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  • 26541-51-5 Structure
  • Basic information

    1. Product Name: N-NITROSOTHIOMORPHOLINE
    2. Synonyms: N-NITROSOTHIOMORPHOLINE;4-Nitrosothiomorpholine
    3. CAS NO:26541-51-5
    4. Molecular Formula: C4H8N2OS
    5. Molecular Weight: 132.18
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 26541-51-5.mol
  • Chemical Properties

    1. Melting Point: 35-37 °C
    2. Boiling Point: 303.8°Cat760mmHg
    3. Flash Point: 137.5°C
    4. Appearance: /
    5. Density: 1.183 (estimate)
    6. Vapor Pressure: 0.00163mmHg at 25°C
    7. Refractive Index: 1.6430 (estimate)
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: -5.00±0.20(Predicted)
    11. CAS DataBase Reference: N-NITROSOTHIOMORPHOLINE(CAS DataBase Reference)
    12. NIST Chemistry Reference: N-NITROSOTHIOMORPHOLINE(26541-51-5)
    13. EPA Substance Registry System: N-NITROSOTHIOMORPHOLINE(26541-51-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 26541-51-5(Hazardous Substances Data)

26541-51-5 Usage

Safety Profile

Questionable carcinogen with experimental carcinogenic data.Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx.

Check Digit Verification of cas no

The CAS Registry Mumber 26541-51-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,5,4 and 1 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 26541-51:
(7*2)+(6*6)+(5*5)+(4*4)+(3*1)+(2*5)+(1*1)=105
105 % 10 = 5
So 26541-51-5 is a valid CAS Registry Number.
InChI:InChI=1/C4H8N2OS/c7-5-6-1-3-8-4-2-6/h1-4H2

26541-51-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-nitrosothiomorpholine

1.2 Other means of identification

Product number -
Other names Morpholine,4-nitrosothio

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:26541-51-5 SDS

26541-51-5Relevant articles and documents

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.

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 the N?H bonds in secondary amines with Fe(NO3)3 ? 9H2O as the nitroso/nitro source through an electrocatalyzed radical coupling reaction was developed. Cyclic aliphatic amines and N-heteroaromatic compounds were N-nitrosated and N-nitrated, respectively, under mild conditions. Control and competition experiments, as well as kinetic studies, demonstrate that N-nitrosation and N-nitration involve two different radical reaction pathways involving N+ and N. radicals. Moreover, the electrocatalysis method enables the preferential activation of the N?H bond over the electrode and thus provides high selectivity for specific N atoms. Finally, this strategy exhibits a broad scope and provides a green and straightforward approach to generate useful N-nitroso/nitro compounds in good yields. (Figure presented.).

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 novel biaryloxazolidinone analogues bearing a hydrazone moiety with potent antibacterial activity. However, the most potent compound OB-104 exhibited undesirable chemical and metabolic instability. Herein, novel biaryloxazolidinone analogues were designed and synthesized to improve the chemical and metabolic stability. Compounds 6a-1, 6a-3, 14a-1, 14a-3 and 14a-7 showed significant antibacterial activity against the tested Gram-positive bacteria as compared to radezolid and linezolid. Further studies indicated that most of them exhibited improved water solubility and chemical stability. Compound 14a-7 had MIC values of 0.125–0.25 μg/mL against all tested Gram-positive bacteria, and showed excellent antibacterial activity against clinical isolates of antibiotic-susceptible and antibiotic-resistant bacteria. Moreover, it was stable in human liver microsome. From a safety viewpoint, it showed non-cytotoxic activity against hepatic cell and exhibited lower inhibitory activity against human MAO-A compared to linezolid. The potent antibacterial activity and all these improved drug-likeness properties and safety profile suggested that compound 14a-7 might be a promising drug candidate for further investigation.

Synthesis and antibacterial activity evaluation of novel biaryloxazolidinone analogues containing a hydrazone moiety as promising antibacterial agents

Wu, Yachuang,Ding, Xiudong,Ding, Liang,Zhang, Yongsheng,Cui, Lei,Sun, Lu,Li, Wei,Wang, Di,Zhao, Yanfang

, p. 247 - 258 (2018/09/18)

A series of linezolid analogues containing a hydrazone moiety were designed, synthesized and evaluated for their antibacterial activity. Most compounds exhibited more potent antibacterial activity against S.aureus, MRSA, MSSA, LREF and VRE pathogens as compared with linezolid and radezolid. Compounds 9a, 9c, 9f, 9g, 10m and 10t were more potent against tested clinical isolates of MRSA, MSSA, VRE and LREF as compared to linezolid. Compound 9a exhibited comparable activity with linezolid against human MAO-A for safety evaluation and showed moderate metabolism in human liver microsome. The most promising compound 9a showed remarkable antibacterial activity against S.aureus, MRSA, MSSA, LREF and VRE pathogens with MIC value of 0.0675 mg/mL, respectively, which was 15- to 30-fold more potent than linezolid.

THERAPEUTIC AGENT FOR CEREBRAL INFARCTION

-

, (2012/08/08)

The invention provides a therapeutic drug for ischemic stroke. The therapeutic drug has the formula (I) wherein each symbol is as defined herein, or a pharmacologically acceptable salt thereof, or a solvate thereof, as an active ingredient.

