3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine (83255-86-1)

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Description

3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine (83255-86-1) video

A number of 3,4-disubstituted pyrazolo[3,4-d]pyrimidine ribonucleosides were synthesized and tested for their biological activity. Glycosylation of persilylated as well as nonsilylated 3-bromoallopurinol with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (4) provided the key intermediate 3-bromo-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrazolo[3,4-d]pyrimidin -4(5H)-one (5a). Similar glycosylations of 3-cyanoallopurinol and 3-(methylthio)allopurinol furnished the corresponding protected N-1 glycosyl derivatives (5b and 5c). Debenzoylation of these nucleosides (5a-c) gave the corresponding 3-bromo, 3-cyano-, and 3-(methylthio)allopurinol nucleosides (6a-c). The site of glycosylation and anomeric configuration of 6a and 6c were assigned on the basis of spectral studies as well as conversion to allopurinol ribonucleoside, whereas the structural assignment of 6b was made by single-crystal X-ray analysis. Conventional functional group transformation of 5a and 5b provided a number of novel 3-substituted allopurinol nucleosides, which included 18a-d. Glycosylation of 4-amino-3-bromopyrazolo[3,4-d]pyrimidine with 4 and subsequent debenzoylation gave 3-bromo-4-aminopyrazolo[3,4-d]pyrimidine ribonucleoside from which 3,4-diamino-β-D-ribofuranosylpyrazolo[3,4-d]pyrimidine was obtained by amination. Thiation of 5b, followed by deblocking, gave 3-cyanothiopurinol ribonucleoside (20). All of these compounds were tested in vitro against certain viruses, tumor cells, and the parasite Leishmania tropica. Among the 3-substituted allopurinol nucleosides, 18b and 18c showed significant activity against Para 3 virus and were found to be potent inhibitors of growth of L1210 and P388 leukemia. Compound 20 exhibited the most significant broad-spectrum in vitro antiviral and antitumor activity. 3-Bromoallopurinol ribonucleoside (6a) was found to be more active than allopurinol ribonucleoside against Leishmania tropica within human macrophages in vitro.

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3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine (83255-86-1) Specifications

CAS 83255-86-1
CAS Min % 97%
CAS Max % 100%
MDL Number MFCD12196922
InChI Key GZQVGSRUUTUJNG-UHFFFAOYSA-N
Chemical Name or Material 3-Bromo-1h-pyrazolo[3,4-d]pyrimidin-4-amine
Infrared Spectrum Authentic
Physical Form Powder or Chunks
Packaging Glass bottle
Molecular Formula C5H4BrN5
Molecular Weight (g/mol) 214.026
SMILES C1=NC2=NNC(=C2C(=N1)N)Br
Color
Melting Point 350°C(lit.)
Assay 97%~100%

 

3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine (83255-86-1) Safety and Handling

(83255-86-1) Hazard description:

♦ Causes skin irritation

♦ Causes serious eye irritation.

3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine Precautionary statement:

♦ Wash hands and face thoroughly after handling.

♦ Wear protective gloves, eye protection

♦ If on skin: Wash with plenty of soap and water. If skin irritation occurs: Get medical advice or attention. Take off contaminated clothing and wash it before reuse.

♦ If in eyes: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice or attention.

WARNING: The information provided on this web site was developed in compliance with European Union (EU) regulations and is correct to the best of our knowledge, information and belief at the date of its publication. The information given is designed only as a guide for safe handling and use. It is not to be considered as either a warranty or quality specification.

3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine (83255-86-1) Articles

Bromopyrazolo[3,4-d]pyrimidine 2′-deoxy-2′-fluoro-β-D-arabinonucleosides: Modified DNA constituents with an unusually rigid sugar N-conformation

Journal of Organic Chemistry 2003

Synthesis, anticancer evaluation, and molecular docking studies of some novel 4,6-disubstituted pyrazolo[3,4-d]pyrimidines as cyclin-dependent kinase 2 (CDK2) inhibitors

Bioorganic Chemistry 2018

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2 reviews for 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine (83255-86-1)

  1. APICMO

    At APICMO, we synthesize and produce large amounts of 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine, among other chemicals. Our products comply with the federal rules and the CGMP manufacturing regulations.

