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901233

(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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About This Item

Empirical Formula (Hill Notation):
C16H14N2S
CAS Number:
1316861-19-4
Molecular Weight:
266.36
UNSPSC Code:
12161600
NACRES:
NA.22
MDL number:
MFCD26793803
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Quality Level

100

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

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.

Other Notes


Technology Spotlight: Homobenzotetramisole (HBTM): A General Organocatalyst for Asymmetric Acylations

[1] Determination of the Absolute Configuration β-Chiral Primary Alcohols Using the Competing Enantioselective Conversion Method

[2] Asymmetric Catalytic Synthesis of Thiochromenes via an Acyl Transfer-Initiated Cascade

[3] Rapid assembly of complex cyclopentanes employing chiral, α, β-unsaturated acylammonium intermediates

[4] Determination of Absolute Configuration Using Kinetic Resolution Catalysts

[5] Kinetic Resolution of Secondary Alcohols Using Amidine-Based Catalysts

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV0374
MKCG0221

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Articles

Homobenzotetramisole (HBTM): A General Organocatalyst for Asymmetric Acylations

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

均苯并四咪唑（HBTM）：一种用于不对称酰基化的通用有机催化剂

作为我们不对称催化产品组合的一部分，我们很自豪地以（R）和（S）对映体形式提供异硫脲有机催化剂均苯并四咪唑（HBTM）。

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.
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
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
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Global Trade Item Number

SKUGTIN
901233-100MG04061835505371