[ CAS No. 100367-37-1 ] {[proInfo.proName]}

Name: 100367-37-1|3-Amino-4-bromophenol|98%
Brand: Ambeed
SKU: A608264
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Quality Control of [ 100367-37-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 100367-37-1 ]

SDS Specification

Alternatived Products of [ 100367-37-1 ]

Product Details of [ 100367-37-1 ]

CAS No. :	100367-37-1	MDL No. :	MFCD09260886
Formula :	C₆H₆BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JJNOHJJIVAVDLP-UHFFFAOYSA-N
M.W :	188.02	Pubchem ID :	24721534
Synonyms :

Calculated chemistry of [ 100367-37-1 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	40.57
TPSA :	46.25 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 :	Yes
Log Kp (skin permeation) :	-6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.28
Log Po/w (XLOGP3) :	1.85
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	1.58
Log Po/w (SILICOS-IT) :	1.34
Consensus Log Po/w :	1.56

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.66
Solubility :	0.407 mg/ml ; 0.00216 mol/l
Class :	Soluble
Log S (Ali) :	-2.44
Solubility :	0.679 mg/ml ; 0.00361 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.32
Solubility :	0.906 mg/ml ; 0.00482 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.18

Safety of [ 100367-37-1 ]

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

Application In Synthesis of [ 100367-37-1 ]

* 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 [ 100367-37-1 ]
Downstream synthetic route of [ 100367-37-1 ]

[ 100367-37-1 ] Synthesis Path-Upstream 1~2

1
[ 78137-76-5 ]
[ 100367-37-1 ]

Yield	Reaction Conditions	Operation in experiment
70.9%	With iron(III) oxide; hydrazine hydrate In ethanol for 1.5 h; Reflux	(3) reduction reaction:The reaction flask was added 13. 1g 3-nitro-4-bromophenol,66g ethanol, stirring to dissolve.Add 1.3g ferric oxide,11.3 g of a hydrazine hydrate solution at a concentration of 80 wtpercent.Stir and heat to reflux. Reflux 1.5h,Sampling, no raw materials, cooling and filtering. The filtrate was concentrated, 16 ml of water was added to the concentrate,With stirring, adjust pH = 7 with 10percent hydrochloric acid. Precipitation of the solid, the crude product was filtered, wet weight 15g.The crude product was recrystallized,Ethanol 17g at 60 ° C, the product just dissolved.Add 17g of water. Stir 10min. After 30min at room temperature, transfer to ice bath for 30min,Precipitated crystals, filtered to give 8 Og light pink product, purity 99percentYield 70.9percent

Reference： [1] Patent: CN102060717, 2017, B, . Location in patent: Paragraph 0007; 0019; 0020

2
[ 591-27-5 ]
[ 100367-37-1 ]
[ 55120-56-4 ]

Reference： [1] Polyhedron, 2013, vol. 52, p. 246 - 254

[ 100367-37-1 ] Synthesis Path-Downstream 1~23

1
[ 100367-37-1 ]
[ 1005787-88-1 ]
[ 1005782-80-8 ]

Yield	Reaction Conditions	Operation in experiment
48%	With potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide;	Example 185 Production of N-[6-(3-amino-4-bromophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide A mixture of N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide (3.28 g, 10 mmol), <strong>[100367-37-1]3-amino-4-bromophenol</strong> (2.82 g, 15 mmol), potassium carbonate (2.76 g, 20 mmol) and N,N-dimethylformamide (20 mL) was stirred at 110 C. for 24 hr, then at 150 C. for 24 hr. The reaction mixture was diluted with water and extracted with a mixed solvent of ethyl acetate/tetrahydrofuran (1:1). The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50?40/100) and recrystallized from ethyl acetate to give the title compound (1.85 g, yield 48%) as a pale-yellow solid. 1H-NMR (DMSO-d6, 300 MHz) delta 0.74-0.88 (4H, m), 1.86-1.98 (1H, m), 5.51 (2H, s), 6.35 (1H, dd, J=8.6, 2.8 Hz), 6.62 (1H, d, J=2.8 Hz), 7.01 (1H, d, J=9.6 Hz), 7.37 (1H, d, J=8.6 Hz), 7.99 (1H, s), 8.02 (1H, d, J=9.6 Hz), 11.08 (1H, s).

