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Type HazMat fee for 500 gram (Estimated)
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Chemical Structure| 1445-91-6 Chemical Structure| 1445-91-6
Chemical Structure| 1445-91-6

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(S)-(-)-Phenylethanol is an endogenous metabolite.

Synonyms: (S)-(-)-1-Phenylethanol; (S)-1-Phenylethanol

4.5 *For Research Use Only !

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Product Citations

Product Citations

Mills, Mitchell ;

Abstract: The development of novel deuterated and fluorinated bioisosteres has significantly impacted the pharmaceutical and agricultural industry and created a growing demand for new synthetic methodology. Both deuterated and fluorinated small molecules exist at the forefront of drug discovery due to their unique ability to attenuate the pharmacokinetic properties of new and currently existing drugs. Selective, highthroughput methods for deuteration and fluorination are scarce in the literature, especially methods that introduce D or F atoms asymmetrically. Benzylic C−H bonds are oftentimes key sites for enzymatic manipulation in metabolic processes, alteration of C−H bonds to C−D or C−F bonds at the benzylic site of organic molecules affects the metabolic process, making this a key site for bioisosterism. Using state-of-the-art methods to synthesize chiral by virtue of deuterium small molecules requires significant synthetic overhead with limited methods for chiral analysis due to the similar nature of H and D. Asymmetric fluorination has been restricted to α,β-unsaturated carbonyl compounds that can transform into metal enolates, and only two literature examples of enantioselective fluorinations of aryl alkenes. Herein, enantioselective methods for both deuteration and fluorination are described. Regio- and enantioselective hydrodeuteration of the π-bond of aryl alkenes was successfully achieved using a chiral Cu−H catalyst with a protic D-source. Molecular rotational resonance (MRR) spectroscopy was utilized as a novel analytical method for determining %ee, absolute stereochemistry, and identifying isotopomers and isotopologues. This substrate scope includes various aromatic and heteroaromatic alkenes with excellent yields and high enantioselectivities. By substituting the protic D-source for Selectfluor, an electrophilic fluorinating reagent, enantioselective fluorination was also achieved. Optimization of the catalytic conditions will reveal the feasibility of achieving high enantioselectivities and yields. In this work, my contributions to both the deuteration and fluorination projects is described.

Purchased from AmBeed: 1445-91-6

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Product Details of (S)-(-)-Phenylethanol

CAS No. :1445-91-6
Formula : C8H10O
M.W : 122.16
SMILES Code : C[C@H](O)C1=CC=CC=C1
Synonyms :
(S)-(-)-1-Phenylethanol; (S)-1-Phenylethanol
MDL No. :MFCD00064264
InChI Key :WAPNOHKVXSQRPX-ZETCQYMHSA-N
Pubchem ID :443135

Safety of (S)-(-)-Phenylethanol

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H311-H315-H318
Precautionary Statements:P501-P264-P280-P361+P364-P332+P313-P302+P352+P312-P305+P351+P338+P310-P405
Class:8(6.1)
UN#:2922
Packing Group:

Application In Synthesis of (S)-(-)-Phenylethanol

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1445-91-6 ]

[ 1445-91-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 93222-42-5 ]
  • [ 98-86-2 ]
  • [ 1445-91-6 ]
  • [ 1517-69-7 ]
  • 2
  • [ 434-45-7 ]
  • [ 1445-91-6 ]
  • [ 10531-50-7 ]
  • [ 340-06-7 ]
  • [ 146801-19-6 ]
  • 3
  • [ 1445-91-6 ]
  • [ 151-10-0 ]
  • [ 85-27-8 ]
  • [ 106552-08-3 ]
  • 4
  • [ 1445-91-6 ]
  • [ 56844-12-3 ]
  • (S)-6-bromo-4-(1-phenylethoxy)thieno[2,3-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With caesium carbonate; In acetonitrile; for 24h;Inert atmosphere; Reflux; General procedure: 6-Bromo-4-chlorothieno[2,3-d]pyrimidine(5a) (200 mg, 0.802 mmol) was mixed with 1-phenylethanol (2a) (118 mg, 0.962 mmol), Cs2CO3( 313 mg, 0.962 mmol) and acetonitrile (2 mL). The reaction was then stirredunder nitrogen atmosphere at reflux and followed by GC. The mixture was cooledto rt, diluted with EtOAc (40 mL), washed with sat. aq. KHCO3 (20mL), water (2×20 mL) and brine (30 mL). The combined organic fractions weredried over Na2SO4 and concentrated in vacuum. Crudeproduct was absorbed onto Celite 545 and purified by silica gel columnchromatography (n-pentane/EtOAc,6/1). This gave 245 mg (0.730 mmol, 91%) of 6a as an off-white solid.
  • 5
  • [ 55589-47-4 ]
  • [ 1445-91-6 ]
  • [ 54010-75-2 ]
  • [ 1539-42-0 ]
  • [ 75-05-8 ]
  • C29H31N5OZn(2+) [ No CAS ]
 

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