5433-01-2

Basic information

• Product Name: 3-Bromocumene
• Synonyms: 3-BROMOISOPROPYLBENZENE;3-BROMOCUMENE;3-ISOPROPYLBROMOBENZENE;1-BROMO-3-ISOPROPYLBENZENE;1-Bromo-3-(1-methylethyl)benzene;Benzene,1-bromo-3-(1-methylethyl)-;cumene,3-bromo-;m-bromocumene
• CAS NO: 5433-01-2
• Molecular Formula: C₉H₁₁Br
• Molecular Weight: 199.09
• Mol File: 5433-01-2.mol

Chemical Properties

• Melting Point: -10°C (estimate)
• Boiling Point: 52-53°C 0,8mm
• Flash Point: 52-53°C/0.8mm
• Appearance: /
• Density: 1,285 g/cm3
• Vapor Pressure: 0.277mmHg at 25°C
• Refractive Index: 1.5302
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Difficult to mix in water.
• BRN: 1858092
• CAS DataBase Reference: 3-Bromocumene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromocumene(5433-01-2)
• EPA Substance Registry System: 3-Bromocumene(5433-01-2)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 22-50/53-51/53-36/38
• Safety Statements: 24/25-61-60-36-26
• RIDADR: 3082
• Hazardous Substances Data: 5433-01-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Bromocumene is used as a key intermediate for the synthesis of various organic compounds. Its unique structure allows for a range of reactions, making it a valuable component in the creation of different molecules.
Used in Pharmaceuticals:
In the pharmaceutical industry, 3-Bromocumene is utilized as a starting material for the production of various drugs. Its reactivity and structural properties enable the development of new medicinal compounds with potential therapeutic applications.
Used in Agrochemicals:
3-Bromocumene is also employed in the agrochemical sector as a precursor for the synthesis of pesticides and other agricultural chemicals. Its role in creating effective and targeted compounds contributes to the industry's goal of enhancing crop protection and yield.
Used in Dyestuffs:
In the dyestuffs industry, 3-Bromocumene serves as a vital raw material for the production of various dyes and pigments. Its chemical properties facilitate the creation of a wide array of colorants used in different applications, such as textiles, plastics, and printing inks.

Synthesis Reference(s)

The Journal of Organic Chemistry, 25, p. 1691, 1960 DOI: 10.1021/jo01080a001

InChI:InChI=1/C9H11Br/c1-7(2)8-4-3-5-9(10)6-8/h3-7H,1-2H3

Upstream product

• 25108-58-1 1-bromo-3-isopropenylbenzene 
• 51605-97-1 2-bromo-4-isopropylaniline 
• 30951-66-7 2-(3-bromophenyl)-2-propanol 
• 98-82-8 Isopropylbenzene 
• 3132-99-8 m-bromobenzoic aldehyde 
• 35739-70-9 dimethyldichlorotitanium(IV) 
• 99-88-7 4-Isopropylaniline 
• 12775-96-1 copper 

Downstream Products

• 5369-16-4 meta-iso-propyl aniline 
• 99723-36-1 1-(3-isopropyl-phenyl)-ethanol 
• 5651-47-8 3-isopropylbenzoic acid 
• 59313-79-0 5-(3-isopropyl-phenyl)-3,7,3',7'-tetramethyl-5H-5λ⁵-[5,5']spirobi(benzo[b]phosphindole) 
• 19789-34-5 3-isopropyl-styrene 
• 112930-12-8 α-(cumen-3'-yl)biphenyl-2-methanol 
• 40751-59-5 3-isopropyl benzonitrile 
• 909416-48-4 1-cyclopentyl-3-(3-isopropyl-phenyl)-propan-1-one 
• 216019-28-2 3-isopropylphenylboronic acid 
• 903583-57-3 2-bromo-3'-isopropyl-biphenyl 
• 112930-15-1 (E,Z)-1-(biphenyl-2'-yl)-1-(cumen-3-yl)buta-1,3-diene 
• 112930-13-9 <(biphenyl-2-yl)cumen-3-yl>methanone 
• 112930-14-0 1-(biphenyl-2-yl)-1-(cumen-3-yl)but-3-en-1-ol 
• 75659-51-7 1-ethynyl-3-isopropyl-benzene 

