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2-Aminoethoxydiphenyl borate

Product Name
2-Aminoethoxydiphenyl borate
CAS No.
524-95-8
Chemical Name
2-Aminoethoxydiphenyl borate
Synonyms
2-APB;NSC 17107;Natural Product;Naturstoffreagenz A;Diphenylborinic acid;NATURAL PRODUCT REAGENT A;AMINOETHOXYDIPHENYLBORANE;2-Aminoethyl diphenyl orate;2-AMINOETHOXYDIPHENYLBORATE;Aminoethyl Diphenylborinate
CBNumber
CB3308983
Molecular Formula
C14H16BNO
Formula Weight
225.09
MOL File
524-95-8.mol
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2-Aminoethoxydiphenyl borate Property

Melting point:
192-194 °C(lit.)
Boiling point:
325.3±34.0 °C(Predicted)
Density 
1.04±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
Soluble in ethanol and methanol.
pka
8.03±0.10(Predicted)
form 
Liquid
color 
Clear colorless to yellow
BRN 
2942273
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
InChIKey
BLZVCIGGICSWIG-UHFFFAOYSA-N
CAS DataBase Reference
524-95-8(CAS DataBase Reference)
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Safety

Risk Statements 
36/37/38
Safety Statements 
22-24/25
WGK Germany 
3
RTECS 
ED6150000
F 
8-21
HS Code 
29310099
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
100065
Product name
2-APB
Purity
A cell-permeable modulator of Ins(1,4,5)P3-induced Ca
Packaging
100mg
Price
$82.8
Updated
2024/03/01
TCI Chemical
Product number
D0281
Product name
2-Aminoethyl Diphenylborinate
Purity
>98.0%(HPLC)(T)
Packaging
10g
Price
$155
Updated
2024/03/01
TCI Chemical
Product number
D0281
Product name
2-Aminoethyl Diphenylborinate
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$332
Updated
2024/03/01
Alfa Aesar
Product number
A16606
Product name
2-Aminoethyl diphenylborinate, 98%
Packaging
5g
Price
$76.5
Updated
2024/03/01
Alfa Aesar
Product number
A16606
Product name
2-Aminoethyl diphenylborinate, 98%
Packaging
25g
Price
$241
Updated
2024/03/01
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2-Aminoethoxydiphenyl borate Chemical Properties,Usage,Production

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.

Chemical Properties

white crystalline powder

Uses

Ca release inhibitor, angiogensin II inhibitor

Uses

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.

Definition

ChEBI: An organoboron compound that is diphenylborane in which the borane hydrogen is replaced by a 2-aminoethoxy group.

Synthesis Reference(s)

Journal of the American Chemical Society, 80, p. 5409, 1958 DOI: 10.1021/ja01553a022
Journal of the American Chemical Society, 80, p. 5409, 1958 DOI: 10.1021/ja01553a022

General Description

A cell-permeable modulator of Ins(1,4,5)P3-induced Ca2+ release. Inhibits Ins(1,4,5)P3-induced Ca2+ release from rat cerebellar microsomal preparations (IC50 = 42 μM) without affecting [3H]-Ins(1,4,5)P3 binding to its receptor. In liver cells, 2-APB inhibits store-operated Ca2+ channels through a mechanism which may involve its binding to either the channel protein or an associated regulatory protein. Has no effect on the Ca2+ release from the ryanodine-sensitive Ca2+ store prepared from rat leg skeletal muscle and heart.

Biological Activity

A functional and membrane permeable D-myo-inositol 1,4,5-trisphosphate (IP 3 ) receptor antagonist (IC 50 = 42 μ M). Stimulates store-operated calcium (SOC) release at low concentrations (< 10 μ M) and inhibits it at higher concentrations (up to 50 μ M). Increases STIM-Orai channel conductance and limits ion selectivity. Modulator of TRP channels; blocks TRPC1, TRPC3, TRPC5, TRPC6, TRPV6, TRPM3, TRPM7, TRPM8 and TRPP2 and at higher concentrations stimulates TRPV1, TRPV2 and TRPV3. Also blocks specific gap channel subtypes.

Biochem/physiol Actions

Membrane-permeable modulator of intracellular IP3-induced calcium release.

storage

Room temperature

References

1) Maruyama et al. (1997) 2APB, 2-aminoethoxydiphenyl borate, a membrane-penetrable modulator of Ins(1,4,5)P3-induced Ca2+ release; J. Biochem., 122 498 2) Varnai et al. (2009) STIM and Orai: the long-awaited constituents of store-operated calcium entry; Trends Pharmacol. Sci., 30 118 3) Togashi et al. (2008) Inhibition of the transient receptor potential cation channel TRPM2 by 2-aminoethoxydiphenyl borate (2-APB); Br. J. Pharmacol., 153 1324 4) Xu et al. (2005) Block of TRPC5 channels by 2-aminoethoxydiphenyl borate: a differential, extracellular and voltage-dependent effect; Br. J. Pharmacol., 145 405 5) Bai et al. (2006) Block of specific gap junction channel subtypes by 2-aminoethoxydiphenyl borate (2-APB); J. Pharmacol. Exp. Ther., 319 1452

