[ CAS No. 20358-06-9 ] {[proInfo.proName]}

Name: 20358-06-9|4-Fluorobenzo[d]thiazol-2-amine|97%
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SKU: A188527
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Quality Control of [ 20358-06-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 20358-06-9 ]

SDS Specification

Alternatived Products of [ 20358-06-9 ]

Product Details of [ 20358-06-9 ]

CAS No. :	20358-06-9	MDL No. :	MFCD04448824
Formula :	C₇H₅FN₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CBVRCEFUXXJLSG-UHFFFAOYSA-N
M.W :	168.19	Pubchem ID :	2049887
Synonyms :

Calculated chemistry of [ 20358-06-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.98
TPSA :	67.15 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) :	-5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.57
Log Po/w (XLOGP3) :	2.13
Log Po/w (WLOGP) :	2.45
Log Po/w (MLOGP) :	1.69
Log Po/w (SILICOS-IT) :	2.85
Consensus Log Po/w :	2.14

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.83
Solubility :	0.249 mg/ml ; 0.00148 mol/l
Class :	Soluble
Log S (Ali) :	-3.17
Solubility :	0.113 mg/ml ; 0.000674 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.88
Solubility :	0.22 mg/ml ; 0.00131 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.14

Safety of [ 20358-06-9 ]

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 [ 20358-06-9 ]

* 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 [ 20358-06-9 ]
Downstream synthetic route of [ 20358-06-9 ]

[ 20358-06-9 ] Synthesis Path-Upstream 1~6

1
[ 20358-06-9 ]
[ 63754-97-2 ]

Reference： [1] Farmaco, Edizione Scientifica, 1977, vol. 32, p. 348 - 354

2
[ 656-32-6 ]
[ 20358-06-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: With bromine In chloroform at 20℃; for 3 h; Heating / reflux Stage #2: With ammonium hydroxide In water	To a suspension of (2-fluorophenyl) thiourea (1.7g, 10.0 mmol) in chloroform [(25ML)] was added a solution of bromine (0.51 mL; 10.0 mmol) dropwise at room temperature. The resulting mixture was heated under reflux for 3 hrs. The solvent was evaporated, water was added and the mixture was neutralized with ammonium hydroxide. The resulting white precipitation was collected by filtration and dried to yield 1.2 g (72percent) of the title compound which was used in the subsequent step without further purification.

Reference： [1] Patent: WO2004/11460, 2004, A2, . Location in patent: Page 57
[2] Synthetic Communications, 1987, vol. 17, # 2, p. 229 - 240
[3] Journal of the Chemical Society [Section] C: Organic, 1969, p. 268 - 272

3
[ 348-54-9 ]
[ 1147550-11-5 ]
[ 20358-06-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With bromine In dichloromethane at 20℃; for 16 h;	General procedure: To a mixture of aniline (1) (2.0 g, 0.021 mol) and ammonium thiocyanate (6.5 g, 0.086 mol), bromine (2.2 mL, 0.043 mol) in dichloromethane (20 mL) and stirred for 16 h at ambient temperature. Later than water was added to the reaction mixture and the product was extracted in dichloromethane (3 × 30 mL). The solvent was evaporated under vacuum to afford the as crude, which was further purified by column chromatography using EtOAc:Hexane (4:6) to give compounds 2a-d.

Reference： [1] Asian Journal of Chemistry, 2015, vol. 27, # 12, p. 4575 - 4578

4
[ 348-54-9 ]
[ 20358-06-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: at 10℃; Stage #2: at 10 - 20℃; for 4 h;	General procedure: A mixture of aniline (0.05mol) and NH₄SCN (19.03g, 0.25mol) in glacial acetic acid (100mL) was cooled to 10°C in an ice bath and stirred for 10–20min. Then bromine (2.82mL, 0.055mol) in glacial acetic acid was added drop wise at such a rate to keep the temperature below 10°C. The mixture was stirred at room temperature for 4h and then poured into hot water (500mL), and basified to pH 11.0 with ammonia solution (NH₄OH). The resulting precipitate was filtered, washed with water and dried to get a light yellow to brown solid. The crude product was purified by chromatography on silica gel using MeOH/CH₂Cl₂ to afford compounds 2a–2k in good yields.

Reference： [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1759 - 1775

5
[ 51085-49-5 ]
[ 20358-06-9 ]

Reference： [1] Synthetic Communications, 1987, vol. 17, # 2, p. 229 - 240

6
[ 348-54-9 ]
[ 20358-06-9 ]

Reference： [1] Journal of the Chemical Society [Section] C: Organic, 1969, p. 268 - 272

[ 20358-06-9 ] Synthesis Path-Downstream 1~46

1
[ 20358-06-9 ]
[ 63754-97-2 ]

Reference： [1]Farmaco, Edizione Scientifica,1977,vol. 32,p. 348 - 354

2
[ 656-32-6 ]
[ 20358-06-9 ]

Yield	Reaction Conditions	Operation in experiment
72%		To a suspension of (2-fluorophenyl) thiourea (1.7g, 10.0 mmol) in chloroform [(25ML)] was added a solution of bromine (0.51 mL; 10.0 mmol) dropwise at room temperature. The resulting mixture was heated under reflux for 3 hrs. The solvent was evaporated, water was added and the mixture was neutralized with ammonium hydroxide. The resulting white precipitation was collected by filtration and dried to yield 1.2 g (72%) of the title compound which was used in the subsequent step without further purification.

Reference： [1]Patent: WO2004/11460,2004,A2 .Location in patent: Page 57
[2]Synthetic Communications,1987,vol. 17,p. 229 - 240
[3]Journal of the Chemical Society C: Organic,1969,p. 268 - 272

3
[ 20358-06-9 ]
[ 126612-94-0 ]
2-Guanidino-thiazole-4-carboxylic acid (4-fluoro-benzothiazol-2-yl)-amide; hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1975 - 1982

4
[ 20358-06-9 ]
[ 73628-29-2 ]

Reference： [1]Synthetic Communications,1987,vol. 17,p. 229 - 240
[2]Journal of Medicinal Chemistry,1991,vol. 34,p. 108 - 122

5
[ 20358-06-9 ]
[ 110821-58-4 ]