18355-96-9

Basic information

• Product Name: 3-((Dimethylamino)propyl)triphenylphosphonium bromide
• Synonyms: (3-BROMIDEPROPYL)TRIPHENYLPHOS-PHONIUM BROMIDE, 98+%;(3-Dimethylamino)propyltriphenylphosphonium bromide;(3-(DiMethylaMino)propyl)triphenylphosphoniuM broMide;(3-(Dimethylamino)propyl)triphenylphosphonium bromide 98%;(3-(Dimethylamino)
• CAS NO: 18355-96-9
• Molecular Formula: Br*C₂₃H₂₇NP
• Molecular Weight: 428.34
• EINECS: 1312995-182-4
• Product Categories: C-C Bond Formation;Olefination;Wittig Reagents
• Mol File: 18355-96-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 193-196 °C
• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• BRN: 4637548
• CAS DataBase Reference: 3-((Dimethylamino)propyl)triphenylphosphonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-((Dimethylamino)propyl)triphenylphosphonium bromide(18355-96-9)
• EPA Substance Registry System: 3-((Dimethylamino)propyl)triphenylphosphonium bromide(18355-96-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 18355-96-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-((Dimethylamino)propyl)triphenylphosphonium bromide is used as a reactant for the preparation of various pharmaceutical compounds, including:
1. Olopatadine hydrochloride: It is used as a reactant in the synthesis of olopatadine hydrochloride, which is an antihistamine drug used for treating allergic conditions such as rhinitis and conjunctivval.
2. Topoisomerase I-targeting antitumor agents: It serves as a reactant in the preparation of topoisomerase I-targeting antitumor agents, which are used in cancer therapy to inhibit the activity of the enzyme topoisomerase I, thereby preventing DNA replication and transcription.
3. C15-C21 stereopentad of discodermolide: It is used in the synthesis of the C15-C21 stereopentad of discodermolide, a complex natural product with potent anti-cancer activity. 3-((Dimethylamino)propyl)triphenylphosphonium bromide is synthesized via cleavage of aminoglycosides, double-bond isomerization, and selective hydroxyl group protection.
4. Diphenyl amine-based sodium channel blockers: It is used as a reactant in the preparation of diphenyl amine-based sodium channel blockers, which are effective against hNav1.2. These blockers have potential applications in the treatment of pain and other neurological disorders.
5. Wittig reaction with benzaldehyde: 3-((Dimethylamino)propyl)triphenylphosphonium bromide is used as a reactant in the Wittig reaction with benzaldehyde, a widely used method in organic chemistry for the synthesis of alkenes from aldehydes and ketones. This reaction is crucial for the preparation of various pharmaceutical compounds and other organic molecules.

InChI:InChI=1/C23H27NP.BrH/c1-24(2)19-12-20-25(21-13-6-3-7-14-21,22-15-8-4-9-16-22)23-17-10-5-11-18-23;/h3-11,13-18H,12,19-20H2,1-2H3;1H/q+1;/p-1

Upstream product

• 27710-82-3 anhydrous 3-(dimethylamino)propyltriphenylphosphonium bromide hydrobromide 
• 603-35-0 triphenylphosphine 
• 3607-17-8 3-bromopropyltriphenylphosphonium bromide 
• 124-40-3 dimethyl amine 

Downstream Products

• 140462-76-6 olopatadine hydrochloride 
• 1585241-59-3 (3E)-4-(3-chlorophenyl)-N,N-dimethyl-4-(2-pyrazinyl)but-3-en-1-ammonium trifluoroacetate 
• 1585241-61-7 (3Z)-4-(3-chlorophenyl)-N,N-dimethyl-4-(2-pyrazinyl)but-3-en-1-ammonium trifluoroacetate 
• 1585241-54-8 (3Z)-4-(3-chlorophenyl)-N,N-dimethyl-4-(4-pyridyl)but-3-en-1-ammonium trifluoroacetate 
• 1585241-56-0 (3E)-4-(3-chlorophenyl)-N,N-dimethyl-4-(4-pyridyl)but-3-en-1-ammonium trifluoroacetate 
• 1585244-34-3 (3E)-4-(3-chlorophenyl)-N,N-dimethyl-4-(3-pyridyl)but-3-en-1-ammonium trifluoroacetate 
• 1585244-36-5 (3Z)-4-(3-chlorophenyl)-N,N-dimethyl-4-(3-pyridyl)but-3-en-1-ammonium trifluoroacetate 
• 1585241-40-2 (E)-4-(2-chlorophenyl)-N,N-dimethyl-4-(2-pyridyl)but-3-en-1-ammonium trifluoroacetate 
• 1585241-35-5 (3E)-4-(3-chlorophenyl)-N,N-dimethyl-4-(2-pyridyl)but-3-en-1-ammoniumtrifluoroacetate 
• 1585241-37-7 (3Z)-4-(3-chlorophenyl)-N,N-dimethyl-4-(2-pyridyl)but-3-en-1-ammonium trifluoroacetate 
• 1585241-30-0 (3E)-4-(4-chlorophenyl)-N,N-dimethyl-4-(2-pyridyl)but-3-en-1-ammonium trifluoroacetate 
• 1585241-32-2 (3Z)-4-(4-chlorophenyl)-N,N-dimethyl-4-(2-pyridyl)but-3-en-1-ammonium trifluoroacetate 
• 1384866-65-2 (E)-methyl 4-{2-[4-(dimethylamino)but-1-enyl]benzyloxy}-3-iodophenylacetate 
• 875050-51-4 (E)-methyl 3-[4-(dimethylamino)but-1-enyl]-4-(2-iodobenzyloxy)phenylacetate 

