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

• ChemBase ID: 103058
• Molecular Formular: C6H8ClN2O5P
• Molecular Mass: 254.564881
• Monoisotopic Mass: 253.98593568
• SMILES: ClP(=O)(N1CCOC1=O)N1CCOC1=O
• Canonical SMILES: O=C1OCCN1P(=O)(N1CCOC1=O)Cl
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(2-oxo-1,3-oxazolidin-3-yl)phosphinoyl chloride
• IUPAC Traditional name: bis(2-oxo-1,3-oxazolidin-3-yl)phosphinoyl chloride
• Synonyms: Bis(2-oxo-3-oxazolidinyl)phosphinic chloride; BOP-Cl; Bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Phosphoric acid bis(2-oxooxazolidide) chloride; N,N-bis-(2-OXO-3-OXAZOLIDINYL)-PHOSPHORODIAMIDIC CHLORIDE; 双(2-氧代-3-噁唑烷基)次磷酰氯; 双(2-氧代'-3-噁唑烷基)次磷酰氯

Database IDs

• CAS Number: 68641-49-6
• MDL Number: MFCD00010077
• Beilstein Number: 3654596
• PubChem SID: 24849128; 162090262; 24856419
• PubChem CID: 152842

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.084358275
• LogD (pH = 7.4): -0.084358275
• Log P: -0.084358275
• Molar Refractivity: 49.5288 cm^3
• Polarizability: 19.79999 Å^3
• Polar Surface Area: 76.15 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 191 °C (dec.)(lit.); ca 195°C dec.

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: SZ5871000
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

Product Information

• Purity: ≥97.0% (AT); 97%
• Empirical Formula (Hill Notation): C6H8ClN2O5P

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

Sigma Aldrich - 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

REFERENCES

• 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.
• 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).
• The mixed anhydride formed with carboxylic acids adds to imines to give ?-lactams: Synthesis, 63 (1982):
  
• These are also formed in high yield by cyclization of ?-amino acids: Bull. Korean Chem. Soc., 12, 457 (1991).