Welcome to LookChem.com Sign In|Join Free

CAS

  • or

930-55-2

Post Buying Request

930-55-2 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

930-55-2 Usage

Description

N-Nitrosopyrrolidine (NPYR) is a nitrosamine compound that is used primarily as a research chemical and is not produced commercially. There is the possibility of generating NPYR after frying in dry-cured bacon. The major amine precursors to NPYR in cooked bacon are free proline in the adipose tissue and to a lesser extent, collagenous connective tissues. When proline peptides were heated with nitrite at pH 3.4, small amounts of NPYR were formed from all tested peptides. There are several potential sources of exposure of man to this group of potent carcinogens. Certain foods were thought to be derived from the interaction of nitrite with secondary amines in the food, either spontaneously or by the agency of bacteria. Recently the possibility that nitrosamines may be formed from secondary amines and nitrite in the gastrointestinal tract has been explored. The acid conditions that prevail in the human stomach favor the nitrosation of dimethylamine. In addition, at neutral pH, many secondary amines can be nitrosated by nitrite or nitrate in the presence of intestinal bacteria, or the cecal contents of the rat, and soluble enzymes which catalyze the N-nitrosation of several secondary amines have been extracted from two microorganisms. The rate of nitrosamine formation depends greatly on the basicity of the amine; the less basic amines such as diphenylamine and pyrrolidine are nitrosated far more readily than the strongly basic dimethylamine and diethylamine.

Chemical Properties

Different sources of media describe the Chemical Properties of 930-55-2 differently. You can refer to the following data:
1. Light-Yellow Oil
2. N-Nitrosopyrrolidine is a yellow liquid.

Uses

Different sources of media describe the Uses of 930-55-2 differently. You can refer to the following data:
1. One of the N-nitroso compounds (NOCs) implicated in human colon carcinogenesis, but the toxicological mechanisms involved have not been elucidated.
2. 1-Nitrosopyrrolidine is one of the N-nitroso compounds (NOCs) implicated in human colon carcinogenesis (1,2,3) but the toxicological mechanisms involved have not been elucidated. Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.

General Description

Yellow liquid found in certain food products and tobacco smoke. Probably a carcinogen.

Reactivity Profile

A cyclic nitrosamine. Nitrated organics, such as N-NITROSOPYRROLIDINE, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction.

Health Hazard

ACUTE/CHRONIC HAZARDS: Flammable.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by ingestion and subcutaneous routes. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also N-NITROSO COMPOUNDS.

Potential Exposure

N-Nitrosopyrrolidine is a cyclic nitrosamine and a research chemical. Not commercially produced in the U.S.

Carcinogenicity

N-Nitrosopyrrolidine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Environmental Fate

It is a yellow liquid at room temperature. It is totally soluble in water with solubility of 1.00×10+6 mg l-1 and also is soluble in organic liquids and lipids. Log Pow is -0.19 that expected to move readily from water to soil, sediment, or biota. According to Henry’s law constant 4.89×10-8 atmm3 mol-1 and vapor pressure 0.06 mmHg in 20 ℃, volatilization from water and solid surface is expected to be rapid and an important fate process.

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard Class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required liquid, n.o.s., Hazard Class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

Toxicity evaluation

2-OHTHF and several other reactive electrophilic intermediates can bind with proteins and form DNA adducts mainly with guanines.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Waste Disposal

Under 40 CFR 261.5 small quantity generators of this waste may qualify for partial exclusion from hazardous waste regulations. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

Check Digit Verification of cas no

The CAS Registry Mumber 930-55-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,3 and 0 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 930-55:
(5*9)+(4*3)+(3*0)+(2*5)+(1*5)=72
72 % 10 = 2
So 930-55-2 is a valid CAS Registry Number.
InChI:InChI=1/C4H8N2O/c7-5-6-3-1-2-4-6/h1-4H2

