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N-tert-butylhydroxylamine (NBHA) is a chemical compound that is extensively used in pharmaceutical applications and organic syntheses. It serves as an antioxidant, inhibitor, or stabilizer and is characterized by its colorless to pale yellow liquid appearance with a slight odor. The chemical formula for NBHA is (CH3)3CONH2. It is highly flammable, which requires specific storage conditions to prevent fire hazards. Additionally, NBHA has carcinogenic potential, and exposure can lead to skin, eye, and respiratory irritations, necessitating careful handling and the use of protective equipment.

16649-50-6

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16649-50-6 Usage

Uses

Used in Pharmaceutical Applications:
N-tert-butylhydroxylamine is used as an antioxidant, inhibitor, or stabilizer in the pharmaceutical industry to enhance the stability and effectiveness of various drugs. Its chemical properties allow it to protect against oxidative damage and improve the shelf life of pharmaceutical products.
Used in Organic Syntheses:
In the field of organic chemistry, N-tert-butylhydroxylamine is employed as a reagent or intermediate in the synthesis of various organic compounds. Its unique chemical structure enables it to participate in a range of reactions, contributing to the development of new molecules with potential applications in various industries.
Used in Antioxidant Formulations:
N-tert-butylhydroxylamine is used as an antioxidant in various formulations, such as in the production of plastics, rubber, and other materials. Its ability to prevent oxidative degradation helps to extend the lifespan and maintain the quality of these products.
Used in Research and Development:
In the scientific community, N-tert-butylhydroxylamine is utilized as a research tool to study the effects of antioxidants, inhibitors, and stabilizers on different chemical systems. Its versatile properties make it a valuable compound for exploring new chemical reactions and understanding the underlying mechanisms.

Check Digit Verification of cas no

The CAS Registry Mumber 16649-50-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,6,4 and 9 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 16649-50:
(7*1)+(6*6)+(5*6)+(4*4)+(3*9)+(2*5)+(1*0)=126
126 % 10 = 6
So 16649-50-6 is a valid CAS Registry Number.
InChI:InChI=1/C4H11NO.ClH/c1-4(2,3)5-6;/h5-6H,1-3H3;1H

16649-50-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name N-tert-butylhydroxylamine

1.2 Other means of identification

Product number -
Other names tert-butylhydroxylamine

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:16649-50-6 SDS

16649-50-6Synthetic route

2-Methyl-2-nitropropane
594-70-7

2-Methyl-2-nitropropane

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

Conditions
ConditionsYield
With acetic acid; zinc In ethanol at 10 - 20℃; for 3h;100%
With ammonia borane; gold on titanium oxide In ethanol at 20℃; for 0.666667h; Inert atmosphere;85%
Reduction;82%
(Z)-1-(1,1-dimethylathyl)-2-phthalimido-diazen-1-oxid
78661-66-2, 78661-76-4, 131229-52-2

(Z)-1-(1,1-dimethylathyl)-2-phthalimido-diazen-1-oxid

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

Conditions
ConditionsYield
With hydrazine hydrate at 5℃;95%
tert-butylamine
75-64-9

tert-butylamine

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

Conditions
ConditionsYield
With urea hydrogen peroxide adduct In diethyl ether at 20℃; for 1h; Catalytic behavior; Inert atmosphere;85%
With urea hydrogen peroxide adduct; sodium tungstate In diethyl ether at 20℃; for 6h;80%
4-hydroxy-3-ethoxybenzaldehyde
121-32-4

