[ CAS No. 26020-48-4 ] {[proInfo.proName]}

Name: 26020-48-4|3,4,5-Trichlorothiophene-2-carboxylic acid|95%
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SKU: A136931
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Quality Control of [ 26020-48-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 26020-48-4 ]

Product Details of [ 26020-48-4 ]

CAS No. :	26020-48-4	MDL No. :	MFCD00092429
Formula :	C₅HCl₃O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FVFYTPFJDMYLJS-UHFFFAOYSA-N
M.W :	231.48	Pubchem ID :	4168584
Synonyms :

Calculated chemistry of [ 26020-48-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.31
TPSA :	65.54 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) :	-5.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	3.68
Log Po/w (WLOGP) :	3.41
Log Po/w (MLOGP) :	2.39
Log Po/w (SILICOS-IT) :	3.94
Consensus Log Po/w :	3.0

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.85

Water Solubility

Log S (ESOL) :	-3.86
Solubility :	0.0317 mg/ml ; 0.000137 mol/l
Class :	Soluble
Log S (Ali) :	-4.75
Solubility :	0.00415 mg/ml ; 0.0000179 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.9
Solubility :	0.294 mg/ml ; 0.00127 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.85

Safety of [ 26020-48-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 26020-48-4 ]

* 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.

Downstream synthetic route of [ 26020-48-4 ]

[ 26020-48-4 ] Synthesis Path-Downstream 1~41

1
[ 6012-97-1 ]
[ 26020-48-4 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; diethyl ether Behandeln der Reaktionsloesung mit Kohlendioxid;
	With diethyl ether; magnesium; methyl iodide Behandeln der Reaktionsloesung mit Kohlendioxid;

Reference： [1]Bachman; Heisey [Journal of the American Chemical Society, 1948, vol. 70, p. 2378]
[2]Steinkopf et al. [Justus Liebigs Annalen der Chemie, 1934, vol. 512, p. 136,156]

2
[ 17249-78-4 ]
[ 124-38-9 ]
[ 26020-48-4 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium 1.) -78 deg C, 3 h, THF; 2.) -78 deg C to RT; Yield given. Multistep reaction;

Reference： [1]Rahman, Mohammed T. [Monatshefte fur Chemie, 1983, vol. 114, p. 249 - 254]

3
[ 17249-78-4 ]
[ 124-38-9 ]
[ 26020-48-4 ]
[ 38458-33-2 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium multistep; 1.) THF, -78 deg C, 18 h; various conc. of n-BuLi, t-BuLi instead n-Buli, further solvent and temp.;

Reference： [1]Rahman, Mohammed T. [Monatshefte fur Chemie, 1983, vol. 114, p. 249 - 254]

4
[ 71105-25-4 ]
[ 26020-48-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sulfuric acid In water; acetic acid for 0.5h; Heating;

5
[ 67-56-1 ]
[ 26020-48-4 ]
[ 81730-18-9 ]

Yield	Reaction Conditions	Operation in experiment
83.1%	With hydrogenchloride for 10h; Heating;
75%	With sulfuric acid for 24h; Reflux;

Reference： [1]Kon'kova, S. G.; Safaryan, A. A.; Akopyan, A. N. [Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, # 2, p. 348 - 351][Zhurnal Organicheskoi Khimii, 1982, # 2, p. 400 - 403]
[2]Wang, Wenyi; Ji, Xingyue; Du, Zhenming; Wang, Binghe [Chemical Communications, 2017, vol. 53, # 8, p. 1370 - 1373]

6
[ 71-23-8 ]
[ 26020-48-4 ]
[ 81730-20-3 ]

Yield	Reaction Conditions	Operation in experiment
84.3%	With hydrogenchloride for 10h; Heating;

7
[ 24422-15-9 ]
[ 26020-48-4 ]
[ 81730-14-5 ]

Yield	Reaction Conditions	Operation in experiment
2 g	at 180℃; for 8h;

8
[ 26020-48-4 ]
[ 111-87-5 ]
[ 81730-25-8 ]

Yield	Reaction Conditions	Operation in experiment
63.2%	With hydrogenchloride at 100 - 105℃; for 10h;

9
[ 26020-48-4 ]
[ 64-17-5 ]
[ 81730-19-0 ]

