9-(Bromomethyl)acridine

Base Information

• Chemical Name: 9-(Bromomethyl)acridine
• CAS No.: 1556-34-9
• Molecular Formula: C14H10 Br N
• Molecular Weight: 272.144
• Hs Code.: 29339900
• European Community (EC) Number: 626-458-7
• DSSTox Substance ID: DTXSID10165917
• Nikkaji Number: J275.477K
• Wikidata: Q83035157
• Mol file: 1556-34-9.mol

Synonyms:9-bromomethylacridine

Chemical Property of 9-(Bromomethyl)acridine

Chemical Property:

• Vapor Pressure: 6.74E-07mmHg at 25°C
• Melting Point: 160-165 °C
• Boiling Point: 420.7°Cat760mmHg
• PKA: 4.84±0.10(Predicted)
• Flash Point: 208.2°C
• PSA: 12.89000
• Density: 1.508g/cm³
• LogP: 4.28290
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 270.99966
• Heavy Atom Count: 16
• Complexity: 221

Purity/Quality:

97% ^*data from raw suppliers

9-(Bromomethyl)acridine ^*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: C1=CC=C2C(=C1)C(=C3C=CC=CC3=N2)CBr
• Uses: 9-(Bromomethyl)acridine is an HPLC derivatizing agent used for fluorescent labeling of carboxylic acid.

Technology Process of 9-(Bromomethyl)acridine

There total 5 articles about 9-(Bromomethyl)acridine 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: 99.0%

9-methyl-acridine (611-64-3) → 9-(bromomethyl)acridine (1556-34-9)

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In chloroform; for 5h; Heating;

DOI:10.1039/b502485d

Reference yield:

diphenylamine (122-39-4) → 9-(bromomethyl)acridine (1556-34-9)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc(II) chloride / 5 h / 180 - 220 °C

2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux

With N-Bromosuccinimide; zinc(II) chloride; dibenzoyl peroxide; In tetrachloromethane;

DOI:10.1039/c3pp25362g

Reference yield:

9-Chloroacridine (1207-69-8) → 9-(bromomethyl)acridine (1556-34-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium ethylate; ethanol

2: aqueous HCl

3: dibenzoyl peroxide; tetrachloromethane; N-bromo-succinimide

With hydrogenchloride; tetrachloromethane; N-Bromosuccinimide; ethanol; sodium ethanolate; dibenzoyl peroxide;

upstream raw materials:

9-methyl-acridine

9-Chloroacridine

acridin-9-yl-malonic acid diethyl ester

diphenylamine

Downstream raw materials:

9-(hydrazinylmethyl)acridine

Refernces

• 1、 Lehr,Kaul. "Chlorpromazine metabolism. IV: Quaternization as a key to determination of picomoles of chlorpromazine and other tertiary amine drugs". . p. 950 - 953. Retrieved 1975.
• 2、 Song, Di,Zhang, Nan,Zhang, Panpan,Zhang, Na,Chen, Weijin,Zhang, Long,Guo, Ting,Gu, Xiaotong,Ma, Shutao. "Design, synthesis and evaluation of novel 9-arylalkyl-10-methylacridinium derivatives as highly potent FtsZ-targeting antibacterial agents". . . Retrieved 2021/05/10.
• 3、 -. "Preparation method of 9-bromomethyl acridine". Paragraph 0027-0060. . Retrieved 2020/08/09.