118-23-0

Basic information

• Product Name: N-2-(4-bromobenzhydryloxy)ethyldimethylamine
• Synonyms: bromazine;bromodiphenhydramine;N-2-(4-bromobenzhydryloxy)ethyldimethylamine;Ethanamine, 2-(4-bromophenyl)phenylmethoxy-N,N-dimethyl-;Bromanautine;Bromo-Benadryl;Histabromamine;Diphenhydramine EP Impurity C
• CAS NO: 118-23-0
• Molecular Formula: C₁₇H₂₀BrNO
• Molecular Weight: 107.9174
• EINECS: 204-238-8
• Mol File: 118-23-0.mol

Chemical Properties

• Boiling Point: 397.3°Cat760mmHg
• Flash Point: 194.1°C
• Appearance: /
• Density: 1.259g/cm³
• PKA: pKa 8.64(H2O t = 25 c = 0.002 to 0.01) (Uncertain)
• CAS DataBase Reference: N-2-(4-bromobenzhydryloxy)ethyldimethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-2-(4-bromobenzhydryloxy)ethyldimethylamine(118-23-0)
• EPA Substance Registry System: N-2-(4-bromobenzhydryloxy)ethyldimethylamine(118-23-0)

Safety Data

• Hazardous Substances Data: 118-23-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-2-(4-bromobenzhydryloxy)ethyldimethylamine is used as an antihistamine for the control of cutaneous allergies. Its antihistaminic properties help alleviate symptoms associated with allergic reactions, such as itching, redness, and swelling.
Used in Antimicrobial Applications:
In the field of antimicrobials, N-2-(4-bromobenzhydryloxy)ethyldimethylamine is utilized for its antimicrobial properties. It can be employed in the development of products that help prevent the growth of harmful microorganisms, contributing to improved hygiene and reduced risk of infection.
Used in Cosmetics Industry:
Given its antihistaminic and antimicrobial properties, N-2-(4-bromobenzhydryloxy)ethyldimethylamine can also be used in the cosmetics industry. It can be incorporated into skincare products to help soothe and protect the skin from allergens and microbial infections, making it a valuable ingredient for sensitive skin care formulations.

Originator

Bromazine,Shanghai Lansheng Corporation

Manufacturing Process

28.1 parts of p-bromobenzhydrylbromide are heated to boiling, under reflux and with stirring, with 50 parts of ethylene chlorohydrin and 5.3 parts of calcined sodium carbonate. The reaction product is extracted with ether and the etheral solution washed with water and dilute hydrochloric acid. The residue from the solution in ether [p-bromobenzhydryl(β-chloroethyl)ether]. 28.1 parts of this ether are heated with 12 parts of dimethylethylamine in a sealed tube for 4 hours at 110°C. The product of the reaction is extracted several time with dilute hydrochloric acid. The acid solution made alkaline, in the cold, with concentrated caustic soda solution, and the base which separates taken up in ether. The ether extract is washed with concentrated potassium carbonate solution, evaporated down, and the residue distilled in vacuo. Boiling point of p-bromo-α-phenylbenzyloxy)-N,N-dimethylethylamine 151-154°C under 0.3 mm. p-Bromo-α-phenylbenzyloxy)-N,N-dimethylethylamine may be used as a hydrochloride.

Therapeutic Function

Antihistaminic

InChI:InChI=1S/C17H20BrNO/c1-19(2)12-13-20-17(14-6-4-3-5-7-14)15-8-10-16(18)11-9-15/h3-11,17H,12-13H2,1-2H3

Upstream product

• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 18066-89-2 1-bromo-4-<(bromophenyl)methyl>benzene 
• 29334-16-5 phenyl(4-bromophenyl)methanol 

Downstream Products

• 1808-12-4 [2-(4-bromo-benzhydryloxy)-ethyl]-dimethyl-amine; hydrochloride 
• 4258-28-0 4-[α-(2-dimethylamino-ethoxy)-benzyl]-phenol 

Relevant articles and documents

Palladium-Catalyzed Synthesis of α-Carbonyl-α′-(hetero)aryl Sulfoxonium Ylides: Scope and Insight into the Mechanism

Despite recent advances, a general method for the synthesis of α-carbonyl-α′-(hetero)aryl sulfoxonium ylides is needed to benefit more greatly from the potential safety advantages offered by these compounds over the parent diazo compounds. Herein, we report the palladium-catalyzed cross-coupling of aryl bromides and triflates with α-carbonyl sulfoxonium ylides. We also report the use of this method for the modification of an active pharmaceutical ingredient and for the synthesis of a key precursor of antagonists of the neurokinin-1 receptor. In addition, the mechanism of the reaction was inferred from several observations. Thus, the oxidative addition complex [(XPhos)PhPdBr] and its dimer were observed by 31P{1H} NMR, and these complexes were shown to be catalytically and kinetically competent. Moreover, a complex resulting from the transmetalation of [(XPhos)ArPdBr] (Ar = p-CF3-C6H4) with a model sulfoxonium ylide was observed by mass spectrometry. Finally, the partial rate law suggests that the transmetalation and the subsequent deprotonation are rate-determining in the catalytic cycle.

Anti-inflammatory effects of two new methyl and morpholine derivatives of diphenhydramine on rats

Diphenhydramines are one of the first-generation histamine H1-receptor antagonists of the ethanolamine class that demonstrate many pharmacological properties including anti-inflammatory effects. In this research, bromo (II) and two new tolyl derivatives of I, (Di [p-tolyl] [dimethylaminoethoxy] methane, III) and (Di [p-tolyl] [2-morpholinoethoxy] methane, IV) were synthesized. Their acute and chronic anti-inflammatory activities were evaluated with the formalin and histamine-induced rat paw edema. The vascular permeability in formalin and histamine-induced paw edema, in xylene-induced ear edema, and in peritonitis after acetic acid application into peritoneal cavity were also measured and compared to II. Cotton pellet-induced granuloma model was selected for inducing chronic inflammations in rats. The newly synthesized analogs of diphenhydramine seemed effective to decrease acute inflammations. It was concluded that the prominent anti-phlogistic effects of the new drugs could be related to its reduction vascular permeability mechanism(s) or to its antagonistic effects on H1 histamine receptors. Springer Science+Business Media, LLC 2011.