Yield	Reaction Conditions	Operation in experiment
68%	With hydrogenchloride for 10h; Heating;

10
[ 26020-48-4 ]
[ 71-41-0 ]
[ 81730-22-5 ]

Yield	Reaction Conditions	Operation in experiment
92.1%	With hydrogenchloride at 100 - 105℃; for 10h;

11
[ 26020-48-4 ]
[ 111-70-6 ]
[ 81730-24-7 ]

Yield	Reaction Conditions	Operation in experiment
71.4%	With hydrogenchloride at 100 - 105℃; for 10h;

13
[ 26020-48-4 ]
[ 111350-85-7 ]
[ 111350-87-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-carbonyldiimidazole 1.) CH₂Cl₂; 2.) reflux, 22 h, CH₂Cl₂; Yield given. Multistep reaction;

Reference： [1]Bader, Axel; Ebel, Klaus; Musso, Hans; Skuballa, Norbert [Chemische Berichte, 1988, vol. 121, p. 327 - 338]

14
[ 26020-48-4 ]
[ 100-51-6 ]
[ 81730-28-1 ]

Yield	Reaction Conditions	Operation in experiment
61.7%	at 100 - 105℃; for 10h;

15
[ 26020-48-4 ]
[ 71-36-3 ]
[ 81730-21-4 ]

Yield	Reaction Conditions	Operation in experiment
86.3%	With hydrogenchloride at 100 - 105℃; for 10h;

16
[ 26020-48-4 ]
[ 111-27-3 ]
[ 81730-23-6 ]

Yield	Reaction Conditions	Operation in experiment
76.1%	With hydrogenchloride at 100 - 105℃; for 10h;

17
[ 26020-48-4 ]
[ 143-08-8 ]
[ 81730-26-9 ]

Yield	Reaction Conditions	Operation in experiment
70.5%	With hydrogenchloride at 100 - 105℃; for 10h;

18
[ 26020-48-4 ]
[ 109-52-4 ]

Yield	Reaction Conditions	Operation in experiment
50.5%	With nickel In ethanol for 27h; Heating;

19
[ 124-38-9 ]
[ 78665-33-5 ]
[ 26020-48-4 ]

Yield	Reaction Conditions	Operation in experiment
74%	With water; hydrogen cation

Reference： [1]Rahman, M. T. [Journal of the Indian Chemical Society, 1981, vol. 58, p. 21 - 23]

Yield	Reaction Conditions	Operation in experiment
	A) 2,3,4-Trichlorthiophen, 1) Mg, C2H4Br2, 2) CO2 (Grignard);
	B) Trichlor-2-thienyl-magnesium-halid (V), CO2;
	2-Chlormethyl-3,4,5-trichlorthiophen, HNO3;

	Trichlor-2-thienyllithium, CO2;
	/BRN= 90239/, Butyl-Li, CO2;

21
[ 26020-48-4 ]
4-{2-[1-methyl-4-(1-methyl-4-(4-amino-2-pyrrolecarboxamido)-2-pyrrolecarboxamido)-2-pyrrolecarboxamido]ethyl}morpholine dihydrochloride [ No CAS ]
4-{2-[1-methyl-4-(1-methyl-4-(1-methyl-4-(3,4,5-trichlorothiophene-2-carboxamido)-2-pyrrolecarboxamido)-2-pyrrolecarboxamido)-2-pyrrolecarboxamido]ethyl}morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25 - 37℃; for 16h;

Reference： [1]Kaizerman, Jacob A.; Gross, Matthew I.; Ge, Yigong; White, Sarah; Hu, Wenhao; Duan, Jian-Xin; Baird, Eldon E.; Johnson, Kirk W.; Tanaka, Richard D.; Moser, Heinz E.; Bürli, Roland W. [Journal of Medicinal Chemistry, 2003, vol. 46, # 18, p. 3914 - 3929]

22
[ 26020-48-4 ]
[ 107-06-2 ]
[ 24422-15-9 ]

