[ CAS No. 71050-40-3 ] {[proInfo.proName]}

Name: 71050-40-3|4-Methoxythiophene-3-carboxylic acid|96%
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3d Animation Molecule Structure of 71050-40-3

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Quality Control of [ 71050-40-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 71050-40-3 ]

Product Details of [ 71050-40-3 ]

CAS No. :	71050-40-3	MDL No. :	MFCD00067997
Formula :	C₆H₆O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KEYPLCJVNVJJQK-UHFFFAOYSA-N
M.W :	158.18	Pubchem ID :	2778379
Synonyms :

Calculated chemistry of [ 71050-40-3 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.17
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	37.77
TPSA :	74.77 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) :	-6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.34
Log Po/w (XLOGP3) :	1.1
Log Po/w (WLOGP) :	1.45
Log Po/w (MLOGP) :	0.29
Log Po/w (SILICOS-IT) :	1.89
Consensus Log Po/w :	1.21

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.75
Solubility :	2.8 mg/ml ; 0.0177 mol/l
Class :	Very soluble
Log S (Ali) :	-2.26
Solubility :	0.864 mg/ml ; 0.00546 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.16
Solubility :	11.1 mg/ml ; 0.07 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.47

Safety of [ 71050-40-3 ]

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 [ 71050-40-3 ]

* 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 [ 71050-40-3 ]
Downstream synthetic route of [ 71050-40-3 ]

[ 71050-40-3 ] Synthesis Path-Upstream 1~2

1
[ 65369-22-4 ]
[ 71050-40-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 12, p. 2446 - 2455
[2] Patent: US5015656, 1991, A,

2
[ 78071-37-1 ]
[ 71050-40-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 12, p. 2446 - 2455

[ 71050-40-3 ] Synthesis Path-Downstream 1~17

1
[ 500-22-1 ]
[ 71050-40-3 ]
4-methoxy-2-(3-pyridoyl)thiophene-3-carboxylic acid [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 236 - 240

3
[ 65369-22-4 ]
[ 71050-40-3 ]

Yield	Reaction Conditions	Operation in experiment
		(b) 4-Methoxy-3-thiophenecarboxylic acid The above compound was prepared from methyl 4-methoxy-3-thiophenecarboxylate by the method of Press, Hofmann and Safu J. Org. Chem. (1979) 44 3292.

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 2446 - 2455
[2]Patent: US5015656,1991,A

4
[ 78071-37-1 ]
[ 71050-40-3 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 2446 - 2455

5
[ 71050-40-3 ]
[ 682358-06-1 ]
[ 682358-47-0 ]

Yield	Reaction Conditions	Operation in experiment
57%		A dry reaction vial with a cap charged with 5-aminoindole 15a (50 mg, 0.15 [MMOL),] 4- methoxy-3-thiophenecarboxylic acid (35.6 mg, 0.22 [MMOL)] and [CH2CI2] (2 mL) was allowed to mix for 10 min. Polystyrenecarbodiimide resin (Argonaut, 1.26 [MMOL/G,] 250 mg, 0.32 [MMOL)] was added and the mixture was allowed to mix for 24 h. Finally tris (2-aminomethyl)-aminopolystyrene resin (Novabiochem, 200-400 mesh, 3.7 [MMOL/G,] 25 mg, 93 pmol) was added to the above vial which was then allowed to stir for 8 h. The reaction mixture was filtered, the resin washed with CH2CI2 (2x3 mL) and the combined organic phases were concentrated and dried in vacuo to give 40.8 mg (57%) of the desired [PRODUCT. 1H] NMR [(CDCL3)No. ] 9.33 (s, [1H),] 8.56 (d, J=8.7 Hz, [1H),] 8.22 (d, J=3.6 Hz, 1H), 8.13 (d, J=1. 8 Hz, 1H), 7.39 (m, 3H), 7.27 (dd, [J=8.] 5,2. 1 Hz, 1H), 6.42 (d, J=4.2 Hz, 1H), 6.37 (s, 1H), 4.05 (s, 3H), 1.85 (s, 3H). MS (m/z) : 459 [(MH+).]

