[ CAS No. 55928-90-0 ] {[proInfo.proName]}

Name: 55928-90-0|5-Bromopyridazin-4-amine|98%
Brand: Ambeed
SKU: A146491
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Quality Control of [ 55928-90-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 55928-90-0 ]

SDS Specification

Alternatived Products of [ 55928-90-0 ]

Product Details of [ 55928-90-0 ]

CAS No. :	55928-90-0	MDL No. :	MFCD18909369
Formula :	C₄H₄BrN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KYXLLQKHVRNCCS-UHFFFAOYSA-N
M.W :	174.00	Pubchem ID :	60026667
Synonyms :

Calculated chemistry of [ 55928-90-0 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	34.14
TPSA :	51.8 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.47 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.07
Log Po/w (XLOGP3) :	-0.15
Log Po/w (WLOGP) :	0.83
Log Po/w (MLOGP) :	0.15
Log Po/w (SILICOS-IT) :	1.02
Consensus Log Po/w :	0.58

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.38
Solubility :	7.27 mg/ml ; 0.0418 mol/l
Class :	Very soluble
Log S (Ali) :	-0.48
Solubility :	57.2 mg/ml ; 0.329 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.14
Solubility :	1.25 mg/ml ; 0.00721 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.72

Safety of [ 55928-90-0 ]

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

Application In Synthesis of [ 55928-90-0 ]

* 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 [ 55928-90-0 ]
Downstream synthetic route of [ 55928-90-0 ]

[ 55928-90-0 ] Synthesis Path-Upstream 1~1

1
[ 20744-39-2 ]
[ 55928-90-0 ]

Yield	Reaction Conditions	Operation in experiment
5.56%	With bromine In acetic acid at 20℃; for 1 h;	5-Bromopyridazin-4-amine: To a solution of pyridazin-4-amine (1.18 g, 12.41 mmol) in Acetic Acid (2.5 mL) was added dibromine (0.638 mL, 12.41 mmol)dropwise at rt in a water bath. After 1 h, 10 N NaOH was added and then extracted with dichloromethane (3x). The combined extracts were dried over sodium sulfate and concentrated in vacuo. The crude product was dissolved in a small amount of dichloromethane and charged to a 40 g silica gel cartridge which was eluted with 0-15percent dichloromethane / methanol over a period of 40 mins. The desired fractions were combined and dried under vacuo to give 3-bromopyridazin-4- amine (0.1 g, 0.575 mmol, 4.63 percent yield)(first eluting) and 5-bromopyridazin-4-amine (0.12 g, 0.690 mmol, 5.56 percent yield)(second eluting). 1H NMR (400 MHz, DMSO-d₆) δ ppm 8.75 (s, 1 H) 8.55 (s, 1 H) 6.72 - 6.79 (m, 2 H).

Reference： [1] Patent: WO2015/69594, 2015, A1, . Location in patent: Page/Page column 196
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 4, p. 1583 - 1598

[ 55928-90-0 ] Synthesis Path-Downstream 1~18

3
[ 849354-28-5 ]
[ 55928-90-0 ]
[ 1562398-97-3 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1583 - 1598

4
[ 20744-39-2 ]
[ 55928-90-0 ]

Yield	Reaction Conditions	Operation in experiment
5.56%	With bromine; In acetic acid; at 20℃; for 1h;	5-Bromo<strong>[20744-39-2]pyridazin-4-amine</strong>: To a solution of <strong>[20744-39-2]pyridazin-4-amine</strong> (1.18 g, 12.41 mmol) in Acetic Acid (2.5 mL) was added dibromine (0.638 mL, 12.41 mmol)dropwise at rt in a water bath. After 1 h, 10 N NaOH was added and then extracted with dichloromethane (3x). The combined extracts were dried over sodium sulfate and concentrated in vacuo. The crude product was dissolved in a small amount of dichloromethane and charged to a 40 g silica gel cartridge which was eluted with 0-15% dichloromethane / methanol over a period of 40 mins. The desired fractions were combined and dried under vacuo to give 3-bromopyridazin-4- amine (0.1 g, 0.575 mmol, 4.63 % yield)(first eluting) and 5-bromo<strong>[20744-39-2]pyridazin-4-amine</strong> (0.12 g, 0.690 mmol, 5.56 % yield)(second eluting). 1H NMR (400 MHz, DMSO-d6) delta ppm 8.75 (s, 1 H) 8.55 (s, 1 H) 6.72 - 6.79 (m, 2 H).

Reference： [1]Patent: WO2015/69594,2015,A1 .Location in patent: Page/Page column 196
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 1583 - 1598

5
[ 24424-99-5 ]
[ 55928-90-0 ]
tert-butyl N-(5-bromopyridazin-4-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		tert-Butyl(5-bromopyridazin-4-yl)carbamate. To <strong>[55928-90-0]5-bromopyridazin-4-amine</strong> (0.1 g, 0.575mmol) and TRIETHYL AMINE (0.104 mL, 0.747 mmol)in DCM (2 mL) at 0 C. Thesolution was stirred at rt for 10 mins then BOC20 (0.147 mL, 0.632 mmol) wasadded. The reaction was stirred at rt for 1 hr. The reaction was diluted withDCM and washed with brine, and dried over sodium sulfate. The crude product wasdissolved in a small amount of dichloromethane and charged to a 24 g silica gelcartridge which was eluted with 0-10% dichloromethane / methanol over a periodof 40 mins. The desired fractions were combined and dried under vacuo to givetert-butyl (5-bromopyridazin-4-yl)carbamate (0.12 g, 0.438 mmol, 76 % yield).MS (ESI) (m/z): 276 (M+H)+.

Reference： [1]Patent: WO2015/69594,2015,A1 .Location in patent: Page/Page column 196; 197

6
[ 55928-90-0 ]
[ 151169-74-3 ]
5-(2,3-dichlorophenyl)pyridazin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; water; at 60℃;	5-Bromopyridazin-4-amine, 2.00 g (11.5 mmol), 2,3-dichlorophenylboronic acid, 3.30 g (17.2 mmol), tris(dibenzylideneacetone)dipalladium, 265 mg (0.3 mmol), tri-tert-butylphosphine tetrafluoroborate, 167 mg (0.6 mmol), and potassium fluoride, 2.00 g (34.7 mmol), were dissolved in 16 mL of tetrahydrofuran and 4 mL of water. The mixture was stirred at 60 C overnight. The solvent was removed in vacuo. Water was added, the mixture was extracted with ethyl acetate and the combined organic phase was dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified with silica gel column chromatograph (dichloromethane / methanol = 20: 1) to give 2.1 g (75%) of the product as a yellow solid. LC-MS (Method Ml): Rt = 0.91 min; m/z = 240 (M+l)+.

Reference： [1]Patent: WO2019/2132,2019,A1 .Location in patent: Page/Page column 181

7
[ 126726-62-3 ]
[ 55928-90-0 ]
5-(prop-1-en-2-yl)pyridazin-4-amine [ No CAS ]