[ CAS No. 88105-22-0 ] {[proInfo.proName]}

Name: 88105-22-0|Methyl 5-iodothiophene-2-carboxylate|95%
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SKU: A206980
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Quality Control of [ 88105-22-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 88105-22-0 ]

SDS Specification

Alternatived Products of [ 88105-22-0 ]

Product Details of [ 88105-22-0 ]

CAS No. :	88105-22-0	MDL No. :	MFCD18072497
Formula :	C₆H₅IO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BRDYIIWMXMXTOD-UHFFFAOYSA-N
M.W :	268.07	Pubchem ID :	13156399
Synonyms :

Calculated chemistry of [ 88105-22-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.17
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.32
TPSA :	54.54 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) :	-6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.27
Log Po/w (XLOGP3) :	2.47
Log Po/w (WLOGP) :	2.14
Log Po/w (MLOGP) :	1.85
Log Po/w (SILICOS-IT) :	3.33
Consensus Log Po/w :	2.41

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.3
Solubility :	0.136 mg/ml ; 0.000506 mol/l
Class :	Soluble
Log S (Ali) :	-3.26
Solubility :	0.147 mg/ml ; 0.00055 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.69
Solubility :	0.542 mg/ml ; 0.00202 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.63

Safety of [ 88105-22-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 88105-22-0 ]

* 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 [ 88105-22-0 ]
Downstream synthetic route of [ 88105-22-0 ]

[ 88105-22-0 ] Synthesis Path-Upstream 1~9

1
[ 88105-22-0 ]
[ 60166-85-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With lithium hydroxide In tetrahydrofuran; water	5-Iodo-thiophene-2-carboxylic acid (P-2). To a solution of lithium hydroxide (0.45 g, 11.19 mmol) in 17.5 mL of water was added compound P-1 (1.0 g, 3.73 mmol) in 35 mL of tetrahydrofuran. The resulting mixture was stirred for 4 hours at room temperature and was then acidified to pH 4 and extracted with ethyl acetate. The organic layer was dried (MgSO₄), filtered and evaporated to yield 0.86 g (91percent yield) of compound P-2 as a white solid. ¹H NMR (400 MHz, CD₃OD) d 7.35 (d, J=3.8 Hz, 1H), 7.43 (d, J=3.9 Hz, 1H).

Reference： [1] Patent: US6274620, 2001, B1,

2
[ 5380-42-7 ]
[ 35475-03-7 ]
[ 88105-22-0 ]

Reference： [1] Synthesis, 1995, # 3, p. 248 - 250
[2] Synthesis, 1995, # 3, p. 248 - 250

3
[ 3437-95-4 ]
[ 67-56-1 ]
[ 56-23-5 ]
[ 35475-03-7 ]
[ 88105-22-0 ]

Reference： [1] Petroleum Chemistry, 2008, vol. 48, # 6, p. 471 - 478

4
[ 5380-42-7 ]
[ 2712-78-9 ]
[ 88105-22-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	With iodine; sodium thiosulfate In tetrachloromethane; dichloromethane	5-Iodo-thiophene-2-carboxylic acid methyl ester (P-1). To a solution of thiophene-2-carboxylic acid methyl ester (5.0 g, 28.7 mmol) in 35 mL of anhydrous carbon tetrachloride was added iodine (3.65 g, 14.37 mmol) and [Bis(trifluoroacetoxy)iodo] benzene (6.67 g, 15.52 mmol). This mixture was stirred overnight at room temperature. Dichloromethane was then added and the mixture was extracted with a solution of sodium thiosulfate 10percent. The organic layer was evaporated and the residue was purified flash chromatography (hexane 40percent:chloroform 60percent) to give a solid which was triturated with pentane in order to remove remaining starting material affording compound P-1 as a white solid (4.8 g, 63percent yield). ¹H NMR (400 MHz, CDCl₃) d 3.89 (s, 3H), 7.28 (d, J=3.9 Hz, 1H), 7.45 (d, J=3.9 Hz, 1H).