Reference： [1]Patent: US2009/137595,2009,A1

2
[ 67-56-1 ]
[ 15997-62-3 ]
[ 100367-37-1 ]
[ 1402597-31-2 ]

Yield	Reaction Conditions	Operation in experiment
90%		Example 22a 2b2a (100g, 531 mmol) and 1b (95 g, 558 mmol) were charged into a clean and dry reactor under nitrogen followed by addition of fluorobenzene (1000 mL). After being heated at 35-37 C for 4 hours, the batch was cooled to 23 C. Concentrated H2S04 (260.82 g, 2659.3 mmol, 5 eq.) was added while maintaining the batch temperature below 35 C. The batch was first heated at 30-35 C for 30 minutes and then at 40- 45 C for 2 hours. 4-Methyl morpholine (215.19 g, 2127 mmol, 4 eq.) was added to the batch while maintaining the temperature below 50 C. Then the batch was agitated for 30 minutes at 40-50 C. eOH (100 mL) was then added while maintaining the temperature below 55 C. After the batch was held at 50-55 C for 2 hours, another portion of MeOH (100 mL) was added. The batch was agitated for another 2 hours at 50-55 C. After fluorobenzene was distilled to a minimum amount, water (1000 mL) was added. Further distillation was performed to remove any remaining fluorobenzene. After the batch was cooled to 30 C, the solid was collected by filtration with cloth and rinsed with water (400 mL) and heptane (200 mL). The solid was dried under vacuum below 50 C to reach KF < 0.1%. Typically, the product 2b was obtained in 90% yield with 98 wt%. 1H NMR (500 MHz, DMSO- d6): delta = 10.83 (s, 1 H), 9.85 (s, bs, 1 H), 7.6 (d, 1 H, JHz), 6.40 (s, 1 H), 4.00 (s, 2 H), 3.61 (s, 3 H).

Reference： [1]Patent: WO2012/138670,2012,A1 .Location in patent: Page/Page column 59

3
[ 591-27-5 ]
[ 100367-37-1 ]
[ 55120-56-4 ]

Reference： [1]Polyhedron,2013,vol. 52,p. 246 - 254

4
[ 100367-37-1 ]
[ 31270-80-1 ]
[ 1609581-20-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With caesium carbonate; In dimethyl sulfoxide; at 130℃; for 18h;	This reaction was carried out in two identical batches. A mixture of 3-am ino-4- bromophenol (13 g, 69 mmol), cesium carbonate (45 g, 140 mmol) and 4-chlorofuro[3,2- c]pyridine (7.0 g, 46 mmol) in dimethyl sulfoxide (200 mL)was heated to 13000 for 18 hours. The two batches were cooled to room temperature and combined, and the mixture was pouredinto ice water (800 mL) and extracted with ethyl acetate (5 x 1200 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (500 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. Purification using silica gel chromatography (Gradient: 17% to 25% ethyl acetate in petroleum ether) provided the product as a white solid. Yield: 25 g, 82 mmol, 89%.

Reference： [1]Patent: WO2014/72881,2014,A1 .Location in patent: Page/Page column 90; 91
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 3753 - 3772

5
[ 100367-37-1 ]
[ 1609577-32-3 ]

Reference： [1]Patent: WO2014/72881,2014,A1
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 3753 - 3772

6
[ 100367-37-1 ]
[ 1609581-21-6 ]

Reference： [1]Patent: WO2014/72881,2014,A1
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 3753 - 3772

7
[ 100367-37-1 ]
[ 1609577-75-4 ]

Reference： [1]Patent: WO2014/72881,2014,A1

8
[ 100367-37-1 ]
[ 1609577-99-2 ]

Reference： [1]Patent: WO2014/72881,2014,A1

9
[ 100367-37-1 ]
methyl 2-(tert-butoxy)-2-((R)-4-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2-methylquinolin-3-yl)acetate [ No CAS ]