[ CAS No. 53312-77-9 ] {[proInfo.proName]}

Name: 53312-77-9|2-Amino-3-chlorobenzonitrile|98%
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Quality Control of [ 53312-77-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 53312-77-9 ]

Product Details of [ 53312-77-9 ]

CAS No. :	53312-77-9	MDL No. :	MFCD03425881
Formula :	C₇H₅ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FAHVRFGAGJMXHW-UHFFFAOYSA-N
M.W :	152.58	Pubchem ID :	12627363
Synonyms :

Calculated chemistry of [ 53312-77-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.57
TPSA :	49.81 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) :	-5.71 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.49
Log Po/w (XLOGP3) :	2.14
Log Po/w (WLOGP) :	1.8
Log Po/w (MLOGP) :	1.39
Log Po/w (SILICOS-IT) :	1.72
Consensus Log Po/w :	1.71

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.58
Solubility :	0.403 mg/ml ; 0.00264 mol/l
Class :	Soluble
Log S (Ali) :	-2.82
Solubility :	0.232 mg/ml ; 0.00152 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.72
Solubility :	0.289 mg/ml ; 0.00189 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.37

Safety of [ 53312-77-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302-H312-H315-H319-H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 53312-77-9 ]

* 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 [ 53312-77-9 ]
Downstream synthetic route of [ 53312-77-9 ]

[ 53312-77-9 ] Synthesis Path-Upstream 1~7

1
[ 32315-10-9 ]
[ 53312-77-9 ]
[ 62484-29-1 ]

Reference： [1] Heterocycles, 2012, vol. 85, # 6, p. 1417 - 1426

2
[ 544-92-3 ]
[ 608-31-1 ]
[ 63069-52-3 ]
[ 53312-77-9 ]

Reference： [1] Journal of the American Chemical Society, 2003, vol. 125, # 47, p. 14296 - 14297

3
[ 676-58-4 ]
[ 53312-77-9 ]
[ 56762-32-4 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 13, p. 4052 - 4056

4
[ 608-31-1 ]
[ 4427-60-5 ]
[ 53312-77-9 ]

Yield	Reaction Conditions	Operation in experiment
33%	at 80 - 170℃; for 20.5 h;	2,6-dichloroaniline in 100 ml round-bottomed flask XXXI4. 84 g, 0.03 mol, 12 ml of N- methylpyrrolidone, referred to as NMP and dissolved at 80 ° C after sufficient stirring, cuprous cyanide was added portionwise 3.5 g, 0.04 mol, added after this system was increased to 150-170 degrees Celsius, the reaction at this temperature for 0.5 hours, cooled to 80 ° C, then cuprous cyanide . 3.5 g, 004 mol was added portionwise, after completion of this heating system 150-170 ° C, for 20 hours; then cooled to 60 ° C, poured into a mixed solvent of 30 ml aqueous ammonia and 30 ml ice water, stirred for 1 hours, filtered, the filtrate was collected by filtration and the resulting precipitate was washed with methylene chloride. The methylene chloride layer is separated, dried over anhydrous sodium sulfate, and concentrated to a volume ratio of ethyl acetate: petroleum ether = 1: 10 Column chromatography of the mixed solvent. The first is to elute 1.1 g of 2,6-dichloro-aniline, and the aniline is 2-chloro-6-cyano XXXIII. 5 g, yield 33percent, and finally is rinsed out 2,6 dicyano aniline XXXII10. 17 g, yield 3.96percent.

Reference： [1] Patent: CN102942565, 2016, B, . Location in patent: Paragraph 0057-0059; 0104-0105

5
[ 544-92-3 ]
[ 608-31-1 ]
[ 63069-52-3 ]
[ 53312-77-9 ]

Reference： [1] Journal of the American Chemical Society, 2003, vol. 125, # 47, p. 14296 - 14297

6
[ 544-92-3 ]
[ 608-31-1 ]
[ 53312-77-9 ]

Reference： [1] Tetrahedron, 2006, vol. 62, # 40, p. 9365 - 9372

7
[ 53312-77-9 ]
[ 397322-82-6 ]

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

[ 53312-77-9 ] Synthesis Path-Downstream 1~58

1
[ 53312-77-9 ]
2-Amino-3-chloro-thiobenzamide [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 65 - 67

2
[ 64-18-6 ]
[ 53312-77-9 ]
8-Chloro-1H-quinazolin-4-one [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 2051 - 2053

3
[ 6881-49-8 ]
[ 53312-77-9 ]
[ 402842-43-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2921 - 2928

4
[ 544-92-3 ]
[ 608-31-1 ]
[ 63069-52-3 ]
[ 53312-77-9 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 14296 - 14297

5
[ 3320-90-9 ]
[ 53312-77-9 ]
[ 866042-71-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3453 - 3458

