Bromopentamethylbenzene

Base Information

• Chemical Name: Bromopentamethylbenzene
• CAS No.: 5153-40-2
• Molecular Formula: C11H15Br
• Molecular Weight: 227.144
• Hs Code.: 2903999090
• European Community (EC) Number: 225-926-4
• NSC Number: 340
• DSSTox Substance ID: DTXSID20199501
• Nikkaji Number: J265.538A
• Wikidata: Q72448949
• Mol file: 5153-40-2.mol

Synonyms:Bromopentamethylbenzene;5153-40-2;1-bromo-2,3,4,5,6-pentamethylbenzene;Pentamethylbromobenzene;Benzene, bromopentamethyl-;1-Bromopentamethylbenzene;C11H15Br;EINECS 225-926-4;MFCD00013523;1-Bromo-2,3,4,5,6-pentamethyl-benzene;NSC340;Brompentamethylbenzol;Maybridge1_002545;DivK1c_001297;SCHEMBL816717;HMS548L15;DTXSID20199501;NSC 340;NSC-340;AKOS004907392;AM82981;CS-W013011;CDS1_000257;AS-11017;AS-81524;SY034558;FT-0623256;1-bromo-2,3,4,5,6-pentamethylbenzene (en);A828645;1-bromo-2,3,4,5,6-pentamethyl-benzene

Chemical Property of Bromopentamethylbenzene

Chemical Property:

• Melting Point: 161-162 °C
• Boiling Point: 286.5 °C at 760 mmHg
• Flash Point: 126 °C
• PSA: 0.00000
• Density: 1.214 g/cm³
• LogP: 3.99110
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 226.03571
• Heavy Atom Count: 12
• Complexity: 139

Purity/Quality:

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

1-Bromo-2,3,4,5,6-pentamethylbenzene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=C(C(=C1C)C)Br)C)C
• Uses: Bromopentamethylbenzene is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff fields.

Technology Process of Bromopentamethylbenzene

There total 7 articles about Bromopentamethylbenzene 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%

pentamethylbenzene, (700-12-9) → 2,3,4,5,6-pentamethylbromobenzene (5153-40-2)

Guidance literature:

With N-Bromosuccinimide; In acetonitrile; at 0 - 20 ℃; for 16h;

DOI:10.1021/ic100521t

Reference yield:

2',3',4',5',6'-pentamethylacetophenone (2040-01-9) → 2,3,4,5,6-pentamethylbromobenzene (5153-40-2) + 2,3,4,5,6-pentamethyl-1-(α-bromoacetyl)benzene (73932-65-7)

Guidance literature:

With bromine; nitric acid; silver nitrate; In 1,4-dioxane; acetic acid; at 30 ℃; for 16h;

DOI:10.1246/bcsj.67.757

Reference yield:

1,2,4,5-tetramethylbenzene (95-93-2) → 2,3,4,5,6-pentamethylbromobenzene (5153-40-2)

Guidance literature:

Multi-step reaction with 3 steps

1: N-Bromosuccinimide / acetonitrile / 8 h / 0 - 20 °C

2: magnesium / tetrahydrofuran / 14 h

3: N-Bromosuccinimide / acetonitrile / 8 h / 0 - 20 °C

With N-Bromosuccinimide; magnesium; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo201144t

upstream raw materials:

pentamethylbenzene,

Bromoform

1,2,3,4,5-pentamethylcyclopentadiene

2',3',4',5',6'-pentamethylacetophenone

Downstream raw materials:

Hexamethylbenzene

ethylpentamethylbenzene

(+/-)-1-hydroxy-1-(pentamethyl-phenyl)-propane

(+/-)-2-hydroxy-2-(pentamethyl-phenyl)-butane

Refernces

• 1、 Baciocchi et al.. "". . p. 1279. Retrieved 1969.
• 2、 Mandal, Susovan,Parida, Keshaba Nanda,Samanta, Subhas,Moorthy, Jarugu Narasimha. "Influence of (2,3,4,5,6-pentamethyl/phenyl)phenyl scaffold: Stereoelectronic control of the persistence of o-quinonoid reactive intermediates of photochromic chromenes". scheme or table. p. 7406 - 7414. Retrieved 2011/11/06.
• 3、 Zysman-Colman, Eli,Arias, Karla,Siegel, Jay S.. "Synthesis of arylbromides from arenes and Nbromosuccinimide bromosuccinimide (NBS) in acetonitrile - A convenient method for aromatic bromination". experimental part. p. 440 - 447. Retrieved 2009/12/01.