methyl 4-(1-methyl-1H-pyrazol-5-yl)benzoate

Base Information

• Chemical Name: methyl 4-(1-methyl-1H-pyrazol-5-yl)benzoate
• CAS No.: 179057-12-6
• Molecular Formula: C12H12 N2 O2
• Molecular Weight: 216.239
• Hs Code.: 2933199090
• DSSTox Substance ID: DTXSID80445051
• Nikkaji Number: J2.993.135F
• Wikidata: Q72493029
• Mol file: 179057-12-6.mol

Synonyms:179057-12-6;methyl 4-(1-methyl-1H-pyrazol-5-yl)benzoate;Methyl 4-(2-methylpyrazol-3-yl)benzoate;Benzoic acid, 4-(1-methyl-1H-pyrazol-5-yl)-, methyl ester;MFCD11846164;4-(2-Methyl-2H-pyrazol-3-yl)-benzoic acid methyl ester;SCHEMBL8808172;DTXSID80445051;AMY32990;ZB1447;DS-4893;Methyl 4-(1-Methyl-5-pyrazolyl)benzoate;SY121225;A3973;CS-0061737;FT-0710733;W17388;2-amino-4-methoxy-4-oxobutanoic?acid?hydrochloride;4-(2-Methyl-2H-pyrazole-3-yl)benzoic acid methyl ester;Z2044793880

Chemical Property of methyl 4-(1-methyl-1H-pyrazol-5-yl)benzoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 357.507°C at 760 mmHg
• PKA: 1.50±0.10(Predicted)
• Flash Point: 170.015°C
• PSA: 44.12000
• Density: 1.16
• LogP: 1.87370
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 216.089877630
• Heavy Atom Count: 16
• Complexity: 249

Purity/Quality:

99%, ^*data from raw suppliers

4-(2-Methyl-2H-pyrazol-3-yl)-benzoic acid methyl ester 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=CC=N1)C2=CC=C(C=C2)C(=O)OC

Technology Process of methyl 4-(1-methyl-1H-pyrazol-5-yl)benzoate

There total 4 articles about methyl 4-(1-methyl-1H-pyrazol-5-yl)benzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

4-methoxycarbonylphenyl bromide (619-42-1) + 1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (847818-74-0) → methyl 4-(1-methyl-1H-pyrazol-5-yl)benzoate (179057-12-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium phosphate tribasic trihydrate; In N,N-dimethyl-formamide; at 0 - 120 ℃; Inert atmosphere;

DOI:10.1016/j.ejmech.2016.03.074

Reference yield: 51.0%

1-methyl-1H-pyrazole (930-36-9) + 4-methoxycarbonylphenyl bromide (619-42-1) → methyl 4-(1-methyl-1H-pyrazol-4-yl)benzoate (1339768-73-8) + methyl 4-(1-methyl-1H-pyrazol-5-yl)benzoate (179057-12-6)

Guidance literature:

With potassium acetate; palladium diacetate; In N,N-dimethyl acetamide; at 150 ℃; for 20h; regioselective reaction; Inert atmosphere;

DOI:10.1055/s-0030-1260076

Reference yield: 34.0%

methylhydrazine (60-34-4) + (E)-methyl 4-(3-(dimethylamino)acryloyl)benzoate (114431-72-0) → 4-(1-methyl-1H-pyrazol-3-yl)benzoic acid methyl ester (179057-11-5) + methyl 4-(1-methyl-1H-pyrazol-5-yl)benzoate (179057-12-6)

Guidance literature:

With acetic acid; for 3h; Ambient temperature;

DOI:10.1021/jm9800853

upstream raw materials:

methylhydrazine

(E)-methyl 4-(3-(dimethylamino)acryloyl)benzoate

ethyl-4-acetylbenzoate

1-methyl-1H-pyrazole

Downstream raw materials:

4-(1-methyl-1H-pyrazol-5-yl)benzoic acid

Refernces

• 1、 Dong, Xiaowu,Zhan, Wenhu,Zhao, Mengting,Che, Jinxin,Dai, Xiaoyang,Wu, Yizhe,Xu, Lei,Zhou, Yubo,Zhao, Yanmei,Tian, Tian,Cheng, Gang,Jin, Zegao,Li, Jia,Shao, Yanfei,He, Qiaojun,Yang, Bo,Weng, Qinjie,Hu, Yongzhou. "Discovery of 3,4,6-Trisubstituted Piperidine Derivatives as Orally Active, Low hERG Blocking Akt Inhibitors via Conformational Restriction and Structure-Based Design". supporting information. p. 7264 - 7288. Retrieved 2019/08/20.
• 2、 Zhan, Wenhu,Xu, Lei,Dong, Xiaowu,Dong, Jun,Yi, Xiao,Ma, Xiaodong,Qiu, Ni,Li, Jia,Yang, Bo,Zhou, Yubo,Hu, Yongzhou. "Design, synthesis and biological evaluation of pyrazol-furan carboxamide analogues as novel Akt kinase inhibitors". . p. 47 - 58. Retrieved 2016/05/11.