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

• ChemBase ID: 94885
• Molecular Formular: C12H22F6N6OP2
• Molecular Mass: 442.2806212
• Monoisotopic Mass: 442.12345193
• SMILES: [P-](F)(F)(F)(F)(F)F.n1(c2ccccc2nn1)O[P+](N(C)C)(N(C)C)N(C)C
• Canonical SMILES: F[P-](F)(F)(F)(F)F.CN([P+](N(C)C)(N(C)C)On1nnc2c1cccc2)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-$l^{5}-phosphanuide; (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-λ^5-phosphanuide
• IUPAC Traditional name: (1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-$l^{5}-phosphanuide; (1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-λ^5-phosphanuide; (1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium hexafluorophosphate
• Synonyms: BOP; Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate; Castro's reagent; BOP reagent; 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate; BOP-Reagent; Castros reagent; BENZOTRIAZOL-1-YLOXY-TRIS-(DIMETHYLAMINO)-PHOSPHONIUM HEXAFLUOROPHOSPHATE; EMCS; N-Succinimidyl 6-maleimidocaproate; 6-Maleimidocaproic acid N-succinimidyl ester; N-(ε-MALEIMIDOCAPROYL-OXY)SUCCINIMIDE; BOP Reagent; (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1H-苯并三唑-1-基氧代三(二甲氨基)磷鎓 六氟磷酸盐; BOP 试剂; 卡特缩合剂; 苯并三氮唑-1-基氧基三(二甲氨基)磷鎓六氟磷酸盐

Database IDs

• CAS Number: 56602-33-6; 55750-63-5
• EC Number: 260-279-1
• MDL Number: MFCD00011948
• Beilstein Number: 4287025
• PubChem SID: 24853542; 162081539
• PubChem CID: 151348
• Chemspider ID: 133386
• Wikipedia Title: BOP_reagent

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.6060943
• LogD (pH = 7.4): -0.6060938
• Log P: -0.6060938
• Molar Refractivity: 92.123 cm^3
• Polarizability: 33.17002 Å^3
• Polar Surface Area: 49.66 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Partially soluble in cold water
• Apperance: White crystalline powder; White Solid
• Melting Point: >130 °C (dec.)(lit.); 131-133°C dec.; 136 - 140 °C; 138(dec.)°C; ca 138°C dec.

Safety Information

• Storage Condition: 0°C, Store Under Nitrogen, Protect from light; 2-8°C; Refrigerator
• Storage Warning: Irritant; Moisture & Light Sensitive
• European Hazard Symbols: Explosive (E); Flammable (F); Irritant (Xi)
• UN Number: 1325; UN1325
• German water hazard class: 3
• Hazard Class: 4.1
• Packing Group: 2; II
• Risk Statements: 11-36/37/38-44; 11-37/38-44; 2-11-37/38-44
• Safety Statements: 26-37-60; 35
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H228-H315-H319-H335; H228-H315-H335
• GHS Precautionary statements: P210-P241-P305+P351+P338-P302+P352-P405-P501A; P210-P261
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 1325 4.1/PG 2
• Supplemental Hazard Statements: Risk of explosion if heated under confinement.
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C12H22F6N6OP2

DETAILS

MP Biomedicals - 02150441

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

MP Biomedicals - 02151585

A heterobifunctional reagent for enzyme immunoassay.

Apollo Scientific Ltd - PC2519

Peptide coupling reagent.

Sigma Aldrich - B2886

Application
Activating reagent for synthesis of peptides and amino acid derivatives

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

Toronto Research Chemicals - 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.

REFERENCES

• Z.J. Cabanthik, et al., J. Membrane Biol., 10: 311, (1972). 15: 207, (1974).
• A. Rothstein, et al., Biochem. Biophys
• Kenner, G.W., Seely, J., J. Am. Chem. Soc., 94, 3259 (1972)
• Castro, B., et al.: Tetrahedron Lett., 1219 (1975)
• Reagent for high yield, low racemization peptide coupling: Tetrahedron Lett., 1219 (1975). See Appendix 6.
• 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).
• 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).
• 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).