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

• ChemBase编号: 94885
• 分子式: C12H22F6N6OP2
• 平均质量: 442.2806212
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-$l^{5}-phosphanuide; (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-λ^5-phosphanuide
• IUPAC传统名: (1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-$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
• 别名: 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; 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

登记号

• CAS号: 56602-33-6; 55750-63-5
• EC号: 260-279-1
• MDL号: MFCD00011948
• Beilstein号: 4287025
• PubChem SID: 24853542; 162081539
• PubChem CID: 151348
• Chemspider ID: 133386
• 维基百科标题: BOP_reagent

理论计算性质

• 质子受体: 6
• 质子供体: 0
• LogD (pH = 5.5): -0.6060943
• LogD (pH = 7.4): -0.6060938
• Log P: -0.6060938
• 摩尔折射率: 92.123 cm^3
• 极化性: 33.17002 Å^3
• 极化表面积: 49.66 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Acetone; Dichloromethane; Partially soluble in cold water
• 外观: White crystalline powder; White Solid
• 熔点: >130 °C (dec.)(lit.); 131-133°C dec.; 136 - 140 °C; 138(dec.)°C; ca 138°C dec.

安全信息

• 保存条件: 0°C, Store Under Nitrogen, Protect from light; 2-8°C; Refrigerator
• 保存注意事项: Irritant; Moisture & Light Sensitive
• 欧盟危险性物质标志: 爆炸性(Explosive) (E); 易燃性(Flammable) (F); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 1325; UN1325
• 德国WGK号: 3
• 联合国危险货物等级: 4.1
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 11-36/37/38-44; 11-37/38-44; 2-11-37/38-44
• 安全公开号: 26-37-60; 35
• TSCA收录: 否
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Danger
• GHS危险声明: H228-H315-H319-H335; H228-H315-H335
• GHS警示性声明: P210-P241-P305+P351+P338-P302+P352-P405-P501A; P210-P261
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 1325 4.1/PG 2
• 欧盟补充危害声明: Risk of explosion if heated under confinement.
• 保存温度: -20°C; 2-8°C

产品相关信息

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

详细说明

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

包装
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.

参考文献

• 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).