Reference： [1]Patent: WO2004/35571,2004,A1 .Location in patent: Page 47

6
[ 71050-40-3 ]
3-hydroxy-4-methoxythiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 23℃;Nitrogen atmosphere;	LAH (1.2 g, 31.6 mmol) was tared and diluted with dry THF (150 ML) under nitrogen. Solid neat <strong>[71050-40-3]4-methoxythiophene-3-carboxylic acid</strong> (2.5 g, 15.8 mmol) was added over 10 portions. Upon completion of gas evolution, the mixture was maintained overnight, TLC monitored (50% EtOAc-hexane), and quenched at 23 C carefully with the dropwise addition of saturated aqueous Rochelle salt (15 mL). The mixture was filtered through a pad of celite, washed with ethyl acetate and concentrated in vacuo. The crude product alcohol (2.35 g, 15.9 mmol) was dissolved in methylene chloride (80 mL), cooled to 0 C, and DMSO (10 mL) was added followed by triethylamine (6.9 mL, 47.9 mmol). Solid sulfur trioxide pyridine complex (7.6 g, 47.9 mmol) was added, and the mixture then warmed to room temperature and maintained 4 h (TLC, 50% EtOAc-hexane). The mixture was quenched with saturated aqueous sodium bicarbonate and partitioned with chloroform. The organic phase was concentrated in vacuo to provide the pure the title compound (2.6 g) in quantitative yield.

Reference： [1]Patent: WO2004/58763,2004,A1 .Location in patent: Page 42

7
[ 71050-40-3 ]
[ 82070-04-0 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran;	LAH (1.2 g, 31.6 mmol) was tared and diluted with dry THF (150 ML) under nitrogen. Solid neat <strong>[71050-40-3]4-methoxythiophene-3-carboxylic acid</strong> (2.5 g, 15.8 mmol) was added over 10 portions. Upon completion of gas evolution, the mixture was maintained overnight, TLC monitored (50% EtOAc-hexane), and quenched at 23 C carefully with the dropwise addition of saturated aqueous Rochelle salt (15 mL). The mixture was filtered through a pad of celite, washed with ethyl acetate and concentrated in vacuo. The crude product alcohol (2.35 g, 15.9 mmol) was dissolved in CH2CI2 (80 mL), cooled to 0 C, and DMSO (10 ML) was added followed by triethylamine (6.9 mL, 47.9 mmol). Solid sulfur trioxide pyridine complex (7.6 g, 47.9 mmol) was added, and the mixture then warmed to room temperature and maintained 4 h (TLC, 50% EtOAc-hexane). The mixture was quenched with saturated aqueous sodium bicarbonate and partitioned with chloroform. The organic phase was concentrated in vacuo to provide the pure the title compound (2.6 g) in quantitative yield.

Reference： [1]Patent: WO2004/58702,2004,A2 .Location in patent: Page 32; 25

8
(2-chlorobenzyl)-[6-(6,7-dimethoxy-quinolin-4-yloxy)-benzothiazol-2-yl]-amine [ No CAS ]
[ 71050-40-3 ]
4-methoxy-thiophene-3-carboxylic acid [6-(6,7-dimethoxy-quinolin-4-yloxy)-benzothiazol-2-yl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; potassium carbonate; In dichloromethane; at 20℃;	Example 2; 4-Methoxy-thiophene-3- carboxylic acid [6- (6, 7- dimethoxy-quinolin-4-yloxy)- benzothiazol-2-yl]-amide; To a mixture of 6- (6, 7-dimethoxy-quinolin-4-yloxy) -benzothiazol-2-ylamine (0.100 g, 0.28 mmol (Example 1, Step a) in dry CH2C12 was added <strong>[71050-40-3]4-methoxy-thiophene-3-carboxylic acid</strong> (0.063 g, 0.3 mmol), PyBOP (0.437 g, 1.2 mmol), and K2CO3 (0.116 g, 1.2 mmol). The mixture was stirred at RT overnight under an inert atmosphere. The mixture was quenched with water and diluted with CH2C12 and transferred to a separation funnel. The organics were collected, dried over Na2SO4, filtered, and concentrated in-vacuo. The crude was purified by silica gel column chromatography (MeOH/CH2C12) to give the product as a rust colored solid. MS (ESI pos. ion) m/z : 494 (M+H). Calc'd Exact Mass for C24Hi9N30sS2 : 493.08.

