[ CAS No. 397322-82-6 ] {[proInfo.proName]}

Name: 397322-82-6|2-Amino-3-chlorobenzaldehyde|98%
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SKU: A157626
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Quality Control of [ 397322-82-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 397322-82-6 ]

Product Details of [ 397322-82-6 ]

CAS No. :	397322-82-6	MDL No. :	MFCD13193431
Formula :	C₇H₆ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FVFGTMXRHNSEMC-UHFFFAOYSA-N
M.W :	155.58	Pubchem ID :	23510442
Synonyms :

Calculated chemistry of [ 397322-82-6 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.24
TPSA :	43.09 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.29
Log Po/w (XLOGP3) :	1.88
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	1.39
Log Po/w (SILICOS-IT) :	1.9
Consensus Log Po/w :	1.64

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.37
Solubility :	0.668 mg/ml ; 0.0043 mol/l
Class :	Soluble
Log S (Ali) :	-2.41
Solubility :	0.61 mg/ml ; 0.00392 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.59
Solubility :	0.402 mg/ml ; 0.00258 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 397322-82-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H317-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 397322-82-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 397322-82-6 ]
Downstream synthetic route of [ 397322-82-6 ]

[ 397322-82-6 ] Synthesis Path-Upstream 1~5

1
[ 397322-82-6 ]
[ 67092-20-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6829 - 6833

2
[ 61487-25-0 ]
[ 397322-82-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With manganese(IV) oxide In dichloromethane at 20℃; for 20 h; Inert atmosphere	General procedure: To a solution of 1a (1.2 g, 7.61 mmol) in CH₂Cl₂ (20 mL) was added MnO₂ (2.6 g, 30.1 mmol) and stirred at rt under an Ar atmosphere. After 23 h with stirring, the reaction mixture was filtrated and evaporated. The residue was crystallized from AcOEt to give 7a (1.0 g, 85percent) as a yellow needle crystal.

Reference： [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831

3
[ 53312-77-9 ]
[ 397322-82-6 ]

Reference： [1] Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 416 - 417

4
[ 22233-52-9 ]
[ 397322-82-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6829 - 6833

5
[ 6388-47-2 ]
[ 397322-82-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831

[ 397322-82-6 ] Synthesis Path-Downstream 1~28

1
[ 397322-82-6 ]
[ 97041-58-2 ]

Yield	Reaction Conditions	Operation in experiment
95%		Example 35 In a similar manner to the preparation of the compound of Example 33-1, 8-chloro-3-methylquinoline (1.09 g, 95%) was obtained from <strong>[397322-82-6]2-amino-3-chlorobenzaldehyde</strong> (1.00 g). 1H NMR (CDCl3, 300 MHz) delta 8.90 (d, 1H, J=2.2 Hz), 7.95 (d, 1H, J=2.2 Hz), 7.77 (dd, 1H, J=1.6, 7.5 Hz), 7.68 (dd, I1H, J=1.6, 7.5 Hz), 7.43 (dd, 1H, J=7.5, 7.5 Hz), 2.55 (s, 3H).

Reference： [1]Patent: US2003/181496,2003,A1

2
[ 123-75-1 ]
[ 397322-82-6 ]
[ 1004781-31-0 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 416 - 417
[2]Synthesis,2013,vol. 45,p. 1730 - 1748

3
[ 53312-77-9 ]
[ 397322-82-6 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 416 - 417

4
[ 397322-82-6 ]
[ 5000-66-8 ]
[ 1064578-06-8 ]

Yield	Reaction Conditions	Operation in experiment
		To pyridine (2.1 ml, 26 mmol) in EtOH (60 ml) was added 2-bromo-l-(2- chlorophenyl)ethanone (6.1 g, 26 mmol) in EtOH (40 ml) dropwise over 10 min. The resulting mixture was heated at 60~70C for 1 hour and cooled to room temperature. To the mixture were added pyridine (1.25 ml), 2-amino-3- chlorobenzaldehyde (3.72g, 24.0mmol) and DMAP (0.05g, cat.). The mixture was heated at reflux for 48 hrs. The reaction mixture was cooled to room temperature and pyrrolidine (4.60ml, 55.0 mmol) was added. After heating at reflux overnight, the resulting mixture was concentrated. The residue was partitioned between saturated aqueous NaHCO3 and CH2Cl2. The combined organic layers were dried, concentrated. Flash chromatography of the residue over silica gel, using 3:7 EtOAc-hexane, gave 8-chloro-2-(2-chlorophenyl)- quinolin-3-amine, 1H-NMR (DMSO-d6) delta 7.67 (d, J= 8.0 Hz, IH), 7.63 (d, J= <n="51"/>8.0 Hz, IH), 7.50-7.57 (m, 3H), 7.46 (d, J= 8.0 Hz, IH), 7.42 (s, 1H),7.39 (t, J- 8.0 Hz, IH), 5.32 (br, 2H). Mass Spectrum (ESI) m/e = 289.0 (M + 1).

Reference： [1]Patent: WO2008/118455,2008,A1 .Location in patent: Page/Page column 49-50

6
[ 397322-82-6 ]
[ 3442-60-2 ]
[ 1403212-82-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With methanesulfonic acid; In ethanol; for 25.5h;Reflux; Inert atmosphere;	General procedure: To a stirred solution of 17 (100 mg, 0.33 mmol) in ethanol (7 mL) were added methanesulfonic acid (100 muL, 1.54 mmol) and 7b (377 mg, 2.44 mmol), and refluxed under an Ar atmosphere. After 25.5 h with stirring, the reaction mixture was basified (pH 9) with saturated NaHCO3 aqueous solution, and extracted with CHCl3 three times. The combined organic extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was chromatographed on silica gel (CHCl3/MeOH/25% ammonia aqueous solution = 100/0/0-100/10/1) to give 18b (123 mg, 88%) as a white amorphous solid.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 5810 - 5831

7
[ 61487-25-0 ]
[ 397322-82-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With manganese(IV) oxide; In dichloromethane; at 20℃; for 20h;Inert atmosphere;	General procedure: To a solution of 1a (1.2 g, 7.61 mmol) in CH2Cl2 (20 mL) was added MnO2 (2.6 g, 30.1 mmol) and stirred at rt under an Ar atmosphere. After 23 h with stirring, the reaction mixture was filtrated and evaporated. The residue was crystallized from AcOEt to give 7a (1.0 g, 85%) as a yellow needle crystal.

Reference： [1]Organic Letters,2019,vol. 21,p. 7143 - 7148
[2]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 5810 - 5831
[3]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5099 - 5105

8
[ 6388-47-2 ]
[ 397322-82-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 5810 - 5831
[2]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5099 - 5105
[3]Organic Letters,2019,vol. 21,p. 7143 - 7148

9
[ 397322-82-6 ]
[ 1403212-88-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 5810 - 5831

10
[ 397322-82-6 ]
C₂₄H₂₃ClN₂O₂*ClH [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 5810 - 5831

11
[ 22233-52-9 ]
[ 397322-82-6 ]