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362425

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

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.

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
  • 2-(benzo[d]thiazol-2-ylsulfonyl)-N-methoxy-N-methylacetamide
  • 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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

362425-25G:
362425-VAR:
362425-5G:
362425-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCH1698
MKBW7565V
MKBT8845V
MKBQ8072V
MKBL8786V

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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
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.
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)

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