Reference： [1] Patent: US6274620, 2001, B1,

5
[ 5380-42-7 ]
[ 144-55-8 ]
[ 2712-78-9 ]
[ 88105-22-0 ]

Reference： [1] Patent: US2011/263494, 2011, A1,

6
[ 5380-42-7 ]
[ 88105-22-0 ]

Reference： [1] Tetrahedron Letters, 1995, vol. 36, # 27, p. 4883 - 4884

7
[ 5380-42-7 ]
[ 88105-22-0 ]

Reference： [1] Synthesis, 1995, # 3, p. 248 - 250

8
[ 5380-42-7 ]
[ 35475-03-7 ]
[ 88105-22-0 ]

Reference： [1] Synthesis, 1995, # 3, p. 248 - 250
[2] Synthesis, 1995, # 3, p. 248 - 250

9
[ 3437-95-4 ]
[ 67-56-1 ]
[ 56-23-5 ]
[ 35475-03-7 ]
[ 88105-22-0 ]

Reference： [1] Petroleum Chemistry, 2008, vol. 48, # 6, p. 471 - 478

[ 88105-22-0 ] Synthesis Path-Downstream 1~31

1
[ 4298-52-6 ]
[ 88105-22-0 ]
[ 125972-77-2 ]
[ 125972-76-1 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4019 - 4025
[2]Journal of Organic Chemistry,1990,vol. 55,p. 4019 - 4025

2
[ 88105-22-0 ]
[ 157223-45-5 ]
methyl 5'-(3-acetoxyprop-1-ynyl)-2,2'-bithienyl-5'-carboxylate [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 1245 - 1250

3
[ 88105-22-0 ]
[ 536-74-3 ]
[ 125972-73-8 ]
[ 125972-75-0 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4019 - 4025

4
[ 5380-42-7 ]
[ 35475-03-7 ]
[ 88105-22-0 ]
methyl 4,5-diiodo-2-thiophene-2-carboxylate [ No CAS ]

Reference： [1]Synthesis,1995,p. 248 - 250
[2]Synthesis,1995,p. 248 - 250

5
[ 5380-42-7 ]
[ 88105-22-0 ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 4883 - 4884

6
[ 5380-42-7 ]
[ 88105-22-0 ]
methyl 4,5-diiodo-2-thiophene-2-carboxylate [ No CAS ]

Reference： [1]Synthesis,1995,p. 248 - 250

Yield	Reaction Conditions	Operation in experiment
7.86 g (79%)		A(2). 5-Iodo-2-thiophenecarboxylic acid, methyl ester To a stirred solution of 9.5 g (37.4 mmol) of Part A(1) acid in 100 mL of DMF was added 10.3 g (74.8 mmol) of K2 CO3 followed by 11.6 mL (186.9 mmol) of methyl iodide and the reaction was allowed to stir under argon at RT overnight. The reaction was diluted with ether and acidified with 1 N HCl solution. The organic layer was separated and washed with water, brine, dried over MgSO4 and evaporated to provide 9.2 g of solid. The crude material was recrystallized from hexane to provide 7.86 g (79%) of title ester as a light brown solid. mp 90-91 C., lit mp 88-90 C. [Gronowitz, S.; Arkin For Keni Vol. 21 (1963)]. TLC Silica gel (3:1 hexane/EtOAc) Rf =0.53. IR (KBr) 3078, 2950, 1712, 1695, 1527, 1265, 752 cm-1. 1 H NMR (CDCl3): delta 7.42 (d, 1H, J=3.5 Hz); 7.25 (d, 1H, J=4 Hz); 3.87 (s, 3H, OCH3) ppm. MS (CI-NH3, +ions) m/e 286 (M+NH4), 268 (M). Anal. calcd. for C6 H5 IO2 S: C, 26.88; H, 1.88; I, 47.34; S, 11.96; Found: C, 26.52; H, 2.09; I, 47.05; S, 11.65.

8
[ 88105-22-0 ]
[ 819863-78-0 ]