1006-23-1

Basic information

• Product Name: 5-Nitroso-2,4,6-triaminopyrimidine
• Synonyms: IFLAB-BB F1918-0051;5-NITROSO-2,4,6-TRIAMINOPYRIMIDINE;5-NITROSO-PYRIMIDINE-2,4,6-TRIAMINE;2,4,6-TRIAMINO-5-NITROSOPYRIMIDINE;6-pyrimidinetriamine,5-nitroso-4;5-nitropyrimidine-2,4,6-triamine;2,4,6-Triamino-5-nitroisopyrimidine;5-NITROSO-2-4-6-TRIAMINOPYRIMIDINE*ISOPA C
• CAS NO: 1006-23-1
• Molecular Formula: C₄H₆N₆O
• Molecular Weight: 154.13
• EINECS: 213-742-7
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Amines;Nucleotides and Nucleosides;Pyrimidines;Nucleic acids;Bases & Related Reagents;Nucleotides
• Mol File: 1006-23-1.mol

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 277.47°C (rough estimate)
• Flash Point: 318.4 °C
• Appearance: orange solid
• Density: 1.4788 (rough estimate)
• Vapor Pressure: 3.78E-15mmHg at 25°C
• Refractive Index: 1.7290 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMF (Slightly, Heated), DMSO (Slightly, Heated)
• PKA: 4.07±0.10(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 5-Nitroso-2,4,6-triaminopyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitroso-2,4,6-triaminopyrimidine(1006-23-1)
• EPA Substance Registry System: 5-Nitroso-2,4,6-triaminopyrimidine(1006-23-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 1006-23-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-Nitroso-2,4,6-triaminopyrimidine is used as a synthetic building block for the development of various organic compounds. Its unique structure and reactivity make it a valuable component in the synthesis of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Nitroso-2,4,6-triaminopyrimidine is utilized as a key intermediate in the synthesis of therapeutic agents. Its incorporation into drug molecules can potentially enhance their efficacy, selectivity, and pharmacokinetic properties, leading to the development of novel drugs with improved therapeutic profiles.
Used in Agrochemical Industry:
5-Nitroso-2,4,6-triaminopyrimidine also finds application in the agrochemical industry, where it is employed in the synthesis of active ingredients for pesticides, herbicides, and other crop protection products. Its use in this context can contribute to the development of more effective and environmentally friendly agrochemicals.
Used in Dye and Pigment Industry:
The compound's distinctive orange color makes it a potential candidate for use in the dye and pigment industry. It can be utilized in the development of new dyes and pigments for various applications, such as textiles, plastics, and printing inks, offering a broader range of color options and improved performance characteristics.
Used in Research and Development:
5-Nitroso-2,4,6-triaminopyrimidine is also valuable in research and development settings, where it can be used to explore new reaction pathways, study the effects of different functional groups on molecular properties, and develop innovative synthetic strategies. Its use in research can lead to the discovery of new compounds with unique properties and potential applications across various industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 1518, 1957 DOI: 10.1021/ja01563a078

Flammability and Explosibility

Notclassified

InChI:InChI=1/C4H6N6O2/c5-2-1(10(11)12)3(6)9-4(7)8-2/h(H6,5,6,7,8,9)

Upstream product

• 1004-38-2 2,4,6-triaminopyrimidine 
• 50-01-1 guanidine hydrochloride 
• 109-77-3 malononitrile 
• 593-85-1 diguanidine carbonate 
• 92972-47-9 guanidine salt of 2-(hydroxyimino)propanedinitrile 

Downstream Products

• 5113-30-4 Methoxytriamteren 
• 396-01-0 triamterene 
• 20460-75-7 5-nitro-2,4,6-triaminopyrimidine-1-oxide 
• 19867-41-5 2,4,6-triamino-5-nitropyrimidine-1,3-dioxide 
• 1904-98-9 2,6-diaminopurine 
• 1369492-52-3 pyrimido[5,4-g]pteridine-2,4,6,8-tetramine p-tosylate (1:1) 
• 63110-97-4 9,11-diaminonaphtho<1,2-g>pteridine 
• 30745-07-4 [1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7-diamine 
• 52011-72-0 2-amino-1H-pyrimidine-4,5,6-trione-5-oxime 
• 1004-74-6 2,4,5,6-tetraaminopyrimidine 
• 15167-22-3 2,4,7-Triamino-pteridin-6-carbonsaeure-amid 
• 19152-93-3 2,4-diamino-6-phenyl-7(8H)-pteridinone 
• 1029-87-4 2,4-Diamino-7-methyl-6-phenyl-pteridin 
• 19153-12-9 6-methyl-7-phenyl-pteridine-2,4-diyldiamine 