Reference： [1]Patent: WO2005/73224,2005,A2 .Location in patent: Page/Page column 53

9
[ 71050-40-3 ]
[ 182564-38-1 ]
[ 182564-11-0 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 178 5-(4-methoxy-3-thienoyl)amino-3-(1-methylpiperidin-4-yl)-1H-indole Beginning with 7.0 mg (0.03 mMol) 5-amino-3-(1-methylpiperidin-4-yl)-1H-indole and 14.2 mg (0.09 mMol <strong>[71050-40-3]4-methoxy-3-thienoic acid</strong>, 12.1 mg of the title compound were recovered. MS(m/e): 369(M+)
		EXAMPLE 178 5-(4-methoxy-3-thienoyl)amino-3-(1-methylpiperidin-4-yl)-1H-indole Beginning with 7.0 mg (0.03 mMol) 5-amino-3-(1-methylpiperidin-4-yl)-1H-indole and 14.2 mg (0.09 mMol) <strong>[71050-40-3]4-methoxy-3-thienoic acid</strong>, 12.1 mg of the title compound were recovered. MS(m/e): 369(M+)

Reference： [1]Patent: US5708008,1998,A
[2]Patent: EP832650,1998,A2

10
[ 71050-40-3 ]
[ 133659-14-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuryl dichloride; In chloroform;	(a) 5-Chloro-<strong>[71050-40-3]4-methoxy-3-thiophenecarboxylic acid</strong> To <strong>[71050-40-3]4-methoxythiophene-3-carboxylic acid</strong> (3.16 g) in chloroform (10 ml) was added freshly distilled sulphuryl chloride (1.8 ml). After the exothermic reaction had subsided the product was extracted into 2N NaOH and washed with chloroform. The aqueous solution was acidified with 2N HCl and extracted into dichloromethane, washed with water, dried over magnesium sulphate and the solvent evaporated. The product was crystallized from dichloromethane/n-hexane.

Reference： [1]Patent: US5015656,1991,A

11
[ 64269-79-0 ]
[ 71050-40-3 ]
5-Chloro-N-[(1-ethyl-2-pyrrolidino)methyl]-4-methoxythiophene-3-carboxamide [ No CAS ]
[ 65369-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	(c) N-[(1-Ethyl-2-pyrrolidino)methyl]-4-methoxythiophene-3-carboxamide 4-Methoxy-3-thiophenecarboxylic acid (800 mg) and carbonyl di-imidazole (800 mg) were stirred under a nitrogen atmosphere in tetrahydrofuran (50 ml) for 1.5 hours. 2-Amino-methyl-1-ethylpyrrolidine (640 mg) was added and the solution stirred for 20 hours and then partitioned between 2N HCl and dichloromethane. The acid solution was basified with 2N NaOH and extracted into dichloromethane, washed with water, dried with MgSO4 and the solvent evaporated to leave the crude product as an oil, which was converted to the fumarate salt crystallising from ethyl acetate, m.p. 126. 5-Chloro-N-[(1-ethyl-2-pyrrolidino)methyl]-4-methoxythiophene-3-carboxamide was similarly prepared m.p. 136 (ethyl acetate).

