3-Chlorodiphenylamine

Names

[ CAS No. ]:
101-17-7

[ Name ]:
3-Chlorodiphenylamine

[Synonym ]:
Benzenamine, 3-chloro-N-phenyl-
(3-Chlor-phenyl)-phenyl-amin
EINECS 202-922-0
3-chloro-N-phenyl-aniline
3-Chloro-N-phenyl-benzenamine
N-(3-Chlorophenyl)aniline
MFCD00000590
N-(m-Chlorophenyl)aniline
(3-chlorophenyl)phenylamine
(3-Cl-C6H4)PhNH
m-Chlorodiphenylamine
3-Chloro-N-phenylaniline
3-Chlorodiphenylamine
Benzenamine,3-chloro-N-phenyl
N-(3-chlorophenyl)-N-phenylamine

Biological Activity

[Description]:

3-Chlorodiphenylamine is a high affinity Ca2+ sensitizer of cardiac muscle. 3-Chlorodiphenylamine is based on diphenylamine and binds to the isolated N-domain of cardiac troponin C (cTnC) (Kd=6 µM). 3-Chlorodiphenylamine is an excellent starting scaffold for the development of more potent Ca2+-sensitizing compounds due to its small size, and can be used for systolic heart failure research[1].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel

[Target]

Kd: 6 µM (N-domain of cardiac troponin C (cTnC)) Kd: 10 µM (cNTnC–cSp chimera)[1]

[In Vitro]

3-Chlorodiphenylamine is able to bind highly (Kd=10 µM) to a chimeric protein consisting of the regulatory N-domain of cTnC (cNTnC) and the switch region of cTnI (cNTnC–cSp chimera)[1]. 3-Chlorodiphenylamine (100 µM) results in a 1.5-fold increase in the Ca2+ sensitivity of force development without altering the maximal or resting forces in skinned ventricular trabeculae[1]. 3-Chlorodiphenylamine (25-100 µM) increases Ca2+ sensitivity of the N-domain of intact cTnC after reconstitution into the cTn complex (cTnC complexed with cTnI and cTnT) in a concentration-dependent manner. It exhibits pCa50s with 6.39±0.01, 6.65±0.01, and 6.73±0.02 in the presence of 25, 50, and 100 µM 3-Chlorodiphenylamine, respectively[1].

[References]

[1]. Svetlana B Tikunova, et al. 3-Chlorodiphenylamine activates cardiac troponin by a mechanism distinct from bepridil or TFP. J Gen Physiol. 2019 Jan 7;151(1):9-17.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
337.8±0.0 °C at 760 mmHg

[ Melting Point ]:
112 °C

[ Molecular Formula ]:
C₁₂H₁₀ClN

[ Molecular Weight ]:
203.667

[ Flash Point ]:
147.4±23.2 °C

[ Exact Mass ]:
203.050171

[ PSA ]:
12.03000

[ LogP ]:
3.86

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.643

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S28-S36/37

[ HS Code ]:
2921440000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2921440000

[ Summary ]:
2921440000. diphenylamine and its derivatives; salts thereof. VAT:17.0%. Tax rebate rate:17.0%. . MFN tariff:6.5%. General tariff:30.0%

Related Compounds

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