1837-91-8

Basic information

• Product Name: 1,2,3,4,5,6-HEXABROMOCYCLOHEXANE
• Synonyms: 1,2,3,4,5,6-hexabromo-cyclohexan;1,2,3,4,5,6-HEXABROMOCYCLOHEXANE;BENZENE HEXABROMIDE;JAK2 INHIBITOR II;trans-α-Benzene hexabromide;1,2,3,4,5,6-Hexabromcyclohexan;NSC 7908
• CAS NO: 1837-91-8
• Molecular Formula: C₆H₆Br₆
• Molecular Weight: 557.54
• EINECS: 250-052-5
• Mol File: 1837-91-8.mol

Chemical Properties

• Melting Point: 218.0 to 223.0 °C
• Boiling Point: 388.9°C at 760 mmHg
• Flash Point: 183.4°C
• Appearance: white to beige/
• Density: 2.894g/cm³
• Vapor Pressure: 6.65E-06mmHg at 25°C
• Refractive Index: 1.699
• Storage Temp.: Store at RT
• Solubility: DMSO: soluble2mg/mL (clear solution, warmed)
• CAS DataBase Reference: 1,2,3,4,5,6-HEXABROMOCYCLOHEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,5,6-HEXABROMOCYCLOHEXANE(1837-91-8)
• EPA Substance Registry System: 1,2,3,4,5,6-HEXABROMOCYCLOHEXANE(1837-91-8)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-36-22
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1837-91-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,2,3,4,5,6-Hexabromocyclohexane is used as a pharmaceutical agent for its inhibitory effect on JAK2 autophosphorylation, which plays a crucial role in various cellular processes and diseases. Its ability to inhibit JAK2 autophosphorylation makes it a potential candidate for the development of drugs targeting conditions related to this pathway.

Biological Activity

Potently and directly inhibits JAK2 tyrosine kinase autophosphorylation, specifically inhibiting ligand-dependent JAK2 activation. A 16-hour treatment with 1 μ M of compound reduces JAK2 tyrosine autophosphorylation levels to ~ 50% while 50 μ M elimates nearly all JAK2 activity. Non-cytotoxic at 100 μ M.

InChI:InChI=1/C6H6Br6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H

Upstream product

• 7726-95-6 bromine 
• 71-43-2 benzene 
• 25283-73-2 3-Methyl-4-phenyl-1,2,5-thiadiazole 

Downstream Products

• 106-37-6 1.4-dibromobenzene 
• 615-54-3 1,2,4-tribromobenzene 
• 10035-10-6 hydrogen bromide 
• 71-43-2 benzene 
• 120-80-9 benzene-1,2-diol 
• 108-86-1 bromobenzene 
• 108-36-1 1,3-dibromobenzene 
• 100-39-0 benzyl bromide 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 583-53-9 2,3-dibromobenzene 
• 87-82-1 hexabromobenzene 

Relevant articles and documents

Photochemical Bromination of Anilides by Benzenehexabromide

Benzenehexabromide was found to afford photochemical bromination of substituted acetanilide in the p-position.The rates of bromination were found to follow the order predicted on the basis of inductive effect of the substituents and similar to the sequence of reactivities observed for bromination of acetanilides with N-bromosuccinimide.Similar results were obtained in the case of p-substituted benzanilides and the reaction shows a good Hammett correlation with the ?+ values for the substituents with a ρ value -0.266.

Bromination of Methyl Substituted 1,2,5-Thiadiazoles with N-Bromosuccinimide

Bromomethyl-1,2,5-thiadiazoles 2a-c were prepared by bromination of methyl-1,2,5-thiadiazoles 1a-c by NBS in refluxing carbon tetrachloride.When bromination of 1a and 1b was carried out under irradiation of tungsten lamp, mixtures of cis-5a and b and tran

Photochemical Bromination of Simple Arenes

Photochemical bromination of benzene, fluorobenzene, chlorobenzene, t-butylbenzene, α,α,α-trifluorotoluene, and (in tetrachloromethane) biphenyl and naphthalene gives substitution products and adducts such as 1,2,3,4,5,6-hexabromocyclohexane (1).The decomposition of (1) and of the analogous chlorobenzene adduct (3) under photochemical conditions gives the parent arene, the monobrominated halogenobenzene, and bromine which may be scavenged by toluene to give benzyl bromide or by benzene to give bromobenzene and dibromobenzenes.Addition is a kinetically controlled process, so that the mechanism of formation of these aryl bromides must be largely through the reversible formation of these adducts.This is consistent with the unusual orientation of apparent attack by bromine upon the arene substrates, since the relative amounts of the isomeric aryl bromides is a consequence of the relative stabilities and ease of elimination of HBr and Br2 from a family of adducts. The range of isomer distribution found within the reaction of each arene with bromine is consistent with two competing processes involved in the formation of the aryl bromides; one of these might by the direct homolytic substitution by bromine atoms upon the arene.