Relevant articles and documents

Process improvement in the production of a pharmaceutical intermediate using a reaction calorimeter for studies on the reaction kinetics of amination of a bromopropyl compound

A synthetic process to produce a pharmaceutical intermediate, [3-(dimethylamino)propyl]triphenylphosphonium bromide (1), was established in the laboratory. Process safety evaluations did not show any severe problems. In order to scale up to plant scale, w

Chlorpheniramine Analogues Reverse Chloroquine Resistance in Plasmodium falciparum by Inhibiting PfCRT

The emergence and spread of malaria parasites that are resistant to chloroquine (CQ) has been a disaster for world health. The antihistamine chlorpheniramine (CP) partially resensitizes CQ-resistant (CQR) parasites to CQ but possesses little intrinsic antiplasmodial activity. Mutations in the parasite's CQ resistance transporter (PfCRT) confer resistance to CQ by enabling the protein to transport the drug away from its site of action, and it is thought that resistance-reversers such as CP exert their effect by blocking this CQ transport activity. Here, a series of new structural analogues and homologues of CP have been synthesized. We show that these compounds (along with other in vitro CQ resistance-reversers) inhibit the transport of CQ via a resistance-conferring form of PfCRT expressed in Xenopus laevis oocytes. Furthermore, the level of PfCRT-inhibition was found to correlate well with both the restoration of CQ accumulation and the level of CQ resensitization in CQR parasites.

Polymorphic forms of olopatadine hydrochloride and methods for producing olopatadine and salts thereof

The present invention provides a novel polymorphic form of olopatadine hydrochloride ([(Z)-3-(dimethylamino)propylidene]-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid hydrochloride), a selective histamine H1-receptor antagonist that is used for the treatment of ocular symptoms of seasonal allergic conjunctivitis. The present invention also provides novel methods for producing olopatadine on a large scale, and in a manner that is cost effective, provides a low level of impurities and eliminates the need to use the costly and dangerous base, butyllithium, which is used in prior art reactions for making olopatadine. The present invention further provides novel processes for carrying out a large scale production of 3-dimethylaminopropyltriphenylphosphonium bromide and its corresponding hydrobromide salt, which are employed in the production of olopatadine, and pharmaceutically acceptable salts of olopatadine.

Discovery of diphenyl amine based sodium channel blockers, effective against hNav1.2

The development of new therapies for chronic pain is an area of unmet medical need. Central to pathways of chronic pain is the upregulation of voltage-gated sodium channels. The use of tricyclic antidepressants, which also have sodium channel activity, in chronic pain therapy prompted us to develop novel compounds from this scaffold. Herein, we show that the tricyclic moiety is not needed for effective inhibition of the [3H]-BTX binding site and sodium currents of hNav1.2. Our lead compound 6, containing a diphenyl amine motif, demonstrated a 53% inhibitory block of Nav1.2 currents at 10 μM, which is greater than 50% increase in current block in comparison to the amitriptyline standard. Altogether our study establishes that the tricyclic motif is unnecessary for hNav1.2 activity and modification of the amine portion is detrimental to sodium channel block.

Therapeutic agents

Compounds of formula I STR1 and pharmaceutically acceptable salts thereof in which R1, R2 and R3 independently represent hydrogen, hydroxy, halo, alkyl or alkoxy; ALK1 represents a C2-6 alkylene chain optionally substituted by one or more C1-2 alkyl groups; Y represents a piperidine ring which is attached through nitrogen to ALK1 ; R4 represents hydrogen or a C1-4 alkyl group; the broken line in --- represents a bond, or is absent and the free valency on Y is taken up by hydrogen and the free valency on CR4 is taken up by hydrogen or a C1-4 alkyl group; ALK2 is absent or represents a C1-4 alkylene chain optionally substituted by one or more C1-2 alkyl groups; and R5 and R6 independently represent hydrogen, alkyl, phenyl, alkyl (optionally substituted) or R5 and R6 together with the nitrogen atom to which they are attached represent a saturated 3-7 membered heterocyclic ring (with a proviso); are disclosed which are antiinflammatory, antiallergic and immunomodulatory agents. Compositions containing these compounds and processes to prepare these compounds are also disclosed.

HIGHLY REACTIVE EQUIVALENTS OF ALLYLIDENETRIPHENYLPHOSPHORANES FOR THE STEREOSPECIFIC SYNTHESIS OF 1,3-DIENES BY CIS-OLEFINATION OF HINDERED ALDEHYDES

Ylides derived from 3-dimethylaminopropyltriphenylphosphonium salts react smoothly and stereospecifically with even hindered aldehydes to form Z-olefins which are easily converted to 1,3-dienes.