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Sigma-Aldrich

2-Chloro-N-methoxy-N-methylacetamide

98%

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About This Item

Linear Formula:
ClCH2CON(OCH3)CH3
CAS Number:
67442-07-3
Molecular Weight:
137.56
MDL number:
MFCD00134232
UNSPSC Code:
12352100
PubChem Substance ID:
24862311
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

Assay

98%

form

solid

mp

39-41 °C (lit.)

functional group

amine
chloro

storage temp.

2-8°C

SMILES string

CON(C)C(=O)CCl

InChI

1S/C4H8ClNO2/c1-6(8-2)4(7)3-5/h3H2,1-2H3

InChI key

SCOJKGRNQDKFRP-UHFFFAOYSA-N

Related Categories

General description

2-Chloro-N-methoxy-N-methylacetamide is a Weinreb amide.[1]

Application

2-Chloro-N-methoxy-N-methylacetamide may be used in the preparation of:
  • 2-heptyl-3-hydroxy-4(1H)-quinolone (Pseudomonas quinolone signal or PQS) and structurally related 2-alkyl-4-quinolones having biological activity[1]
  • 2-(benzo[d]thiazol-2-ylsulfonyl)-N-methoxy-N-methylacetamide[2]
  • α-chloro-ketone, starting reagent for the one-pot synthesis of 2-heptyl-3-hydroxyl-4(1H)-quinolone (PQS), signalling molecule in the quorum sensing of Pseudomonas aeruginosa[3]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

219.2 °F - closed cup

Flash Point(C)

104 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT9316
MKCH1698
MKBW7565V
MKBT8845V
MKBQ8072V

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New Reagent for Convenient Access to the a, ?-Unsaturated N-Methoxy-N-methyl-amide Functionality by a Synthesis Based on the Julia Olefination Protocol.
Narayana Manjunath B, et al
European Journal of Organic Chemistry, 12, 2851-2855 (2006)
James T Hodgkinson et al.
Organic & biomolecular chemistry, 9(1), 57-61 (2010-10-23)
Expedient syntheses of Pseudomonas quinolone signal (PQS) and related structural analogues using microwave and flow methods are reported.
James T Hodgkinson et al.
Nature protocols, 7(6), 1184-1192 (2012-05-29)
An optimized procedure for the efficient preparation of 2-heptyl-3-hydroxy-4(1H)-quinolone (Pseudomonas quinolone signal or PQS) and a diverse range of structurally related 2-alkyl-4-quinolones with biological activity is presented. The two-step synthesis begins with the formation of α-chloro ketones by the coupling

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