3D Mol Similar

3-Pyridylboronic acid

Iupac Name：pyridin-3-ylboronic acid

CAS No.: 1692-25-7

Molecular Weight：122.918

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

Introduction: Boronic acid derivatives and their binding affinities with diols. View more+

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1. Names and Identifiers

1.1 Name: 3-Pyridylboronic acid
1.2 Synonyms: (3-Pyridinyl)boronic acid 3-Pyridineboronic acid 3-Pyridylboronic acid B-3-Pyridinylboronic acid Boronic acid, 3-pyridinyl- Boronic acid, B-3-pyridinyl- Dihydroxy(3-pyridyl)borane Puridin-3-yl-boronicacid PYRIDIN-3-BORONIC ACID PYRIDIN-3-YL-3-BORONIC ACID PYRIDIN-3-YLBORONIC ACID Pyridine-3-boronic Acid (contains varying amounts of Anhydride) PYRIDYL-3-BORONIC ACID RARECHEM AH PB 0251

1.3 CAS No.: 1692-25-7

1.4 CID: 2734378

1.5 EINECS(EC#): 605-544-8

1.6 Molecular Formula: C5H6BNO2 (isomer)

1.7 Inchi: InChI=1S/C5H6BNO2/c8-6(9)5-2-1-3-7-4-5/h1-4,8-9H

1.8 InChkey: ABMYEXAYWZJVOV-UHFFFAOYSA-N

1.9 Canonical Smiles: B(C1=CN=CC=C1)(O)O

1.10 Isomers Smiles: B(C1=CN=CC=C1)(O)O

2. Properties

2.1 Density: 1.22

2.1 Melting point: >300℃

2.1 Boiling point: 308.8oC at 760 mmHg

2.1 Refractive index: 1.534

2.1 Flash Point: 140.5oC

2.1 Precise Quality: 123.04900

2.1 PSA: 53.35000

2.1 logP: -1.23860

2.1 Solubility: Slightly soluble in methanol.

2.2 Appearance: White to yellow-orange Powder, Crystals and/or Chunks

2.3 Storage: Keep Cold.

2.4 Chemical Properties: Light Yellow Powder

2.5 Color/Form: Pale-yellow to Yellow-brown Solid

2.6 pKa: 4.00±0.10(Predicted)

2.7 Water Solubility: Slightly soluble in methanol.

2.8 StorageTemp: 0-6°C

3. Use and Manufacturing

3.1 Methods of Manufacturing: General Procedure for the Preparation of Pyridin-3-yl-Boronic Acids (1-6).; [0275] Compounds 1-6 were prepared by the esterification of the appropriate lithiopyridine followed by hydrolysis as previously reported (Cai et al., Tetrahedron Lett. 43: 4285-4287 (2002) ). The synthesis of pyridin-3-yl-3-boronic acid (1) is representative of compounds 2-6. [0276]/Pyridin-3-yl-3-boronic acid (1). A 500 mL 3-neck flask was charged with toluene (85 mL), cooled to below-60 °C and a solution of n-BuLi (1.6 M in hexanes, 48.6 mL, 77.8 mmol) was added dropwise over 10 min. After the internal temperature reached-60 °C a solution of 3-bromopyridine (6.8 mL, 70.7 mmol) in toluene (30 mL) was added drop wise to keep the internal temperature below-50 °C. A brownish-black solid precipitated and the resultant slurry was stirred for 20 min. THF (30 mL) was added drop-wise to keep the internal temperature below-50 °C and the resultant slurry was stirred for 15 min. To the slurry was added triisopropyl borate (19.6 mL, 84.9 mmol) in one portion via syringe. The solution was warmed to-15 °C, quenched with HCl (aq) (2.7 N, 70.0 mL) and transferred to a separatory funnel. The aqueous layer was collected and the organic layer was washed with water (10 mL), the combined aqueous layers were neutralized to pH 7 with NaOH (aq) (10 N) and extracted with THF (200 mL x 1, 125 mL x 2). The combined organics were concentrated in vacuo and the residue was dissolved in THF/CH30H (1: 1, 140 mL), filtered and diluted to 300 mL with CH3CN. The solvent was switched to CH3CN by distillation and concentrated to 100 mL. The solids were collected by filtration to afford the title compound 1 (6.4 g, 73percent yield) as an off white solid : 1H NMR (CD30D) 6 8.64 (br s, 1H), 8.50 (m, 1H), 8.38 (br s, 1H), 7.65 (br s, 1H). This material was used directly in Suzuki cross coupling reactions.

