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6638-79-5

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6638-79-5 Usage

Chemical Properties

N,O-Dimethylhydroxylamine hydrochloride is white to off-white crystals or crystalline powder

Uses

Different sources of media describe the Uses of 6638-79-5 differently. You can refer to the following data:
1. N,O-Dimethylhydroxylamine hydrochloride is used for preparation of an inhibitor of the NLS-derived BC peptides.
2. 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.
3. Reagent for the preparation of Weinreb amides recently used in the synthesis of 2-acyloxazoles from 2-oxazolemagnesium chloride.

Check Digit Verification of cas no

The CAS Registry Mumber 6638-79-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,6,3 and 8 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 6638-79:
(6*6)+(5*6)+(4*3)+(3*8)+(2*7)+(1*9)=125
125 % 10 = 5
So 6638-79-5 is a valid CAS Registry Number.
InChI:InChI=1/C2H7NO.ClH/c1-3-4-2;/h3H,1-2H3;1H

6638-79-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (D1899)  N,O-Dimethylhydroxylamine Hydrochloride  >98.0%(T)

  • 6638-79-5

  • 25g

  • 180.00CNY

  • Detail
  • TCI America

  • (D1899)  N,O-Dimethylhydroxylamine Hydrochloride  >98.0%(T)

  • 6638-79-5

  • 100g

  • 520.00CNY

  • Detail
  • TCI America

  • (D1899)  N,O-Dimethylhydroxylamine Hydrochloride  >98.0%(T)

  • 6638-79-5

  • 500g

  • 1,790.00CNY

  • Detail
  • Alfa Aesar

  • (A17469)  N,O-Dimethylhydroxylamine hydrochloride, 98%   

  • 6638-79-5

  • 5g

  • 311.0CNY

  • Detail
  • Alfa Aesar

  • (A17469)  N,O-Dimethylhydroxylamine hydrochloride, 98%   

  • 6638-79-5

  • 25g

  • 818.0CNY

  • Detail
  • Alfa Aesar

  • (A17469)  N,O-Dimethylhydroxylamine hydrochloride, 98%   

  • 6638-79-5

  • 100g

  • 2305.0CNY

  • Detail
  • Aldrich

  • (D163708)  N,O-Dimethylhydroxylaminehydrochloride  98%

  • 6638-79-5

  • D163708-5G

  • 325.38CNY

  • Detail
  • Aldrich

  • (D163708)  N,O-Dimethylhydroxylaminehydrochloride  98%

  • 6638-79-5

  • D163708-25G

  • 1,248.39CNY

  • Detail
  • Aldrich

  • (D163708)  N,O-Dimethylhydroxylaminehydrochloride  98%

  • 6638-79-5

  • D163708-100G

  • 2,543.58CNY

  • Detail

6638-79-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N,O-Dimethylhydroxylamine hydrochloride

1.2 Other means of identification

Product number -
Other names DMH HYDROCHLORIDE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6638-79-5 SDS

6638-79-5Synthetic route

N,0-dimethylhydroxylamine
1117-97-1

N,0-dimethylhydroxylamine

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

Conditions
ConditionsYield
With hydrogenchloride37.1 g
4-amino-2-ethylsulfanylpyrimidine-5-carboxylic acid metoxymethylamide
741712-36-7

4-amino-2-ethylsulfanylpyrimidine-5-carboxylic acid metoxymethylamide

1-bromo-4,5-difluoro-2-methoxybenzene
202865-58-5

1-bromo-4,5-difluoro-2-methoxybenzene

A

(4-amino-2-ethylsulfanylpyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone
741713-37-1

(4-amino-2-ethylsulfanylpyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone

B

(4-amino-2-ethylsulfanylpyrimidin-5-yl)(4,5-difluoro-2-methoxyphenyl)methanone
741713-33-7

(4-amino-2-ethylsulfanylpyrimidin-5-yl)(4,5-difluoro-2-methoxyphenyl)methanone

C

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

Conditions
ConditionsYield
Stage #1: 1-bromo-4,5-difluoro-2-methoxybenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃;
Stage #2: 4-amino-2-ethylsulfanylpyrimidine-5-carboxylic acid metoxymethylamide In tetrahydrofuran; hexane at -78 - -35℃; for 2h;
trimethylaluminum
75-24-1

trimethylaluminum

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

Conditions
ConditionsYield
With hydroxylamine hydrochloride In tetrahydrofuran; toluene at 0℃; Inert atmosphere;
N-methoxy-N-methylbenzenesulfonamide

N-methoxy-N-methylbenzenesulfonamide

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

Conditions
ConditionsYield
Stage #1: N-methoxy-N-methylbenzenesulfonamide With iodine; magnesium In methanol for 0.5h; Sonication;
Stage #2: With hydrogenchloride In water pH=1;
46%
2-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-N-methoxy-N-methyl-acetamide

