2-Aminoethyl diphenylborinate

Base Information

• Chemical Name: 2-Aminoethyl diphenylborinate
• CAS No.: 524-95-8
• Molecular Formula: C14H16BNO
• Molecular Weight: 225.098
• Hs Code.: 29310099
• European Community (EC) Number: 208-366-5
• NSC Number: 17107
• UNII: E4ES684O93
• DSSTox Substance ID: DTXSID0040389
• Nikkaji Number: J42.786A
• Wikipedia: 2-Aminoethoxydiphenyl_borate
• Wikidata: Q4596857
• Pharos Ligand ID: XJS2H8DY719A
• ChEMBL ID: CHEMBL169233
• Mol file: 524-95-8.mol

Synonyms:2-aminoethyl diphenylborinate;2-APB cpd

Chemical Property of 2-Aminoethyl diphenylborinate

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0.000232mmHg at 25°C
• Melting Point: 192-194 °C(lit.)
• Refractive Index: 1.559
• Boiling Point: 325.3 °C at 760 mmHg
• PKA: 8.03±0.10(Predicted)
• Flash Point: 150.6 °C
• PSA: 35.25000
• Density: 1.04 g/cm³
• LogP: 1.46790
• Storage Temp.: 2-8°C
• Solubility.: Soluble in ethanol and methanol.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 225.1324943
• Heavy Atom Count: 17
• Complexity: 182

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-APB ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Boron)
• Canonical SMILES: B(C1=CC=CC=C1)(C2=CC=CC=C2)OCCN
• Description: 2-Aminoethyl diphenylborinate (2-APB) is a modulator of intracellular calcium levels and transient receptor potential (TRP) channels. It inhibits calcium release induced by inositol-1,4,5-triphosphate (IP3) in rat cerebellar microsomes (IC50 = 42 μM) without affecting IP3 binding to its receptor. 2-APB inhibits store-operated calcium entry (SOCE) in DT40 cells (IC50 = 4.8 μM), as well as inhibits TRP canonical 6 (TRPC6) and TRP melastatin 8 (TRPM8) and activates TRP vanilloid 1 (TRPV1), TRPV2, and TRPV3 in vitro. It also inhibits calcium transients induced by the sarcoplasmic/endoplasmic reticulum Ca2+-ATPase (SERCA) inhibitor thapsigargin in DDT1 MF-2 cells when used at a concentration of 75 μM. 2-APB inhibits differentiation of primary mouse brown adipocytes when used at concentrations ranging from 30 to 300 μM and reduces adipocyte triglyceride levels at 100 μM. It also increases the expression of Ucp1 and Pparg in primary mouse brown adipocytes. 2-APB (10 mg/kg) reduces protein levels of TRP melastatin 2 (TRPM2) in the rat hippocampus and improves learning and memory deficits induced by amyloid-β (25-35) in rats.
• Uses: Ca release inhibitor, angiogensin II inhibitor 2-Aminoethyl diphenylborinate is used for the densitometric determination of flavonoids and TRP activator. It is also used to manipulate intracellular release of calcium ions and in preparation of apoptotic inducers. It serves as a reactant for preparation of apoptotic inducers and in membrane-permeable SOCE (store operated calcuym entry) inhibitor.

Technology Process of 2-Aminoethyl diphenylborinate

There total 13 articles about 2-Aminoethyl diphenylborinate 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: 75.0%

oxybis(diphenylborane) (4426-21-5) + ethanolamine (141-43-5) → diphenylborinic acid (2622-89-1) + 2-Aminoethoxydiphenylborane (524-95-8)

Guidance literature:

In acetonitrile; for 1h; cooling;

DOI:10.1124/mol.105.015701

Reference yield: 35.0%

bromobenzene (108-86-1,52753-63-6) + Trimethyl borate (121-43-7,63156-11-6) + ethanolamine (141-43-5) → 2-Aminoethoxydiphenylborane (524-95-8)

Guidance literature:

bromobenzene; Trimethyl borate; With iodine; magnesium; In tetrahydrofuran; at 40 ℃; for 2h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 0.5h; Inert atmosphere;

ethanolamine; In ethyl acetate; at 20 ℃; Inert atmosphere;

DOI:10.1039/c5cc06177f

Reference yield:

triphenylborane.sodium hydroxide (856622-73-6) + diethyl ether (60-29-7,927820-24-4) + ethanolamine (141-43-5) → 2-Aminoethoxydiphenylborane (524-95-8)

Guidance literature:

With hydrogenchloride;

upstream raw materials:

diphenylborinic acid

ethanolamine

triphenylborane

isobutyl diphenylborinate

Downstream raw materials:

oxybis(diphenylborane)

[N-(2-hydroxy-2-phenyl-ethyl)-N,N-dimethyl-hydraziniumato^(1-)-N',O]-diphenyl-boron

2,2,4-triphenyl-3-oxa-1-aza-6-azonia-2-borata-spiro[5.6]dodecane

diphenylborinic acid 2-methyl-1-morpholin-4-yloxy-propyl ester

Refernces

• 1、 Chen, Xiaofeng,Ke, Haihua,Chen, Yao,Guan, Changwei,Zou, Gang. "Cross-coupling of diarylborinic acids and anhydrides with arylhalides catalyzed by a phosphite/N-heterocyclic carbene co-supported palladium catalyst system". . p. 7572 - 7578. Retrieved 2012/10/29.
• 2、 Dobrydneva, Yuliya,Abelt, Christopher J.,Dovel, Beth,Thadigiri, Celina M.,Williams, Roy L.,Blackmore, Peter F.. "2-Aminoethoxydiphenyl borate as a prototype drug for a group of structurally related calcium channel blockers in human platelets". . p. 247 - 256. Retrieved 2007/10/03.