR
1,2-PHENYLENE PHOSPHOROCHLORIDATE(1499-17-8)13CNMR
1,2-PHENYLENE PHOSPHOROCHLORIDATE(1499-17-8)IR1
1,2-PHENYLENE PHOSPHOROCHLORIDATE(1499-17-8)IR2
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