Piperidine, 1-nitroso-
- Name Piperidine, 1-nitroso-
- CAS 100-75-4
- Purity 99%
Product Details
Manufacturer supply good quality Piperidine, 1-nitroso- 100-75-4 with stock
- Molecular Formula: C5H10 N2 O
- Molecular Weight: 114.147
- Appearance/Colour: light yellow oily liquid
- Vapor Pressure: 0.103mmHg at 25°C
- Melting Point: 170℃ (decomposition)
- Refractive Index: 1.4933 (589.3 nm 19℃)
- Boiling Point: 229.8 ºC
- PKA: -3.18±0.20(Predicted)
- Flash Point: 92.8 ºC
- PSA： 32.67000
- Density: 1.06 g/mL(lit.)
- LogP: 1.09160
Piperidine, 1-nitroso-(Cas 100-75-4) Usage
|
Synthesis Reference(s) |
Chemical and Pharmaceutical Bulletin, 36, p. 459, 1988 DOI: 10.1248/cpb.36.459 |
|
Air & Water Reactions |
Water soluble. |
|
Reactivity Profile |
N-NITROSOPIPERIDINE may react with strong oxidizing agents, especially peroxyacids. . |
|
Health Hazard |
ACUTE/CHRONIC HAZARDS: When heated to decomposition N-NITROSOPIPERIDINE emits highly toxic fumes. |
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Fire Hazard |
Flash point data are not available for N-NITROSOPIPERIDINE, but N-NITROSOPIPERIDINE is probably combustible. |
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Safety Profile |
Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by ingestion, intravenous, and subcutaneous routes. An experimental teratogen. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also N-NITROSO COMPOUNDS. |
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Potential Exposure |
N-Nitrosopiperidine is found in some foods and tobacco smoke. Used as a research chemical. |
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Carcinogenicity |
N-Nitrosopiperidine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals. |
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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 |
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Incompatibilities |
Nitrated organics range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction. Reaction with aliphatic amines can release carcinogenic nitrosamines. 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. Light and UV may cause decomposition |
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Waste Disposal |
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. Under 40 CFR 261.5 small quantity generators of this waste may qualify for partial exclusion from hazardous waste regulations. |
|
Definition |
ChEBI: N-nitrosopiperidine is a nitrosamine that is piperidine in which the hydrogen attached to the nitrogen is replaced by a nitroso group. One of the many carcinogens detected in cigarette smoke, it is found in meat, cheese and spices that have been treated with the preservative sodium nitrite. It has a role as a carcinogenic agent, an apoptosis inducer, a mutagen and an environmental contaminant. It is a nitrosamine and a piperidine. |
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General Description |
Light yellow oil or liquid. May be a carcinogen. |
InChI:InChI=1/C5H10N2O/c8-6-7-4-2-1-3-5-7/h1-5H2
100-75-4 Relevant articles
The Use of Potassium/Sodium Nitrite as a Nitrosating Agent in the Electrooxidative N-Nitrosation of Secondary Amines
Chen, Zuxing,Gao, Meng,Lu, Cuifen,Ma, Chao,Ruan, Mengyao,Wang, Feiyi,Wang, Ying,Yang, Guichun,You, Shiqi
, p. 3289 - 3293 (2021)
We report herein on the electrochemical ...
Oxone-sodium nitrite mediated N-nitrosamines formation under mild conditions from secondary amines
Gaur, Pinki,Banerjee, Shaibal
, p. 2270 - 2279 (2019)
Herein, we report an efficient synthesis...
Synthesis and properties of 2-hydroxyethyl derivatives of methylene-bis(1-oxy-3, 3-dialkyl-1-triazene 2-oxides)
Smirnov,Nikitin,Gordeev,Pokhvisneva,Ternikova,Luk’yanov
, p. 2706 - 2711 (2015)
Synthetic approach to 2-hydroxyethyl der...
The mild N-nitrosation of secondary amines with trichloro nitromethane
Demir,Mahasneh,Aksoy,Gercek
, p. 2607 - 2611 (1992)
Reaction of trichloronitromethane with s...
THE OXIDATION OF HYDROXYLAMINE BY FREMY'S SALT. PREPARATION OF N-NITROSAMINES AND TETRAZENES
Tato, M. P. Vazquez,Castedo, Luis,Riguera, Ricardo
, p. 623 - 626 (1985)
Treatment of secondary amines with Fremy...
Silica chloride/NaNO2 as a novel heterogeneous system for the nitrosation of secondary amines under mild conditions
Zolfigol, Mohammad Ali,Shirini, Farhad,Ghorbani Choghamarani, Arash
, p. 1809 - 1813 (2002)
Secondary amines can be readily converte...
Synthesis of N,N-dialkylnitramines from secondary ammonium nitrates in liquid or supercritical carbon dioxide
Kuchurov,Fomenkov,Zlotin
, p. 2058 - 2062 (2009)
An efficient explosion-proof method was ...