2-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-N-methoxy-N-methyl-acetamide

A

[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-acetic acid

[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-acetic acid

B

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

phenylacetic acid
103-82-2

phenylacetic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N-methoxy-N-methyl-2-phenylacetamide
95092-10-7

N-methoxy-N-methyl-2-phenylacetamide

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide 1) -10 deg C, 0.5 h, 2) r.t., 2.5 h;100%
With sodium hydroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; water at 20℃; for 3.5h; pH=4.5;100%
Stage #1: phenylacetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran for 1h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With trimethylamine In tetrahydrofuran; acetonitrile for 20h;
97%
indole-3-acetic acid
87-51-4

indole-3-acetic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

2-(1H-indol-3-yl)-N-methoxy-N-methyl-acetamide
132922-37-3

2-(1H-indol-3-yl)-N-methoxy-N-methyl-acetamide

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; for 1h;100%
Stage #1: indole-3-acetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;
97%
With triethylamine; dicyclohexyl-carbodiimide In dichloromethane for 2h; Ambient temperature;84%
t-Boc-L-valine
13734-41-3

t-Boc-L-valine

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

tert-butyl (S)-1-(N-methoxy-N-methylcarbamoyl)-2-methylpropylcarbamate
87694-52-8

tert-butyl (S)-1-(N-methoxy-N-methylcarbamoyl)-2-methylpropylcarbamate

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 4℃;100%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃;100%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;100%
N-(tert-butyloxycarbonyl)-L-isoleucine
13139-16-7

N-(tert-butyloxycarbonyl)-L-isoleucine

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N-(tert-butoxycarbonyl)-L-isoleucine N'-methoxy-N'-methylamide
87694-51-7

N-(tert-butoxycarbonyl)-L-isoleucine N'-methoxy-N'-methylamide

Conditions
ConditionsYield
Stage #1: N-(tert-butyloxycarbonyl)-L-isoleucine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With 4-methyl-morpholine In dichloromethane at 0 - 25℃; for 14h; Inert atmosphere;
100%
Stage #1: N-(tert-butyloxycarbonyl)-L-isoleucine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With 4-methyl-morpholine In dichloromethane at 25℃; for 14h; Inert atmosphere;
100%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 2h;91%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide
87694-50-6

N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide

Conditions
ConditionsYield
Stage #1: N-tert-butoxycarbonyl-L-leucine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With 4-methyl-morpholine In dichloromethane at 0 - 25℃; for 14h; Inert atmosphere;
100%
Stage #1: N-tert-butoxycarbonyl-L-leucine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With 4-methyl-morpholine In dichloromethane at 25℃; for 14h; Inert atmosphere;
100%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane100%
L-N-Boc-Ala
15761-38-3

L-N-Boc-Ala

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

tert-butyl {(S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate
146553-06-2, 87694-49-3

tert-butyl {(S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane100%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;100%
With 1,1'-carbonyldiimidazole In dichloromethane for 16h;99%
cyclohexanone-4-carboxylic acid ethyleneacetal
66500-55-8

cyclohexanone-4-carboxylic acid ethyleneacetal

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N-Methoxy-N-methyl-1,4-dioxaspiro<4.5>decane-8-carboxamide

N-Methoxy-N-methyl-1,4-dioxaspiro<4.5>decane-8-carboxamide

Conditions
ConditionsYield
Stage #1: cyclohexanone-4-carboxylic acid ethyleneacetal With 1,1'-carbonyldiimidazole In dichloromethane for 1.66667h; Large scale;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane for 24.25h; Large scale;
100%
With 1,1'-carbonyldiimidazole 1.) CHCl3, 2.) r.t., 18 h; Yield given. Multistep reaction;
Stage #1: cyclohexanone-4-carboxylic acid ethyleneacetal With 1,1'-carbonyldiimidazole In dichloromethane for 1.33333h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane for 24h;
N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

Nα-(t-butyloxycarbonyl)-Nω-(4-methoxy-2,3,6-trimethylbenzenesulphonyl)-L-arginine
102185-38-6

Nα-(t-butyloxycarbonyl)-Nω-(4-methoxy-2,3,6-trimethylbenzenesulphonyl)-L-arginine

N-α-(t-butyloxycarbonyl)-N'-ω'-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-L-arginine-N,O-dimethylhydroxyamide
142801-55-6

N-α-(t-butyloxycarbonyl)-N'-ω'-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-L-arginine-N,O-dimethylhydroxyamide

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2h;100%
With N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;93%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 4.5h;92%
N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

(2R)-3-(biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid
128779-47-5

(2R)-3-(biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid

(R)-α-<<(1,1-dimethylethoxy)carbonyl>amino>-N-methoxy-N-metyl<1,1'-biphenyl>-4-propanamide
162972-36-3