4-hydroxy-3-ethoxybenzaldehyde

1-Iodohexane
638-45-9

1-Iodohexane

A

α-(3-ethoxy-4-hexyloxyphenyl)-N-tert-butylnitrone
223649-89-6

α-(3-ethoxy-4-hexyloxyphenyl)-N-tert-butylnitrone

B

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

Conditions
ConditionsYield
With sodium hydroxide In ethanol; ethyl acetateA 57.2%
B n/a
diethyl ether
60-29-7

diethyl ether

ethyl nitrite
109-95-5

ethyl nitrite

tert-butylmagnesium chloride
677-22-5

tert-butylmagnesium chloride

A

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

B

N,N-di-tert-butylhydroxylamine
10531-39-2

N,N-di-tert-butylhydroxylamine

C

N-nitroso-N-tert-butylhydroxylamine
75005-93-5

N-nitroso-N-tert-butylhydroxylamine

Conditions
ConditionsYield
at -30℃;
2-tert-butyl-3-methoxy-oxaziridine
49680-37-7, 103202-91-1, 103202-96-6

2-tert-butyl-3-methoxy-oxaziridine

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

Conditions
ConditionsYield
(i) TsOH, CH2Cl2, H2O, benzene, (ii) NaOH; Multistep reaction;
tert-butylmagnesium chloride
677-22-5

tert-butylmagnesium chloride

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

Conditions
ConditionsYield
With nitrosylchloride In diethyl ether
(Z)-N-benzylidene-2-methylpropan-2-amine oxide
3376-24-7, 52392-70-8, 85225-53-2

(Z)-N-benzylidene-2-methylpropan-2-amine oxide

A

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With water at 25℃; Rate constant; hydrolysis;
N-tert-butyl-α-phenylnitrone
3376-24-7

N-tert-butyl-α-phenylnitrone

A

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With hydrogenchloride In water at 25℃; Rate constant; in presence of NaCl, n-butylammonium chloride, didodecyldimethylammonium chloride (DdDMAC), dodecylammonium chloride (DdAC); effect of colloidal phase;
With dodecylammonium chloride In hydrogenchloride at 25℃; Rate constant; pH = 1;
With water; sodium hydroxide pH=10 - 12; Kinetics; Reagent/catalyst; pH-value;
N-<(4-Methylphenyl)methylene>-2-methyl-2-propanamine N-oxide
40117-29-1, 127895-99-2

N-<(4-Methylphenyl)methylene>-2-methyl-2-propanamine N-oxide

A

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

B

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

Conditions
ConditionsYield
With water at 25℃; Rate constant; hydrolysis;
(Z)-N-tert-butyl-1-(4-methoxyphenyl)methanimine oxide
127896-00-8, 40117-28-0

(Z)-N-tert-butyl-1-(4-methoxyphenyl)methanimine oxide

A

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

B

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With water at 25℃; Rate constant; hydrolysis;
(Z)-N-4-fluorobenzylidene-t-butanamine oxide
85623-70-7, 127896-06-4

(Z)-N-4-fluorobenzylidene-t-butanamine oxide

A

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

B

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

Conditions
ConditionsYield
With water at 25℃; Rate constant; hydrolysis;
N-tert-butyl α-(4-ethylphenyl) nitrone
85623-71-8, 137957-42-7

N-tert-butyl α-(4-ethylphenyl) nitrone

A

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

B

4-ethylbenzylaldehyde
4748-78-1

4-ethylbenzylaldehyde

Conditions
ConditionsYield
With water at 25℃; Rate constant; hydrolysis;
2-tert-butyl-3-phenyl-oxazirane

2-tert-butyl-3-phenyl-oxazirane

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

Conditions
ConditionsYield
With sulfuric acid
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

Conditions
ConditionsYield
With sulfuric acid In methanol; water at 4℃; for 18h;
N-(tert-butyl)-O-benzoylhydroxylamine
51339-03-8

N-(tert-butyl)-O-benzoylhydroxylamine

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

Conditions
ConditionsYield
With potassium hydroxide at 20℃;
N-tertiary butyl hydroxyl amine acetate

N-tertiary butyl hydroxyl amine acetate

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

Conditions
ConditionsYield
With sodium hydrogencarbonate
2-Methyl-2-nitropropane
594-70-7

