[ CAS No. 4565-31-5 ] {[proInfo.proName]}

Name: 4565-31-5|5-Formylthiophene-2-carboxylic acid|97%
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SKU: A263847
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Quality Control of [ 4565-31-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4565-31-5 ]

SDS Specification

Alternatived Products of [ 4565-31-5 ]

Product Details of [ 4565-31-5 ]

CAS No. :	4565-31-5	MDL No. :	MFCD00191437
Formula :	C₆H₄O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VFEAMMGYJFFXKV-UHFFFAOYSA-N
M.W :	156.16	Pubchem ID :	818882
Synonyms :

Calculated chemistry of [ 4565-31-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	36.67
TPSA :	82.61 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) :	-6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.91
Log Po/w (XLOGP3) :	1.26
Log Po/w (WLOGP) :	1.26
Log Po/w (MLOGP) :	-0.07
Log Po/w (SILICOS-IT) :	2.05
Consensus Log Po/w :	1.08

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.84
Solubility :	2.26 mg/ml ; 0.0145 mol/l
Class :	Very soluble
Log S (Ali) :	-2.59
Solubility :	0.398 mg/ml ; 0.00255 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.97
Solubility :	16.5 mg/ml ; 0.106 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.13

Safety of [ 4565-31-5 ]

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 [ 4565-31-5 ]

* 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 [ 4565-31-5 ]
Downstream synthetic route of [ 4565-31-5 ]

[ 4565-31-5 ] Synthesis Path-Upstream 1~8

1
[ 4565-31-5 ]
[ 50340-79-9 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 1, p. 17 - 28
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 12, p. 5982 - 5986

2
[ 67808-64-4 ]
[ 4565-31-5 ]

Yield	Reaction Conditions	Operation in experiment
59%	With potassium hydroxide; water In tetrahydrofuran	The compound 25 (2 g, 12.8 mmol) was dissolved in 200 ml of mixture solvent (THF: H20=1 : 1) and HYDROLYZATION was conducted by adding KOH (1.1 g, 19.2 MMOL). After the completion of the reaction, THF was removed under reduced pressure. The water layer was titrated with 1N HC1 solution in pH 1-2 and then extracted with ethyl acetate (200 ml X 5) to obtain the desirable compound 25 (1.2 g, yield 59percent). 1H NMR (300MHZ, CDC13) 10.00 (s, 1H), 7.93-7. 92 (d, J=3.92Hz, 1H), 7.78-7. 77 (d, J=3.9Hz, 1H). I3C NMR (300MHZ, CDC13) 182. 2, 163. 70, 141. 57, 139. 70, 133. 79, 132. 79.

Reference： [1] Patent: WO2004/37808, 2004, A1, . Location in patent: Page 14-15; 93

3
[ 932-95-6 ]
[ 4565-31-5 ]

Reference： [1] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 602 - 607

4
[ 58268-08-9 ]
[ 124-38-9 ]
[ 4565-31-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6572 - 6576[2] Angew. Chem., 2018, vol. 130, p. 6682 - 6686,5
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2265 - 2279

5
[ 124-38-9 ]
[ 104208-13-1 ]
[ 4565-31-5 ]

Reference： [1] Tetrahedron, 1985, vol. 41, # 18, p. 3803 - 3812
[2] Tetrahedron, 2001, vol. 57, # 38, p. 8145 - 8150

6
[ 98-03-3 ]
[ 4565-31-5 ]

Reference： [1] Tetrahedron, 1985, vol. 41, # 18, p. 3803 - 3812
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6572 - 6576[3] Angew. Chem., 2018, vol. 130, p. 6682 - 6686,5

7
[ 4565-31-5 ]
[ 74-88-4 ]
[ 67808-64-4 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium carbonate In N,N-dimethyl-formamide at 25℃; for 20 h;	Step 1. Methyl 5-formyl-2-thiophenecarboxylateA mixture of 5-formyl-2-thiophene carboxylic acid (2.34 g, 15 mmol) and sodium carbonate (5.57 g, 52.5 mmol) in DMF (25 ml) at 25 ⁰C was treated with iodomethane (1.15 ml, 18 mmol) and the mixture was stirred for 20 h before being quenched with the addition of water and saturated aqueous NH₄Cl. The resulting solid precipitate was collected by filtration to give methyl 5-formyl-2- thiophenecarboxylate as a solid. The filtrate was extracted with EtOAc (3 x 30 ml) and the combined organic extracts were washed with water and brine, dried (Na₂SO₄), concentrated under reduced pressure, and subjected to flash chromatography to give solid material that was combined with the solid collected by precipitation to give methyl 5-formyl-2-thiophenecarboxylate as a white solid (1.60 g, 62percent): ESI-MS (m/z): 171.2 (M+H⁺).