The use of Nafion-H/NaNO2 as an efficient procedure for the chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions
Zolfigol, Mohammad Ali,Habibi, Davood,Mirjalili, BiBi Fatemeh,Bamoniri, Abdolhamid
, p. 3345 - 3349 (2003)
A combination of Nafion-H and sodium nit...
N-nitrosation of secondary amines using p-TSA-NaNO2 as a novel nitrosating agent under mild conditions
Borikar, Sanjay P.,Paul, Vincent
, p. 654 - 660 (2010)
A combination of p-toluenesulfonic acid ...
-
Makhova et al.
, (1978)
-
The reaction of peroxynitrite with morpholine (secondary amines) revisited: The overlooked hydroxylamine formation
Kirsch, Michael,Korth, Hans-Gert,Wensing, Angela,Lehnig, Manfred,Sustmann, Reiner,De Groot, Herbert
, p. 2399 - 2424 (2006)
The reaction of peroxynitrite/peroxynitr...
Nitrosation of Amines in Nonaqueous Solvents. 2. Solvent-Induced Mechanistic Changes
Garcia-Rio,Leis,Iglesias
, p. 4712 - 4720 (1997)
We studied the nitrosation of amines (py...
-
Lovejoy,Vosper
, p. 2325 (1968)
-
Alumina-methanesulfonic acid (AMA)/NaNO2 as an efficient procedure for the chemoselectivite N-nitrosation of secondary amines
Niknam, Khodabakhsh,Zolfigol, Mohammad Ali
, p. 2311 - 2319 (2006)
A combination of alumina/methanesulfonic...
Ph3P/Br2/n-Bu4NNO2 as an efficient system for the preparation of N-nitrosamines and azides
Iranpoor, Nasser,Firouzabadi, Habib,Nowrouzi, Najmeh
, p. 4242 - 4244 (2008)
The combination PPh3/Br2/n-Bu4NNO2 was d...
Kinetics of the Aminolysis and Hydrolysis of Alkyl Nitrites: Evidence for an Orbital Controlled Mechanism
Garcia-Santos,Calle,Gonzalez-Mancebo,Casado
, p. 997 - 1003 (1996)
The kinetics of the nitrosation of piper...
N-nitrosation of secondary amines with [NO+·Crown·H (NO3)2-]
Zolfigol,Zebarjadian,Chehardoli,Keypour,Salehzadeh,Shamsipur
, p. 3619 - 3620 (2001)
-
Silica sulfuric acid/NaNO2 as a novel heterogeneous system for the chemoselective N-nitrosation of secondary amines under mild conditions
Zolfigol, Mohammad Ali,Bamoniri, Abdolhamid
, p. 1621 - 1624 (2002)
Neat chlorosulfonic acid reacts with sil...
Molybdate sulfuric acid/NaNO2: A novel heterogeneous system for the N-nitrosation of secondary amines under mild conditions
Montazerozohori, Morteza,Karami, Bahador
, p. 2922 - 2926 (2006)
Wet molybdate sulfuric acid (=dioxo[bis(...
Nitrosation of Amines in Non-Aqueous Solvents - Difference between N-N=O and O-N=O Nitroso Donors
Garcia-Rio, Luis,Leis, Jose R.,Moreira, Jose A.,Serantes, David
, p. 614 - 622 (2004)
A kinetic study has been carried out on ...
N-nitrosation of secondary amines under mild and heterogeneous conditions
Zolfigol,Bagherzadeh,Choghamarani,Keypour,Salehzadeh
, p. 1161 - 1166 (2001)
A combination of potassium monopersulfat...
A combined experimental and DFT mechanistic study for the unexpected nitrosolysis of: N -hydroxymethyldialkylamines in fuming nitric acid
Zhang, Yu,Zou, Po,Han, Yingbin,Geng, Yongliang,Luo, Jun,Zhou, Baojing
, p. 19310 - 19316 (2018)
The reaction of dimorpholinomethane in f...
Comparative study of nitroso group transfer in colloidal aggregates: Micelles, vesicles and microemulsions
Garcia-Rio,Herves,Mejuto,Perez-Juste,Rodriguez-Dafonte
, p. 372 - 380 (2003)
A kinetic study was carried out on nitro...
Cyclodextrins as enzyme models in nitrosation and in acid-base- catalyzed reactions of alkyl nitrites
Iglesias, Emilia
, p. 13057 - 13069 (1998)
The widely studied cyclodextrin-mediated...
Thermal Decomposition of Nitramines: Dimethylnitramine, Diisopropylnitramine, and N-Nitropiperidine
Oxley, J. C.,Hiskey, M.,Naud, D.,Szekeres, R.
, p. 2505 - 2509 (1992)
Kinetics and activation parameters of th...
Transfer of the Nitroso Group in Water/AOT/Isooctane Microemulsions: Intrinsic and Apparent Reactivity
Garcia-Rio, Luis,Leis, J. Ramon,Pena, M. Elena,Iglesias, Emilia
, p. 3437 - 3442 (1993)
The kinetics of the transfer of the nitr...
Efficient and chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions with sodium nitrite and oxalic acid two hydrate
Zolfigol, Mohammad Ali
, p. 905 - 910 (1999)
Secondary amines can be quantitatively c...
