[ CAS No. 26165-66-2 ]

Name: 26165-66-2|Methyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate|98%
Brand: Ambeed
SKU: A355559
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Quality Control of [ 26165-66-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 26165-66-2 ]

SDS Specification

Alternatived Products of [ 26165-66-2 ]

Product Details of [ 26165-66-2 ]

CAS No. :	26165-66-2	MDL No. :	MFCD01125267
Formula :	C₁₄H₁₅NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FFRKCMKOLMHBCM-UHFFFAOYSA-N
M.W :	229.27 g/mol	Pubchem ID :	738398
Synonyms :

Calculated chemistry of [ 26165-66-2 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.21
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	66.98
TPSA :	31.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.96
Log Po/w (XLOGP3) :	2.97
Log Po/w (WLOGP) :	2.88
Log Po/w (MLOGP) :	2.45
Log Po/w (SILICOS-IT) :	2.87
Consensus Log Po/w :	2.83

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.41
Solubility :	0.0885 mg/ml ; 0.000386 mol/l
Class :	Soluble
Log S (Ali) :	-3.29
Solubility :	0.118 mg/ml ; 0.000514 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.16
Solubility :	0.0159 mg/ml ; 0.0000695 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.76

Safety of [ 26165-66-2 ]

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 [ 26165-66-2 ]

* 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 [ 26165-66-2 ]

[ 26165-66-2 ] Synthesis Path-Downstream 1~20

Yield	Reaction Conditions	Operation in experiment
41%	With Hf/SBA-15⁽²⁰⁾ at 150℃; for 6h; Inert atmosphere;	28 Example 1 General procedure: Put 140 mg Hf/SBA-15(20) (that is, the Si/Hf ratio is 20),1.5 mL 2,5-dimethylfuran,0.5 mmol aniline into the pressure tube,The molar ratio of hafnium metal to aniline in the catalyst is 18.2%,Under the atmosphere of N2 protection, the reaction was carried out at 150°C with a stirring speed of 800 rpm for 6 hours,The reaction product was confirmed by nuclear magnetic analysis that the main product was indeed 2,5-dimethyl-1-phenyl-1H-pyrrole, as shown in Figure 1.With naphthalene as an internal standard, the yield of 2,5-dimethyl-1-phenyl-1H-pyrrole was 97.3% by gas chromatography quantitative analysis.
	Entspr. Saeure, ROH;

2
[ 26165-66-2 ]
[ 26165-67-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrazine hydrate In ethanol Reflux;	3.2.4. 4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzoic acid hydrazide (18) A mixture of methyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate (16) (2.29 g, 10 mmol) and hydrazine hydrate(2.25 g, 45 mmol) in 96% ethanol (10 mL) was heated at reflux temperature overnight. The solid that separatedon cooling was filtered and recrystallized to give colorless crystals (1.95 g, 85%), mp 164-165 °C (ethanol) (lit.35mp 148 °C); 1 H NMR (DMSO-d6 , 400 MHz): 1.97 (s, 6H), 4.54 (s, 2H, exchangeable with D), 5.81 (s, 2H),7.34 (d, J = 8.4 Hz, 2H), 7.94 (d, J = 8.4 Hz, 2H), 9.89 (s, 1H, exchangeable with D); 13 C NMR (DMSO-d6 ,100 MHz): 12.9, 106.4, 127.5, 127.8, 128.0, 132.4, 140.6, 165.2. Anal. Calcd. for C13 H15 N3 O: C, 68.10; H,6.59; N, 18.33. Found: C, 68.25; H, 6.71; N, 18.48.
	With hydrazine hydrate In ethanol for 1h; Reflux;

Reference： [1]Roman, Gheorghe; Bostănaru, Andra-Cristina; Năstasă, Valentin; Mareş, Mihai [Turkish Journal of Chemistry, 2019, vol. 43, # 2, p. 531 - 546]
[2]Location in patent: experimental part Dong, Ming-Xin; Zhang, Jian; Peng, Xu-Qing; Lu, Hong; Yun, Liu-Hong; Jiang, Shibo; Dai, Qiu-Yun [European Journal of Medicinal Chemistry, 2010, vol. 45, # 9, p. 4096 - 4103]

3
[ 123-54-6 ]
[ 619-45-4 ]
[ 26165-66-2 ]

Yield	Reaction Conditions	Operation in experiment
	In acetic acid Reflux;

Reference： [1]Location in patent: scheme or table Dong, Ming-Xin; Zhang, Jian; Peng, Xu-Qing; Lu, Hong; Yun, Liu-Hong; Jiang, Shibo; Dai, Qiu-Yun [European Journal of Medicinal Chemistry, 2010, vol. 45, # 9, p. 4096 - 4103]

