22061-78-5

Basic information

• Product Name: 2-bromo-3-methyl-phenol
• Synonyms: 2-bromo-3-methyl-phenol;2-Bromo-3-hydroxytoluene;Phenol, 2-broMo-3-Methyl-
• CAS NO: 22061-78-5
• Molecular Formula: C₇H₇BrO
• Molecular Weight: 187.04
• Product Categories: Halides;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 22061-78-5.mol

Chemical Properties

• Melting Point: 58.5-59 °C
• Boiling Point: 215.2 °C at 760 mmHg
• Flash Point: 83.9 °C
• Appearance: /
• Density: 1.554 g/cm³
• Vapor Pressure: 0.102mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 8.54±0.10(Predicted)
• CAS DataBase Reference: 2-bromo-3-methyl-phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-3-methyl-phenol(22061-78-5)
• EPA Substance Registry System: 2-bromo-3-methyl-phenol(22061-78-5)

Safety Data

• Hazardous Substances Data: 22061-78-5(Hazardous Substances Data)

Usage

Uses

2-Bromo-3-methylphenol is a reagent used in chemoselective and regioselective oxybromination of phenols with dioxygen

InChI:InChI=1/C7H7BrO/c1-5-3-2-4-6(9)7(5)8/h2-4,9H,1H3

Upstream product

• 2835-97-4 2-amino-3-methylphenol 
• 108-39-4 3-methyl-phenol 
• 54879-20-8 2-bromo-3-methylaniline 
• 7664-93-9 sulfuric acid 
• 7446-11-9 sulfur trioxide 
• 7726-95-6 bromine 
• 591-24-2 3-Methylcyclohexanone 
• 4920-77-8 3-methyl-2-nitrophenol 
• 570-24-1 2-Methyl-6-nitroaniline 
• 50868-73-0 2-methoxy-6-methylbenzeneamine 
• 38197-43-2 2-bromo-3-methylanisole 
• 95-46-5 2-methylphenyl bromide 

Downstream Products

• 38197-43-2 2-bromo-3-methylanisole 
• 4743-48-0 2-formyl-6-hydroxy-benzoic acid 
• 33528-09-5 methyl 6-methylsalicylate 
• 31490-86-5 2-acetoxy-6-methylbenzoic acid 
• 68040-67-5 methyl 2-acetoxy-6-methylbenzoate 
• 1379772-91-4 N-ethyl-3,6-dimethyldibenz[b,f][1,4]oxazepin-11(10H)-one 
• 1379773-13-3 N-ethyl-2-(2-bromo-3-methylphenoxy)-4-methylbenzamide 
• 25181-65-1 2-(2-bromo-3-methylphenoxy)acetic acid 
• 1374574-57-8 3-bromo-6-methoxy-2-methylbenzonitrile 

Relevant articles and documents

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol

Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.

Examination of Selectivity in the Oxidation of ortho- and meta-Disubstituted Benzenes by CYP102A1 (P450 Bm3) Variants

Cytochrome P450 CYP102A1 (P450 Bm3) variants were used to investigate the products arising from the P450 catalysed oxidation of a range of disubstituted benzenes. The variants used all generated increased levels of metabolites compared to the wild-type enzyme. With ortho-halotoluenes up to six different metabolites could be identified whereas the oxidation of 2-methoxytoluene generated only two aromatic oxidation products. Addition of an ethyl group markedly shifted the selectivity for oxidation to the more reactive benzylic position. Epoxidation of an alkene was also preferred to aromatic oxidation in 2-methylstyrene. Significant minor products arising from the migration of one substituent to a different position on the benzene ring were formed during certain P450-catalysed substrate turnovers. For example, 2-bromo-6-methylphenol was formed from the turnover of 2-bromotoluene and the dearomatisation product 6-ethyl-6-methylcyclohex-2,4-dienone was generated from the oxidation of 2-ethyltoluene. The RLYF/A330P variant altered the product distribution enabling the generation of certain metabolites in higher quantities. Using this variant produced 4-methyl-2-ethylphenol from 3-ethyltoluene with ≥90 % selectivity and with a biocatalytic activity suitable for scale-up of the reaction.

1,2-asymmetric induction in diastereoselective zwitterionic aza-Claisen rearrangements: Key steps in optically active alkaloid synthesis

The zwitterionic aza-Claisen rearrangement of optically active N-allylpyrrolidines and α-phenoxyacetyl fluorides proceeds with complete simple diastereoselectivity (internal asymmetric induction) and complete 1,2-asymmetric induction to generate a new C-C bond adjacent to a chiral C-N-Boc functionality. The resulting γ,δ-unsaturated amides were cyclised to give the corresponding pyrrolizidinones, which enabled the determination of the relative configuration of the stereotriads. Vinyl group degradation and a final lactam reduction gave an optically active analogue of (+)-petasinine (a pyrrolizidine alkaloid). Furthermore, the stereotriad-containing amides should be useful key intermediates for the total synthesis of optically active elaeocarpin (an indolizidine alkaloid). Copyright

Copper-catalyzed cross-coupling interrupted by an opportunistic smiles rearrangement: An efficient domino approach to dibenzoxazepinones

Unexpected Smiles! An unusual and highly regioselective synthesis of dibenzoxazepinones by a domino sequence assisted by an unexpected Smiles rearrangement is reported. The process is effective on electronically differentiated phenols and shows a high tolerance to variation in the benzamide substituents. A plausible path for the reaction, supported by preliminary mechanistic data, is offered. Copyright

Design of living ring-opening alkyne metathesis

It's alive: A ring-strained alkyne based on dibenzo[a,e][8]annulene undergoes ringopening metathesis polymerization (ROMP) to give a high-molecular-weight poly(ortho-phenylene) featuring alternating ethyl and ethynyl linkers along the polymer backbone. The molybdenumalkylidyne- based catalyst system discriminates between strained and unstrained alkynes to yield a living polymer with an unparalleled low polydispersity.

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

Compounds of formula (I): wherein R4, R6 and R7 are defined herein, are useful as inhibitors of HIV replication.

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

Compounds of formula (I): wherein c, X, Y, R2, R4 and R5 are defined herein, are useful as inhibitors of HIV replication.

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

The present invention relates to compounds of formula (I) wherein c, X, Y, R2, R3, R4 and R6 are as defined herein, compositions and uses thereof for treating human immunodeficiency virus (HIV) infection. In particular, the present invention provides novel inhibitors of HIV integrase, pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HIV infection

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

Compounds of formula I : wherein c, R2, R3, R4, R5, R6, R7 and R8 are defined herein, are useful as inhibitors of HIV replication.

An efficient, rapid, and regioselective bromination of anilines and phenols with 1-butyl-3-methylpyridinium tribromide as a new reagent/solvent under mild conditions

1-Butyl-3-methylpyridinium tribromide, [BMPy]Br3 proves to be a highly efficient, regioselective reagent/solvent for nuclear bromination of various anilines and phenols. The synthesis and characterization of the room temperature ionic liquid [BMPy]Br3 (2) is described. The bromination was carried out in the absence of organic solvents and in most cases the only extraction solvent needed was water. The spent 1-butyl-3-methylpyridinium bromide (1) was easily recycled.