[ CAS No. 131184-73-1 ] {[proInfo.proName]}

Name: 131184-73-1|(2-Aminothiazol-5-yl)methanol|97%
Brand: Ambeed
SKU: A253025
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Quality Control of [ 131184-73-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 131184-73-1 ]

SDS Specification

Alternatived Products of [ 131184-73-1 ]

Product Details of [ 131184-73-1 ]

CAS No. :	131184-73-1	MDL No. :	MFCD06203018
Formula :	C₄H₆N₂OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	TZEMBFLDHOUKNI-UHFFFAOYSA-N
M.W :	130.17	Pubchem ID :	11217273
Synonyms :

Calculated chemistry of [ 131184-73-1 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.25
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	32.65
TPSA :	87.38 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.93
Log Po/w (XLOGP3) :	-0.24
Log Po/w (WLOGP) :	0.07
Log Po/w (MLOGP) :	-1.08
Log Po/w (SILICOS-IT) :	1.29
Consensus Log Po/w :	0.19

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.89
Solubility :	16.7 mg/ml ; 0.128 mol/l
Class :	Very soluble
Log S (Ali) :	-1.14
Solubility :	9.49 mg/ml ; 0.0729 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.73
Solubility :	24.4 mg/ml ; 0.187 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.22

Safety of [ 131184-73-1 ]

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 [ 131184-73-1 ]

* 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 [ 131184-73-1 ]
Downstream synthetic route of [ 131184-73-1 ]

[ 131184-73-1 ] Synthesis Path-Upstream 1~3

1
[ 1003-61-8 ]
[ 131184-73-1 ]

Yield	Reaction Conditions	Operation in experiment
43%	With sodium tetrahydroborate In methanol for 1 h; Cooling with ice	2-Amino-5-formylthiazole (11.5 g, 90 mmol) was dissolved in methanol (120 mL), and sodium borohydride (5.11 g, 135 mmol) was added thereto while cooling with ice, followed by stirring at the same temperature for 1 hour. Acetone (6 mL) and water (10 mL) were added to the reaction mixture, followed by stirring. The residue obtained by evaporating the reaction mixture under reduced pressure was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:15), thereby giving the title compound (5.09 g, 43percent) as a white solid.

Reference： [1] Farmaco, 1989, vol. 44, # 11, p. 1011 - 1030
[2] Patent: US2013/165438, 2013, A1, . Location in patent: Paragraph 0349

2
[ 32955-21-8 ]
[ 131184-73-1 ]

Yield	Reaction Conditions	Operation in experiment
225 mg	With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2.25 h; Inert atmosphere; Reflux	[00363] A suspension of ethyl 2-amino-1,3-thiazole-5-carboxylate (1.72 g, 10 mmol) in anhydrous THF (100 mL) was cooled in an ice bath and treated with LiAIH4 (0.76 g, 20 mmol) portionwise, under nitrogen. The reaction mixture was warmed to room temperature and stirred for 90 minutes. After this time, additional LiAIH4 (0.76 g, 20 mmol) was added and thesuspension was heated to reflux for 45 minutes. After this time, the suspension was cooled in an ice bath and cautiously treated with ice chips, followed by concentrated aqueous ammonium hydroxide solution (10 mL) and stirred for 60 hours. The orange suspension was filtered through CeliteTM, washing with MeOH. The filtrate was evaporated under reduced pressure, adsorbed onto silica and purified by flash column chromatography, eluting with MeOH/DCM (5-10percent), with the desired fractions combined and concentrated under reduced pressure to afford the title compound (225 mg). LCMS method: Method 5, RT: 0.55 mm, Ml: 131 [M+1]

Reference： [1] Patent: WO2016/124938, 2016, A1, . Location in patent: Paragraph 00363-00364

3
[ 765-34-4 ]
[ 131184-73-1 ]

Reference： [1] Patent: US6265553, 2001, B1,

[ 131184-73-1 ] Synthesis Path-Downstream 1~37

1
[ 1003-61-8 ]
[ 131184-73-1 ]