Yield	Reaction Conditions	Operation in experiment
22.0 g (>98% wt)	With thionyl chloride In N,N-dimethyl-formamide	7 3,4,5-Trichloro-2-thiophenecarbonyl chloride EXAMPLE 7 3,4,5-Trichloro-2-thiophenecarbonyl chloride A mixture of 20.4 g (0.088 mole) of 3,4,5-trichloro-2-thiophenecarboxylic acid, 7.3 mL (0.1 mole) of thionyl chloride, 0.2 mL of DMF and 80 mL of 1,2-dichloroethane was heated at reflux temperature for 3 h. The reaction mixture became a clear solution after 1 h of heating. The mixture was allowed to cool to RT, concentrated in vacuo and exposed to high vacuum to give 22.0 g (>98% wt) an oil which solidified upon standing to an off-white powder, mp 37°-41° C.
22.0 g (>98% wt)	With thionyl chloride In N,N-dimethyl-formamide	4.C C. C. 3,4,5-Trichloro-2-thiophenecarbonyl chloride A mixture of 20.4 g (0.088 mole) of 3,4,5-trichloro-2-thiophenecarboxylic acid, 7.3 mL (0.1 mole) of thionyl chloride, 0.2 mL of DMF and 80 mL of 1,2-dichloroethane was heated at reflux temperature for 3 h. The reaction mixture became a clear solution after 1 h of heating. The mixture was allowed to cool to RT, concentrated in vacuo and exposed to high vacuum to give 22.0 g (>98% wt) an oil which solidified upon standing to an off-white powder, mp 37°-41° C.

Reference： [1]Current Patent Assignee: CORTEVA INC - US6096898, 2000, A
[2]Current Patent Assignee: CORTEVA INC - US6329528, 2001, B1

23
[ 26020-48-4 ]
[ 53399-81-8 ]
[ 1159205-87-4 ]
[ 1159205-86-3 ]
[ 1159205-88-5 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium(II) trifluoroacetate; 1-Adamantanecarboxylic acid; p-benzoquinone In 1,4-dioxane; dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 1h; Inert atmosphere; optical yield given as %de; regioselective reaction;

Reference： [1]Hu, Peng; Kan, Jian; Su, Weiping; Hong, Maochun [Organic Letters, 2009, vol. 11, # 11, p. 2341 - 2344]

24
[ 26020-48-4 ]
[ 17249-78-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With acetic acid; silver carbonate In dimethyl sulfoxide at 120℃; for 16h;
58%	With copper(l) iodide; triethylamine In dimethyl sulfoxide at 140℃; for 20h; Inert atmosphere; Schlenk technique;

Reference： [1]Lu, Pengfel; Sanchez, Carolina; Cornella, Josep; Larrosa, Igor [Organic Letters, 2009, vol. 11, # 24, p. 5710 - 5713]
[2]Li, Zhaojie; Fu, Zhengjiang; Zhang, Haixia; Long, Jiao; Song, Yuanyuan; Cai, Hu [New Journal of Chemistry, 2016, vol. 40, # 4, p. 3014 - 3018]

25
[ 26020-48-4 ]
[ 17249-78-4 ]
[ 34721-65-8 ]

Yield	Reaction Conditions	Operation in experiment
66%	With palladium(II) trifluoroacetate; silver carbonate In dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 16h; Inert atmosphere;

Reference： [1]Cornella, Josep; Lahlali, Hicham; Larrosa, Igor [Chemical Communications, 2010, vol. 46, # 43, p. 8276 - 8278]

26
[ 26020-48-4 ]
[ 727385-55-9 ]
[ 1222773-95-6 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 1h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Rai, Ganesha; Kenyon, Victor; Jadhav, Ajit; Schultz, Lena; Armstrong, Michelle; Jameson, J. Brian; Hoobler, Eric; Leister, William; Simeonov, Anton; Holman, Theodore R.; Maloney, David J. [Journal of Medicinal Chemistry, 2010, vol. 53, # 20, p. 7392 - 7404]

27
[ 54022-99-0 ]
[ 26020-48-4 ]
[ 1393456-36-4 ]

Yield	Reaction Conditions	Operation in experiment
55%	With dichloro bis(acetonitrile) palladium(II); silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;

Reference： [1]Hu, Peng; Shang, Yaping; Su, Weiping [Angewandte Chemie - International Edition, 2012, vol. 51, # 24, p. 5945 - 5949]