3.2 Usage: Boronic acid derivatives and their binding affinities with diols.

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: R22;R36/37/38

4.1 Safety Statements: S26;S3;S36/37/39

4.1 Hazard Class: IRRITANT, KEEP COLD

4.1 Hazard Declaration: H302

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501

4.1 WGK Germany: 3

4.1 Safety: Hazard Codes:Xn,Xi,C,F
Risk Statements:36/37/38-22-34-11
36/37/38:Irritating to eyes, respiratory system and skin
22:Harmful if swallowed
34:Causes burns
11:Highly Flammable
Safety Statements:36/37/39-3-26-45-16
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
3:Keep in a cool place
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
16:Keep away from sources of ignition - No smoking
WGK Germany:3
HazardClass:IRRITANT, KEEP COLD
Hazard Note:Irritant

4.2 Specification: Light Yellow Powder
usageEng:Boronic acid derivatives and their binding affinities with diols.
Safety Statements:36/37/39-3-26-45-16
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
3:Keep in a cool place
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
16:Keep away from sources of ignition - No smoking

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation 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. P337+P313 If eye irritation persists: Get medical advice/attention. 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. Synthesis Route

1692-25-7Total: 8 Synthesis Route

626-55-1 270 Suppliers

1692-25-7 317 Suppliers

Literatures:
Matondo, Hubert; Souirti, Souad; Baboulene, Michel Synthetic Communications, 2003 , vol. 33, # 5 p. 795 - 800
Yield: ~72%

626-55-1 270 Suppliers

109-72-8 213 Suppliers

1692-25-7 317 Suppliers

Literatures:
Cai, Dongwei; Larsen, Robert D; Reider, Paul J Tetrahedron Letters, 2002 , vol. 43, # 23 p. 4285 - 4287
Yield: ~96%

626-55-1 270 Suppliers

121-43-7 121 Suppliers

1692-25-7 317 Suppliers

Literatures:
US5981550 A1, ; US 5981550 A
Yield: null

View all

7. Precursor and Product

precursor:

64-17-5

594-19-4

149817-62-9

201733-56-4

109-72-8

865-34-9

121-43-7

626-55-1

5419-55-6

product :

65523-65-1

19733-56-3

3613-73-8

64368-85-0

4282-46-6

404844-11-7

39574-18-0

5094-12-2

19686-05-6

10296-29-4

832695-63-3

923293-14-5

859239-18-2

70539-84-3

837376-53-1

134363-45-4

82261-42-5

181633-36-3

21298-53-3

160688-99-3

875798-79-1

1120-90-7

217188-15-3

372-47-4

152459-95-5

View all

8. Other Information

8.0 Usage: Reactant used for preparation of phosphine-free Suzuki-Miyaura cross-coupling reactions, regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intermolecular aminocarbonylation and annulation, N-arylation using copper acetylacetonate catalys, copper-mediated cyanation and regioselective cyanation of electron-rich benzenes, New linear poly(phenylpyridyl) chains by Suzuki coupling and Oligopyridyl foldamers as mimics of a-helix twist.

8.1 Storage Conditions: General Procedure for the Preparation of Pyridin-3-yl-Boronic Acids (1-6).; [0275] Compounds 1-6 were prepared by the esterification of the appropriate lithiopyridine followed by hydrolysis as previously reported (Cai et al., Tetrahedron Lett. 43: 4285-4287 (2002) ). The synthesis of pyridin-3-yl-3-boronic acid (1) is representative of compounds 2-6. [0276]/Pyridin-3-yl-3-boronic acid (1). A 500 mL 3-neck flask was charged with toluene (85 mL), cooled to below-60 °C and a solution of n-BuLi (1.6 M in hexanes, 48.6 mL, 77.8 mmol) was added dropwise over 10 min. After the internal temperature reached-60 °C a solution of 3-bromopyridine (6.8 mL, 70.7 mmol) in toluene (30 mL) was added drop wise to keep the internal temperature below-50 °C. A brownish-black solid precipitated and the resultant slurry was stirred for 20 min. THF (30 mL) was added drop-wise to keep the internal temperature below-50 °C and the resultant slurry was stirred for 15 min. To the slurry was added triisopropyl borate (19.6 mL, 84.9 mmol) in one portion via syringe. The solution was warmed to-15 °C, quenched with HCl (aq) (2.7 N, 70.0 mL) and transferred to a separatory funnel. The aqueous layer was collected and the organic layer was washed with water (10 mL), the combined aqueous layers were neutralized to pH 7 with NaOH (aq) (10 N) and extracted with THF (200 mL x 1, 125 mL x 2). The combined organics were concentrated in vacuo and the residue was dissolved in THF/CH30H (1: 1, 140 mL), filtered and diluted to 300 mL with CH3CN. The solvent was switched to CH3CN by distillation and concentrated to 100 mL. The solids were collected by filtration to afford the title compound 1 (6.4 g, 73percent yield) as an off white solid : 1H NMR (CD30D) 6 8.64 (br s, 1H), 8.50 (m, 1H), 8.38 (br s, 1H), 7.65 (br s, 1H). This material was used directly in Suzuki cross coupling reactions.

8.2 Mesh Entry Terms: 3-pyridineboronic acid

9. Computational chemical data

Molecular Weight: 122.918g/mol
Molecular Formula: C₅H₆BNO₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 123.0491586
Monoisotopic Mass: 123.0491586
Complexity: 89
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 53.4
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: AAADcYJiMAAAAAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAABgAAoHAAACAAACADBEgQ8gJIIEACgADBnRACCgCAxAiAI2CA4ZJgIIOLAkZGEIAhggADIyAYQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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3-Pyridylboronic acid 1692-25-7 high purity low price hot sell in stock