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686271

Sigma-Aldrich

(S)-4-Chloro-α-methylbenzyl alcohol

95%

Synonym(s):

(S)-1-(4-Chlorophenyl)ethanol, (S)-4′-Chloro-1-phenylethanol

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About This Item

Linear Formula:
ClC6H4CH(CH3)OH
CAS Number:
99528-42-4
Molecular Weight:
156.61
MDL number:
MFCD06797296
UNSPSC Code:
12352101
PubChem Substance ID:
329761034
NACRES:
NA.22

assay

95%

form

liquid

optical activity

[α]20/D -48.0°, c = 1 in chloroform

refractive index

n20/D 1.544

density

1.175 g/mL at 25 °C

SMILES string

C[C@H](O)c1ccc(Cl)cc1

InChI

1S/C8H9ClO/c1-6(10)7-2-4-8(9)5-3-7/h2-6,10H,1H3/t6-/m0/s1

InChI key

MVOSNPUNXINWAD-LURJTMIESA-N

Application

(S)-4-Chloro-α-methylbenzyl alcohol can be used as a chiral building block in:
  • The enantioselective synthesis of (-)-(S,S)-clemastine.
  • The enantioselective and geometrically defined synthesis of chloro methylbenzyl pinacol boronic ester via lithiation−borylation methodology.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

>230.0 °F

flash_point_c

> 110 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Stereospecific conversion of alcohols into pinacol boronic esters using lithiation-borylation methodology with pinacolborane
Roesner S, et al.
Chemical Communications (Cambridge, England), 50(31), 4053-4055 (2014)
Anne M Fournier et al.
Organic letters, 12(10), 2222-2225 (2010-04-22)
The first enantioselective synthesis of the antihistamine agent clemastine, as its (S,S)-stereoisomer, has been achieved by ether formation between a proline-derived chloroethylpyrrolidine and an enantiomerically enriched tertiary alcohol. The tertiary alcohol was formed from the carbamate derivative of alpha-methyl-p-chlorobenzyl alcohol

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