Reference： [1]Patent: US5015656,1991,A

12
[ 71050-40-3 ]
[ 959992-80-4 ]
C₂₆H₂₉N₃O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 17 - 25℃; for 12h;	Example 5.1; N-r(4-methoxythiophen-3-yl)carbonyll-0-f2-(5,6,7,8-tetrahydro-l,8-naphthyridin-2- vQethyll -L-tyrosineTo a solution of methyl O-[2-(5,6,7,8-tetrahydro-l,8-naphthyridin-2-yl)ethyl]-L- tyrosinate (200 mg, 0.56 mmol) in DMF (1.2 ml)were added 4-methoxythiophene-3- carboxylic acid (98 mg, 0.62 mmol), 4-methylmorpholine (68 mul, 0.62 mmol) and TBTU (234 mg, 0.73 mmol). The reaction mixture was stirred at room temperature for 12 hours. Then NaOH 6N (0.38 ml, 2.25 mmol) was added, and the mixture was stirred for one hour. After filtration, the residue was purified by Cl 8 reverse phase chromatography (basic conditions) to afford the title compound (190 mg, 70 %.); Mass spectrum [M+H]+ = 482; 1H NMR Spectrum ODMSOd^) 1.70-1.79 (m, 2H), 2.57-2.63 (m, 2H), 2.86 (t, 2H), 3.01 (dd, IH), 3.06 (dd, IH), 3.20-3.25 (m, 2H), 3.81 (s, 3H), 4.19 (t, 2H), 4.49-4.56 (m, IH), 6.35 (d, IH), 6.36 (s, IH), 6.77 (d, IH), 6.84 (d, 2H), 7.04 (d, IH), 7.10 (d, 2H), 7.78 (d, IH), 8.02 (d, IH).

Reference： [1]Patent: WO2008/93065,2008,A1 .Location in patent: Page/Page column 145

13
[ 71050-40-3 ]
[ 1198409-41-4 ]
[ 1198434-58-0 ]

Yield	Reaction Conditions	Operation in experiment
		Example 101 lambda/-[6-(1H-lndol-4-yl)-1H-indazol-4-yl]-4-(methyloxy)-3-thiophenecarboxamide <n="190"/> 4-(Methyloxy)-3-thiophenecarboxylic acid (35mg) was treated with lambda/-[(dimethylamino)(3H- [1 ,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-lambda/-methylmethanaminium hexafluorophosphate (84mg) in DMF (250mul) and DIPEA (69mul). The reaction mixture was shaken for five min prior to treatment with 6-(1 H-indol-4-yl)-1 H-indazol-4-amine (25mg) in DMF (250mul). The reaction mixture was left to stand at 220C for 18h. The solvent was removed in vacuo and the product re-dissolved in chloroform (0.3ml) prior to application on to an aminopropyl SPE cartridge (0.5g) that had been preconditioned with methanol and then chloroform. The product was eluted after 2 hr with ethyl acetate / methanol (1 :1 , 3ml), and concentrated under a stream of nitrogen using blow down apparatus. Purification by mass directed preparative HPLC (Method C) gave the title compound. LC/MS R1 1.08min m/z 389 [MH+]. Method B

Reference： [1]Patent: WO2009/147188,2009,A1 .Location in patent: Page/Page column 187-188

14
[ 598-32-3 ]
[ 71050-40-3 ]
C₁₀H₁₂O₃S [ No CAS ]
C₁₀H₁₂O₃S [ No CAS ]

Reference： [1]Chemical Science,2018,vol. 9,p. 5289 - 5294

15
[ 71050-40-3 ]
[ 591-87-7 ]
2-allyl-4-methoxy-thiophene-3-carboxylic acid [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 14580 - 14584
Angew. Chem.,2018,vol. 130,p. 14788 - 14792,5

16
[ 71050-40-3 ]
[ 106-38-7 ]
2-(4-methylphenyl)-4-methoxy-3-thiophenecarboxylic acid methyl ester [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3925 - 3929

17
[ 71050-40-3 ]
[ 106-38-7 ]
C₁₃H₁₂O₃S [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3925 - 3929

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H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 71050-40-3 ] {[proInfo.proName]}

Quality Control of [ 71050-40-3 ]

Related Doc. of [ 71050-40-3 ]

Product Details of [ 71050-40-3 ]

Calculated chemistry of [ 71050-40-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 71050-40-3 ]

Application In Synthesis of [ 71050-40-3 ]

[ 71050-40-3 ] Synthesis Path-Upstream 1~2

[ 71050-40-3 ] Synthesis Path-Downstream 1~17

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry