76116-20-6

Basic information

• Product Name: (R)-1-(2-BROMOPHENYL)ETHANOL
• Synonyms: (R)-(+)-2-BROMO-ALPHA-METHYLBENZYL ALCOHOL;(R)-2-BROMO-ALPHA-METHYLBENZYL ALCOHOL;(R)-1-(2-BROMOPHENYL)ETHANOL;(R)-(-)-2-BROMO-1-PHENYLETHANOL;(r)-(+)-2-bromo-α-methylbenzyl alcohol;(R)-2-BROMO-ALPHA-METHYLBENZYL ALCOHOL, 95%, 98% EE;(R)-2-Bromo-alpha-methylbenzyl alcohol, 98% ee;(R)-1-(2-BroMohenyl)ethanol
• CAS NO: 76116-20-6
• Molecular Formula: C₈H₉BrO
• Molecular Weight: 201.06
• Product Categories: chiral;Chiral Reagent;Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 76116-20-6.mol
• Article Data: 196

Chemical Properties

• Melting Point: 54-56 °C(lit.)
• Boiling Point: 243.5 °C at 760 mmHg
• Flash Point: 113.3 °C
• Appearance: /
• Density: 1.47g/cm³
• Vapor Pressure: 0.0172mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.01±0.20(Predicted)
• CAS DataBase Reference: (R)-1-(2-BROMOPHENYL)ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(2-BROMOPHENYL)ETHANOL(76116-20-6)
• EPA Substance Registry System: (R)-1-(2-BROMOPHENYL)ETHANOL(76116-20-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 76116-20-6(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

It is the most important dyestuff intermediate.

InChI:InChI=1/C8H9BrO/c1-6(10)7-4-2-3-5-8(7)9/h2-6,10H,1H3/t6-/m1/s1

Upstream product

• 1973-22-4 1-bromo-2-ethylbenzene 
• 5411-56-3 1-(2-bromophenyl)ethanol 
• 97-72-3 2-Methylpropionic anhydride 
• 2142-69-0 2-bromophenyl methyl ketone 
• 2039-88-5 2-bromostyrene 
• 544-97-8 dimethyl zinc(II) 
• 6630-33-7 ortho-bromobenzaldehyde 
• 67-63-0 isopropyl alcohol 
• 88-65-3 2-bromobenzoic-acid 
• 7154-66-7 2-bromobenzoic acid chloride 
• 118-92-3 anthranilic acid 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 113641-96-6 o-bromoacetophenone trimethylsilyl enol ether 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 1073106-89-4 (S)-1-(ortho-bromophenyl)ethyl (R)-α-methoxy-α-trifluoromethylphenylacetate 
• 1326723-10-7 (S)-1-(ortho-bromophenyl)ethyl (S)-α-methoxy-α-trifluoromethylphenylacetate 
• 1429127-78-5 1-bromo-2-[(1R)-1-chloroethyl]benzene 
• 1429127-65-0 C₁₉H₂₄BrN₅OS₂ 
• 1429127-82-1 (2R)-2-[(2-chloro-5-{[(1S)-1-(2-bromophenyl)ethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol 
• 1429127-79-6 1-bromo-2-[(1S)-1-chloroethyl]benzene 
• 1429127-66-1 C₁₉H₂₄BrN₅OS₂ 
• 166191-24-8 (S)-1-bromo-2-(1-methoxyethyl)benzene 

Relevant articles and documents

Cinchona-Alkaloid-Derived NNP Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of Ketones

Most ligands applied for asymmetric hydrogenation are synthesized via multistep reactions with expensive chemical reagents. Herein, a series of novel and easily accessed cinchona-alkaloid-based NNP ligands have been developed in two steps. By combining [Ir(COD)Cl]2, 39 ketones including aromatic, heteroaryl, and alkyl ketones have been hydrogenated, all affording valuable chiral alcohols with 96.0-99.9% ee. A plausible reaction mechanism was discussed by NMR, HRMS, and DFT, and an activating model involving trihydride was verified.

Arene-Immobilized Ru(II)/TsDPEN Complexes: Synthesis and Applications to the Asymmetric Transfer Hydrogenation of Ketones

The Noyori-Ikariya (arene)Ru(II)/TsDPEN precatalyst has been anchored to amorphous silica and DAVISIL through the η6-coordinated arene ligand via a straightforward synthesis and the derived systems, (arene)Ru(II)/TsDPEN@silica and (arene)Ru(II)/TsDPEN@DAVISIL, form highly efficient catalysts for the asymmetric transfer hydrogenation of a range of electron-rich and electron-poor aromatic ketones, giving good conversion and excellent ee's under mild reaction conditions. Moreover, catalyst generated in situ immediately prior to addition of substrate and hydrogen donor, by reaction of silica-supported [(arene)RuCl2]2 with (S,S)-TsDPEN, was as efficient as that generated from its preformed counterpart [(arene)Ru{(S,S)-TsDPEN}Cl]@silica. Gratifyingly, the initial TOFs (up to 1085 h?1) and ee's (96–97 %) obtained with these catalysts either rivalled or outperformed those previously reported for catalysts supported by either silica or polymer immobilized through one of the nitrogen atoms of TsDPEN. While the high ee's were also maintained during recycle studies, the conversion dropped steadily over the first three runs due to gradual leaching of the ruthenium.

Ruthenium-catalyzed hydrogenation of aromatic ketones using chiral diamine and monodentate achiral phosphine ligands

The Ru-catalyzed asymmetric hydrogenation of ketones with chiral diamine and monodentate achiral phosphine has been developed. A wide range of ketones were hydrogenated to afford the corresponding chiral secondary alcohols in good to excellent enantioselectivities (up to 98.1% ee). In addition, an appropriate mechanism for the asymmetric hydrogenation was proposed and verified by NMR spectroscopy.