2-Methyl-2-nitropropane

A

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

B

tert-butylamine
75-64-9

tert-butylamine

Conditions
ConditionsYield
With 5% Pd/SiO2; hydrogen In isopropyl alcohol at 20℃; under 750.075 Torr; for 30h;A 89 %Spectr.
B 9 %Spectr.
N-(4-pyridylmethylene)-t-butylamine N,N'-dioxide
66893-81-0

N-(4-pyridylmethylene)-t-butylamine N,N'-dioxide

A

isonicotinaldehyde 1-oxide
7216-42-4

isonicotinaldehyde 1-oxide

B

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

Conditions
ConditionsYield
With water; sodium hydroxide at 40℃; pH=10 - 12; Kinetics; pH-value; Reagent/catalyst;
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

3-methallyloxy-propionaldehyde
76618-56-9

3-methallyloxy-propionaldehyde

N-tert-Butyl-6-methyl-4-oxa-6-hepten-1-imin-N-oxid
127355-32-2

N-tert-Butyl-6-methyl-4-oxa-6-hepten-1-imin-N-oxid

Conditions
ConditionsYield
With magnesium sulfate In chloroform for 24h; Ambient temperature;100%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

2-Methyl-4-thia-6-heptenal
127355-02-6

2-Methyl-4-thia-6-heptenal

N-tert-Butyl-2-methyl-4-thia-6-hepten-1-imin-N-oxid
127355-25-3

N-tert-Butyl-2-methyl-4-thia-6-hepten-1-imin-N-oxid

Conditions
ConditionsYield
With magnesium sulfate In chloroform for 24h; Ambient temperature;100%
1-nitroethylene
3638-64-0

1-nitroethylene

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

N-tert-Butyl-N-(2-nitroethyl)hydroxylamin

N-tert-Butyl-N-(2-nitroethyl)hydroxylamin

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;99%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

tert-butyl vinyl ketone
2177-30-2

tert-butyl vinyl ketone

tert-Butyl<2-(tert-butylhydroxyamino)ethyl>keton

tert-Butyl<2-(tert-butylhydroxyamino)ethyl>keton

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;99%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

methyl 2-bromoacrylate
4519-46-4

methyl 2-bromoacrylate

2-Brom-3-(tert-butylhydroxyamino)propionsaeure-methylester

2-Brom-3-(tert-butylhydroxyamino)propionsaeure-methylester

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;99%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

3-allylsulfanyl-propionaldehyde
22842-59-7

3-allylsulfanyl-propionaldehyde

N-tert-Butyl-4-thia-6-hepten-1-imin-N-oxid
127355-24-2

N-tert-Butyl-4-thia-6-hepten-1-imin-N-oxid

Conditions
ConditionsYield
With magnesium sulfate In chloroform for 24h; Ambient temperature;99%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

N-tert-Butyl-N-<2-(phenylsulfonyl)ethyl>hydroxylamin

N-tert-Butyl-N-<2-(phenylsulfonyl)ethyl>hydroxylamin

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;99%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

α-thiophenyl-acrylonitrile
2974-73-4

α-thiophenyl-acrylonitrile

3-(tert-Butylhydroxyamino)-2-(phenylthio)propiononitril

3-(tert-Butylhydroxyamino)-2-(phenylthio)propiononitril

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;99%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

(E)-8-Oxo-5-thia-2-octensaeure-tert-butylester
127355-04-8

(E)-8-Oxo-5-thia-2-octensaeure-tert-butylester

8-(tert-Butylimino)-5-thia-2-octensaeure-tert-butylester-N-oxid
127355-27-5

8-(tert-Butylimino)-5-thia-2-octensaeure-tert-butylester-N-oxid

Conditions
ConditionsYield
With magnesium sulfate In chloroform for 24h; Ambient temperature;99%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

3-Thia-5-heptenal
332837-04-4

3-Thia-5-heptenal

(5E,Z)-N-tert-Butyl-3-thia-5-hepten-1-imin-N-oxid
127355-07-1, 127355-08-2

(5E,Z)-N-tert-Butyl-3-thia-5-hepten-1-imin-N-oxid

Conditions
ConditionsYield
With magnesium sulfate In chloroform for 24h; Ambient temperature;99%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