4
[ 110-13-4 ]
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[ 26165-66-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With MIL-53(Al) In neat (no solvent) at 80℃; for 0.25h; Sonication;
96%	With Cl^(1-)C₅H₁₄NO⁽¹⁺⁾3ZnCl₂ In neat (no solvent) for 0.166667h; Sealed tube; Sonication; Green chemistry;
84%	With 1-allyl-3-methylimidazolium tetrafluoromethanesulfonate; zinc(II) chloride at 80℃; for 1h; Sonication;	General procedure for Paal-Knorr reaction General procedure: A solution of aniline (1 mmol, 0.094 g), acetonylacetone (1.2 mmol, 0.136 g) and ZnCl2(10 mol%, 0.0136 g) in the presence of [AMIm](OTf) (0.1 g) was sonicated at 80 C for the appropriate time indicated. The completion of the reaction was monitored by thin layer chromatography (TLC) and GC. The reaction mixture was extracted with diethylether (10 x 5 mL). The combined organic extract was washed with water (10 mL), dried with anhydrous sodium sulfate, filtered and dried under vacuum at 30 C. The residue was purified by chromatography on silica gel using ethyl acetate-hexane (1:9). The product was characterized by 1H and 13C NMR.

81%	With toluene-4-sulfonic acid In toluene at 150℃; for 1h; Sealed tube; Microwave irradiation;
75%	In ethanol; acetic acid for 6h; Reflux;	3.2.2. Methyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate (16) A solution of methyl 4-aminobenzoate (3.02 g, 20 mmol), 2,5-hexanedione (2.28 g, 20 mmol), and glacial acetic acid (0.5 mL) in 96% ethanol (20 mL) was heated at reflux temperature for 6 h, and then the solvent was partially removed under reduced pressure. The solid that separated on cooling was filtered and recrystallized from 2-propanol to give tan crystals (3.44 g, 75%), mp 92-93 °C (lit.35 mp 88 °C); 1 H NMR (DMSO-d6 , 400MHz): 1.99 (s, 6H), 3.89 (s, 3H), 5.84 (s, 2H), 7.43 (d, J = 8.8 Hz, 2H), 8.07 (d, J = 8.8 Hz, 2H); 13 CNMR (DMSO-d6 , 100 MHz): 12.9, 52.3, 106.7, 127.5, 128.2, 128.6, 130.2, 142.5, 165.7. Anal. Calcd. forC14 H15 NO2 : C, 73.34; H, 6.59; N, 6.11. Found: C, 73.24; H, 6.51; N, 6.03.

Reference： [1]Nguyen, Hai Truong; Thuy Nguyen, Linh Ho; Le Hoang Doan, Tan; Tran, Phuong Hoang [RSC Advances, 2019, vol. 9, # 16, p. 9093 - 9098]
[2]Truong Nguyen, Hai; Nguyen Chau, Duy-Khiem; Tran, Phuong Hoang [New Journal of Chemistry, 2017, vol. 41, # 21, p. 12481 - 12489]
[3]Nguyen, Hai Truong; Ngo, Dung Kim Thi; Chau, Khiem Duy Nguyen; Tran, Phuong Hoang [Organic Preparations and Procedures International, 2021, vol. 53, # 2, p. 157 - 165]
[4]Walia, Amit; Kang, Soosung; Silverman, Richard B [Journal of Organic Chemistry, 2013, vol. 78, # 21, p. 10931 - 10937]
[5]Roman, Gheorghe; Bostănaru, Andra-Cristina; Năstasă, Valentin; Mareş, Mihai [Turkish Journal of Chemistry, 2019, vol. 43, # 2, p. 531 - 546]

5
[ 26165-66-2 ]
[ 619-45-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	With hydrogenchloride In methanol at 120℃; for 0.333333h; Microwave irradiation;

Reference： [1]Walia, Amit; Kang, Soosung; Silverman, Richard B [Journal of Organic Chemistry, 2013, vol. 78, # 21, p. 10931 - 10937]

6
[ 109-49-9 ]
[ 619-45-4 ]
[ 26165-66-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With palladium(II) trifluoroacetate; oxygen In toluene at 100℃;	General procedure for the preparation of pyrroles 3. General procedure: All the reactions were carried out under aerobic atmosphere. To a solution of substrate 5-hexen-2-one 1 (0.6 mmol, 1.2 mmol for the diamines substrates) and amines 2 (0.5 mmol) in toluene (2.0 mL) was added to Pd(OCOCF3)2 (0.05 mmol, 16.5 mg). The mixture with O2 balloon was stirred at 100 °C overnight. The substrate was consumed completely monitored by TLC. The mixture was cooled to room temperature, filtered through celite, washed with ethylacetate and concentrated under vacuum. The resulting residue was purified by column chromatography using hexane/ethyl acetate (v/v, 20/1 to 10/1) as the eluent to give the desired product.

Reference： [1]Chen, Xi; Yang, Meng; Zhou, Min [Tetrahedron Letters, 2016, vol. 57, # 47, p. 5215 - 5218]

7
[ 26165-66-2 ]
4-allyl-3-[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]-1H-1,2,4-triazole-5-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: hydrazine hydrate / ethanol / Reflux 2: ethanol / 1 h / Reflux 3: potassium hydroxide / water / 3 h / Reflux