4-Carboxyphenylboronic acid

Iupac Name：4-boronobenzoic acid

Molecular Weight：165.939

Modify Date.: 2022-11-23 17:37

Introduction: 4-Carboxyphenylboronic acid is a highly versatile reagent. It is a reagent used in various reactions including condensation reactions with stabilizer chains at the surface of polystyrene latex, Suzuki coupling reactions, esterification, derivatization of polyvinylamine, synthesis of isotopically labeled mercury and functionalization of poly-SiNW for detection of dopamine. It is reagents used for Suzuki-Miyaura cross-coupling, induction of pH sensitivity on fluorescence lifetime of quantum dots by NIR fluorescent dyes, bio-supported palladium nanoparticles as phosphine-free catalyst for Suzuki reaction in water and Chan-Lam-type Copper (Cu)-catalyzed S-arylation with aryl boronic acids at room temperature. It is reagents used for the preparation of isoquinolones via regioselective Suzuki-Miyaura cross-coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation, amprenavir-based P1-substituted bi-aryl derivatives as ultra-potent HIV-1 protease inhibitors, phenols via visible-light initiated aerobic oxidative hydroxylation of arylboronic acids using air as oxidant catalyzed by Ruthenium (Ru)-complex, glucose sensitive boronic acid-bearing block copolymers, trisulfonated calixarene upper-rim sulfonamido derivatives and their complexation with the trimethyllysine epigenetic mark. It can also be used as a corrosion inhibitor for steel. View more+

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1. Names and Identifiers

1.1 Name: 4-Carboxyphenylboronic acid
1.2 Synonyms: [4-(Formyloxy)phenyl]boronic acid 4-(dihydroxyboranyl)benzoic acid 4-(Dihydroxyboronyl)benzoic acid, 4-Boronobenzoic acid 4-(Dihydroxyboryl)benzoic acid 4-16-00-01683 4-Boronobenzoic acid 4-borono-benzoicaci 4-Carboxybenzeneboronic Acid AKOS BRN-0008 Benzoic acid, 4-borono- Benzoic acid, 4-borono- (9CI) Benzoic acid, p-borono- (6CI,7CI,8CI) Boronic acid, B-[4-(formyloxy)phenyl]- MFCD00151801 OTAVA-BB BB7110951390 p-Boronobenzoic acid p-Carboxybenzeneboronic acid P-CARBOXYPHENYLBORONIC ACID RARECHEM AH PB 0147 TIMTEC-BB SBB003899 ZERENEX ZX001647

1.3 CAS No.: 14047-29-1

1.4 CID: 312183

1.5 EINECS(EC#): 604-189-6

1.6 Molecular Formula: C7H7BO4 (isomer)

1.7 Inchi: InChI=1S/C7H7BO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,11-12H,(H,9,10)

1.8 InChkey: SIAVMDKGVRXFAX-UHFFFAOYSA-N

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

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

2. Properties

2.1 Density: 1.3

2.1 Melting point: 238-240℃

2.1 Boiling point: 325.1°Cat760mmHg

2.1 Refractive index: 1.585

2.1 Flash Point: 150.4°C

2.1 Precise Quality: 166.04400

2.1 PSA: 77.76000

2.1 logP: -0.93540

2.1 Appearance: Off-white to light beige Powder

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: Off-white to light beige powder

2.4 Color/Form: Off-white to light beige

2.5 pKa: 4.08±0.10(Predicted)

2.6 Water Solubility: Very soluble

2.7 Stability: Stable under normal temperatures and pressures.

2.8 StorageTemp: Keep in dark place,Sealed in dry,Room Temperature

3. Use and Manufacturing

3.1 Usage: suzuki reaction

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Hazard Class: IRRITANT

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: 2

4.1 RTECS: CY8925000

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

View all

6. Synthesis Route

14047-29-1Total: 10 Synthesis Route

586-76-5 187 Suppliers

14047-29-1 330 Suppliers

Literatures:
Li, Wenjie; Nelson, Dorian P.; Jensen, Mark S.; Hoerrner, R. Scott; Cai, Dongwei; Larsen, Robert D.; Reider, Paul J. Journal of Organic Chemistry, 2002 , vol. 67, # 15 p. 5394 - 5397
Yield: ~42%

