43204-63-3

Basic information

• Product Name: bis(2-bromoethyl)ammonium bromide
• Synonyms: bis(2-bromoethyl)ammonium bromide;BIS(2-BROMOETHYL)AMINEHYDROBROMICACIDSALT;2-BROMO-N-(2-BROMOETHYL)ETHANAMINE HYDROBROMIDE;Bis(2-bromoethyl)amine·hydrobrominate;Bis(2-bromoethyl)amine hydrobromide;EthanaMine, 2-broMo-N-(2-broMoethyl)-, hydrobroMide;2,2'-Dibromodiethylamine Hydrobromide;Bis(2-bromoethyl)ammonium hydrobromide
• CAS NO: 43204-63-3
• Molecular Formula: 2BrH*C₄H₉Br₂N
• Molecular Weight: 311.8409
• EINECS: 256-142-0
• Mol File: 43204-63-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 203-205℃
• Boiling Point: 239.4°C at 760mmHg
• Flash Point: 98.6°C
• Appearance: /
• Density: 1.779g/cm³
• Vapor Pressure: 0.0402mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: bis(2-bromoethyl)ammonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: bis(2-bromoethyl)ammonium bromide(43204-63-3)
• EPA Substance Registry System: bis(2-bromoethyl)ammonium bromide(43204-63-3)

Safety Data

• Hazardous Substances Data: 43204-63-3(Hazardous Substances Data)

Usage

Description

Bis(2-bromoethyl)ammonium bromide, also known as 2,2''-Dibromodiethylamine Hydrobromide, is a chemical compound with the formula (BrCH2CH2)2NH2+Br-. It is a bromoalkylating agent that is widely used in the synthesis of various pharmaceutical compounds due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
Bis(2-bromoethyl)ammonium bromide is used as a key intermediate in the synthesis of quinone phosphorodiamidate drugs. These drugs target DT-diaphorase, an enzyme that is overexpressed in solid tumors, making it a potential therapeutic approach for cancer treatment.
Used in Anticancer Applications:
Bis(2-bromoethyl)ammonium bromide is utilized in the development of anticancer agents that specifically target DT-diaphorase, an enzyme associated with various solid tumors. By inhibiting this enzyme, the compound can potentially slow down or halt the growth of cancer cells.
Used in Antidepressant Drug Preparation:
Bis(2-bromoethyl)ammonium bromide is also used in the preparation of anti-depressive drugs, specifically for the treatment of major depressive disorders. It is an essential component in the synthesis of Trazadone, a medication used to treat depression and other mood disorders.
Used in Trazadone Impurity:
As a Trazadone Impurity, Bis(2-bromoethyl)ammonium bromide is an important compound in the quality control and regulatory processes of pharmaceutical manufacturing. Ensuring the purity and safety of the final drug product is crucial, and the presence of this impurity can be monitored and controlled during the production process.

InChI:InChI=1/C4H9Br2N/c5-1-3-7-4-2-6/h7H,1-4H2

Upstream product

• 2488-95-1 1,2-bis(2'-hydroxyethyl)-hydrazine 
• 78265-92-6 1-Phthalyl-2,2-di(2-bromethyl)hydrazin 
• 111-42-2 2,2'-iminobis[ethanol] 

Downstream Products

• 101266-21-1 1-(2-allylmercapto-phenyl)-piperazine 
• 40818-92-6 1-(2-ethylmercapto-phenyl)-piperazine 
• 100862-54-2 1-(2-butylmercapto-phenyl)-piperazine 
• 91561-55-6 1-(5-chloro-2-ethylsulfanyl-phenyl)-piperazine 
• 52605-47-7 1-(2-propylmercapto-phenyl)-piperazine 
• 57536-86-4 1-naphtylpiperazine 
• 35386-24-4 1-(2-Methoxyphenyl)piperazine 
• 1013-24-7 1-(2-methylsulfanylphenyl)piperazine 
• 39593-08-3 (4-methylphenyl)piperazine 
• 6269-89-2 1-(4-Nitrophenyl)piperazine 
• 92-54-6 4-phenyl-1-piperazine 
• 4432-90-0 bis(2-phenylaminoethyl)amine 
• 13339-02-1 1-(2-aminophenyl)piperazine 
• 57536-91-1 1-naphthalen-2-yl-piperazine 

Relevant articles and documents

Development of novel quinone phosphorodiamidate prodrugs targeted to DT-diaphorase

A series of naphthoquinone and benzimidazolequinone phosphorodiamidates has been synthesized and studied as potential cytotoxic prodrugs activated by DT-diaphorase. Reduction of the quinone moiety in the target compounds was expected to provide a pathway for expulsion of the phosphoramide mustard alkylating agent. All of the compounds synthesized were excellent substrates for purified human DT-diaphorase (k(cat)/K(m) = 3 x 107 - 3 x 108 M-1 s-1). The naphthoquinones were toxic to both HT-29 and BE human colon cancer cell lines in a clonogenic assay; however, cytotoxicity did not correlate with DT-diaphorase activity in these cell lines. The benzimidazolequinone analogues were 1-2 orders of magnitude less cytotoxic than the naphthoquinone analogues. Chemical reduction of the naphthoquinone led to rapid expulsion of the phosphorodiamidate anion; in contrast, the benzimidazole reduction product was stable. Michael addition of glutathione and other sulfur nucleophiles provides an alternate mechanism for activation of the naphthoquinone phosphorodiamidates, and this mechanism may contribute to the cytotoxicity of these compounds.

Tricyclic analgesics

A tricyclic compound of Formula (I): wherein: R1 is hydrogen or hydroxy; R2 is hydrogen or hydroxy; or R1 and R2 together are oxygen; A is a bond, CH2, CH CH3, CH2 CH2 or C(CH3)2; R3 and R4 are the same or different and are hydrogen, halo, C1-C6 alkyl, C1-C4 alkoxy, trifluoromethyl NO2, COR6, COOR6 or NR6R7, wherein R6 and R7 are the same or different and are hydrogen, C1-C6 alkyl or benzyl; R5 is hydrogen, C1-6 alkyl, C2-6 alkenyl, C3-6 cycloalkyl, (O═C)—C1-6 alkyl, (O═C)—C2-6 alkenyl, (O═C)—C3-6 cycloalkyl wherein said alkyl, alkenyl and cycloalkyl groups can be substituted by 1, 2 or 3 groups selected from halo, C3-C6 cycloalkyl, phenyl or substituted phenyl, and salts thereof, are particularly useful for treating, among other indications, neuropathic pain and other CNS disorders.

Synthese von N,N-Di(2-bromethyl)hydrazin

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