6
[ 53312-77-9 ]
[ 124-68-5 ]
[ 913731-14-3 ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 9365 - 9372

7
[ 544-92-3 ]
[ 608-31-1 ]
[ 53312-77-9 ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 9365 - 9372

8
[ 53312-77-9 ]
2-[(8-chloro-2-phenyl-4-quinolyl)amino]-2-methylpropan-1-ol [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 9365 - 9372

9
[ 53312-77-9 ]
[ 875629-19-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3453 - 3458

10
[ 53312-77-9 ]
(3-Chloro-2-pyrrol-1-yl-benzyl)-[1-(4-ethyl-phenyl)-meth-(E)-ylidene]-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3453 - 3458

11
[ 53312-77-9 ]
10-chloro-4-(4-ethyl-phenyl)-5,6-dihydro-4H-benzo[f]pyrrolo[1,2-a][1,4]diazepine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3453 - 3458

12
[ 53312-77-9 ]
[ 402842-59-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2921 - 2928

13
[ 53312-77-9 ]
[ 402842-75-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2921 - 2928

14
[ 53312-77-9 ]
10-amino-8-chloro-2-oxo-1,2,3,4-tetrahydro-2λ⁴-thia-9-aza-anthracen-4-ol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2921 - 2928

15
[ 53312-77-9 ]
[ 74409-85-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 65 - 67

16
[ 53312-77-9 ]
[ 26803-78-1 ]

Yield	Reaction Conditions	Operation in experiment
		To a mixture of 2-amino-3- chlorobenzonitrile (500 mg, 3.3 mmol), sodium azide (4.3 mmol, 1.3 eq.), and triethylamine hydrochloride (4.3 mmol, 1.3 eq.) in a sealed tube, 8 mL of toluene was added. The tube was tightly capped and the reaction was stirred and heated to 1000C overnight. The mixture was cooled to room temperature, diluted with another 10 mL of toluene, transferred to a separatory funnel and washed 3 x 20 mL with water. The EPO <DP n="62"/>aqueous extractions were collected and acidified to a pH of 4 with concentrated HCl. The solid was collected by filtration, washed with acetonitrile, and dried under vacuum to afford 581 mg of 2-chloro-6-(lH-tetrazol-5-yl)aniline. MS (EI) for C7H6ClN5: 196 (MH+).

Reference： [1]Patent: WO2007/44724,2007,A2 .Location in patent: Page/Page column 60-61

17
[ 53312-77-9 ]
[ 397322-82-6 ]

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

18
[ 53312-77-9 ]
[ 79-22-1 ]
[ 100-58-3 ]
[ 69565-43-1 ]

Yield	Reaction Conditions	Operation in experiment
		Reference Synthesis Example 1 (Preparation of 8-chloro-4-phenyl-2(1H)-quinazolinone (compound No. II-11)) To 7.10 g of phenylmagnesium bromide (32% THF solution) was added dropwise a solution of 953 mg of <strong>[53312-77-9]2-<strong>[53312-77-9]amino-3-chlorobenzonitrile</strong></strong> in THF (7 ml) at room temperature, followed by heating under reflux for 30 minutes. To the resulting reaction product was added dropwise 885 mg of methyl chlorocarbonate under ice cooling, followed by heating under reflux for 40 minutes. The resulting reaction solution was cooled and poured into 40 ml of 2N-hydrochloric acid, and 8 g of sodium bicarbonate and 20 ml of MTBE were added thereto, followed by stirring. Precipitated crystals were collected by filtration to obtain 1.30 g of the titled compound. 1H NMR (DMSO-d6): 7.24(1H, t, J = 8.0 Hz), 7.57-7.70 (6H, m), 7.90-7.93 (1H, m), 11.45 (br. s).

Reference： [1]Patent: EP2100507,2009,A1 .Location in patent: Page/Page column 34

19
[ 1378039-78-1 ]
[ 53312-77-9 ]
[ 1378040-21-1 ]

Yield	Reaction Conditions	Operation in experiment
	With titanium tetrachloride; triethylamine; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere;	Method 2:Example 95 :3-Chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)-pyrazolo[4,3-c]pyridin-2-yl]-benzonitrileStep 1 : 2- { [1 -(4-Azido-5-fluoropyridin-3-yl)-meth-(£')-ylidene] -amino}-3-chlorobenzonitrileA solution of 4-azido-5-fluoropyridine-3-carbaldehyde (2.86 g, 17.2 mmol) and <strong>[53312-77-9]2-<strong>[53312-77-9]amino-3-chlorobenzonitrile</strong></strong> (2.62 g, 17.2 mmol) in DCM (60 mL) was cooled to 0 C under an atmosphere of nitrogen. Triethylamine (7.2 mL, 51.6 mmol) was added, followed by drop wise additiona of titanium (IV) chloride solution (1 N in DCM, 10.3 mL, 10.3 mmol). The reaction mixture was stirred at 0 C for 2 hours, then at room temperature overnight. The resultant mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residue obtained was used in the following step without further purification