2-(Phenylseleno)-2-propensaeure-methylester
75804-36-3

2-(Phenylseleno)-2-propensaeure-methylester

3-(tert-Butylhydroxyamino)-2-(phenylseleno)propionsaeure-mehylester

3-(tert-Butylhydroxyamino)-2-(phenylseleno)propionsaeure-mehylester

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;99%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

t-butylnitrite
917-95-3

t-butylnitrite

Conditions
ConditionsYield
With carbon nanotube-rhodium nanohybrid; air In chloroform; water at 20℃; for 12h;99%
With benzeneseleninic anhydride In tetrahydrofuran for 0.0166667h; Ambient temperature;96 % Spectr.
In water at 25℃; pH 8.8, controlled potential electrolysis, glassy carbon plate electrode; Yield given;
With sodium hypobromide at -10 - -5℃;
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

acrylonitrile
107-13-1

acrylonitrile

3-(tert-Butylhydroxyamino)propiononitril

3-(tert-Butylhydroxyamino)propiononitril

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;99%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

3-(tert-Butylhydroxyamino)propionsaeure-methylester
95503-43-8

3-(tert-Butylhydroxyamino)propionsaeure-methylester

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;99%
In diethyl ether Ambient temperature;84%
2-Hydroxy-4-methoxybenzaldehyde
673-22-3

2-Hydroxy-4-methoxybenzaldehyde

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

α-(2-hydroxy-4-methoxyphenyl)-N-tert-butylnitrone
255052-05-2

α-(2-hydroxy-4-methoxyphenyl)-N-tert-butylnitrone

Conditions
ConditionsYield
for 0.0583333h; Ionic liquid; Microwave irradiation;99%
72.9%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

C-(4-pyridyl)-N-(tert-butyl)nitrone
69396-90-3

C-(4-pyridyl)-N-(tert-butyl)nitrone

Conditions
ConditionsYield
for 0.0833333h; Ionic liquid; Microwave irradiation;99%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

vanillin
121-33-5

vanillin

C12H17NO3
938041-25-9

C12H17NO3

Conditions
ConditionsYield
for 0.0666667h; Ionic liquid; Microwave irradiation;99%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

4-((4-fluorobenzyl)oxy)benzaldehyde
56442-17-2

4-((4-fluorobenzyl)oxy)benzaldehyde

α-[4-(4-fluorobenzyloxy)phenyl]-N-tert-butylnitrone
223650-14-4

α-[4-(4-fluorobenzyloxy)phenyl]-N-tert-butylnitrone

Conditions
ConditionsYield
toluene-4-sulfonic acid98.5%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

5-chlorosalicyclaldehyde
635-93-8

5-chlorosalicyclaldehyde

α-(5-chloro-2-hydroxyphenyl)-N-tert-butylnitrone
255051-96-8

α-(5-chloro-2-hydroxyphenyl)-N-tert-butylnitrone

Conditions
ConditionsYield
With hydrogenchloride; silica gel In methanol98.5%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

1-vinylsulfonylpropane
20295-18-5

1-vinylsulfonylpropane

2-(N-tert-butylhydroxyamino)-1-(propylsulfonyl)ethane
126713-12-0

2-(N-tert-butylhydroxyamino)-1-(propylsulfonyl)ethane

Conditions
ConditionsYield
In dichloromethane at 0℃;98%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

(E)-3-(but-2-en-1-yloxy)propanal
127355-05-9

(E)-3-(but-2-en-1-yloxy)propanal

N-tert-Butyl-4-oxa-6-octen-1-imin-N-oxid
127355-33-3

N-tert-Butyl-4-oxa-6-octen-1-imin-N-oxid

Conditions
ConditionsYield
With magnesium sulfate In chloroform for 24h; Ambient temperature;98%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