-
Warthesen et al. ?
, p. 898,900 (1975)
-
Selective N-nitrosation of amines, N-alkylamides and N-alkylureas by N2O4 supported on cross-linked polyvinylpyrrolidone (PVP-N2O4)
Iranpoor, Nasser,Firouzabadi, Habib,Pourali, Ali-Reza
, p. 1591 - 1597 (2003)
N2O4 was supported on the cross-linked p...
Nitrosation of Amines in Nonaqueous Solvents, 1. Evidence of a Stepwise Mechanism
Garcia Rio,Leis,Iglesias
, p. 4701 - 4711 (1997)
We studied the nitrosation of piperidine...
-
Oae,S. et al.
, p. 913 - 917 (1978)
-
A screening procedure for the formation of nitroso derivatives and mutagens by drug-nitrite interaction
Takeda,Kanaya
, p. 3399 - 3404 (1982)
A general procedure for screening for th...
In situ generated amine as a Lewis base catalyst in the reaction of 3,7-dinitro-1,3,5,7-tetraazabicyclo[3.3.1]nonane in nitric acid: Experimental and DFT study
Zhang, Yu,Chi, Guoli,He, Ying,Xu, Zishuai,Zhang, Luyao,Luo, Jun,Zhou, Baojing
, (2019)
The problem how ammonium nitrate affects...
Iodide-catalyzed synthesis of N-nitrosamines via C-N cleavage of nitromethane
Zhang, Jie,Jiang, Jiewen,Li, Yuling,Wan, Xiaobing
, p. 11366 - 11372 (2013)
An iodide-catalyzed process to synthesiz...
Differences in the activity of neutral and ionized β-cyclodextrin on the nitrosation of amines by phenylpropyl nitrites
Iglesias
, p. 1025 - 1035 (2000)
The influence of β-cyclodextrin (β-CD) o...
Efficient procedure for chemoselective N-nitrosation of secondary amines with trichloromelamine-NaNO2
Bamoniri,Zolfigol,Mirjalili,Fallah
, p. 1393 - 1396 (2007)
A combination of trichloromelamine and s...
Fremy's Salt (Potassium Nitrosodisulphonate): A Nitrosating Reagent for Amines
Castedo, Luis,Riguera, Ricardo,Vazquez, M. Pilar
, p. 301 - 302 (1983)
Treatment of secondary and tertiary amin...
-
Lijinsky
, p. 384,388 (1966)
-
Trichloroisocyanuric acid/NaNo2 as a novel heterogeneous system for the N-nitrosation of N,N-dialkylamines under mild conditions
Zolfigol, Mohammad Ali,Choghamarani, Arash Ghorbani,Hazarkhani, Hassan
, p. 1002 - 1004 (2002)
A combination of trichloroisocyanuric ac...
-
Challis,Outram
, p. 707 (1978)
-
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...
Electrochemical Nonacidic N-Nitrosation/N-Nitration of Secondary Amines through a Biradical Coupling Reaction
Zhao, Ji-Ping,Ding, Lu-jia,Wang, Peng-Cheng,Liu, Ying,Huang, Min-Jun,Zhou, Xin-Li,Lu, Ming
supporting information, p. 5036 - 5043 (2020/07/13)
An acid-free N-nitrosation/nitration of ...
Optimization of biaryloxazolidinone as promising antibacterial agents against antibiotic-susceptible and antibiotic-resistant gram-positive bacteria
Wu, Yachuang,Ding, Xiudong,Yang, Yifeng,Li, Yingxiu,Qi, Yinliang,Hu, Feng,Qin, Mingze,Liu, Yajing,Sun, Lu,Zhao, Yanfang
, (2019/10/23)
We previously discovered a series of nov...
100-75-4 Process route
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626-67-5
N-methylcyclohexylamine
-
-
100-75-4
N-nitrosopiperidine
-
-
50-00-0,30525-89-4,61233-19-0
formaldehyd
| Conditions | Yield |
|---|---|
|
With
potassium nitrososulfonate; sodium carbonate;
|
20%
|
-
-
110-89-4
piperidine
-
-
80-11-5
N-methyl-N-nitrosotoluene-p-sulfonamide
-
-
100-75-4
N-nitrosopiperidine
-
-
640-61-9
N-methyl-p-toluenesulfonylamide
| Conditions | Yield |
|---|---|
|
With
sodium bis(2-ethylhexyl)-sulfosuccinate;
In
2,2,4-trimethylpentane;
at 25 ℃;
Rate constant;
also in water;
|
|
|
In
ethanol; water;
Rate constant;
Kinetics;
transnitrosation reaction; further secondary amines; effect of alcohol concentration;
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100-75-4 Upstream products
-
110-89-4
piperidine
-
6091-45-8
piperidinium nitrate
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108-24-7
acetic anhydride
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20591-07-5
piperidine; nitrite
100-75-4 Downstream products
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2213-43-6
1-Aminopiperidine
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110-89-4
piperidine
-
880-09-1
di(N-piperidinyl)methane
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1055-23-8
9,9'-bianthracene
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