2,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane

Base Information

• Chemical Name: 2,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane
• CAS No.: 120666-13-9
• Molecular Formula: C9H21 N4 P
• Molecular Weight: 216.266
• UNII: LK9MJR52XE
• DSSTox Substance ID: DTXSID90400494
• Nikkaji Number: J631.080J
• Wikipedia: Verkade_base
• Wikidata: Q27283044
• Mol file: 120666-13-9.mol

Synonyms:P(CH(3)NCH(2)CH(2))(3)N;proazaphosphatrane

Chemical Property of 2,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane

Chemical Property:

• Vapor Pressure: 0.01mmHg at 25°C
• Melting Point: 110-115 °C(lit.)
• Boiling Point: 263.9°Cat760mmHg
• PKA: 10.43±0.20(Predicted)
• Flash Point: 113.4°C
• PSA: 26.55000
• Density: g/cm³
• LogP: 0.08950
• Sensitive.: moisture sensitive, store cold
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 216.15038368
• Heavy Atom Count: 14
• Complexity: 168

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane VERKADE SUPERBASE ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CCN2CCN(P1N(CC2)C)C
• Uses: 2,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (CAS# 120666-13-9) is a useful catalyst for the direct α-?arylation of nitriles with aryl chlorides and aryl bromides. It is also used as a catalyst in carbon dioxide reduction to methylamines under metal-free conditions.

Technology Process of 2,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane

There total 9 articles about 2,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane 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: 81.0%

bis(diethylamino)chlorophosphine (685-83-6) + tris[2-(methylamino)ethyl]amine (65604-89-9) → proazaphosphatrane (120666-13-9)

Guidance literature:

With potassium tert-butylate; In acetonitrile; 1) 1h, RT, 2) 1 h, RT;

DOI:10.1016/S0040-4039(00)60476-8

Reference yield: 69.0%

2,8,9-Trimethyl-2,8,9-triaza-5-azonia-1λ5-phospha-tricyclo[3.3.3.01,5]undecane → C9H21(2)HN4P(1+) + proazaphosphatrane (120666-13-9)

Guidance literature:

With potassium tert-butylate; In dimethylsulfoxide-d6; at 20 ℃;

DOI:10.1016/j.tetlet.2011.05.127

Reference yield: 53.0%

2,8,9-Trimethyl-2,8,9-triaza-5-azonia-1λ5-phospha-tricyclo[3.3.3.01,5]undecane; chloride (120710-16-9) → proazaphosphatrane (120666-13-9)

Guidance literature:

With sodium hydroxide; at 200 ℃;

DOI:10.1021/ja00191a081

upstream raw materials:

bis(diethylamino)chlorophosphine

tris[2-(methylamino)ethyl]amine

2,8,9-Trimethyl-2,8,9-triaza-5-azonia-1λ⁵-phospha-tricyclo[3.3.3.0^1,5]undecane; chloride

Hexamethylphosphorous triamide

Downstream raw materials:

Phenyl-(2,8,9-trimethyl-2,5,8,9-tetraaza-1λ⁵-phospha-bicyclo[3.3.3]undec-1-ylidene)-amine

C₁₈H₃₀N₅P

(R)-2-[4-(N-phenylcarbonylamidino)-phenylaminomethyl]-1-methyl-5-[1-(n-butyloxycarbonylmethylamino)-1-(pyrrolidinocarbonyl)-ethyl]-benzimidazole

Refernces

• 1、 Makita, Yoshimasa,Furuyoshi, Kenta,Ikeda, Keisuke,Fujita, Tomoyuki,Fujiwara, Shin-Ichi,Ehara, Masahiro,Ogawa, Akiya. "Synthesis and characterization of a cyclotriveratrylene-capped azaphosphatrane". . p. 4129 - 4131. Retrieved 2011.
• 2、 Li, Chunyang,Manick, Anne-Doriane,Yang, Jian,Givaudan, David,Biletskyi, Bohdan,Michaud-Chevalier, Sabine,Dutasta, Jean-Pierre,Hérault, Damien,Bugaut, Xavier,Chatelet, Bastien,Martinez, Alexandre. "The Chloroazaphosphatrane Motif for Halogen Bonding in Solution". . p. 11964 - 11973. Retrieved 2021/08/20.