α-(5-Bromo-2-hydroxyphenyl)-N-tert-butylnitrone
255052-12-1

α-(5-Bromo-2-hydroxyphenyl)-N-tert-butylnitrone

Conditions
ConditionsYield
for 0.0666667h; Ionic liquid; Microwave irradiation;98%
68.7%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

(Z)-N-tert-butyl-α-(pyridin-3-yl)-nitrone
1001387-10-5, 72877-60-2

(Z)-N-tert-butyl-α-(pyridin-3-yl)-nitrone

Conditions
ConditionsYield
With sodium acetate at 140℃; for 0.0666667h; microwave irradiation;97%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

C12H10F3NO2

C12H10F3NO2

C16H19F3N2O2

C16H19F3N2O2

Conditions
ConditionsYield
In ethanol at 20℃; for 18h;97%
In ethanol at 20℃; for 18h;97%
4-(n-Propylaminocarbonyloxy)-3,5-di-tert-butylbenzaldehyde

4-(n-Propylaminocarbonyloxy)-3,5-di-tert-butylbenzaldehyde

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

α-[4-(n-propylaminocarbonyloxy)-3,5-di-tert-butylphenyl]-N-tert-butylnitrone

α-[4-(n-propylaminocarbonyloxy)-3,5-di-tert-butylphenyl]-N-tert-butylnitrone

Conditions
ConditionsYield
In benzene96.6%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

methyl vinyl ketone
78-94-4

methyl vinyl ketone

<2-(tert-Butylhydroxyamino)ethyl>methylketon

<2-(tert-Butylhydroxyamino)ethyl>methylketon

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;96%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

thiopivaloyl (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphinan-2-yl) sulfide
463962-25-6

thiopivaloyl (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphinan-2-yl) sulfide

N-tert-butyl-O-thiopivaloylhydroxylamine
463962-35-8

N-tert-butyl-O-thiopivaloylhydroxylamine

Conditions
ConditionsYield
With triethylamine In chloroform for 0.25h;96%
With triethylamine96%
N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

p-butoxybenzaldehyde
5736-88-9

p-butoxybenzaldehyde

α-(4-Butoxyphenyl)-N-tert-butylnitrone
1097948-53-2

α-(4-Butoxyphenyl)-N-tert-butylnitrone

Conditions
ConditionsYield
96%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

N-tert-Butylhydroxylamine
16649-50-6

N-tert-Butylhydroxylamine

α-(2-hydroxy-5-methoxyphenyl)-N-tert-butylnitrone
255052-02-9

α-(2-hydroxy-5-methoxyphenyl)-N-tert-butylnitrone

Conditions
ConditionsYield
for 0.0833333h; Ionic liquid; Microwave irradiation;96%
68.1%

16649-50-6Relevant academic research and scientific papers

Oxidation of primary amines to N-monoalkylhydroxylamines using sodium tungstate and hydrogen peroxide-urea complex

Heydari, Akbar,Aslanzadeh, Saied

, p. 1223 - 1225 (2005)

The sodium tungstate-catalyzed (10 mol %) oxidation of primary amines with a urea-hydrogen peroxide complex (UHP) gives the corresponding N-monoalkylhydroxylamines, which are important biologically active compounds, in good to excellent yields. The method is applicable for a wide range of primary amines, including chiral benzylic amines, α-1,2-hydroxylamine and α-amino esters.

Das Hydrierprodukt eines β-Nitro-N-nitrosoamins ist kein 1,2,3-Triazolidin, sondern ein β-Hydroxylamino-N-nitrosoamin

Egger, Notker,Hoesch, Lienhard,Dreiding, Andre S.

, p. 2558 - 2562 (1982)

It is shown, by spectroscopy, that the product of catalytic hydrogenation of N,2-dimethyl-2-nitro-N-nitrosopropylamine (1) consists of a 5:1 mixture of (E)- and (Z)-2-hydroxylamino-N,2-dimethyl-N-nitrosopropylamine (3) and does not contain - as had been claimed - any 1,2-dihydroxy-1,2,3-triazolidine (2).Thus there is still no evidence for the existence of the N(OH)N(OH) functionality.The structure of intermediates on the way to 1 are also revised.