2-Aminoethoxydiphenyl borate Preparation Products And Raw materials

Raw materials

PHENYLMAGNESIUM BROMIDE Monoethanolamine Tributyl borate TRIPHENYLBORANE Diethyl ether Benzene

Preparation Products

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2-Aminoethoxydiphenyl borate Suppliers

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View Lastest Price from 2-Aminoethoxydiphenyl borate manufacturers

Career Henan Chemical Co
Product
(2-AMINOETHOXY)DIPHENYLBORANE 524-95-8
Price
US $0.01/KG
Min. Order
1KG
Purity
98%; 99%
Supply Ability
500g;1kg； 25kg
Release date
2020-01-09

524-95-8, 2-Aminoethoxydiphenyl borateRelated Search:

Dimethyl carbonate 3,4-DIHYDROXYBENZYLAMINE HYDROBROMIDE TRIPROPYL BORATE N-(4-AMINOBUTYL)-2-NAPHTHALENESULFONAMIDE HYDROCHLORIDE 2-(1,3-DIMETHYL-2,6-DIOXO-1,2,3,6-TETRAHYDRO-7H-PURIN-7-YL)-N-(4-ISOPROPYLPHENYL)ACETAMIDE Niguldipine (hydrochloride) 2-Propenoic acid, 3,3'-(1,3-phenylene)bis- Methanone, (3,4-dihydro-2(1H)-isoquinolinyl)[2-[(4-methoxyphenyl)amino]-4-thiazolyl]- MSK-195 L-Menthol 2-Aminoethoxydiphenyl borate Diphenylphosphinic Chloride 6-[(DIPHENYLBORYL)OXY]-6-OXO-1,5-HEXANEDIAMINE 1-[(DIPHENYLBORYL)OXY]-1-OXO-3-PHENYL-2-PROPANAMINE SPECS AO-164/42302603 SPECS AO-164/42302642 SPECS AI-942/13332058

  • NATURAL PRODUCT REAGENT A
  • b-(2-aminoethoxy)diphenylborane
  • 2-Aminoethyl diphenyl orate
  • (2-Aminoethoxy)diphenylborane ,98%
  • 2,2-DIPHENYL-1,3,2-OXAZA-BOROLIDINE INTERNAL SALT
  • 2-APB
  • 2-AMINOETHYL DIPHENYL BORATE
  • 2-AMINOETHYL DIPHENYLBORINATE
  • (2-AMINOETHOXY)DIPHENYLBORANE
  • 2-AMINOETHOXYDIPHENYLBORATE
  • BETA-AMINOETHYL DIPHENYLBORINATE
  • DIPHENYLBORIC ACID 2-AMINOETHYL ESTER
  • DIPHENYLBORIC ACID ETHANOLAMINE COMPLEX
  • DIPHENYLBORINIC ACID 2-AMINOETHYL ESTER
  • DIPHENYLBORINIC ACID ETHANOLAMINE ESTER
  • Diphenylborinic acid 2-aMinoethyl ester, 98% 10GR
  • Diphenylborinic acid 2-aMinoethyl ester, 98% 25GR
  • Diphenylborinic acid 2-aMinoethyl ester, 98% 5GR
  • (2-Aminoethoxy)diphenylborane Diphenylborinic Acid 2-Aminoethyl Ester
  • AMINOETHOXYDIPHENYLBORANE
  • 2- aMinoethylbiphenylboric acidester
  • Naturstoffreagenz A
  • NSC 17107
  • Natural Product
  • diphenyl-borinicaci2-aminoethylester
  • o-(2-aminoethyl)diphenyl-borinicaci
  • Borinic acid, diphenyl-, 2-aminoethyl ester
  • Diphenylborinic acid
  • 2-Aminoethyl diphenylborinate, Diphenylboric acid 2-aminoethyl ester, Natural product Reagent A
  • 2-(Diphenylboryloxy)ethanamine
  • 2-(Diphenylboryloxy)ethylamine
  • Diphenylborinic acid 2-aminoethyl ester,98%
  • 2-Aminoethyl diphenyl borate, 2-APB, Diphenylboric acid 2-aminoethyl ester, Diphenylborinic acid
  • 2-Aminoethyl Diphenylborinate &gt
  • Aminoethyl Diphenylborinate
  • 2-AMINOETHYLDIPHENYL BORATE FOR SYNTHESI
  • Borinic acid, B,B-diphenyl-, 2-aminoethyl ester
  • 2-Aminoethyl diphenylborinate (2-APB)
  • 2-diphenylboranyloxyethanamine
  • 2-Aminoethoxydiphenyl borate|||2-APB
  • 2-APB, Ca2+ release modulator
  • 2-Aminoethyl diphenylborinate, 10 mM in DMSO
  • 524-95-8
  • C6H52BOCH2CH2NH2
  • C14H16BNO
  • B1C14H16N1O1
  • Others
  • Organometallic Reagents
  • Analytical Chromatography Product Catalog
  • Analytical Reagents
  • Boronic Acids and Derivatives
  • AMINE
  • Borinic Acids
  • B (Classes of Boron Compounds)
  • Signalling
  • Aromatic Esters
  • Borinic Acids
  • B (Classes of Boron Compounds)