4-Isopropoxyphenylboronic acid

Base Information

• Chemical Name: 4-Isopropoxyphenylboronic acid
• CAS No.: 153624-46-5
• Molecular Formula: C9H13BO3
• Molecular Weight: 180.011
• Hs Code.: 29319090
• European Community (EC) Number: 639-275-2
• DSSTox Substance ID: DTXSID60395202
• Nikkaji Number: J2.152.806D
• Wikidata: Q72485604
• Mol file: 153624-46-5.mol

Synonyms:4-Isopropoxyphenylboronic acid;153624-46-5;4-isopropoxylphenylboronic acid;(4-isopropoxyphenyl)boronic acid;4-Isopropoxybenzeneboronic acid;(4-propan-2-yloxyphenyl)boronic Acid;4-iso-Propoxyphenylboronic acid;MFCD03427051;BORONIC ACID, [4-(1-METHYLETHOXY)PHENYL]-;4-Isopropoxyphebylboronic acid;[4-(propan-2-yloxy)phenyl]boronic acid;4-(1-METHYLETHOXY)PHENYLBORONIC ACID;4-ISOPROPYLOXYPHENYLBORONIC ACID;SCHEMBL9279;4isopropoxyphenylboronic acid;4-Isopropoxyphenylboronicacid;4-isopropoxybenzenboronic acid;4-isopropoxy phenylboronic acid;4-isopropoxyphenyl boronic acid;4-isopropoxy benzeneboronic acid;4-(isopropoxy)phenylboronic acid;DTXSID60395202;CJUHQADBFQRIMC-UHFFFAOYSA-N;4-(1-methylethoxyl)phenylboronic acid;AKOS004114099;CS-W007585;[4-(1-methylethoxy)phenyl]boronic acid;NCGC00249553-01;AC-24816;AS-11014;SY017470;AM20060521;FT-0618823;I0806;EN300-221063;A809452;J-515595;Z381513180

Chemical Property of 4-Isopropoxyphenylboronic acid

Chemical Property:

• Appearance/Colour: White to off-white or light tan powder
• Vapor Pressure: 0.00012mmHg at 25°C
• Melting Point: 150-154 °C
• Refractive Index: 1.511
• Boiling Point: 321.9 °C at 760 mmHg
• PKA: 8.78±0.17(Predicted)
• Flash Point: 148.5 °C
• PSA: 49.69000
• Density: 1.1 g/cm₃
• LogP: 0.15360
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 180.0957744
• Heavy Atom Count: 13
• Complexity: 142

Purity/Quality:

99% ^*data from raw suppliers

4-Isopropoxyphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)OC(C)C)(O)O
• Uses: Reactant for:? ;Microwave-mediated click-chemistry synthesis of glyco-porphyrin derivatives with in vitro photo-cytotoxicity for application in photodynamic therapy1? ;Palladium-catalyzed oxidative cross-coupling reactions2? ;Ruthenium-catalyzed hydrogenation reactions3? ;Stereoselective rhodium-catalyzed arylation4? ;Palladium acetate catalyzed C-glycosidation5 suzuki reaction 4-Isopropoxyphenylboronic Acid is used to synthesize potent cytotoxic analogues of the marine alkaloid Lamellarin D. It is also used to synthesize cyclooxygenase-2 (COX-2) inhibitors.

Technology Process of 4-Isopropoxyphenylboronic acid

There total 3 articles about 4-Isopropoxyphenylboronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.0%

1-bromo-4-isopropoxybenzene (6967-88-0) → 4-(isopropoxy)phenylboronic acid (153624-46-5)

Guidance literature:

1-bromo-4-isopropoxybenzene; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃;

With Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;

DOI:10.1016/j.tet.2007.10.105

Reference yield:

Trimethyl borate (121-43-7,63156-11-6) + 1-bromo-4-isopropoxybenzene (6967-88-0) → 4-(isopropoxy)phenylboronic acid (153624-46-5)

Guidance literature:

Reference yield:

→ potassium iodide + 4-(isopropoxy)phenylboronic acid (153624-46-5)

Guidance literature:

upstream raw materials:

1-bromo-4-isopropoxybenzene

Trimethyl borate

Downstream raw materials:

N-(3,4-Dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]-4'-(1-methylethoxy)[1,1'-biphenyl]-2-sulfonamide

1-(4-isopropoxy-phenyl)-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid methyl ester

1,2-bis-(4-isopropoxy-phenyl)-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid methyl ester

1-(4-isopropoxyphenyl)-1H-indole-2,3-dione

Refernces

• 1、 Fukuda, Tsutomu,Sudo, Ei-ichi,Shimokawa, Kozue,Iwao, Masatomo. "Palladium-catalyzed cross-coupling of N-benzenesulfonyl-3,4-dibromopyrrole and its application to the total syntheses of lamellarins O, P, Q, and R". . p. 328 - 338. Retrieved 2008/04/01.
• 2、 -. "PHENYL SULFONAMIDE ENDOTHELIN ANTAGONISTS". . . Retrieved 2008/06/13.