CAS 68641-49-6|BOP-Cl|双(2-氧代'-3-噁唑烷基)次磷酰氯|Bis(2-oxo-3-oxazolidinyl)phosphinic chloride|bis(2-oxo-1,3-oxazolidin-3-yl)phosphinoyl chloride|bis(2-oxo-1,3-oxazolidin-3-yl)phosphinoyl chlorid...

General Information

Structure

Molecular Formula

C₆H₈ClN₂O₅P

Molecular Mass

254.564881

Exact Mass

253.98593568

Charge

InChI

InChI=1S/C6H8ClN2O5P/c7-15(12,8-1-3-13-5(8)10)9-2-4-14-6(9)11/h1-4H2

InChIKey

KLDLRDSRCMJKGM-UHFFFAOYSA-N

Canonic Smiles

O=C1OCCN1P(=O)(N1CCOC1=O)Cl

Isomeric Smiles

ClP(=O)(N1CCOC1=O)N1CCOC1=O

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-0.084358275

LogD (pH = 7.4)

-0.084358275

Log P

-0.084358275

Molar Refractivity

49.5288

Polarizability

19.79999

Polar Surface Area

76.15

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

BOP-Cl双(2-氧代'-3-噁唑烷基)次磷酰氯Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideN,N-bis-(2-OXO-3-OXAZOLIDINYL)-PHOSPHORODIAMIDIC CHLORIDEBis(2-oxo-3-oxazolidinyl)phosphinic chloridePhosphoric acid bis(2-oxooxazolidide) chloride双(2-氧代-3-噁唑烷基)次磷酰氯

IUPAC Traditional name

bis(2-oxo-1,3-oxazolidin-3-yl)phosphinoyl chloride

IUPAC name

bis(2-oxo-1,3-oxazolidin-3-yl)phosphinoyl chloride

Names and Identifiers

Registration numbers

CAS Number

68641-49-6

Beilstein Number

3654596

MDL Number

MFCD00010077

PubChem SID

2485641916209026224849128

PubChem CID

152842

Registration numbers

Properties

Product Information

Certificate of Analysis

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Purity

97%

≥97.0% (AT)

Empirical Formula (Hill Notation)

C6H8ClN2O5P

Physical Property

Melting Point

191 °C (dec.)(lit.)

ca 195°C dec.

Properties

Related Proteins

No Data Available

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Molecular Spectra

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Molecule Details

MP Biomedicals

02150475

Peptide coupling reagent.

Sigma Aldrich

270962

Application
Reagent for activating carboxyl groups and coupling peptides.
Packaging
5 g in glass bottle

15140

Other Notes
Reagent for activating the carboxylic group, synthesis of amides 1,2; Esters 3; Peptides 4
Packaging
5, 25 g in glass bottle

Molecule Details

References

PubChem Literature

From Data Sources

• Diago-Meseguer, J., et al., Synthesis, 547 (1980).

• Coupling reagent for which the rates of reaction with various nucleophiles are sufficiently different to permit a genuine "one-step" coupling of carboxylic acids with amines: Synthesis, 547 (1980). Particularly suitable for coupling N-alkyl amino acids: J. Org. Chem., 51, 3350 (1986). For discussion of strategies for one-step coupling in synthesis of amides, see: Synthesis, 413 (1984), and of the scope and limitations of the reagent in peptide coupling, see: Int. J. Pept. Prot. Res., 29, 574 (1987); J. Org. Chem., 55, 2895 (1990). See also Appendix 6.

• The mixed anhydride formed with carboxylic acids adds to imines to give ?-lactams: Synthesis, 63 (1982):

• For use in the direct selective 5'-acylation of nucleosides by carboxylic acids, (without 3'-protection), see: Tetrahedron, 44, 229 (1988). For high yield dehydration of carboxylic acids to anhydrides, see: Synthesis, 616 (1981). Also used in macrolide cyclization: J. Am. Chem. Soc., 104, 6818 (1982), and in formation of acyclic esters: Synth. Commun., 14, 515 (1984).

• These are also formed in high yield by cyclization of ?-amino acids: Bull. Korean Chem. Soc., 12, 457 (1991).

References

Bioactivity

PubChem BioAssay

Bioactivity