N,O-Dimethylhydroxylamine hydrochloride, 98%, Thermo Scientific Chemicals
N,O-Dimethylhydroxylamine hydrochloride, 98%, Thermo Scientific Chemicals
Thermo Scientific Chemicals

N,O-Dimethylhydroxylamine hydrochloride, 98%, Thermo Scientific Chemicals

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100 g
5 g
25 g
Catalog number A17469.22
also known as A17469-22
Price (USD)/ Each
275.65
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306.00 
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Quantity:
100 g
Request bulk or custom format
Price (USD)/ Each
275.65
Online exclusive
306.00 
Save 30.35 (10%)
Add to cart
N,O-Dimethylhydroxylamine hydrochloride, 98%, Thermo Scientific Chemicals
Catalog numberA17469.22
Price (USD)/ Each
275.65
Online exclusive
306.00 
Save 30.35 (10%)
-
Add to cart
Chemical Identifiers
CAS6638-79-5
SpecificationsSpecification SheetSpecification Sheet
FormCrystalline powder
Melting Point (clear melt)110-117?C
Assay (Titration ex Chloride)≥97.5 to ≤102.5%
Water Content (Karl Fischer Titration)<1.0%
Appearance (Color)White to pale cream
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N,O-Dimethylhydroxylamine hydrochloride is used as a reagent in the preparation of 2-acyloxazoles from 2-oxazolemagnesium chloride and N-methoxy-N-methyl-3-oxo-butyramide from diketene. It is also used in amide coupling reactions to form Weinreb amides, which are useful in the Weinreb ketone synthesis. In addition, it is used in the preparation of an inhibitor of the NLS-derived BC peptides.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
N,O-Dimethylhydroxylamine hydrochloride is used as a reagent in the preparation of 2-acyloxazoles from 2-oxazolemagnesium chloride and N-methoxy-N-methyl-3-oxo-butyramide from diketene. It is also used in amide coupling reactions to form Weinreb amides, which are useful in the Weinreb ketone synthesis. In addition, it is used in the preparation of an inhibitor of the NLS-derived BC peptides.

Solubility
Soluble in water, dimethyl sulfoxide and methanol.

Notes
Hygroscopic. Store in a cool place. Incompatible with strong oxidizing agents.
RUO – Research Use Only

General References:

  1. The N-methoxy-N-methylamides (Weinreb amides) of carboxylic acids, N-protected amino acids and peptides are readily prepared from the acid chloride or mixed anhydride, or from the acid in the presence of 2-Chloro-1-methyl pyridinium iodide, A12820 : Synth. Commun., 25, 1277 (1995); or BOP Reagent ( 1H-Benzotriazol-1-yl oxytris(dimethyl amino) phosphonium hexafluorophosphate, A16140 ): J. Org. Chem., 61, 4999 (1996). The products undergo a number of useful transformations, e.g.:
  2. Reaction with Grignard or organolithium reagents gives ketones: Tetrahedron Lett., 22, 3815 (1981). Reduction with Lithium aluminum hydride, A18116 , gives the aldehyde: Synthesis, 676 (1983). For subsequent conversion of Boc-amino acid derived aldehydes and ketones to pyrrole derivatives, see: J. Org. Chem., 61, 4999 (1996). Coupling with alkyl acetoacetates gives ß δ -diketo esters: Tetrahedron Lett., 29, 6467 (1988). For conversion to ɑ -diketones or ɑ -keto esters, see: J. Org. Chem., 54, 3913 (1989).
  3. Burk, M.; Wilson, N.; Herzon, S. B. Multigram synthesis of 1-O-acetyl-3-O-(4-methoxybenzyl)-4-N-(9-fluorenylmethoxycarbonyl)-4-N-methyl-l-pyrrolosamine. Tetrahedron Lett. 2015, 56 (23), 3231-3234.
  4. Prosser, A. R.; Liotta, D. C. One-pot transformation of esters to analytically pure ketones: Methodology and application in process development. Tetrahedron Lett. 2015, 56 (23), 3005-3007.