(3-(Dimethylamino)propyl)triphenylphosphonium bromide

Base Information

• Chemical Name: (3-(Dimethylamino)propyl)triphenylphosphonium bromide
• CAS No.: 18355-96-9
• Molecular Formula: C23H27BrNP
• Molecular Weight: 428.352
• Hs Code.: 2931900090
• European Community (EC) Number: 605-998-7
• DSSTox Substance ID: DTXSID90580684
• Mol file: 18355-96-9.mol

Synonyms:18355-96-9;(3-(Dimethylamino)propyl)triphenylphosphonium bromide;Phosphonium, [3-(dimethylamino)propyl]triphenyl-, bromide (1:1);3-(dimethylamino)propyl-triphenylphosphanium;bromide;[3-(Dimethylamino)propyl]triphenylphosphonium bromide;MFCD00012200;(3-Dimethylamino)propyltriphenylphosphonium bromide;C23H27BrNP;3-dimethylaminopropyltriphenylphosphonium bromide;SCHEMBL190865;(3-(Dimethylamino)propyl)triphenylphosphoniumbromide;DTXSID90580684;SSWPSKSQQSJKKF-UHFFFAOYSA-M;AKOS015917632;SY283964;D97351;(3-dimethylaminopropyl) triphenylphophonium bromide;A880818;J-011759;(3-(Dimethylamino)propyl)triphenyl-phosphonium bromide;[3-(Dimethylamino)propyl](triphenyl)phosphanium bromide

Chemical Property of (3-(Dimethylamino)propyl)triphenylphosphonium bromide

Chemical Property:

• Melting Point: 193-196 °C
• PSA: 16.83000
• LogP: 0.93620
• Storage Temp.: Inert atmosphere,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 427.10645
• Heavy Atom Count: 26
• Complexity: 317

Purity/Quality:

99%+ ^*data from raw suppliers

(3-(Dimethylamino)propyl)triphenylphosphonium bromide 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
• Uses: (3-(Dimethylamino)propyl)triphenyl-phosphonium Bromide is used in preparation of olopatadine hydrochloride. Reactant for preparation of:Topoisomerase I-targeting antitumor agentsC15-C21 stereopentad of discodermolide via cleavage of aminoglycosides, double-bond isomerization, and selective hydroxyl group protectionDiphenyl amine based sodium channel blockers, effective against hNav1.2Reactant for Wittig reaction with benzaldehyde

Technology Process of (3-(Dimethylamino)propyl)triphenylphosphonium bromide

There total 4 articles about (3-(Dimethylamino)propyl)triphenylphosphonium bromide 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: 96.0%

3-bromopropyltriphenylphosphonium bromide (3607-17-8) + dimethyl amine (124-40-3) → (3-dimethylaminopropyl)-triphenylphosphoniumbromide (18355-96-9)

Guidance literature:

In methanol; water; at 80 ℃; for 18h; Sealed tube;

DOI:10.1021/ml5000228

Reference yield: 94.4%

anhydrous 3-(dimethylamino)propyltriphenylphosphonium bromide hydrobromide (27710-82-3) → (3-dimethylaminopropyl)-triphenylphosphoniumbromide (18355-96-9)

Guidance literature:

With sodium carbonate; In isopropyl alcohol; at 50 ℃; for 6h; Product distribution / selectivity;

Reference yield:

triphenylphosphine (603-35-0) → (3-dimethylaminopropyl)-triphenylphosphoniumbromide (18355-96-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / benzene / 15 h / 80 °C

2: 83 percent / ethanol / 15 h / 23 °C

In ethanol; benzene;

DOI:10.1016/S0040-4039(00)98914-7

upstream raw materials:

3-bromopropyltriphenylphosphonium bromide

dimethyl amine

triphenylphosphine

anhydrous 3-(dimethylamino)propyltriphenylphosphonium bromide hydrobromide

Downstream raw materials:

(3E)-4-(4-chlorophenyl)-N,N-dimethyl-4-(2-pyridyl)but-3-en-1-ammonium trifluoroacetate

(3Z)-4-(4-chlorophenyl)-N,N-dimethyl-4-(2-pyridyl)but-3-en-1-ammonium trifluoroacetate

(3E)-4-(3-chlorophenyl)-N,N-dimethyl-4-(2-pyridyl)but-3-en-1-ammoniumtrifluoroacetate

(3Z)-4-(3-chlorophenyl)-N,N-dimethyl-4-(2-pyridyl)but-3-en-1-ammonium trifluoroacetate

Refernces

• 1、 Deane, Karen J.,Summers, Robert L.,Lehane, Adele M.,Martin, Rowena E.,Barrow, Russell A.. "Chlorpheniramine Analogues Reverse Chloroquine Resistance in Plasmodium falciparum by Inhibiting PfCRT". supporting information. p. 576 - 581. Retrieved 2014/06/09.
• 2、 Hudgens, Debjani P.,Taylor, Catherine,Batts, Timothy W.,Patel, Manoj K.,Brown, Milton L.. "Discovery of diphenyl amine based sodium channel blockers, effective against hNav1.2". . p. 8366 - 8378. Retrieved 2008/02/05.