930-55-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Nitrosopyrrolidine

1.2 Other means of identification

Product number -
Other names N-NITROSOPYRROLIDINE

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:930-55-2 SDS

930-55-2Synthetic route

pyrrolidine
123-75-1

pyrrolidine

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

Conditions
ConditionsYield
With sulfuric acid; silica gel; sodium nitrite In dichloromethane at 20℃; for 0.166667h;98%
With cross-linked polyvinylpyrrolidone*N2O4; dinitrogen tetraoxide In dichloromethane at 20℃;98%
With toluene-4-sulfonic acid; sodium nitrite In dichloromethane at 20℃; for 0.0833333h; chemoselective reaction;97%
C6H12NO(1+)*CH3O4S(1-)
73722-93-7

C6H12NO(1+)*CH3O4S(1-)

A

pyrrolidine
123-75-1

pyrrolidine

B

1-pyrrolidinecarboxaldehyde
3760-54-1

1-pyrrolidinecarboxaldehyde

C

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

Conditions
ConditionsYield
With sodium nitrite In waterA n/a
B 70%
C n/a
pyrrolidine
123-75-1

pyrrolidine

bromonitromethane
563-70-2

bromonitromethane

A

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

B

formaldehyd
50-00-0

formaldehyd

Conditions
ConditionsYield
In acetonitrile at 70℃; for 168h;A 62%
B n/a
1,4-diaminobutane
110-60-1

1,4-diaminobutane

A

pyrrolidine
123-75-1

pyrrolidine

B

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

Conditions
ConditionsYield
With sodium nitroprusside at 20℃; Cyclization;A 50%
B n/a
pyrrolidine
123-75-1

pyrrolidine

A

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

B

fluoro-pyrrolidine
125227-85-2

fluoro-pyrrolidine

Conditions
ConditionsYield
With trifluoroamine oxide at -15℃; for 1.5h;A 20%
B 30%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

Conditions
ConditionsYield
With dinitrogen tetraoxide In tetrachloromethane 40 - 50 deg C, 20 deg C, 15 min;30%
With nitric acid; acetic anhydride 1.) 50 deg C, 30 min, 2.) room temp., 16 h;13%
O2-chloromethyl 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate
340728-86-1, 960231-74-7

O2-chloromethyl 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate

1-hydroxy-[3-(2-hydroxyethyl)-3-methyl]-1-triazene 2-oxide sodium salt
742081-66-9

1-hydroxy-[3-(2-hydroxyethyl)-3-methyl]-1-triazene 2-oxide sodium salt

A

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

B

N-(2-hydroxyethyl)-N-methyl-N-nitrosamine
26921-68-6

N-(2-hydroxyethyl)-N-methyl-N-nitrosamine

Conditions
ConditionsYield
With sodium carbonate In acetonitrile at 0 - 20℃; for 7h;A 30%
B 20%
Benzyl-[1-pyrrolidin-1-yl-meth-(E)-ylidene]-amine
62453-13-8

Benzyl-[1-pyrrolidin-1-yl-meth-(E)-ylidene]-amine

acetic acid
64-19-7

acetic acid

A

1-pyrrolidinecarboxaldehyde
3760-54-1

1-pyrrolidinecarboxaldehyde

B

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

C

Benzyl acetate
140-11-4

Benzyl acetate

D

benzyl formate
104-57-4

benzyl formate

E

benzyl nitrite
935-05-7

benzyl nitrite

F

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With cis-nitrous acid at 37℃; Product distribution; further products; time course;A 1.4%
B 23%
C 13%
D 6.5%
E 4%
F 6%
With cis-nitrous acid at 37℃; Product distribution; Mechanism; further products; time course;A 1.4%
B 23%
C 13%
D 6.5%
E 4%
F 6%
piperylin
25924-78-1

piperylin

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

Conditions
ConditionsYield
With perchloric acid; sodium nitrite In water at 100℃; for 2h; Product distribution; other reaction conditions;2.2%
With perchloric acid; sodium nitrite In water at 100℃; for 2h;2.2%
pyrrolidine
123-75-1

pyrrolidine

n-propyl nitrite
543-67-9

n-propyl nitrite

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

Conditions
ConditionsYield
With sodium perchlorate at 25℃; Rate constant;
pyrrolidine
123-75-1

pyrrolidine

n-propyl nitrite
543-67-9

n-propyl nitrite

A

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

B

propan-1-ol
71-23-8

propan-1-ol

Conditions
ConditionsYield
With sodium hydroxide In water at 25℃; Rate constant; Thermodynamic data; ΔH(excit.) and ΔS(excit.); var. solvent system and temp.;
pyrrolidine
123-75-1