28
[ 26020-48-4 ]
methyl 3,4,5-trichlorothiophene-2-carboxylate 1,1-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sulfuric acid / 24 h / Reflux 2: trifluoroacetyl peroxide / dichloromethane / 48 h / 20 °C

Reference： [1]Wang, Wenyi; Ji, Xingyue; Du, Zhenming; Wang, Binghe [Chemical Communications, 2017, vol. 53, # 8, p. 1370 - 1373]

29
[ 26020-48-4 ]
[ 115269-99-3 ]
(E)-N,N-bis(tert-butoxycarbonyl)-3-(3,4,5-trichlorothiophen-2-yl)prop-2-en-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With palladium(II) trifluoroacetate; silver carbonate In tetrahydrofuran; dimethyl sulfoxide at 100℃; for 8h; Inert atmosphere; stereoselective reaction;	4.2. General procedure for the decarboxylative arylation of olefins with aryl carboxylic acids General procedure: To an oven-dried pressure tube were sequentially added aryl carboxylic acid 1 (0.2 mmol), olefin 2 (0.24 mmol), Pd(TFA)2 (3.33 mg, 5.0 mol%), Ag2CO3 (55.2 mg, 0.2 mmol), THF (2.0 mL) and DMSO (0.10 mL) under nitrogen at room temperature. After degassing three times, the reaction mixture was heated at 100 °C for 8 h, and then was cooled to room temperature. Water (20.0 mL)was added, and the mixture was extracted with ethyl acetate (3 5.0 mL). The combined organic layer was washed with brine, dried over anhydrious Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate) to give the pure target product.

Reference： [1]Qin, Xubo; Chen, Changjun; Zhang, Lingjuan; Xu, Jianbin; Pan, Yixiao; Zhao, Haoqiang; Han, Jiahong; Li, Huanrong; Xu, Lijin [Tetrahedron, 2017, vol. 73, # 16, p. 2242 - 2249]

30
[ 5428-09-1 ]
[ 26020-48-4 ]
(E)-2-(3-(3,4,5-trichlorothiophen-2-yl)allyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With palladium(II) trifluoroacetate; silver carbonate In tetrahydrofuran; dimethyl sulfoxide at 100℃; for 8h; Inert atmosphere; stereoselective reaction;	4.2. General procedure for the decarboxylative arylation of olefins with aryl carboxylic acids General procedure: To an oven-dried pressure tube were sequentially added aryl carboxylic acid 1 (0.2 mmol), olefin 2 (0.24 mmol), Pd(TFA)2 (3.33 mg, 5.0 mol%), Ag2CO3 (55.2 mg, 0.2 mmol), THF (2.0 mL) and DMSO (0.10 mL) under nitrogen at room temperature. After degassing three times, the reaction mixture was heated at 100 °C for 8 h, and then was cooled to room temperature. Water (20.0 mL)was added, and the mixture was extracted with ethyl acetate (3 5.0 mL). The combined organic layer was washed with brine, dried over anhydrious Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate) to give the pure target product.

Reference： [1]Qin, Xubo; Chen, Changjun; Zhang, Lingjuan; Xu, Jianbin; Pan, Yixiao; Zhao, Haoqiang; Han, Jiahong; Li, Huanrong; Xu, Lijin [Tetrahedron, 2017, vol. 73, # 16, p. 2242 - 2249]

31
[ 26020-48-4 ]
C₂₅H₃₉N₃O₁₀P^(1-)*Na⁽¹⁺⁾ [ No CAS ]
C₃₀H₃₈Cl₃N₃O₁₁PS^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃;

Reference： [1]Yuhas, Shelby C.; Laverty, Daniel J.; Lee, Huijin; Majumdar, Ananya; Greenberg, Marc M. [Journal of the American Chemical Society, 2021, vol. 143, # 21, p. 8099 - 8107]

32
[ 26020-48-4 ]
N-(2-amino-2-sulfanylideneethyl)-3,4,5-trichlorothiophene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / tetrahydrofuran; ethyl acetate / 20 h / 20 °C 2: water; lithium hydroxide / tetrahydrofuran / 4 h / 20 °C 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; ammonium chloride / dichloromethane / 2 h / 20 °C / Inert atmosphere 4: Lawessons reagent / toluene / 5 h / 60 °C / Inert atmosphere