CAS 56602-33-6|CAS 55750-63-5|(1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-$l^{5}-phosphanuide|BOP|Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate...

General Information

Structure

Molecular Formula

C₁₂H₂₂F₆N₆OP₂

Molecular Mass

442.2806212

Exact Mass

442.12345193

Charge

InChI

InChI=1S/C12H22N6OP.F6P/c1-15(2)20(16(3)4,17(5)6)19-18-12-10-8-7-9-11(12)13-14-18;1-7(2,3,4,5)6/h7-10H,1-6H3;/q+1;-1

InChIKey

MGEVGECQZUIPSV-UHFFFAOYSA-N

Canonic Smiles

F[P-](F)(F)(F)(F)F.CN([P+](N(C)C)(N(C)C)On1nnc2c1cccc2)C

Isomeric Smiles

[P-](F)(F)(F)(F)(F)F.n1(c2ccccc2nn1)O[P+](N(C)C)(N(C)C)N(C)C

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-0.6060943

LogD (pH = 7.4)

-0.6060938

Log P

-0.6060938

Molar Refractivity

92.123

Polarizability

33.17002

Polar Surface Area

49.66

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

(1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-$l^{5}-phosphanuide (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-λ⁵-phosphanuide

Synonyms

BOPBenzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphateCastros reagentBENZOTRIAZOL-1-YLOXY-TRIS-(DIMETHYLAMINO)-PHOSPHONIUM HEXAFLUOROPHOSPHATEEMCSN-Succinimidyl 6-maleimidocaproateBOP-ReagentBOP reagentN-(ε-MALEIMIDOCAPROYL-OXY)SUCCINIMIDE6-Maleimidocaproic acid N-succinimidyl esterCastro's reagent苯并三氮唑-1-基氧基三(二甲氨基)磷鎓六氟磷酸盐BOP Reagent卡特缩合剂(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphateBOP 试剂(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate1H-苯并三唑-1-基氧代三(二甲氨基)磷鎓六氟磷酸盐

IUPAC Traditional name

(1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-$l^{5}-phosphanuide (1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-λ⁵-phosphanuide (1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium hexafluorophosphate

Names and Identifiers

Registration numbers

CAS Number

PubChem CID

Chemspider ID

Wikipedia Title

MDL Number

Beilstein Number

EC Number

PubChem SID

Registration numbers

Properties

Related Proteins

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Molecular Spectra

No Data Available

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Molecule Details

Apollo Scientific

PC2519

Peptide coupling reagent.

MP Biomedicals

02151585

A heterobifunctional reagent for enzyme immunoassay.

02150441

Peptide coupling agent. Also used to prepare amino acid phenyl esters.

Wikipedia

BOP_reagent

Sigma Aldrich

226084

Packaging
1, 5 g in glass bottle
Application
Reagent for: Peptide coupling1 Synthesis of esters2 Esterification of carboxylic acids3,4 Plasmid CAN-encapsulating liposomes5 Synthesis of magnolamide for antioxidative activity6Catalyst for preparation of 9-acridinecaroboxamide derivative7

B2886

Application
Activating reagent for synthesis of peptides and amino acid derivatives

TRC

B207000

A peptide coupling reagent. Can be used in the preparation of phenyl esters of amino acids which have been shown to be valuable as blocked derivatives of amino acids in the field of peptide synthesis.

Molecule Details

References

PubChem Literature

From Data Sources

• Z.J. Cabanthik, et al., J. Membrane Biol., 10: 311, (1972). 15: 207, (1974).

• A. Rothstein, et al., Biochem. Biophys

• Castro, B., et al.: Tetrahedron Lett., 1219 (1975)

• Kenner, G.W., Seely, J., J. Am. Chem. Soc., 94, 3259 (1972)

• Reagent for high yield, low racemization peptide coupling: Tetrahedron Lett., 1219 (1975). See Appendix 6.

• The carboxyphosphonium salts formed by reaction with carboxylic acids can be reduced with NaBH₄, providng a mild method for reduction of acids to alcohols: Tetrahedron lett., 39, 3319 (1998).

• Mild and efficient reagent for the preparation of esters from carboxylic acids and alcohols: Tetrahedron Lett., 36, 4253 (1995); for esterification of amino acids at low temperatures, see: Tetrahedron Lett., 35, 5603 (1994); for use in formation of mixed phosphonate diesters, see: J. Org. Chem., 60, 5214 (1995).

• Promotes the reaction of aliphatic primary amines with CS₂ to give isothiocyanates which can be isolated in high yield or reacted in situ with nucleophiles: J. Chem. Soc., Chem. Commun., 1995 (1995).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

(1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-$l^{5}-phosphanuide (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-λ⁵-phosphanuide

Synonyms

IUPAC Traditional name

Registration numbers

CAS Number

PubChem CID

Chemspider ID

Wikipedia Title

MDL Number

Beilstein Number

EC Number

PubChem SID

Molecule Details

PC2519

Peptide coupling reagent.

MP Biomedicals

02151585

A heterobifunctional reagent for enzyme immunoassay.

02150441

Peptide coupling agent. Also used to prepare amino acid phenyl esters.

Wikipedia

BOP_reagent

Sigma Aldrich

226084

B2886

Application
Activating reagent for synthesis of peptides and amino acid derivatives

TRC

B207000

References

PubChem Literature

From Data Sources

• Z.J. Cabanthik, et al., J. Membrane Biol., 10: 311, (1972). 15: 207, (1974).

• A. Rothstein, et al., Biochem. Biophys

• Castro, B., et al.: Tetrahedron Lett., 1219 (1975)

• Kenner, G.W., Seely, J., J. Am. Chem. Soc., 94, 3259 (1972)

• Reagent for high yield, low racemization peptide coupling: Tetrahedron Lett., 1219 (1975). See Appendix 6.

• The carboxyphosphonium salts formed by reaction with carboxylic acids can be reduced with NaBH₄, providng a mild method for reduction of acids to alcohols: Tetrahedron lett., 39, 3319 (1998).

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:94885