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901233

Sigma-Aldrich

(2R)-2-Phenyl-3,4-dihydro-2H-pyrimido[2,1-b][1,3]benzothiazole

≥95%

Synonym(s):

(R)-2-Phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine, (R)-Homobenzotetramisole, Birman (R)-HBTM

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25 G
$40.20
100 G
$81.20

About This Item

Empirical Formula (Hill Notation):
C16H14N2S
CAS Number:
Molecular Weight:
266.36
MDL number:
UNSPSC Code:
12161600
NACRES:
NA.22

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Quality Level

assay

≥95%

form

powder or chunks

mp

145-147 °C

functional group

phenyl
thioether

storage temp.

2-8°C

SMILES string

C12=CC=CC=C1SC3=N[C@@H](C4=CC=CC=C4)CCN23

InChI

1S/C16H14N2S/c1-2-6-12(7-3-1)13-10-11-18-14-8-4-5-9-15(14)19-16(18)17-13/h1-9,13H,10-11H2/t13-/m1/s1

InChI key

ZMYZJAQMQBHNLH-CYBMUJFWSA-N

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1 of 4

This Item
MABS1118WH0055294M2F2055
Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

200

biological source

rabbit

biological source

mouse

biological source

mouse

biological source

mouse

shipped in

wet ice

shipped in

ambient

shipped in

dry ice

shipped in

dry ice

Gene Information

human ... FBXW7(55294)

Gene Information

human ... FBXW7(55294)

Gene Information

human ... FBXW7(55294)

Gene Information

human ... FBXW7(55294)
mouse ... Fbxw7(50754)

technique(s)

immunohistochemistry: suitable, western blot: suitable

technique(s)

western blot: suitable

technique(s)

immunohistochemistry (formalin-fixed, paraffin-embedded sections): suitable, indirect ELISA: suitable, western blot: 1-5 μg/mL

technique(s)

immunocytochemistry: 10-20 μg/mL using human A431 or HeLa cells, indirect ELISA: suitable, western blot: 5-10 μg/mL using human A431 cell extracts

application

This chiral isothiourea homobenzotetramisole ((R)-HBTM) developed by the Birman lab is an organocatalyst that has been used for kinetic resolution, determination of absolute configuration, and nucleophile-catalysed, Michael–aldol-b-lactonization (NCMAL). This same product was previously listed as L511730, and the complementary (S)-HBTM organocatalyst (900542) is also available.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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    Alexander J Wagner et al.
    The Journal of organic chemistry, 78(9), 4594-4598 (2013-04-19)
    A new implementation of the competing enantioselective conversion (CEC) method was developed to qualitatively determine the absolute configuration of enantioenriched secondary alcohols using thin-layer chromatography. The entire process for the method requires approximately 60 min and utilizes micromole quantities of
    Nicholas A Ahlemeyer et al.
    Organic letters, 18(14), 3454-3457 (2016-07-08)
    A novel, reagent-free catalytic transformation of α,β-unsaturated thioesters into 2-substituted thiochromenes has been developed, with carbon dioxide as the only byproduct. Amidine-based catalysts, particularly homobenzotetramisole and its analogues, achieve high enantioselectivities and yields in this process.
    Alexander S Burns et al.
    Organic letters, 19(11), 2953-2956 (2017-05-17)
    A method for determining the absolute configuration of β-chiral primary alcohols has been developed. Enantioenriched alcohols were acylated in the presence of either enantiomer of the enantioselective acylation catalyst HBTM, and the faster reaction was determined by measuring product conversion
    Matthew A Perry et al.
    Organic letters, 15(3), 472-475 (2013-01-18)
    A simple method for determining the absolute configuration of oxazolidinones, lactams, and their derivatives using kinetic resolution catalysts is described. The optically pure substrates were acylated using the (S)-HBTM and the (R)-HBTM catalyst, and the faster reaction was determined. An
    Beatrice Ranieri et al.
    The Journal of organic chemistry, 78(12), 6291-6296 (2013-05-22)
    A concise approach to the synthesis of homobenzotetramisole and derivatives is described. Our strategy features a one-pot acylation-cyclization of 2-aminobenzothiazole with α,β-unsaturated acid chlorides to afford annulated pyrimidones. Subsequent Grignard addition followed by acid-promoted dehydration and reduction provides good overall

    Articles

    We are proud to offer the isothiourea organocatalyst homobenzotetramisole (HBTM) as part of our asymmetric catalysis portfolio in both (R) and (S) enantiomeric forms.

    Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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