Ultrasonic promoted synthesis of Ag nanoparticle decorated thiourea-functionalized magnetic hydroxyapatite: A robust inorganic-organic hybrid nanocatalyst for oxidation and reduction reactions

Bahadorikhalili, Saeed,Arshadi, Hosein,Afrouzandeh, Zahra,Ma'mani, Leila

, p. 8840 - 8848 (2020/06/08)

In this research, ultrasonic synthesis is applied for the fabrication of a novel catalyst, based on immobilization of silver nanoparticles (AgNPs) on thiourea functionalized magnetic hydroxyapatite. A recoverable Ag nano-catalyst is constructed by decoration of AgNPs on the surface of thiourea modified magnetic hydroxyapatite. Magnetic hydroxyapatite is used as an organic-inorganic hybrid support for the catalyst. The organic-inorganic hybrid support is prepared by co-precipitation, followed by its surface modification through covalent functionalization of 1-(3,5-bis(trifluoromethyl)phenyl)-3-propyl)thiourea. The fabricated catalyst has been characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), powder X-ray diffraction (XRD), nuclear magnetic resonance (NMR), Fourier-transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA) and Brunauer-Emmett-Teller (BET) analysis. The nanoparticles are mostly tubular in shape and their particle sizes are smaller than 100 nm. This nanocatalyst shows efficient and robust catalytic activity in different reactions, including selective reduction of 4-nitrophenol (4NP) and oxidation of primary amines by applying NaBH4and urea hydrogen peroxide (UHP) as reagents, respectively. The catalyst shows good reusability in 10 sequential reaction runs.

TREATMENT OF DRUG RESISTANT GLIOMAS

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Page/Page column 21-22, (2019/04/16)

The present disclosure describes the use of 2,4-disulfonyl phenyl tert-butyl nitrone (2,4- ds-PBN) in the treatment of temozolomide drug resistant gliomas. The 2,4-ds-PBN may be used combined with other chemo- and radiotherapies and surgery, including temozolomide, to reduce glioma occurrence, recurrence, spread, growth, metastasis, and vascularization, and to inhibit development of temozolomide resistance.

Formation of radicals during heating lysine and glucose in solution with an intermediate water activity

Yin,Andersen,Thomsen,Skibsted,Hedegaard

, p. 643 - 650 (2013/08/23)

Heating glucose with lysine under alkaline conditions (pH 7.0-10.0) was found to take place with consumption of oxygen together with formation of brown-colored compounds. Highly reactive intermediary radicals were detected when lysine and glucose were heated at intermediate water activity at pH 7.0 and 8.0. The detection was based on initial trapping of highly reactive radicals by ethanol followed by spin trapping of 1-hydroxyethylradicals with α-(4-pyridyl N-oxide)-N-tert-butylnitrone (POBN) and Electron Spin Resonance (ESR) spectroscopy. The generation of reactive intermediary radicals from the Maillard reactions was favored by enhancing alkaline conditions (pH 8.0) and stimulated by presence of the transition metal ion Fe2+. The stability of the nitrone spin traps, N-tert-butyl-α-phenylnitrone and POBN was examined in buffered aqueous solutions within the pH range 1-12, and found to be less temperature dependent at acidic pH compared to alkaline conditions. A low rate (kobs) of hydrolysis of POBN was found at the used experimental conditions of 70°C and pH 7.0 and 8.0, which made this spin trap method suitable for the detection of radicals in the Maillard reaction system.

