5-Pyrimidinylboronic acid

Iupac Name：pyrimidin-5-ylboronic acid

Molecular Weight：123.906

Modify Date.: 2022-11-22 16:53

Introduction: suzuki reaction 5-Pyrimidinylboronic acid Preparation Products And Raw materials Raw materials View more+

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1. Names and Identifiers

1.1 Name: 5-Pyrimidinylboronic acid
1.2 Synonyms: 4(5)-METHYL-1H-IMIDAZOLE-2-CARBALDEHYDE 4-METHYL-1H-IMIDAZOLE-2-CARBALDEHYDE 5-Fluoro-2-methoxypyridine-4-boronic acid 5-Pyrimidineboronic Acid 5-Pyrimidylboronic Acid 5-Pyrimidylboronic Acid (contains varying amounts of Anhydride) Boronic acid, 5-pyrimidinyl- (9CI) Boronic acid, B-5-pyrimidinyl- MFCD05864565 Pyrimidin-5-ylboronic acid Pyrimidine 5-boronic acid Pyrimidine-5-Boronic Pyrimidine-5-boronic acid PYRIMIDINYL-5-BORONIC ACID

1.3 CAS No.: 109299-78-7

1.4 CID: 2795193

1.5 Molecular Formula: C4H5BN2O2 (isomer)

1.6 Inchi: InChI=1S/C4H5BN2O2/c8-5(9)4-1-6-3-7-2-4/h1-3,8-9H

1.7 InChkey: HZFPPBMKGYINDF-UHFFFAOYSA-N

1.8 Canonical Smiles: B(C1=CN=CN=C1)(O)O

1.9 Isomers Smiles: B(C1=CN=CN=C1)(O)O

2. Properties

2.1 Density: 1.33

2.1 Melting point: >300°C

2.1 Boiling point: 334.7 °Cat760mmHg

2.1 Refractive index: 1.534

2.1 Flash Point: 156.2 °C

2.1 Precise Quality: 124.044411

2.1 PSA: 66.24000

2.1 logP: -1.84360

2.1 Solubility: Soluble in Ether, MeOH, DMSO, THF.

2.2 Appearance: off-white powder

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: Off-white powder

2.5 Color/Form: BRIGHT YELLOW-ORANGE AMORPHOUS SOLID

2.6 Decomposition: When heated to decomposition it emits toxic fumes of nitroxides.

2.7 pKa: 5.23±0.10(Predicted)

2.8 Water Solubility: Soluble in Ether, MeOH, DMSO, THF.

2.9 Stability: STABLE IN AIR WHEN PROTECTED FROM LIGHT & MOISTURE; STRONG LIGHT &/OR MOIST AIR CAUSES IT TO DARKEN /HYDROCHLORIDE/

2.10 StorageTemp: Inert atmosphere,2-8°C

3. Use and Manufacturing

3.1 GHS Classification: Signal: Warning
GHS Hazard Statements
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H362 (100%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]

Precautionary Statement Codes
P201, P202, P260, P263, P264, P270, P280, P281, P305+P351+P338, P308+P313, P337+P313, P405, and P501

3.2 Methods of Manufacturing: 5-Pyrimidineboronic acid; 'BuLi (3.02 ml, 2M solution in hexane, 7.55 mmol) was added dropwise to a stirring solution of 5-bromopyrimidine (1 g, 6.29 mmol) and triisopropylborate (1.46 ml, 7.55 mmol) in anhydrous toluene (16 ml) and anhydrous THF (4 ml) at-70°C under a nitrogen atmosphere. The reaction mixture was stirred at-70°C for 30 mins and then removed from the cold bath. When the internal temp. reached-20°C, the reaction was quenched by the dropwise addition of 2M HCI (10 ml). The mixture was allowed to warm to RT and then separated. The aqueous phase was taken to pH 5.5 with 2M KOH and extracted into THF (3 x 25 ml). The combined organic extracts were dried (MgS04), filtered and concentrated in vacuo to provide a colourless solid. The solid was slurried in acetonitrile (2 ml), collected by filtration and dried on the sinter to give the target boronic acid as a brilliant white solid (340 mg, 44percent). 8H(MeOD; 250MHz) 8.98 (2H, s), 9.14 (1H, s).To a solution of compound 5-bromopyrimidine (8 g, 50 mmol), trimethyl borate (4.6g, 60 mmol) in toluene and THF (150 mL, V/V=4: 1) was added n-BuLi (24 mL, 60 mmol, 2.5 M in hexane) at

3.3 Usage: suzuki reaction 5-Pyrimidinylboronic acid Preparation Products And Raw materials Raw materials

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R22;R36/37/38

4.1 Safety Statements: S22;S26;S36/37/39

4.1 Hazard Class: IRRITANT

4.1 Hazard Declaration: H315

4.1 Caution Statement: P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

4.1 Safety: Hazard Codes: Xi, Xn
Risk Statements: 22-36/37/38
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-26-36/37/39-36
S22:Do not breathe dust.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S36:Wear suitable protective clothing.
Hazard Note: Irritant
HazardClass: IRRITANT

4.2 Specification: 5-Pyrimidinylboronic acid (CAS NO.109299-78-7) is also named as Acide pyrimidin-5-ylboronique ; boronic acid, B-5-pyrimidinyl- ; Pyrimidin-5-ylboronic acid ; Pyrimidine-5-boronic acid . 5-Pyrimidinylboronic acid (CAS NO.109299-78-7) is off-white powder.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Serious eye damage, Category 1

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H315 Causes skin irritation H318 Causes serious eye damage H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026 P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

7. Synthesis Route

109299-78-7Total: 2 Synthesis Route

4595-59-9 234 Suppliers

109299-78-7 178 Suppliers

Literatures:
Matondo, Hubert; Souirti, Souad; Baboulene, Michel Synthetic Communications, 2003 , vol. 33, # 5 p. 795 - 800
Yield: ~70%

4595-59-9 234 Suppliers

121-43-7 121 Suppliers

109299-78-7 178 Suppliers

Literatures:
PROGENICS PHARMACEUTICALS, INC. Patent: WO2009/155527 A2, 2009 ; Location in patent: Page/Page column 133-134 ; WO 2009/155527 A2
Yield: ~62%

8. Precursor and Product

precursor:

121-43-7

4595-59-9

product :

58759-01-6

34771-45-4

1134120-67-4

64858-29-3

832695-81-5

1242733-91-0

1134120-65-2

791-28-6

9. Other Information

9.0 Usage: Pyrimidine 5-boronic acid could be used in an analogous one-pot copper-catalyzed DBAD coupling and condensation. The widely utilized Suzuki-Miyaura coupling allows for the coupling of boronic acids with carbon halides and surrogates.

9.1 Uses: 5-Pyrimidylboronic Acid, is one of the new heteroarylpyrimidine derivatives via Suzuki cross-coupling reactions.

9.2 Chemical Properties: Off-white powder

9.3 Uses: suzuki reaction

10. Computational chemical data

Molecular Weight: 123.906g/mol
Molecular Formula: C₄H₅BN₂O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 124.0444076
Monoisotopic Mass: 124.0444076
Complexity: 84.6
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 66.2
Heavy Atom Count: 9
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYJjMAAAAAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAABgAAoHAAACAAACADBEgQtkJYIEACgABBnZACAgCkRAKABUCAoRBCACIBASUAEBAgIAAJAACAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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