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10905

Sigma-Aldrich

Chloroacetone

produced by Wacker Chemie AG, Burghausen, Germany, ≥96.0% (GC)

Synonym(s):

MCA, 1-Chloropropan-2-one, Chloro-2-propanone

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About This Item

Linear Formula:
ClCH2COCH3
CAS Number:
78-95-5
Molecular Weight:
92.52
Beilstein/REAXYS Number:
605369
EC Number:
201-161-1
MDL number:
MFCD00000936
UNSPSC Code:
12352100
PubChem Substance ID:
57646839
NACRES:
NA.22

grade

produced by Wacker Chemie AG, Burghausen, Germany

Quality Level

100

assay

≥96.0% (GC)

contains

~0.1% Drapex 39 as stabilizer

refractive index

n20/D 1.432 (lit.)

bp

120 °C (lit.)

solubility

H2O: soluble 10 parts
alcohol: miscible
chloroform: miscible
diethyl ether: miscible

density

1.162 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(=O)CCl

InChI

1S/C3H5ClO/c1-3(5)2-4/h2H2,1H3

InChI key

BULLHNJGPPOUOX-UHFFFAOYSA-N

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General description

Chloroacetone undergoes direct aldol reaction with 4-nitrobenzaldehyde catalyzed by L-proline amides. It reacts with carboxylic acids to form ester derivatives.

Application

Chloroacetone was used in microbial asymmetric reduction of chloracetone to synthesize chiral 1,2-epoxy propane. It was used in analysis of acids by gas chromatography. It was also used in the syntheis of methylthiazole derivatives by reacting with 1-((3-(naphtho[2,1-b]furan-2-yl)-1-phenyl-1H-pyrazol-4-yl) methylene)-2-phenylhydrazone.

Other Notes

prices for bulk quantities on request

signalword

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

95.0 °F - closed cup

flash_point_c

35 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Analysis of carboxylic acids by gas chromatography. Derivatisation using chloroacetone.
McCalley DV, et al.
Chromatographia, 18(6), 309-312 (1984)
Ashraf H F Abd El-Wahab et al.
Molecules (Basel, Switzerland), 16(1), 307-318 (2011-01-27)
Vilsmeier formylation of 2-(1-phenylhydrazonoethyl)naphtho[2,1-b]furan (2) gave 3-naphtho[2,1-b]furan-2-yl-1-phenyl-1H-pyrazole-4-carbaldehyde (3), which was reacted with C- and N-nucleophiles to afford naphthofuranpyrazol derivatives 4-8. Treatment of 2-[(3-(naphtho[2,1-b]furan-2-yl)-1-phenyl-1H-pyrazol-4-yl)methylene]-malononitrile (4a) with reactants having active hydrogen and Et₃N gave the corresponding pyrazoline, pyran and chromene addition product
Synthesis of optically pure 1, 2-epoxypropane by microbial asymmetric reduction of chloroacetone.
Weijers CAGM, et al.
Applied Microbiology and Biotechnology, 38(3), 297-300 (1992)
L-Proline amide-catalyzed direct asymmetric aldol reaction of aldehydes with chloroacetone.
He L, et al.
Tetrahedron, 62(2), 346-351 (2006)
Bridget W Alligood et al.
The Journal of chemical physics, 135(3), 034302-034302 (2011-07-27)
We use a combination of crossed laser-molecular beam scattering experiments and velocity map imaging experiments to investigate the three primary photodissociation channels of chloroacetone at 193 nm: C-Cl bond photofission yielding CH(3)C(O)CH(2) radicals, C-C bond photofission yielding CH(3)CO and CH(2)Cl
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