Facile reduction of nitroarenes into anilines and nitroalkanes into hydroxylamines via the rapid activation of ammonia· borane complex by supported gold nanoparticles

Vasilikogiannaki, Eleni,Gryparis, Charis,Kotzabasaki, Vasiliki,Lykakis, Ioannis N.,Stratakis, Manolis

supporting information, p. 907 - 911 (2013/05/08)

Gold nanoparticles supported on titania catalyse, even at a ppm loading level, the quantitative reduction of nitroarenes into anilines and nitroalkanes into alkylhydroxylamines by the ammonia× borane complex. No dehalohalogenation was seen in the case of chloro- or bromonitroarenes, while ester, cyano, or carboxylic acid functionalities also remain intact. The nitroarene to aniline reduction pathway does not require nitrosoarenes as intermediate products. Copyright

Synthesis and biological evaluations of novel apocynin analogues

Lu, Xiaoyu,Wan, Sainan,Jiang, Jie,Jiang, Xiaojian,Yang, Wenjing,Yu, Pei,Xu, Lipeng,Zhang, Zaijun,Zhang, Gaoxiao,Shan, Luchen,Wang, Yuqiang

experimental part, p. 2691 - 2698 (2011/06/27)

We have designed and synthesized a series of novel apocynin analogues, and evaluated their biological activity. Compound 10, an apocynin dimer analogue, compound 12, the lipoic acid (LA) and apocynin conjugate, were the most potent in protecting cells from lipopolysaccharide (LPS)-induced cytotoxicity, had significant activity scavenging ROS induced by LPS, and greatly decreased LPS-induced P67phox protein expression. SAR analysis suggests that modification of apocynin can increase its activity. Our results demonstrate that arming apocynin with a powerful antioxidant such as lipoic acid is a valid strategy to design new apocynin analogues with enhanced biological activity.

NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS

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Page/Page column 37; 77, (2010/04/23)

Disclosed herein are cannabinoid receptor ligands of formula (I) wherein A1, A5, Rx, X4, and z are as defined in the specification. Compositions comprising such compounds, and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

Selective synthesis of N-Alkyl hydroxylamines by hydrogenation of nitroalkanes using supported palladium catalysts

Takenaka, Yasumasa,Kiyosu, Takahiro,Choi, Jun-Chul,Sakakura, Toshiyasu,Yasuda, Hiroyuki

experimental part, p. 1166 - 1168 (2011/12/02)

The selective hydrogenation of nitroalkanes to the corresponding N-alkyl hydroxylamines is achieved at room temperature with excellent yields (up to 98 %), by using common supported palladium catalysts. The reaction temperature is key to the highly selective formation of the hydroxylamines, which proceeds smoothly in a H2 atmosphere without additives. The catalyst can be recycled up to five times.

Spin trapping of Au-H intermediate in the alcohol oxidation by supportedand unsupported gold catalysts

Conte, Marco,Miyamura, Hiroyuki,Kobayashi, Shu,Chechik, Victor

supporting information; experimental part, p. 7189 - 7196 (2009/09/30)

Electron paramagnetic resonance (EPR) spectroscopy and spin trapping were used to explore the mechanism of alcohol oxidation over gold catalysts. Reaction of secondary alcohols with supported and unsupported gold catalysts (e.g., Au/CeO2, polymer-Incarcerated Au nanoparticles,PPh 3-protected Au nanoparticles) In the presence of spin tr aps led to the formation of a hydrogen spin adduct. Using Isotope labeling, we confirmed that the hydrogen In the spin adduct originates from the cleavage of the C-H bond In the alcohol molecule. The formation of thehydrogen spin adduct most likely results from the abstraction of hydrog en from the Au surface by a spin trap. These results thus strongly suggest Intermediate formation of Au-H species during alcohol oxidation. The role of oxygen In this mechanism Is to restore the catalytic activity rather than oxidize alcohol. This was further confirmed by carrying out gold-catalyzed alcohol oxidation In the absence of oxygen, with nitroxidesas hydrogen abstractors. The support (e.g., metal oxides) can activate oxygen and act as an H abstractor from the gold surface and hence lead t o a faster recovery of the activity. Peroxyl radicals were also observedduring alcohol oxidation, consistent with a free-radical autoxidation m echanism. However, this mechanism Is likely to be a minor side reaction,which does not lead to the formation of an appreciable amount of oxidat ion products.

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