3-(BROMOMETHYL)PYRENE

Base Information

• Chemical Name: 3-(BROMOMETHYL)PYRENE
• CAS No.: 2595-90-6
• Molecular Formula: C17H11 Br
• Molecular Weight: 295.178
• Hs Code.: 2902900000
• European Community (EC) Number: 803-708-5
• DSSTox Substance ID: DTXSID50361552
• Nikkaji Number: J900.394K
• Wikidata: Q72447804
• Mol file: 2595-90-6.mol

Synonyms:1-(Bromomethyl)pyrene;1-Pyrenylmethyl bromide; 3-(Bromomethyl)pyrene

Chemical Property of 3-(BROMOMETHYL)PYRENE

Chemical Property:

• Vapor Pressure: 1.22E-07mmHg at 25°C
• Melting Point: 145-147°C
• Refractive Index: 1.844
• Boiling Point: 443.3°Cat760mmHg
• Flash Point: 225.5°C
• PSA: 0.00000
• Density: 1.541g/cm³
• LogP: 5.47890
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 294.00441
• Heavy Atom Count: 18
• Complexity: 313

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-(Bromomethyl)pyrene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C3C(=C1)C=CC4=C(C=CC(=C43)C=C2)CBr
• Uses: 1-(Bromomethyl)pyrene is widely used in the synthesis of fluorophores for the fluorescent sensing of variety of analytes including metal ions like Cd2+, Zn2+ and adenosine triphosphate (ATP) sensing at physiological pH. It is also used in the synthesis of photoinitiators (PIs) for the radical polymerization of acrylates and the cationic polymerization of epoxy-silicone and vinyl ethers.

Technology Process of 3-(BROMOMETHYL)PYRENE

There total 4 articles about 3-(BROMOMETHYL)PYRENE 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: 97.0%

1-pyrenemethanol (24463-15-8) → 1-bromomethylpyrene (2595-90-6)

Guidance literature:

With phosphorus tribromide; In toluene; at 0 - 20 ℃; for 1h;

DOI:10.1002/anie.201202947

Reference yield: 85.0%

methanol (67-56-1) + pyrene (129-00-0) → 1-bromomethylpyrene (2595-90-6)

Guidance literature:

With phosphorus tribromide; In toluene; for 5h; Inert atmosphere; Sealed tube; Schlenk technique; Cooling with ice;

DOI:10.1039/d1ra05328k

Reference yield:

pyrene-1-aldehyde (3029-19-4) → 1-bromomethylpyrene (2595-90-6)

Guidance literature:

Multistep reaction; (i) LiAlH₄, Et₂O, (ii) PBr₃, Py;

upstream raw materials:

1-methylpyrene

pyrene-1-aldehyde

1-pyrenemethanol

methanol

Downstream raw materials:

pyren-1-ylmethyltriphenylphosphonium bromide

3-(1-pyrenylmethyloxy)benzyl alcohol

Refernces

• 1、 Ma, Boling,Zeng, Fang,Li, Xizhen,Wu, Shuizhu. "A facile approach for sensitive, reversible and ratiometric detection of biothiols based on thymine-mediated excimer-monomer transformation". . p. 6007 - 6009. Retrieved 2012.
• 2、 Jiao, Dezhi,Geng, Jin,Loh, Xian Jun,Lee, Tung-Chun,Scherman, Oren A.,Das, Debapratim. "Supramolecular peptide amphiphile vesicles through host-guest complexation". . p. 9633 - 9637,5. Retrieved 2012.
• 3、 Biswas, Rakesh,Ghosh, Surya,Bhaumik, Shubhra Kanti,Banerjee, Supratim. "Selective recognition of ATP by multivalent nano-assemblies of bisimidazolium amphiphiles through “turn-on” fluorescence response". . p. 2728 - 2738. Retrieved 2020.
• 4、 Ji, Hai-Feng,Dabestani, Reza,Brown, Gilbert M.,Hettich, Robert L.. "Spacer length effect on the photoinduced electron transfer fluorescent probe for alkali metal ions". . p. 513 - 516. Retrieved 1999.
• 5、 Xu, Zhaochao,Singh, N. Jiten,Lim, Jeesun,Pan, Jie,Ha, Na Kim,Park, Sungsu,Kim, Kwang S.,Yoon, Juyoung. "Unique sandwich stacking of pyrene-adenine-pyrene for selective and ratiometric fluorescent sensing of ATP at physiological pH". . p. 15528 - 15533. Retrieved 2009.
• 6、 Ghosh, Ashutosh,Kanti Seth, Sourav,Purkayastha, Pradipta. "Controlled Formation of Hydrated Micelles by the Intervention of Cyclodextrins". . p. 130 - 135. Retrieved 2019.
• 7、 Zeng, Lintao,Wu, Jiasheng,Dai, Qing,Liu, Weimin,Wang, Pengfei,Lee, Chun-Sing. "Sensing of bacterial endotoxin in aqueous solution by supramolecular assembly of pyrene derivative". . p. 4014 - 4017. Retrieved 2010.
• 8、 Chang, Tao,Fu, Xiying,Hao, Yongjing,Kang, Lianwei,Li, Xiaopeng,Panchal, Balaji,Qin, Shenjun,Tian, Tian,Zhu, Zheng. "Pyrene-based ammonium bromides combined with g-C3N4for the synergistically enhanced fixation reaction of CO2and epoxides". . p. 30222 - 30228. Retrieved 2021/10/20.