Reference： [1]Patent: WO2012/66061,2012,A1 .Location in patent: Page/Page column 179-180

20
[ 32315-10-9 ]
[ 53312-77-9 ]
[ 62484-29-1 ]

Reference： [1]Heterocycles,2012,vol. 85,p. 1417 - 1426

21
[ 53312-77-9 ]
[ 74-88-4 ]
[ 1294507-95-1 ]

Yield	Reaction Conditions	Operation in experiment
88%		To a solution of <strong>[53312-77-9]2-<strong>[53312-77-9]amino-3-chlorobenzonitrile</strong></strong> (5.0 g, 32.9 mmol) in dry DMF (60 mL) was added NaH (1.97 g, 60%, 49.3 mmol) at 0 C. Then, the mixture was stirred at 0 C for 15 min. Mel (4.67 g, 32.9 mmol) was added and the mixture was stirred at rt for 2 hrs. The reaction solution was quenched with saturated NH4C1 solution, diluted with EtOAc (200 mL), washed with H20 (2x) and brine (2x), dried (Na2S04), filtered, and concentrated. The residue was purified by silica gel column chromatography (EtOAc/PE=0~5%) to give 3-chloro-2- (methylamino)benzonitrile (4.8 g, 88%) as a white solid. ESI-MS (EI+, m/z): 167.0 [M+1]+.
88%		To a solution of <strong>[53312-77-9]2-<strong>[53312-77-9]amino-3-chlorobenzonitrile</strong></strong> (5.0 g, 32.9 mmol) in dry DMF (60 mL) was added NaH (1.97 g, 60%, 49.3 mmol) at 0 C. Then, the mixture was stirred at 0 C for 15 min. Mel (4.67 g, 32.9 mmol) was added and the mixture was stirred at rt for 2 hrs. The reaction solution was quenched with saturated NH4C1 solution, diluted with EtOAc (200 mL), washed with H20 (2x) and brine (2x), dried (Na2S04), filtered, and concentrated. The residue was purified by silica gel column chromatography (EtOAc/PE=0~5%) to give 3-chloro-2- (methylamino)benzonitrile (4.8 g, 88%) as a white solid. ESI-MS (EI+, m/z): 167.0 [M+1]+.

Reference： [1]Patent: WO2014/152213,2014,A2 .Location in patent: Page/Page column 46; 47
[2]Patent: WO2014/152278,2014,A2 .Location in patent: Page/Page column 45; 46

22
[ 53312-77-9 ]
8-chloro-3-(2-(3,5-dimethylphenylamino)thiazol-4-yl)-1-methylquinolin-2(1H)-one [ No CAS ]

Reference： [1]Patent: WO2014/152213,2014,A2

23
[ 53312-77-9 ]
3-(2-bromoacetyl)-8-chloro-1-methylquinolin-2(1H)-one [ No CAS ]

Reference： [1]Patent: WO2014/152213,2014,A2

24
[ 53312-77-9 ]
3-acetyl-8-chloro-1-methylquinolin-2(1H)-one [ No CAS ]

Reference： [1]Patent: WO2014/152213,2014,A2

25
[ 53312-77-9 ]
3-chloro-2-(methylamino)benzaldehyde [ No CAS ]

Reference： [1]Patent: WO2014/152213,2014,A2

26
[ 53312-77-9 ]
2-(9H-carbazol-9-yl)-N-(2-chloro-6-cyanophenyl)acetamide [ No CAS ]

Reference： [1]ChemMedChem,2015,vol. 10,p. 1489 - 1497

27
[ 53312-77-9 ]
[ 79-04-9 ]
2-chloro-N-(2-chloro-6-cyanophenyl)acetamide [ No CAS ]

Reference： [1]ChemMedChem,2015,vol. 10,p. 1489 - 1497

28
C₄H₁₀NPol [ No CAS ]
[ 53312-77-9 ]
C₁₁H₁₂ClN₄Pol [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 65540 - 65545

29
[ 53312-77-9 ]
2-((8-chloro-2-(1-fluorocyclobutyl)-4-(4-(2-methoxyphenyl)piperidin-1-yl)quinazolin-6-yl)(methyl)amino)ethanol [ No CAS ]

Reference： [1]Patent: WO2015/200534,2015,A2
[2]Patent: WO2015/200534,2015,A2

30
[ 53312-77-9 ]
2-({8-chloro-2-(1-fluorocyclopropyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl}-N-methylamino)ethanol [ No CAS ]