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Sigma-Aldrich

2-Chloro-2,2-difluoroacetophenone

95%

Sinonimo/i:

2-Chloro-2,2-difluoro-1-phenylethanone, Chlorodifluoromethyl phenyl ketone, α-Chloro-α,α-difluoroacetophenone

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About This Item

Formula condensata:
C6H5COCF2Cl
Numero CAS:
384-67-8
Peso molecolare:
190.57
Beilstein:
2251448
Numero MDL:
MFCD00042123
Codice UNSPSC:
12352101
ID PubChem:
329768330
NACRES:
NA.22

Saggio

95%

Forma fisica

liquid

Impiego in reazioni chimiche

reaction type: C-C Bond Formation

Indice di rifrazione

n20/D 1.4954
n20/D 1.497 (lit.)

P. eboll.

94-96 °C/35 mmHg (lit.)

Densità

1.293 g/mL at 25 °C (lit.)
1.3178 g/mL at 25 °C

Stringa SMILE

FC(F)(Cl)C(=O)c1ccccc1

InChI

1S/C8H5ClF2O/c9-8(10,11)7(12)6-4-2-1-3-5-6/h1-5H
MNOONJNILVDLSW-UHFFFAOYSA-N

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Descrizione generale

2-Chloro-2,2-difluoroacetophenone is a difluorocarbene reagent, which is generally used in the synthesis of 2,2-difluoro enol silyl ethers, and gem -difluoromethene derived compounds.

Applicazioni

2-Chloro-2,2-difluoroacetophenone can be used:
  • As a reagent in the difluoromethylation of various phenols to yield aryl difluoromethyl ethers.
  • As a precursor in the Baylis-Hillman reaction of fluoroalkyl ketones to obtain chlorodifluoromethyl containing products.
  • As a substrate in the synthesis of propargyl alcohols using a novel ruthenium catalyst.

Reagent is an effective product for the synthesis of difluoromethylated phenols in the presence of mild base and aqueous solvent.

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

160.0 °F

Punto d’infiammabilità (°C)

71.1 °C

Certificati d'analisi (COA)

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2-Chloro-2, 2-difluoroacetophenone: a non-ODS-based difluorocarbene precursor and its use in the difluoromethylation of phenol derivatives
Zhang L, et al.
The Journal of Organic Chemistry, 71(26), 9845-9848 (2006)
Study of Fluorocarbonyls for the Baylis- Hillman Reaction
Ram Reddy MV, et al.
The Journal of Organic Chemistry, 67(15), 5382-5385 (2002)
2-Chloro-2,2-difluoroacetophenone
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2009)
Octahedral ruthenium complex with exclusive metal-centered chirality for highly effective asymmetric catalysis
Zheng Y, et al.
Journal of the American Chemical Society, 139(12), 4322-4325 (2017)
Laijun Zhang et al.
The Journal of organic chemistry, 71(26), 9845-9848 (2006-12-16)
A novel and non-ODS-based (ODS = ozone-depleting substance) preparation of 2-chloro-2,2-difluoroacetophenone (1) was achieved in high yield by using 2,2,2-trifluoroacetophenone as the starting material. Compound 1 was found to act as a good difluorocarbene reagent, which readily reacts with a

Contenuto correlato

Hu Group – Professor Product Portal

The major research interests of Prof. Jinbo Hu's lab include the development of new fluorination reagents and reactions, especially the difluoromethylation, difluoromethylenation, and monofluoromethylation methods.

Il team dei nostri ricercatori vanta grande esperienza in tutte le aree della ricerca quali Life Science, scienza dei materiali, sintesi chimica, cromatografia, discipline analitiche, ecc..

Contatta l'Assistenza Tecnica.