Reference： [1] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 1, p. 17 - 28
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 12, p. 5982 - 5986
[3] Patent: WO2008/124582, 2008, A1, . Location in patent: Page/Page column 130
[4] Patent: US5047554, 1991, A,
[5] Patent: US2006/293343, 2006, A1, . Location in patent: Page/Page column 89
[6] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2265 - 2279
[7] Patent: WO2005/79791, 2005, A1, . Location in patent: Page/Page column 125-126
[8] Patent: WO2006/123639, 2006, A1, . Location in patent: Page/Page column 135-136

8
[ 67-56-1 ]
[ 4565-31-5 ]
[ 67808-64-4 ]

Yield	Reaction Conditions	Operation in experiment
0.45 g	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 5 - 20℃; for 1 h;	In a reaction vessel,5-formylthiophene-2-carboxylic acid (0.50 g),4-dimethylaminopyridine (0.11 g), methanol (0.87 g) and chloroform (12 mL) were added,It was cooled to 5 ° C.To this was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.74 g).After stirring at room temperature for 1 hour,3 mol / L hydrochloric acid (8 mL) was added.The reaction solution was extracted with chloroform,The organic layer was washed with saturated brine.The organic phase was dried over anhydrous sodium sulfate,The solvent was distilled off to obtain a crude product.This was purified with a silica gel column (chloroform)To give a yellow product (5-formylthiophene-2-carboxylic acid methyl ester, 0.45 g).

Reference： [1] Patent: JP2015/86268, 2015, A, . Location in patent: Paragraph 0125-0127

[ 4565-31-5 ] Synthesis Path-Downstream 1~88

1
[ 67-56-1 ]
[ 4565-31-5 ]
5-(Hydroxy-methoxy-methyl)-thiophene-2-carboxylic acid [ No CAS ]
[ 154935-51-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1083 - 1086

2
[ 6066-82-6 ]
[ 4565-31-5 ]
5-Formyl-thiophene-2-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1992,vol. 73,p. 41 - 48

3
[ 4565-31-5 ]
[ 811-98-3 ]
[ 119291-48-4 ]
[ 119291-46-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1083 - 1086

4
[ 4565-31-5 ]
[ 1134-35-6 ]
4-(5-Carboxythienyl)-ethenyl-4'-methyl-2,2'-bipyridin [ No CAS ]
[ 114527-31-0 ]

Reference： [1]Monatshefte fur Chemie,1988,vol. 119,p. 1 - 16

5
[ 124-38-9 ]
[ 104208-13-1 ]
[ 4565-31-5 ]

Reference： [1]Tetrahedron,1985,vol. 41,p. 3803 - 3812
[2]Tetrahedron,2001,vol. 57,p. 8145 - 8150

6
[ 4565-31-5 ]
[ 541-41-3 ]
C₉H₈O₅S [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1992,vol. 73,p. 41 - 48

7
[ 498532-06-2 ]
[ 4565-31-5 ]
[ 858671-10-0 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 5331 - 5334

8
[ 98-03-3 ]
benzylmagnesium halide [ No CAS ]
[ 4565-31-5 ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 8145 - 8150

9
[ 4565-31-5 ]
1,6-bis(5-ethoxycarbonyl-2-thienyl)hexa-1,5-diene-3,4-dione [ No CAS ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 8145 - 8150

10
[ 4565-31-5 ]
4',4''-bis(5-ethoxycarbonyl-2-thienyl)-2,2':6',2'':6'',2'''-quaterpyridine [ No CAS ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 8145 - 8150

11
[ 4565-31-5 ]
C₂₄H₁₄Cl₂N₂O₂S₂ [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1988,vol. 119,p. 1 - 16

12
[ 4565-31-5 ]
4,4'-<(5-Diethoxycarbonylthienyl)-ethenyl>-2,2'-bipyridin [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1988,vol. 119,p. 1 - 16

13
[ 98-03-3 ]
[ 4565-31-5 ]

Reference： [1]Tetrahedron,1985,vol. 41,p. 3803 - 3812
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 6572 - 6576
Angew. Chem.,2018,vol. 130,p. 6682 - 6686,5

14
[ 4565-31-5 ]
[ 2325-98-6 ]