(S)-1-(2-Bromophenyl)Ethanol

Base Information

• Chemical Name: (S)-1-(2-Bromophenyl)Ethanol
• CAS No.: 114446-55-8
• Molecular Formula: C₈H₉BrO
• Molecular Weight: 201.063
• Hs Code.: 29062900
• European Community (EC) Number: 624-057-1
• DSSTox Substance ID: DTXSID40921381
• Nikkaji Number: J267.440H
• Wikidata: Q72449404
• Mol file: 114446-55-8.mol

Synonyms:(S)-1-(2-Bromophenyl)Ethanol;114446-55-8;(1S)-1-(2-bromophenyl)ethanol;(1S)-1-(2-bromophenyl)ethan-1-ol;(S)-(-)-2-Bromo-alpha-methylbenzyl alcohol;MFCD00004509;1-(2-bromophenyl)ethan-1-ol;SCHEMBL1328402;(S)-1-(o-Bromophenyl)ethanol;DTXSID40921381;DZLZSFZSPIUINR-LURJTMIESA-N;AMY10619;SC1257;(S)-(-)-1-(2-bromophenyl)ethanol;AKOS012521502;CS-W015567;AS-64830;EN300-100384;(S)-(-)-2-Bromo- alpha -methylbenzyl alcohol;A803185;(S)-(-)-2-Bromo-alpha-methylbenzyl alcohol, 98%;Benzenemethanol, 2-bromo-alpha-methyl-, (alphaS)-;J-502341;Z1127664292

Chemical Property of (S)-1-(2-Bromophenyl)Ethanol

Chemical Property:

• Appearance/Colour: off-white to light yellow crystalline powder
• Vapor Pressure: 0.0172mmHg at 25°C
• Melting Point: 56-58 °C(lit.)
• Refractive Index: 1.572
• Boiling Point: 243.5 °C at 760 mmHg
• PKA: 14.01±0.20(Predicted)
• Flash Point: 113.3 °C
• PSA: 20.23000
• Density: 1.47 g/cm³
• LogP: 2.50240
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 199.98368
• Heavy Atom Count: 10
• Complexity: 105

Purity/Quality:

99% ^*data from raw suppliers

(S)-(?)-2-Bromo-α-methylbenzyl alcohol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1Br)O
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1Br)O
• Uses: Used in the synthesis of chiral boronic acids, which serve as reagents for enantiomeric purity determination of diols by H-NMR.

Technology Process of (S)-1-(2-Bromophenyl)Ethanol

There total 38 articles about (S)-1-(2-Bromophenyl)Ethanol 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%

2-bromophenyl methyl ketone (2142-69-0) → (1S)-1-(2-bromophenyl)ethanol (5411-56-3,76116-20-6,118375-26-1,114446-55-8)

Guidance literature:

With hydrogen; potassium hydroxide; 9-amino-9-deoxyepicinchonine; In isopropyl alcohol; at 40 ℃; for 5h; under 45004.5 Torr; optical yield given as %ee; enantioselective reaction; Autoclave;

DOI:10.1016/j.catcom.2009.12.024

Reference yield: 54.0%

1-(2-bromophenyl)ethanol (5411-56-3) → 2-bromophenyl methyl ketone (2142-69-0) + (1S)-1-(2-bromophenyl)ethanol (5411-56-3,76116-20-6,118375-26-1,114446-55-8) + (1R)-1-(2-bromophenyl)ethan-1-ol (5411-56-3,114446-55-8,118375-26-1,76116-20-6)

Guidance literature:

With sodium hydrogencarbonate; sodium bromide; chiral 4,1'-dinaphthyl-3,2'-cyclo[C(Me)2-N(oxyl)-C(Me)2]; In dichloromethane; water; at -15 ℃; for 1.5h; Title compound not separated from byproducts; Electrolysis;

DOI:10.1016/S0040-4039(00)01419-2

Reference yield: 54.0%

1-(2-bromophenyl)ethanol (5411-56-3) → 2-bromophenyl methyl ketone (2142-69-0) + (1S)-1-(2-bromophenyl)ethanol (5411-56-3,76116-20-6,118375-26-1,114446-55-8) + (1R)-1-(2-bromophenyl)ethan-1-ol (5411-56-3,114446-55-8,118375-26-1,76116-20-6)

Guidance literature:

With sodium hydrogencarbonate; sodium bromide; chiral 4,1'-dinaphthyl-3,2'-cyclo[C(Me)2-N(oxyl)-C(Me)2]; In dichloromethane; water; at -15 ℃; for 1.5h; Title compound not separated from byproducts; Electrolysis;