(R)-α-<<(1,1-dimethylethoxy)carbonyl>amino>-N-methoxy-N-metyl<1,1'-biphenyl>-4-propanamide

Conditions
ConditionsYield
With 2-(6-chloro-1H-benzotriazole-1-yl)21,1,3,3-tetramethylaminiumhexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 16h; Ambient temperature;97%
Stage #1: N,O-dimethylhydroxylamine*hydrochloride; (2R)-3-(biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid With 4-methyl-morpholine In dichloromethane at -15℃; for 0.0833333h; Inert atmosphere;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -15 - 20℃; for 5.5h; Inert atmosphere;
87%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Inert atmosphere;22.7 g
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

(9H-fluoren-9-yl)methyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate
156939-65-0

(9H-fluoren-9-yl)methyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;100%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;98%
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With trichloroacetonitrile; triphenylphosphine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
89%
Boc-Nle-OH
6404-28-0

Boc-Nle-OH

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N-Methoxy-N-methyl 2(S)-(tert-butoxycarbonylamino) hexanamide
104062-69-3

N-Methoxy-N-methyl 2(S)-(tert-butoxycarbonylamino) hexanamide

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane100%
Stage #1: Boc-Nle-OH With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -15℃; for 0.5h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at -15 - 20℃; for 17h;
94%
Stage #1: Boc-Nle-OH With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.25h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 20℃;
85%
N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

Fmoc-Lys(tert-butoxycarbonyl)
71989-26-9

Fmoc-Lys(tert-butoxycarbonyl)

(S)-N-α-(fluorenylmethyloxycarbonyl)-N-ε-(tert-butyloxycarbonyl)-lysine N-methoxy-N-methylamide
151145-21-0

(S)-N-α-(fluorenylmethyloxycarbonyl)-N-ε-(tert-butyloxycarbonyl)-lysine N-methoxy-N-methylamide

Conditions
ConditionsYield
Stage #1: Fmoc-Lys(tert-butoxycarbonyl) With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-d6-formamide at 0℃; for 0.5h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 3.5h;
100%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide98%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane96%
2-furancarbonyl chloride
527-69-5

2-furancarbonyl chloride

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N-methoxy-N-methyl-2-furancarboxamide
95091-92-2

N-methoxy-N-methyl-2-furancarboxamide

Conditions
ConditionsYield
With pyridine; sodium carbonate In tetrahydrofuran at 20℃; Inert atmosphere;100%
With triethylamine In dichloromethane Ambient temperature;92%
With potassium carbonate In 2-methyltetrahydrofuran; water at 0 - 20℃;92%
3-methylthenoyl chloride
61341-26-2

3-methylthenoyl chloride

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N-methoxy-N-methyl-3-methylthiophene-2-carboxamide
181868-50-8

N-methoxy-N-methyl-3-methylthiophene-2-carboxamide

Conditions
ConditionsYield
With triethylamine In chloroform at 0 - 20℃; Inert atmosphere;100%
With triethylamine In chloroform at 0 - 20℃;100%
With pyridine In dichloromethane for 2h; Ambient temperature; Yield given;
With triethylamine In chloroform at 0 - 20℃;28.8 g
N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester
95514-03-7

(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester

(S)-3-(tert-butyldiphenylsilyloxy)-N-methoxy-N,2-dimethylpropanamide
185996-35-4

(S)-3-(tert-butyldiphenylsilyloxy)-N-methoxy-N,2-dimethylpropanamide

Conditions
ConditionsYield
With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;100%
With isopropylmagnesium chloride In tetrahydrofuran at -20 - -5℃;99%
With trimethylaluminum In dichloromethane; toluene for 4h; Heating;60%
N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

4-fluorobenzoyl chloride
403-43-0

4-fluorobenzoyl chloride

4-fluoro-N-methoxy-N-methylbenzamide
116332-54-8

4-fluoro-N-methoxy-N-methylbenzamide

Conditions
ConditionsYield
With triethylamine In dichloromethane for 0.5h;100%
With triethylamine In dichloromethane100%
With triethylamine In dichloromethane at 0 - 18℃; for 16.5h; Inert atmosphere;99%
3-(tert-butyloxycarbonylamino)propionic acid
3303-84-2

3-(tert-butyloxycarbonylamino)propionic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

[2-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester
142570-56-7

[2-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: 3-(tert-butyloxycarbonylamino)propionic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -15℃; for 0.25h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at -15 - 20℃; for 16h;
100%
Stage #1: 3-(tert-butyloxycarbonylamino)propionic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane
99%
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -15 - 20℃; Inert atmosphere;95%
5-methyl-benzofuran-2-carbonyl chloride
90723-52-7