pyrrolidine

n-Butyl nitrite
544-16-1

n-Butyl nitrite

A

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

B

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With sodium hydroxide In water at 25℃; Rate constant;
pyrrolidine
123-75-1

pyrrolidine

N-methyl-N-nitrosotoluene-p-sulfonamide
80-11-5

N-methyl-N-nitrosotoluene-p-sulfonamide

A

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

B

N-methyl-p-toluenesulfonylamide
640-61-9

N-methyl-p-toluenesulfonylamide

Conditions
ConditionsYield
With sodium bis(2-ethylhexyl)-sulfosuccinate In 2,2,4-trimethylpentane at 25℃; Rate constant; also in water;
In 1,4-dioxane; water at 25℃; Rate constant;
pyrrolidine
123-75-1

pyrrolidine

2-hydroxyethyl nitrite
70434-12-7

2-hydroxyethyl nitrite

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

Conditions
ConditionsYield
With sodium perchlorate at 25℃; Rate constant;
1-[N-(4-chloro-phenyl)-formimidoyl]-pyrrolidine
7549-99-7

1-[N-(4-chloro-phenyl)-formimidoyl]-pyrrolidine

A

1-pyrrolidinecarboxaldehyde
3760-54-1

1-pyrrolidinecarboxaldehyde

B

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

C

N-(4-chlorophenyl)formamide
2617-79-0

N-(4-chlorophenyl)formamide

D

4-chloro-aniline
106-47-8

4-chloro-aniline

E

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With cis-nitrous acid In acetic acid at 37℃; Product distribution; Mechanism;
pyrrolidine
123-75-1

pyrrolidine

S-nitroso-N-acetylpenicillamine
67809-83-0

S-nitroso-N-acetylpenicillamine

A

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

B

1-Amino-1-carboxy-2-methyl-propane-2-thiol anion
1060936-14-2

1-Amino-1-carboxy-2-methyl-propane-2-thiol anion

Conditions
ConditionsYield
With sodium hydroxide; ethylenediaminetetraacetic acid In water at 25℃; pH=11.57; Kinetics; Further Variations:; Reagents; Nitrosation;
1-nitropyrrolidine
3760-55-2

1-nitropyrrolidine

A

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

B

N2, N2O, CO2, CO

N2, N2O, CO2, CO

Conditions
ConditionsYield
In acetone at 240℃; Rate constant; Thermodynamic data; decomposition in sealed tube;
pyrrolidine
123-75-1

pyrrolidine

A

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

B

1-nitropyrrolidine
3760-55-2

1-nitropyrrolidine

Conditions
ConditionsYield
With diethylenetriaminopentaacetic acid; peroxynitrite In phosphate buffer at 37℃; for 0.25h; pH=7.4; Product distribution; Further Variations:; pH-values;
pyrrolidine-1-d1
694-00-8

pyrrolidine-1-d1

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

Conditions
ConditionsYield
With 4-nitro-benzenesulfonic acid-(methyl-nitroso-amide) In cyclohexane at 25℃; Kinetics;
acetic acid
64-19-7

acetic acid

1-[1-(phenylimino)ethyl]pyrrolidine

1-[1-(phenylimino)ethyl]pyrrolidine

A

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

B

N-(acetyl)pyrrolidine
4030-18-6

N-(acetyl)pyrrolidine

C

Phenyl acetate
122-79-2

Phenyl acetate

D

phenol
108-95-2

phenol

Conditions
ConditionsYield
With sodium hydroxide; sodium nitrite In water at 25℃; pH=3.7; Kinetics;
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

10-(bromomethyl)-2,3,6-trimethoxyphenanthrene
585573-79-1

10-(bromomethyl)-2,3,6-trimethoxyphenanthrene

1-nitroso-2-[(2,3,6-trimethoxy-10-phenanthryl)methyl]pyrrolidine
1150647-87-2

1-nitroso-2-[(2,3,6-trimethoxy-10-phenanthryl)methyl]pyrrolidine

Conditions
ConditionsYield
Stage #1: N-nitrosopyrrolidine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 10-(bromomethyl)-2,3,6-trimethoxyphenanthrene In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
93%
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

