183911

Sigma-Aldrich

Methyl 2-chloroacetoacetate

Linear Formula:
CH3COCH(Cl)CO2CH3
CAS Number:
Molecular Weight:
150.56
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

refractive index

n20/D 1.446 (lit.)

bp

137 °C (lit.)

mp

−33-−32.7 °C (lit.)

density

1.236 g/mL at 25 °C (lit.)

SMILES string

COC(=O)C(Cl)C(C)=O

InChI

1S/C5H7ClO3/c1-3(7)4(6)5(8)9-2/h4H,1-2H3

InChI key

GYQRIAVRKLRQKP-UHFFFAOYSA-N

Application

Methyl 2-chloroacetoacetate was used in one-pot synthesis of 2-arylimidazole-4-carboxylic acids. It was also used in synthesis of 3,5-disubstituted 1,2,4-triazoles.

Packaging

25 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3334

WGK Germany

WGK 3

Flash Point(F)

161.6 °F - closed cup

Flash Point(C)

72 °C - closed cup

'One-flask'synthesis to 3, 5-disubstituted 1, 2, 4-triazoles from aldehydes with hydrazonoyl hydrochlorides via 1, 3-dipolar cycloaddition.
Tseng W-C, et al.
Tetrahedron, 67(29), 5339-5345 (2011)
Joshua C Yoburn et al.
Organic letters, 7(17), 3801-3803 (2005-08-12)
A versatile, one-pot synthesis of 2-arylimidazole-4-carboxylic acids from arylamidines and methyl-2-chloroacetoacetate is described. The transformation is chemoselective, and reaction conditions are mild. Moreover, the flexibility of the strategy offers rapid access to two important classes of biaryl compounds, both 2-arylimidazoles...

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