    This chemical falls under the categories of heterocycles, nucleosides,pyrimidines, pyridines, and their related building blocks. It is useful for research, development, or production.

    Product specifications

    Chemical name 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine
    IUPAC name 3-Bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine
    CAS value Min % – 97

    Max % – 100

    CAS no. 83255-86-1
    Synonyms · 3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine
    · 1H-pyrazolo[3,4-d]pyrimidin-4-amine, 3-bromo
    · 3-bromo-4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidine
    · 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine
    · 7-bromo-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,6,9-tetraen-5-amine
    · 1h-pyrazolo[3,4-d]pyrimidin-4-amine
    · 3-bromo-1H-pyrazol[3,4-d]pyrimidin-4-amine
    · 3-bromopyrazolo[5,4-d]pyrimidine-4-ylamine
    Molecular weight (g/mol) 214.0228
    Molecular formula C5H4BrN5
    Formula weight (g/mol) 214.023
    Monoisotopic mass (g/mol) 212.965
    Structural formula 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine (83255-86-1)
    Physical state Solid chunks or powder
    Chemical purity 97%
    Density (g/cm3) 2.14
    Melting point (˚C) 350°C
    Packaging Glass bottle

    Chemical and Physical Properties of 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine

    1. Bonding
    Hydrogen bond Acceptor count – 5 units

    Donor count – 3 units

    Rotatable bond 0
    Covalent 1 unit
    1. Appearance

    3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine is available in powder form or a solid chunk.

    1. Sensitivity

    The product is sensitive to light, heat, and moisture. When exposed to any of these conditions, 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-aminemight decompose.

    Computed Properties

    Property Name Property value
    Exact Mass (g/mol) 212.965
    Complexity 154
    Topological polar surface area 80.5 A^2
    Isotope Atom Count 0
    Defined Bond Stereocenter Count 0
    Defined Atom Stereocenter Count 0
    Undefined Atom Stereocenter Count 0
    Undefined Bond Stereocenter Count 0
    Formal Charge 0
    Heavy Atom Count 11
    XLogP3-AA 0.8
    Compound Is Canonicalized Yes
    Refractive index 1.851
    Molar volume (cm3) 100
    Molar refractivity (cm3) 44
    Surface tension (dyne/cm) 117.8
    Specific gravity (g/ml) 2.14

    Uses of 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine

    APICMO hazard icons

    • Pharmaceutical applications such as inhibition of Src kinases
    • A product for research and development
    • Synthesis of other chemicals

    Hazards associated with Poor Handling of 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine

    3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine may be hazardous to the human health. Therefore, it should be handled by an experienced researcher or under the close supervision of a qualified professional. Here are some of the dangers of mishandling the product:

    • Causes skin allergies when in direct contact with the body
    • Severe eye irritation or total damage
    • Harmful to the respiratory tract if inhaled
    • Toxic when swallowed

    Safety Measures when Dealing with 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine

    1. When Handling the Chemical

    When working with 3-Bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine, observe the following precautions:

    • Work in a well-ventilated room
    • Wear protective clothing to cover your entire body including the hands, feet, skin, and the face to avoid getting in contact with the product
    • Do not eat, taste, or drink anything on the laboratory
    • Use a chemical fume chamber

    2. After Use

    After working out your research, development or product synthesis, consider the following:

    • Store the remaining chemical in a tightly closed container
    • The storage space should be cool and dry
    • Dispose of the container or the end products according to the federal or local regulations governing the waste disposal
    • Thoroughly wash your hands and face with enough water
    • Launder on contaminated clothes before reusing
    • Clean and ventilate the working bench

    3. When not in Use

    When out of use, take note of the precautions below:

    • Store under low temperatures, preferably in a refrigerator
    • Keep it locked in a tightly closed container

    4. Personal Protective Equipment

    Always put on full body protection to minimize possible dangers or accidents.