N-aminopyrrolidine
16596-41-1

N-aminopyrrolidine

Conditions
ConditionsYield
With carbon dioxide; water; ammonium chloride; zinc at 35℃; under 1500.15 Torr; for 1.5h; Autoclave; Green chemistry;92%
With titanium(III) chloride In water for 1h; Ambient temperature;56%
With lithium aluminium tetrahydride In diethyl ether Reduction; Heating;
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

10-(bromomethyl)-2,3,5,6-tetramethoxyphenanthrene
1150647-85-0

10-(bromomethyl)-2,3,5,6-tetramethoxyphenanthrene

1-nitroso-2-[(2,3,5,6-tetramethoxy-10-phenanthryl)methy]pyrrolidine
1150647-88-3

1-nitroso-2-[(2,3,5,6-tetramethoxy-10-phenanthryl)methy]pyrrolidine

Conditions
ConditionsYield
Stage #1: N-nitrosopyrrolidine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 10-(bromomethyl)-2,3,5,6-tetramethoxyphenanthrene In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
90%
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

1-nitropyrrolidine
3760-55-2

1-nitropyrrolidine

Conditions
ConditionsYield
With potassium sulfate; potassium hydrogensulfate; potassium peroxomonosulfate; acetone In phosphate buffer pH=7 - 8.5;88%
With dihydrogen peroxide; trifluoroacetic anhydride In dichloromethane; water at 0℃; Product distribution / selectivity; Reflux;80%
With dihydrogen peroxide65%
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

9-(bromomethyl)-2,3,6,7-tetramethoxyphenanthrene
1150647-83-8

9-(bromomethyl)-2,3,6,7-tetramethoxyphenanthrene

1-nitroso-2-[(2,3,6,7-tetramethoxy-9-phenanthryl)methyl]pyrrolidine
1150647-86-1

1-nitroso-2-[(2,3,6,7-tetramethoxy-9-phenanthryl)methyl]pyrrolidine

Conditions
ConditionsYield
Stage #1: N-nitrosopyrrolidine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 9-(bromomethyl)-2,3,6,7-tetramethoxyphenanthrene In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
81%
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

pyrrolidine
123-75-1

pyrrolidine

Conditions
ConditionsYield
With isocyanate de chlorosulfonyle In diethyl ether for 10h; Ambient temperature;78%
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

[(5,10,15,20-tetraphenylporphyrinato)Fe(THF)2]ClO4
165605-12-9

[(5,10,15,20-tetraphenylporphyrinato)Fe(THF)2]ClO4

[(5,10,15,20-tetraphenylporphyrinato)Fe(N-nitrosopyrrolidine)2]ClO4
1226896-74-7

[(5,10,15,20-tetraphenylporphyrinato)Fe(N-nitrosopyrrolidine)2]ClO4

Conditions
ConditionsYield
In toluene byproducts: C4H8O; (N2, Schlenk) to a toluene-soln. of complex was added nitrosoamine-compound, the mixt. was stirred for 45 min; the solvent was reduced in vol., hexane was added, -22°C overnight, crystals were filtered, washed with hexane, dried in vac.;72%
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

1-indene
95-13-6

1-indene

A

(Z)-2-(pyrrolidin-1-yl)-2,3-dihydro-1H-inden-1-one oxime

(Z)-2-(pyrrolidin-1-yl)-2,3-dihydro-1H-inden-1-one oxime

B

(E)-2-(pyrrolidin-1-yl)-2,3-dihydro-1H-inden-1-one oxime

(E)-2-(pyrrolidin-1-yl)-2,3-dihydro-1H-inden-1-one oxime

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 23℃; for 48h; Irradiation; Inert atmosphere; Sealed tube; Overall yield = 72 percent; regioselective reaction;A 30%
B 42%
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