Relevant articles and documents

Synthetic method of triamterene intermediate

The invention improves a synthesis method of triamterene from an intermediate to a triamterene finished product. The method adopts guanidine hydrochloride as a starting material to prepare 5-nitroso-2, 4, 6-triaminopyrimidine, and comprises the following steps: (1) sequentially adding water and malononitrile into a reaction kettle, stirring for 25 minutes for dissolving, starting nitrogen protection, adding a sodium nitrite saturated solution at 20 DEG C, dropwise adding 8% HCl at the same time for adjusting the pH value to 3-4, after the sodium nitrite aqueous solution is dropwise added, keeping the temperature for 2.5 hours at 18 DEG C, wherein the dosage weight ratio of the water to the sodium nitrite to the malononitrile to the 8% hydrochloric acid is as follows: the use mass ratio of the sodium nitrite to the malononitrile to the 8% hydrochloric acid is 2.5:1.15:1:0.35; and (2) adding guanidine hydrochloride solid into the solution obtained in the step (1), and stirring for 30 minutes, and adding NaCO3 solid to adjust the pH value to 9-10, wherein the weight ratio of guanidine hydrochloride to sodium carbonate to malononitrile in (1) is as follows: guanidine hydrochloride to malononitrile to sodium carbonate is 1.60:1:(0.10-0.12). According to the method, the synthesis risk of the triamterene intermediate is reduced, wastewater generated in the refining process is reduced, and safe production, energy conservation and emission reduction are facilitated.

Imidazopyridine- and purine-thioacetamide derivatives: Potent inhibitors of nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1)

Nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1) belongs to the family of ecto-nucleotidases, which control extracellular nucleotide, nucleoside, and (di)phosphate levels. To study the (patho)physiological roles of NPP1 potent and selective inhibitors with drug-like properties are required. Therefore, a compound library was screened for NPP1 inhibitors using a colorimetric assay with p-nitrophenyl 5′-thymidine monophosphate (p-Nph-5′-TMP) as an artificial substrate. This led to the discovery of 2-(3H-imidazo[4,5-b]pyridin-2-ylthio)-N-(3,4-dimethoxyphenyl)acetamide (5a) as a hit compound with a Ki value of 217 nM. Subsequent structure-activity relationship studies led to the development of purine and imidazo[4,5-b]pyridine analogues with high inhibitory potency (Ki values of 5.00 nM and 29.6 nM, respectively) when assayed with p-Nph-5′-TMP as a substrate. Surprisingly, the compounds were significantly less potent when tested versus ATP as a substrate, with Ki values in the low micromolar range. A prototypic inhibitor was investigated for its mechanism of inhibition and found to be competitive versus both substrates.

Preparation of 2,4,5,6-tetraaminopyrimidine from 2,4,6-triaminopyrimidine

An improved process for the production of STR1 FROM STR2 WHICH PRODUCES BUT DOES NOT ISOLATE AN INTERMEDIATE STR3 WHICH COMPOUND IS RETAINED IN SITU AND MINIMIZES THE COMPLEX POLYMER FORM OF A THREE-DIMENSIONAL NETWORK OF AZO LINKAGES FORMED BY THE NITROSO AND AMINO GROUPS. These groups, as they appear in the nitroso intermediate, have carcinogenic possibilities. It has been found that the nitroso compound will precipitate as a stirrable slurry if the temperature parameter is kept low at about 0°-20° C. A preferred route for the production of the nitroso compound from the triamino starting material utilizes as reactants 1.0-1.05 moles of sodium nitrite and 1.5 moles of HOAc in water (HCl may be substituted for HOAc). In the second state of this sequential reaction, the reduction of nitroso is carried out by a reducing agent and one preferred agent is sodium dithionite. Catalytic agents such as Raney nickel and hydrazine or nickel salts, e.g., nickel chloride, and sodium borohydride may also be used. The present process is an improvement in part of the technique of Piper and Montgomery, J. Het. Chem., 11:279 (1974), which process is designed specially to produce the antifolate methotrexate as an end product and is an improvement of the method of application Ser. No. 742,450 of Ellard filed Nov. 17, 1976, entitled "Improved Synthesis of Methotrexate", U.S. Pat. No. 4,080,825.