DOI:10.1016/S0040-4039(00)01419-2

upstream raw materials:

2-bromophenyl methyl ketone

1-(2-bromophenyl)ethanol

dimethyl zinc(II)

ortho-bromobenzaldehyde

Downstream raw materials:

(2R)-2-{[(1R)-1-(2-bromo phenyl)ethoxy]methyl}oxirane

(3S)-2-fluoro-1-(4-bromophenyl)-3-(2-bromophenyl)but-1-ene

(3S)-2-fluoro-1-(4-bromophenyl)-3-(2-bromophenyl)but-1-ene

(S)-bis(acetato-O)[2-(1-methoxyethyl)phenyl]iodine

Refernces

• 1、 Kawakami, Yuji,Borissova, Antonia,Chapman, Michael R.,Goltz, Gert,Koltsova, Eleonora,Mitrichev, Ivan,Blacker, A. John. "Continuous Flow Asymmetric Transfer Hydrogenation with Long Catalyst Lifetime and Low Metal Leaching". . p. 7499 - 7505. Retrieved 2019.
• 2、 Liu, Pei Nian,Deng, Jin Gen,Tu, Yong Qiang,Wang, Shao Hua. "Highly efficient and recyclable heterogeneous asymmetric transfer hydrogenation of ketones in water". . p. 2070 - 2071. Retrieved 2004.
• 3、 Chen, Jiachen,Hou, Huacui,Ling, Fei,Nian, Sanfei,Wu, Feifei,Xu, Min,Yi, Xiao,Zhong, Weihui. "Manganese-Catalyzed Enantioselective Hydrogenation of Simple Ketones Using an Imidazole-Based Chiral PNN Tridentate Ligand". . p. 285 - 289. Retrieved 2020.
• 4、 Liu, Jianhong,Fan, Binbin,Liang, Dong,Shi, Xiufeng,Li, Ruifeng,Chen, Hua. "Asymmetric hydrogenation of aromatic ketones by chiral (1S,2S)-DPEN-Ru(II)Cl2(TPP)2 encapsulated in SBA-16". . p. 373 - 377. Retrieved 2010.
• 5、 Kurbanoglu, Esabi B.,Zilbeyaz, Kani,Kurbanoglu, Namudar I.,Kilic, Hamdullah. "Asymmetric reduction of acetophenone analogues by Alternaria alternata using ram horn peptone". . p. 2332 - 2335. Retrieved 2007.
• 6、 Wei, Juan,Zhang, Xiaomin,Zhang, Xiaoming,Zhao, Yaopeng,Li, Ruixiang,Yang, Qihua. "Facile synthesis of hybrid core-shell nanospheres for the asymmetric transfer hydrogenation of aromatic ketones". . p. 1368 - 1374. Retrieved 2014.
• 7、 Li, Aipeng,Ye, Lidan,Guo, Fei,Yang, Xiaohong,Yu, Hongwei. "Biocatalytic anti-Prelog reduction of prochiral ketones with whole cells of a newly isolated strain Empedobacter brevis ZJUY-1401". . p. 31 - 37. Retrieved 2015.
• 8、 Hosoda, Naoya,Kamito, Hideaki,Takano, Miki,Takebe, Yoshitaka,Yamaguchi, Yoshitaka,Asami, Masatoshi. "Erratum: Synthesis of chiral 2-(anilinophenylmethyl)pyrrolidines and 2-(anilinodiphenylmethyl)pyrrolidine and their application to enantioselective borane reduction of prochiral ketones as chiral catalysts (Tetrahedron (2013) 69:6 (1739-1746))". . p. 2509 - 2509. Retrieved 2013.
• 9、 Wang, Jinbo,Feng, Jian,Qin, Ruixiang,Fu, Haiyan,Yuan, Maolin,Chen, Hua,Li, Xianjun. "Asymmetric hydrogenation of aromatic ketones catalyzed by achiral monophosphine TPPTS-stabilized Ru in ionic liquids". . p. 1643 - 1647. Retrieved 2007.
• 10、 Abdlhmed Al-bayati, Yaser W.,Karaka?, Duygu Elma,Meri?, Nermin,Aydemir, Murat,Durap, Feyyaz,Baysal, Ak?n. "Ferrocene based chiral binuclear η6-benzene-Ru(II)-phosphinite complexes: Synthesis, characterization and catalytic activity in asymmetric reduction of ketones". . . Retrieved 2018.