5-methyl-benzofuran-2-carbonyl chloride

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

5-Methyl-benzofuran-2-carboxylic acid methoxy-methyl-amide
194471-27-7

5-Methyl-benzofuran-2-carboxylic acid methoxy-methyl-amide

Conditions
ConditionsYield
With triethylamine In dichloromethane for 0.5h; Ambient temperature;100%
N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

Heptanoic acid chloride
2528-61-2

Heptanoic acid chloride

heptanoic acid N,O-dimethylhydroxyamide
104863-66-3

heptanoic acid N,O-dimethylhydroxyamide

Conditions
ConditionsYield
With pyridine100%
With pyridine In dichloromethane at 20℃; for 1h;93%
With TEA In dichloromethane92%
N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid
84358-13-4

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate
139290-70-3

tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride; N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid With triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 0.166667h;
Stage #2: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide)
Stage #3: With hydrogenchloride In water
100%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 48h;99%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;99%
N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

3-(tert-butyldimethylsilanyloxy)-4,4-dimethyldihydro-2(3H)-furan-2-one
133094-78-7

3-(tert-butyldimethylsilanyloxy)-4,4-dimethyldihydro-2(3H)-furan-2-one

(R)-2-(tert-butyldimethylsilyloxy)-4-hydroxy-N-methoxy-N,3,3-trimethylbutanamide
218434-95-8

(R)-2-(tert-butyldimethylsilyloxy)-4-hydroxy-N-methoxy-N,3,3-trimethylbutanamide

Conditions
ConditionsYield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride; 3-(tert-butyldimethylsilanyloxy)-4,4-dimethyldihydro-2(3H)-furan-2-one With isopropylmagnesium chloride In tetrahydrofuran at 0℃;
Stage #2: With water In tetrahydrofuran at 0℃; pH=7; aq. phosphate buffer;
100%
With trimethylaluminum In hexane; benzene for 1h; Ambient temperature;98%

6638-79-5Relevant articles and documents

PHENYLPYRAZOLE COMPOUND AND METHOD FOR CONTROLLING PLANT DISEASE

-

, (2021/10/22)

The present invention provides a method for controlling a plant disease which comprises applying a compound represented by formula (I) [wherein Z represents a C1-C6 chain hydrocarbon group and the like, R1 and R2 are identical to or different from each other and represent a hydrogen atom or a fluorine atom, and R3, R4, R5, R6 and R7 are identical to or different from each other and represent a C1-C6 chain hydrocarbon group and the like] to a plant or a soil, which has excellent control efficacies against plant diseases.

Deoxyalkoxyamination of Alcohols for the Synthesis of N-Alkoxy-N-alkylbenzenesulfonamides

Sun, Qi-An,Lu, Ze-Hai,Pu, Xiao-Qiu,Hu, Hui-Lian,Zhang, Jia-heng,Yang, Xian-Jin

supporting information, p. 3920 - 3927 (2018/07/31)

A novel protocol for the deoxyalkoxyamination of alcohols has been developed, using N-alkoxybenzenesulfonimide (NOSI) as both a sulfonyl transfer reagent and an alkoxyamine source, accessing a diverse range of N-alkoxy-N-alkylbenzenesulfonamides with excellent isolated yields. This method is characterized by metal-free reaction, scalability, and waste-balance. Chiral substrates are converted with excellent levels of stereochemical inversion. NOSI could be generated in situ during the reaction as a stable reagent if a three-component one-pot reaction was designed. Exploiting this approach to run intramolecular reactions offered various N-protected isoxazolidines. In addition, valuable O-alkyl hydroxylamines (or isoxazolidines) were obtained through a neutral strategy of desulfonylation of the products.

Studies on transannulation reactions across a nine-membered ring: The synthesis of natural product-like structures

Iqbal, Mudassar,Black, Richard J. G.,Winn, Joby,Reeder, Andrew T.,Blake, Alexander J.,Clarke, Paul A.

experimental part, p. 5062 - 5078 (2011/08/21)

A series of diverse natural product-like structures have been synthesised by the use of a number of novel transannulation reactions across a cyclononene ring. Transannular cyclisations through oxygen functionality have generated a number of bicyclo[5.3.1]systems containing bridged cyclic ethers and bicyclo[5.2.2]lactones, as well as a tetrahydrofuran-containing bridged analogue of hexacyclinic acid. An unprecedented Bronsted acid mediated transannular cyclisation between proximal carbons generated bicyclo[4.3.0] nonanes which form the core of the pinguisane and austrodorane families of sesquiterpenoids. In all cases the key factor that determined the mode of reactivity was the conformation of the nine-membered ring and the distance between the reacting centres. The Royal Society of Chemistry 2011.

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