Tri(dimethylamino)benzotriazol-1-yloxyphosphonium hexafluorophosphate

Base Information

• Chemical Name: Tri(dimethylamino)benzotriazol-1-yloxyphosphonium hexafluorophosphate
• CAS No.: 56602-33-6
• Molecular Formula: C12H22N6OP^.PF6
• Molecular Weight: 442.284
• Hs Code.: 29339980
• European Community (EC) Number: 260-279-1
• NSC Number: 367086
• DSSTox Substance ID: DTXSID60205170
• Wikipedia: BOP_reagent
• Wikidata: Q4385302
• Mol file: 56602-33-6.mol

Synonyms:benzotriazol-1-yloxy-tris(dimethylamino)phosphonium;benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate;benzotriazol-1-yloxy-tris(dimethylamino)phosphonium tetrafluoroborate;BOP reagent;BTZO-TDMAP

Chemical Property of Tri(dimethylamino)benzotriazol-1-yloxyphosphonium hexafluorophosphate

Chemical Property:

• Appearance/Colour: white to off-white powder
• Melting Point: >130 °C (dec.)(lit.)
• Flash Point: 138 °C
• PSA: 76.84000
• LogP: 4.60470
• Storage Temp.: 2-8°C
• Sensitive.: Moisture & Light Sensitive
• Solubility.: methanol: 25 mg/mL, clear
• Water Solubility.: Soluble in methanol, acetone and dichloromethane. Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 5
• Exact Mass: 442.12345231
• Heavy Atom Count: 27
• Complexity: 368

Purity/Quality:

99% ^*data from raw suppliers

(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,E,F
• Statements: 37/38-44-36/37/38-11-2
• Safety Statements: 24/25-37/39-36-26-35-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
• Uses: Peptide coupling reagent which suppresses racemization. 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate is 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. 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate is used as a reagent for peptide coupling, lactonization, selective esterification, amidation of alfa amino acids without racemization and synthesis of magnolamide for antioxidative activity and catalyst for 9-acridinecaroboxamide derivative. It is also used as a precursor for the synthesis of phenyl esters of amino acids. It acts as a substitute for (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) reagent.

Technology Process of Tri(dimethylamino)benzotriazol-1-yloxyphosphonium hexafluorophosphate

There total 3 articles about Tri(dimethylamino)benzotriazol-1-yloxyphosphonium hexafluorophosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N,N,N,N,N,N-hexamethylphosphoric triamide (680-31-9) → (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (56602-33-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / potassium hexafluorophosphate; oxalyl chloride; DMF / acetonitrile / 4 h / 0 - 20 °C

2: TEA / acetone / 1 h

With potassium hexafluorophosphate; oxalyl dichloride; TEA; N,N-dimethyl-formamide; In acetone; acetonitrile;

DOI:10.1080/10426500307942

Reference yield:

benzotriazol-1-ol (2592-95-2) + chlorotris(dimethylamino)phosphonium hexafluorophosphate → (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (56602-33-6)

Guidance literature:

With TEA; In acetone; for 1h;

DOI:10.1080/10426500307942

Reference yield:

→ (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (56602-33-6)

Guidance literature:

upstream raw materials:

benzotriazol-1-ol

N,N,N,N,N,N-hexamethylphosphoric triamide

Downstream raw materials:

(S)-2-[(5S,6S)-6-((1E,5E)-(3S,4R)-4-Hydroxy-1,3,5-trimethyl-hepta-1,5-dienyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl]-2-(4-methoxy-benzyloxy)-butyric acid benzotriazol-1-yl ester

N,N,N,N,N,N-hexamethylphosphoric triamide

1-(4-nitro-benzoyloxy)-1H-benzotriazole

N-[2-[[(1S,2R)-2-[(4-Chlorobenzoyl)amino]cyclopentyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide

Refernces

• 1、 -. "Novel spiro compounds". . . Retrieved 2008/06/13.