Yield	Reaction Conditions	Operation in experiment
72.7%	With methanol; sodium tetrahydroborate; at 0℃; for 3h;	At 0 C,Compound2-amino-5-Aldehydethiazole (12.0 g, 90 mmol) was dissolved in anhydrous methanol (250 mL), and sodium borohydride (10.0 g, 90 mmol) was slowly added and stirred for 3.0 h.The reaction was quenched by the addition of distilled water (20 mL).Dichloromethane extraction (50 mL × 3), anhydrous sodium sulfate (10 g), dried.Concentration gave 8.8 g of a yellow-brown solid.Yield: 72.7%.
43%	With sodium tetrahydroborate; In methanol; for 1h;Cooling with ice;	2-Amino-5-formylthiazole (11.5 g, 90 mmol) was dissolved in methanol (120 mL), and sodium borohydride (5.11 g, 135 mmol) was added thereto while cooling with ice, followed by stirring at the same temperature for 1 hour. Acetone (6 mL) and water (10 mL) were added to the reaction mixture, followed by stirring. The residue obtained by evaporating the reaction mixture under reduced pressure was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:15), thereby giving the title compound (5.09 g, 43%) as a white solid.

Reference： [1]Patent: CN104744446,2019,B .Location in patent: Paragraph 1250; 1262-1264
[2]Il Farmaco,1989,vol. 44,p. 1011 - 1030
[3]Patent: US2013/165438,2013,A1 .Location in patent: Paragraph 0349

2
[ 1001-58-7 ]
[ 131184-73-1 ]
[ 131184-75-3 ]

Reference： [1]Il Farmaco,1989,vol. 44,p. 1011 - 1030

3
[ 156-57-0 ]
[ 131184-73-1 ]
2-<(2-amino-5-thiazolyl)methylthio>ethylamine dibromide [ No CAS ]

Reference： [1]Il Farmaco,1989,vol. 44,p. 1011 - 1030

4
[ 765-34-4 ]
[ 131184-73-1 ]

Yield	Reaction Conditions	Operation in experiment
	With thiourea;	EXAMPLE 2 Preparation of 2-amino-5-hydroxymethylthiazole: The epoxy propanal solution from example 1 is cooled to 0 C. With vigorous stirring, 76 g (1.00 mole) of thiourea was added in portions. After the addition is complete the water is removed under vacuum on a rotatory evaporator. A red-brown oil is isolated as the product (91.3 g).

Reference： [1]Patent: US6265553,2001,B1

5
[ 1151240-86-6 ]
[ 131184-73-1 ]
[ 1151240-67-3 ]

Yield	Reaction Conditions	Operation in experiment
1.25%	With potassium carbonate; In acetonitrile; at 40℃; for 48h;	Example 46: {2-[({1-[(3,4-Dichlorophenyl)methyl]-1 H-1 ,2,3-triazol-4-yl}methyl)amino]- 1 ,3-thiazol-5-yl}methanolTo a solution of 4-(bromomethyl)-1-[(3,4-dichlorophenyl)methyl]-1 H-1 ,2,3-triazole (Intermediate 17) (0.21 g, 0.65 mmol) in acetonitrile was added (2-amino-1 ,3-thiazol-5- yl)methanol (0.175 g, 2 eq) followed by potassium carbonate (0.185 g, 2 eq) The reaction was stirred at 400C for 2 days. After evaporation, the residue was dissolved in ether and ethyl acetate and washed with water. The organic phase was dried over sodium sulphate, filtered and evaporated. The compound was purified by flash chromatography eluting with DCM/MeOH (92/8). The title compound was obtained as an <n="56"/>ochre powder (3 mg, 1.25%). HRMS calculated for Ci4H13CI2N5OS (M+H)+ 370.0296, found: 370.0297, Rt: 2.35 min. LC/MS: m/z 370 (M+H)+ Rt: 2.60 min.

Reference： [1]Patent: WO2009/60054,2009,A1 .Location in patent: Page/Page column 54-55

6
[ 288-13-1 ]
[ 131184-73-1 ]
[ 1194551-59-1 ]