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Merck
CN

414131

1-Bromopinacolone

≥97%

Synonym(s):

1-Bromo-3,3-dimethyl-2-butanone, Bromomethyl tert-butyl ketone

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About This Item

Linear Formula:
(CH3)3CCOCH2Br
CAS Number:
5469-26-1
Molecular Weight:
179.05
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24865895
EC Number:
226-794-0
Beilstein/REAXYS Number:
506485
MDL number:
MFCD00000206

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Product Name

1-Bromopinacolone, ≥97%

InChI key

SAIRZMWXVJEBMO-UHFFFAOYSA-N

InChI

1S/C6H11BrO/c1-6(2,3)5(8)4-7/h4H2,1-3H3

SMILES string

CC(C)(C)C(=O)CBr

assay

≥97%

form

liquid

refractive index

n20/D 1.466 (lit.)

bp

188-194 °C (lit.)

mp

−10 °C (lit.)

density

1.331 g/mL at 25 °C (lit.)

functional group

bromo
ketone

storage temp.

−20°C

Quality Level

200

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Application

1-Bromopinacolone is the suitable reagent for the synthesis of a photolabile azido derivative of the kaurene oxidase inhibitor 1-(4- chlorophenyl)4,4-dimethyl-2-(1,2,4-triazol-1-yl) pentan-3-ol (paclobutrazol). It may be used as reagent in the synthesis of 2-t-butyl-6-benzoylimidazo[1,2-b]pyridazine.

General description

1-Bromopinacolone is an α-bromoketone-aldehyde. Coupling of 1-bromopinacolone with various aldehyde electrophiles catalyzed by SmI2 has been reported. It acts as reversible competitive inhibitor for acetylcholinesterase, during hydrolysis of acetylcholine.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

167.0 °F - closed cup

flash_point_c

75 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCBT6036
BCBC7504V
BCBC7504
1452204V
1452204

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Brian A Sparling et al.
Organic letters, 10(6), 1291-1294 (2008-02-28)
Highly substituted, very hindered enones were synthesized using a two-step procedure that utilizes a diiodosamarium-promoted Reformatsky-type coupling and dehydration using Martin sulfurane. Both alpha-chloro- and alpha-bromoketones were coupled with a variety of carbonyl nucleophiles to form the intermediate beta-hydroxyketones, occurring
Methyl imidazo [1,2-b] pyridazine-2-carbamates and related compounds as potential antifilarial agents
Mourad AE, et al.
Journal of Heterocyclic Chemistry, 29, 1583-1583 (1992)
D L Hallahan et al.
Plant physiology, 88(4), 1425-1429 (1988-12-01)
A photolabile azido derivative of the kaurene oxidase inhibitor 1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-l-yl) pentan-3-ol (paclobutrazol) has been synthesized for use as a photoaffinity labeling agent. The compound was tested as an inhibitor of the oxidation of ent-kaurene catalyzed by cell-free preparations from endosperm
S G Cohen et al.
Biochimica et biophysica acta, 997(3), 167-175 (1989-08-31)
1-Bromo-2-[14C]pinacolone, (CH3)3C14COCH2Br [( 14C]BrPin), was prepared from [1-14C]acetyl chloride and tert-butylmagnesium chloride with cuprous chloride catalyst, followed by bromination. It was examined as an active-site directed label for acetylcholinesterase (acetylcholine acetylhydrolase, EC 3.1.1.7) (AcChE). AcChE, isolated from Torpedo nobiliana, has
E Salih et al.
Biochimica et biophysica acta, 1208(2), 324-331 (1994-10-19)
To characterize the structure of the active site of acetylcholinesterase (AChE) from the electric organ of E. electricus, we identified sites of incorporation of two active-site affinity labels, [3H]diisopropyl fluorophosphate ([3H]DFP), and 1-bromo-2-[14C]pinacolone ([14C]BrPin). AChE was isolated, purified, inactivated and
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