5720-05-8 265 Suppliers

14047-29-1 330 Suppliers

Literatures:
Percec, Virgil; Won, Betty C.; Peterca, Mihai; Heiney, Paul A. Journal of the American Chemical Society, 2007 , vol. 129, # 36 p. 11265 - 11278
Yield: ~69%

4294-57-9 31 Suppliers

14047-29-1 330 Suppliers

Literatures:
Journal of Organic Chemistry, , vol. 38, p. 4016 - 4021
Yield: null

View all

7. Precursor and Product

precursor:

4294-57-9

5720-05-8

87199-16-4

624-38-4

124-38-9

586-76-5

1072960-67-8

121-43-7

106-38-7

126747-14-6

87199-17-5

product :

6427-66-3

114879-31-1

116378-39-3

123088-59-5

19188-42-2

91062-38-3

114691-92-8

426268-06-6

4334-88-7

1073353-57-7

5730-75-6

397843-67-3

5730-76-7

1073353-55-5

99768-12-4

92-89-7

619-58-9

85107-54-6

180516-87-4

207279-31-0

938043-31-3

5748-43-6

View all

8. Other Information

8.0 BRN: 3031088

8.1 Description: 4-Carboxyphenylboronic acid is a highly versatile reagent. It is a reagent used in various reactions including condensation reactions with stabilizer chains at the surface of polystyrene latex, Suzuki coupling reactions, esterification, derivatization of polyvinylamine, synthesis of isotopically labeled mercury and functionalization of poly-SiNW for detection of dopamine. It is reagents used for Suzuki-Miyaura cross-coupling, induction of pH sensitivity on fluorescence lifetime of quantum dots by NIR fluorescent dyes, bio-supported palladium nanoparticles as phosphine-free catalyst for Suzuki reaction in water and Chan-Lam-type Copper (Cu)-catalyzed S-arylation with aryl boronic acids at room temperature. It is reagents used for the preparation of isoquinolones via regioselective Suzuki-Miyaura cross-coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation, amprenavir-based P1-substituted bi-aryl derivatives as ultra-potent HIV-1 protease inhibitors, phenols via visible-light initiated aerobic oxidative hydroxylation of arylboronic acids using air as oxidant catalyzed by Ruthenium (Ru)-complex, glucose sensitive boronic acid-bearing block copolymers, trisulfonated calixarene upper-rim sulfonamido derivatives and their complexation with the trimethyllysine epigenetic mark. It can also be used as a corrosion inhibitor for steel.

8.2 Reference

Nam, N. D., et al. "A study of 4-carboxyphenylboronic acid as a corrosion inhibitor for steel in carbon dioxide containing environments." Corrosion Science 76.10(2013):257-266.
Vollmueller, Frank, et al. "Cyclization of 4-carboxyphenylboronic acid with hydrazide derivative; hydrolysis; catalytic esterification." US, US 6197967 B1. 2001.

8.3 Chemical Properties: Off-white to light beige powder

8.4 Uses: suzuki reaction

8.5 Uses: Intermediates of Liquid Crystals

8.6 Reference

Nam, N. D., et al. "A study of 4-carboxyphenylboronic acid as a corrosion inhibitor for steel in carbon dioxide containing environments." Corrosion Science 76.10(2013):257-266.
Vollmueller, Frank, et al. "Cyclization of 4-carboxyphenylboronic acid with hydrazide derivative; hydrolysis; catalytic esterification." US, US 6197967 B1. 2001.

8.7 Uses: 4-Carboxyphenylboronic acid is a reagent used in suzuki coupling reactions.

9. Computational chemical data

Molecular Weight: 165.939g/mol
Molecular Formula: C₇H₇BO₄
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 166.0437389
Monoisotopic Mass: 166.0437389
Complexity: 163
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 77.8
Heavy Atom Count: 12
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: AAADcYJgOAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAoGgAACAAADACAmAAwCIAAAgCIAiDSCAACAAAkAAAIiAEACMgIJjKAFRCAcQAkwAEImYeIyCCOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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4-Carboxyphenylboronic acid