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414131

Sigma-Aldrich

1-Bromopinacolone

≥97%

Sinônimo(s):

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

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About This Item

Fórmula linear:
(CH3)3CCOCH2Br
Número CAS:
5469-26-1
Peso molecular:
179.05
Beilstein:
506485
Número CE:
226-794-0
Número MDL:
MFCD00000206
Código UNSPSC:
12352100
ID de substância PubChem:
24865895
NACRES:
NA.22

Nível de qualidade

200

Ensaio

≥97%

forma

liquid

índice de refração

n20/D 1.466 (lit.)

pb

188-194 °C (lit.)

pf

−10 °C (lit.)

densidade

1.331 g/mL at 25 °C (lit.)

grupo funcional

bromo
ketone

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

InChI

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

chave InChI

SAIRZMWXVJEBMO-UHFFFAOYSA-N

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Descrição geral

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.

Aplicação

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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

10 - Combustible liquids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

167.0 °F - closed cup

Ponto de fulgor (°C)

75 °C - closed cup

Equipamento de proteção individual

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificados de análise (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.
The Journal of biological chemistry, 257(23), 14087-14092 (1982-12-10)
1-Bromopinacolone, BrPin, acts initially as a reversible competitive inhibitor for acetylcholinesterase, KI = 0.18 mM in hydrolysis of acetylcholine. Unlike bromoacetone, with time it acts as an irreversible covalent inhibitor. BrPin has a hydrolytic half-life of 30 h at the
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
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