Conditions | Yield |
---|---|
With hydrogenchloride | 37.1 g |
4-amino-2-ethylsulfanylpyrimidine-5-carboxylic acid metoxymethylamide
1-bromo-4,5-difluoro-2-methoxybenzene
A
(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
C
N,O-dimethylhydroxylamine*hydrochloride
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride In tetrahydrofuran; toluene at 0℃; Inert atmosphere; |
N,O-dimethylhydroxylamine*hydrochloride
Conditions | Yield |
---|---|
Stage #1: N-methoxy-N-methylbenzenesulfonamide With iodine; magnesium In methanol for 0.5h; Sonication; Stage #2: With hydrogenchloride In water pH=1; | 46% |
B
N,O-dimethylhydroxylamine*hydrochloride
phenylacetic acid
N,O-dimethylhydroxylamine*hydrochloride
N-methoxy-N-methyl-2-phenylacetamide
Conditions | Yield |
---|---|
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
N,O-dimethylhydroxylamine*hydrochloride
2-(1H-indol-3-yl)-N-methoxy-N-methyl-acetamide
Conditions | Yield |
---|---|
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
N,O-dimethylhydroxylamine*hydrochloride
tert-butyl (S)-1-(N-methoxy-N-methylcarbamoyl)-2-methylpropylcarbamate
Conditions | Yield |
---|---|
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
N,O-dimethylhydroxylamine*hydrochloride
N-(tert-butoxycarbonyl)-L-isoleucine N'-methoxy-N'-methylamide
Conditions | Yield |
---|---|
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
N,O-dimethylhydroxylamine*hydrochloride
N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide
Conditions | Yield |
---|---|
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 dichloromethane | 100% |
L-N-Boc-Ala
N,O-dimethylhydroxylamine*hydrochloride
tert-butyl {(S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate
Conditions | Yield |
---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane | 100% |
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
N,O-dimethylhydroxylamine*hydrochloride
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
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
(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
Conditions | Yield |
---|---|
With 2-(6-chloro-1H-benzotriazole-1-yl)21,1,3,3-tetramethylaminiumhexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane | 100% |
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
N,O-dimethylhydroxylamine*hydrochloride
(9H-fluoren-9-yl)methyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate
Conditions | Yield |
---|---|
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
N,O-dimethylhydroxylamine*hydrochloride
N-Methoxy-N-methyl 2(S)-(tert-butoxycarbonylamino) hexanamide
Conditions | Yield |
---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane | 100% |
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
Fmoc-Lys(tert-butoxycarbonyl)
(S)-N-α-(fluorenylmethyloxycarbonyl)-N-ε-(tert-butyloxycarbonyl)-lysine N-methoxy-N-methylamide
Conditions | Yield |
---|---|
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-formamide | 98% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane | 96% |
2-furancarbonyl chloride
N,O-dimethylhydroxylamine*hydrochloride
N-methoxy-N-methyl-2-furancarboxamide
Conditions | Yield |
---|---|
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
N,O-dimethylhydroxylamine*hydrochloride
N-methoxy-N-methyl-3-methylthiophene-2-carboxamide
Conditions | Yield |
---|---|
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
(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester
(S)-3-(tert-butyldiphenylsilyloxy)-N-methoxy-N,2-dimethylpropanamide
Conditions | Yield |
---|---|
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
4-fluorobenzoyl chloride
4-fluoro-N-methoxy-N-methylbenzamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 0.5h; | 100% |
With triethylamine In dichloromethane | 100% |
With triethylamine In dichloromethane at 0 - 18℃; for 16.5h; Inert atmosphere; | 99% |
3-(tert-butyloxycarbonylamino)propionic acid
N,O-dimethylhydroxylamine*hydrochloride
[2-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
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
N,O-dimethylhydroxylamine*hydrochloride
5-Methyl-benzofuran-2-carboxylic acid methoxy-methyl-amide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 0.5h; Ambient temperature; | 100% |
N,O-dimethylhydroxylamine*hydrochloride
Heptanoic acid chloride
heptanoic acid N,O-dimethylhydroxyamide
Conditions | Yield |
---|---|
With pyridine | 100% |
With pyridine In dichloromethane at 20℃; for 1h; | 93% |
With TEA In dichloromethane | 92% |
N,O-dimethylhydroxylamine*hydrochloride
N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid
tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate
Conditions | Yield |
---|---|
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
3-(tert-butyldimethylsilanyloxy)-4,4-dimethyldihydro-2(3H)-furan-2-one
(R)-2-(tert-butyldimethylsilyloxy)-4-hydroxy-N-methoxy-N,3,3-trimethylbutanamide
Conditions | Yield |
---|---|
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% |
The IUPAC name of N,O-Dimethylhydroxylamine hydrochloride is N-methoxymethanamine hydrochloride. With the CAS registry number 6638-79-5, it is also named as Methanamine, N-methoxy-, hydrochloride; (Methoxyamino)methanhydrochlorid. The product's categories are API intermediates, amination, hydroxylamines, hydroxylamines (N-substituted), hydroxylamines (O-substituted), synthetic organic chemistry, active esters/additives, coupling and synthetic reagents. Furthermore, it is white to off-white crystals or crystalline powder which is soluble in water.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.11; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.04; (4)ACD/LogD (pH 7.4): 0.11; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 23.11; (7)ACD/KOC (pH 7.4): 27.16; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Enthalpy of Vaporization: 25.19 kJ/mol; (12)Vapour Pressure: 1710 mmHg at 25°C; (13)Rotatable Bond Count: 1; (14)Exact Mass: 97.029442; (15)MonoIsotopic Mass: 97.029442; (16)Topological Polar Surface Area: 21.3; (17)Heavy Atom Count: 5.
Uses of N,O-Dimethylhydroxylamine hydrochloride: It is used in pharmaceutical and pesticide synthesis. And it is also used in organic synthesis. For example: It can react with diketene to get N-methoxy-N-methyl-3-oxo-butyramide. This reaction needs reagent NEt3 and solvent toluene and methanol at temperature of 0-5°C. The reaction time is 30 min. The yield is 86%.
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin, so people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.
People can use the following data to convert to the molecule structure.
1. SMILES: Cl.O(NC)C;
2. InChI: InChI=1/C2H7NO.ClH/c1-3-4-2;/h3H,1-2H3;1H.
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