    • Eye protection

    Put on safety glasses to prevent 3-Bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine or its by-products from entering the eyes and causing irritation.

    • Skin protection

    Wear a full suit to cover any naked part of the flesh.Put on rubber or impervious footwear and chemical-resistant gloves.

    • Face protection

    Wear appropriate face masks with air-purifying capabilities to filter out dust, mist, fumes, or any other element.

    • Respiratory protection

    To prevent inhalation of harmful fumes, which might irritate the respiratory tract, consider putting on a respirator with HEPA filters.

    5. First Aid Measures

    These emergency cares should immediately be administered after they occur. However, they are never a substitute for medical care. If the symptoms persist, consider visiting a physician.

    In order to administer the first aid on time, your laboratory should be equipped with a safety shower, chemical fume chamber, exhaust ventilation, and eye washer.

    • Contact with skin

    Rinse the affected spot with plenty of running water and mild soap for about 10 minutes. The water ought to be cold. If irritation or corrosion persists, seek the advice of a medic.

    • Inhalation

    Move to a room with enough ventilation or an open place with maximum energy supply. In case the victim has difficulties in breathing, put them in oxygen before seeking further medical attention.

    • Ingestion

    Wash the mouth thoroughly with enough cold water for several minutes. You can also drink plenty of water. If the symptoms persist, seek advice from a medic.

    • Eye contact

    If you have contact lenses, remove them before washing the eyes with enough water for about 10 minutes.

    6. Storage and Handling

    • Handling

    3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine should be handled by an expert who’s aware of the risks involved and how well they can avoid them. Always wear proper body suits as per the occupational safety standards and work in an area with sufficient ventilation.

    Avoid inhaling any dust or fumes emitted by the chemicals. One of the combustion products of 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amineare hydrogen bromide and bromine, which are toxic when inhaled. The vapors irritate both the eyes and the respiratory tract.

    • Storage

    Store 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine is a tightly closed container and lock it up in a safe place with maximum ventilation. Keep it out of reach of unauthorized personnel.

    7. Stability and Reactivity

    3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine is sensitive to light, heat, and moisture.

    8. Firefighting controls

    If the product or a secondary chemical triggers fire, put out the flame using carbon dioxide, alcohol, dry powder or polymer foam. Use protective attires during the firefighting operation. Below are some of the combustion products of 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine:

    • Hydrogen bromide
    • Bromine
    • Carbon
    • Carbon monoxide
    • Carbon dioxide
    • Nitrogen
    • Oxides of nitrogen

    9. Spillages

    If in a solid state, scoop the chunks and dispose of appropriately. When in liquid form, do not let it flow down the water drainage or any other channel. Wipe out the spill with an absorbent material, get rid of the container as per the disposal regulations, wash the working bench, and ventilate it.

    10. Chemical Disposal

    Dispose of 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine according to the local, state, or federal regulations, covering the mode of chemical waste disposal.

    11. Shipping information

    There are no known hazards of transporting 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine either by ground or air.

    Regulatory Information

    3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine complies with the state and federal laws governing chemical threshold level, and neither does it exceed the maximum CAS reporting levels as per SARA title III regulations.

    Bibliography

    1. National Centre For Biotechnology Information, US. National Library Of Medicine, Pubchem, 3-Bromo-2H-Pyrazolo[3,4-D]Pyrimidin-4-Amine, Sections 1-10.
    2. Volkan Kisakürek, M. Volkan Kisakürek, Perspectives in Nucleoside and Nucleic Acid Chemistry, page 1-5
    3. Office of Toxic Substances, ‎United States. Environmental Protection Agency. Office of Pollution Prevention and Toxics – 1995, page 56
  2. Rated 5 out of 5

    Apicmo

    The best 3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-amine and service i have ever had,Nice experience

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