Relevant articles and documents

Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents

β-Substituted aldehydes constitute a very important class of compounds found in nature. Synthesis of this motif can be envisioned by C-C bond formation on enals. For this purpose, we report herein the development of enantioselective copper-catalyzed conjugate addition of various organometallic reagents to α,β-unsaturated aldehydes with (R)-H8BINAP, (R)-TolBINAP, and (R)-SEGPHOS as chiral ligands. Three sets of conditions were successfully developed and several enals were used. Reactivity and regio- and enantioselectivities were strongly dependent on reaction conditions and substrates. Good to excellent regio- and enantioselectivities were obtained with zinc reagents R2Zn and aluminum reagents R3Al. However, the asymmetric conjugate addition of Grignard reagents afforded only moderate to good regio- and enantioselectivities.

Enantioselective copper-catalyzed conjugate addition of trimethylaluminium to β,γ-unsaturated α-ketoesters

Not a cop out: The copper-catalyzed asymmetric conjugate addition of organometallic reagents to Michael acceptors is an important methodology for forming a C-C bond in an enantioselective manner. Such an addition of Me 3Al to β,γ-unsaturated α-

Bromination of alkylbenzenes in 1-butyl-3-methylimidazolium bromide and its dibromide complex

Alkylbenzenes were subjected to bromination with molecular bromine using 1-butyl-3-methylimidazolium bromide as solvent. A complex of 1-butyl-3-methylimidazolium bromide with bromine was synthesized. It ensured bromination of alkylbenzenes with no bromine and solvent. The results of bromination in binary solvents and ionic liquids, 1-butyl-3-methylimidazolium bromide and tribromide were compared. The bromination of ethylbenzene with 1-butyl-3-methylimidazolium tribromide was accompanied by formation of a considerable amount of α-bromoethylbenzene, which is not typical of electrophilic aromatic substitution process.

Preparation of substituted bridged indenyl and related ligands

A process for preparing a chelating ligand of the formula (II) from a chelating ligand of the formula (I) via an sp2-sp2 or sp2-sp3 coupling reaction with an organometallic compound of the formula (III). wherein

Substituted 1,3-thiazole compounds, their production and use

(1) A 1,3-thiazole compound of which the 5-position is substituted with a 4-pyridyl group having a substituent including no aromatic group or (2) a 1,3-thiazole compound of which the 5-position is substituted with a pyridyl group having at the position adjacent to a nitrogen atom of the pyridyl group a substituent including no aromatic group has an excellent p38 MAP kinase inhibitory activity.

Bromination of alkylbenzenes in organic solvents. Substrate and position selectivity and effects of substituents

The relative reactivity and the orientation of the entering group in the reaction of bromine with alkylbenzenes (C1-C4 alkyl groups, the last two with normal and iso structures) in organic solvents (acetic acid, acetic anhydride, nitromethane) under polythermal conditions (25-75 deg C) are determined mainly by the steric effects of the substituents.Nathan-Baker position and substrate effects are observed.Correlations close to linear are observed between the orientation (in the form of log 2P/O, where P and O are the relative amounts of the isomers in their reaction mixture) and the purely steric constants of the alkyl groups Es0.The substrate selectivity depends nonlinearly and inversely on Es0.The sensitivity of the orientation to change in the steric characteristics of the substituents shows an extremal dependence on the temperature with a maximum at about 50 deg C.

Direct Geminal Dimethylation of Aromatic Aldehydes with Dichlorodimethyltitanium

Aromatic aldehydes react specifically with (CH3)2TiCl2 to form the geminal dimethylated products.