A

1-benzamidopyrrolidine
1134-70-9

1-benzamidopyrrolidine

B

N-pyrrolidino-dibenzamide
5455-25-4

N-pyrrolidino-dibenzamide

Conditions
ConditionsYield
With acetic acid; zinc Behandeln des Reaktionsprodukts mit Benzoylchlorid und wss. Natronlauge.;
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

amyl iodide
628-17-1

amyl iodide

2-Pentyl-N-nitrosopyrrolidin
74856-38-5

2-Pentyl-N-nitrosopyrrolidin

Conditions
ConditionsYield
With lithium diisopropyl amide 1.) 45 min, -78 deg C, THF, HMPT, 2.) -78 degC, 4 h; Yield given. Multistep reaction;
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

A

pyrrolidine
123-75-1

pyrrolidine

B

N-aminopyrrolidine
16596-41-1

N-aminopyrrolidine

Conditions
ConditionsYield
With titanium(III) chloride; ammonium acetate In water for 1h; Product distribution; Ambient temperature; variation of reaction conditions ( pH<1, pH=9.4 );A 0.1 % Chromat.
B 98 % Chromat.
With hydrogenchloride; zinc In water for 24h; Product distribution; Ambient temperature;A 3 % Chromat.
B 98 % Chromat.
With potassium hydroxide; aluminium In water for 24h; Product distribution; Ambient temperature;A 15 % Chromat.
B 87 % Chromat.
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

C4H9N2O(1+)*C4H8N2O*F6P(1-)
114552-67-9

C4H9N2O(1+)*C4H8N2O*F6P(1-)

Conditions
ConditionsYield
With hexafluorophosphoric acid In diethyl ether
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

C-nitrosopyrrolidine

C-nitrosopyrrolidine

Conditions
ConditionsYield
at -253.2℃; Irradiation;
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

N-nitroso-1-phosphonooxypyrrolidine

N-nitroso-1-phosphonooxypyrrolidine

Conditions
ConditionsYield
In phosphate buffer at 20 - 25℃; pH=7.4; phosphorylation; UV-irradiation;

930-55-2Relevant articles and documents

Versatile new reagent for nitrosation under mild conditions

Galloway, Jordan D.,Sarabia, Cristian,Fettinger, James C.,Hratchian, Hrant P.,Baxter, Ryan D.

supporting information, p. 3253 - 3258 (2021/05/06)

Here we report a new chemical reagent for transnitrosation under mild experimental conditions. This new reagent is stable to air and moisture across a broad range of temperatures and is effective for transnitrosation in multiple solvents. Compared with traditional nitrosation methods, our reagent shows high functional group tolerance for substrates that are susceptible to oxidation or reversible transnitrosation. Several challenging nitroso compounds are accessed here for the first time, including 15N isotopologues. X-ray data confirm that two rotational isomers of the reagent are configurationally stable at room temperature, although only one isomer is effective for transnitrosation. Computational analysis describes the energetics of rotamer interconversion, including interesting geometry-dependent hybridization effects.

Visible-Light-Induced Photoaddition of N-Nitrosoalkylamines to Alkenes: One-Pot Tandem Approach to 1,2-Diamination of Alkenes from Secondary Amines

Patil, Dilip V.,Si, Tengda,Kim, Hun Young,Oh, Kyungsoo

supporting information, p. 3105 - 3109 (2021/05/05)

The generation of aminium radical cation species from N-nitrosoamines is disclosed for the first time through visible-light excitation at 453 nm. The developed visible-light-promoted photoaddition reaction of N-nitrosoamines to alkenes was combined with the o-NQ-catalyzed aerobic oxidation protocol of amines to telescope the direct handling of harmful N-nitroso compounds, where the desired α-amino oxime derivatives were obtained in a one-pot tandem N-nitrosation and photoaddition sequence.

Substrate promiscuity of ortho-naphthoquinone catalyst: Catalytic aerobic amine oxidation protocols to deaminative cross-coupling and n-nitrosation

Kim, Hun Young,Oh, Kyungsoo,Si, Tengda

, p. 9216 - 9221 (2019/10/08)

ortho-Naphthoquinone-based organocatalysts have been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite species that in situ oxidized the amines to the corresponding N-nitroso compounds. Without using harsh oxidants in a stoichiometric amount, the present catalytic aerobic oxidation protocol utilizes the substrate promiscuity feature to provide a facile access to amine oxidation products under mild reaction conditions.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 930-55-2