Reactivity of nitrogen nucleophiles towards S-nitrosopenicillamine

Munro, Andrew P.,Williams, D. Lyn H.

, p. 1989 - 1993 (2007/10/03)

We report the results of a kinetic study of the reactions of a number of nitrogen nucleophiles with the nitrosothiol S-nitrosopenicillamine (SPEN). The range of nucleophiles includes primary, secondary and tertiary aliphatic amines, together with hydrazine, hydroxylamine, azide ion, ammonia, semicarbazide, thiomorpholine and S-methylcysteine. Secondary amines form N-nitrosamines quantitatively. As expected, reaction occurs via the free base forms of the nucleophiles and consequently most of the reactions take place readily only at relatively high pH. Experiments were carried out with [nucleophile] ? [RSNO], and for many reactions, plots of the first order rate constant vs. [nucleophile] were linear. For ammonia and the primary amines, however, this plot tended to level off at high [nucleophile] and an explanation is offered involving the reversible formation of an inactive RSNO-amine complex, for which there is spectral evidence, in parallel with the main reaction. For the secondary amines there is a reasonably good Broensted plot with a β value of ~0.2. The much greater reactivities of S-methylcysteine and thiomorpholine, compared to those of primary amines and morpholine respectively are consistent with initial attack at the sulfur atom, followed by an internal rearrangement. Over the whole range of nucleophiles studied there is a reasonable correlation with the Ritchie N+ parameter, and not with the Pearson n scale. Comparisons are made with the corresponding reactions of alkyl nitrites and N-methyl-N-nitrosotoluene-p-sulfonamide (MNTS).

Reactivity of Nucleophilic Nitrogen Compounds towards the Nitroso Group

Garcia-Rio, Luis,Iglesias, Emilia,Leis, J. Ramon,Pena, M. Elena,Rios, Ana

, p. 29 - 37 (2007/10/02)

We discuss the reactivity of 43 nucleophilic nitrogen compounds towards the nitroso group of N-methyl-N-nitrosotoluene-p-sulfonamide (MNTS), and in some cases with alkyl nitrites.The series of nucleophiles considered is structurally very varied, includes members exhibiting the alpha effect, and covers 8 pKa units and a range of reactivities of almost five orders of magnitude.The values of solvent isotope effects and activation parameters have been measured and throw light on the structure of the transition states involved.Reactivities do not correlate well with thebasicity of the nucleophile, largely owing to the behaviour of primary amines, ammonia and nucleophiles with an alpha effect.Application of the curve crossing model suggests a relationship with vertical ionization potentials.The relationship with Ritchie's N+ scale is discussed, and interesting correlations with the reactivities of the same nucleophiles in various other chemical processes are noted.

Studies on Internal Nitroso Group Transfer. Nitrosation of Thiomorpholine

Coello, Adela,Meijide, Francisco,Tato, Jose Vazquez

, p. 1677 - 1680 (2007/10/02)

The kinetics of nitrosation of thiomorpholine have been studied under different experimantal conditions.At low nitrite concentration and high acidity the reaction rate is first order with respect to nitrite and thiomorpholine and independent of acidity.The results are interpreted through a mechanism in which the S-nitroso intermediate with a deprotonated amino group must acquire a boat conformation to facilitate the migration of the NO group from the sulphur to the nitrogen atom.The mechanism is supported by the low isotope effect observed when the reaction is studied in D2O.In the pH range 2.3-3.6 and high nitrite concentration, the reaction rate is second order with respect to nitrite, the accepted mechanism being the nitrosation of deprotonated thiomorpholine by dinitrogen trioxide.

ALPHA-MERCAPTOMETHYL-BENZENE PROPANAMIDES, PHARMACEUTICAL COMPOSITIONS AND USE

-

, (2008/06/13)

Novel α-mercaptomethyl-benzene propanamides of the formula STR1 wherein R 1 is selected from the group consisting of hydrogen and STR2 R 1 ' is selected from the group consisting of alkyl of 1 to 5 carbon atoms and aryl optionally substituted with at least one member of the group consisting of--OH,--NO 2, halogen and alkyl and alkoxy of 1 to 5 carbon atoms, X and X' are individually selected from the group consisting of hydrogen, alkyl and alkoxy of 1 to 5 carbon atoms,--OH, halogen and--CF 3, R 2 is selected from the group consisting of pyrrolidinyl, morpholinyl, piperidinyl, piperazinyl, tetrahydrothiazinyl and hexahydroazepinyl, all optionally substituted with at least one member of the group consisting of alkyl and alkoxy of 1 to 5 carbon atoms,--OH,--NO. sub.2,--CF 3, halogen and acyl of an organic carboxylic acid of 1 to 7 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having analgesic activity, antidepression and anxiolytic properties.

On the Reactivity of Thiomorpholine and Alkyl Substituted Thiomorpholines 4. (On the Joint Action of Elementary Sulfur and Gaseous Ammonia on Ketones, 94.)

Asinger, Friedrich,Saus, Alfons,Wachtendonk, Magdalena von

, p. 385 - 398 (2007/10/02)

Thiomorpholine as well as alkyl substituted thiomorpholines and their S-dioxides, respectively, are transformed into the corresponding N-Aminothiomorpholines by nitrosation (1-5) followed by the reduction with zinc in acetic acid/acetic acid anhydride und

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