Penicillanic acid

Base Information

• Chemical Name: Penicillanic acid
• CAS No.: 87-53-6
• Molecular Formula: C8H11 N O3 S
• Molecular Weight: 201.246
• Hs Code.: 2934999090
• European Community (EC) Number: 201-750-3
• UNII: PIS09H0QIX
• DSSTox Substance ID: DTXSID90236038
• Nikkaji Number: J192.646B
• Wikidata: Q27117271
• Metabolomics Workbench ID: 55683
• ChEMBL ID: CHEMBL325758
• Mol file: 87-53-6.mol

Synonyms:Acid, Penicillanic;Penicillanic Acid

Chemical Property of Penicillanic acid

Chemical Property:

• Vapor Pressure: 2.26E-08mmHg at 25°C
• Melting Point: 208-209 °C
• Boiling Point: 423.8°C at 760 mmHg
• PKA: 2.43±0.50(Predicted)
• Flash Point: 210.1°C
• PSA: 82.91000
• Density: 1.46g/cm³
• LogP: 0.46130
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 201.04596439
• Heavy Atom Count: 13
• Complexity: 289

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C(N2C(S1)CC2=O)C(=O)O)C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)CC2=O)C(=O)O)C

Technology Process of Penicillanic acid

There total 17 articles about Penicillanic acid 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: 88.0%

6-Aminopenicillanic Acid (551-16-6) → penicillanic acid (87-53-6,820211-53-8)

Guidance literature:

6-Aminopenicillanic Acid; With sulfuric acid; sodium nitrite; In water; at -10 - 5 ℃; for 1h;

With sodium hypophosphite; In water; at -5 - 30 ℃; for 2h;

Reference yield: 76.0%

6α-Bromopenicillanic acid (205320-26-9) → penicillanic acid (87-53-6,820211-53-8)

Guidance literature:

With dipotassium hydrogenphosphate; In water; at 0 - 10 ℃; electroreduction;

DOI:10.1248/cpb.36.1976

Reference yield: 75.0%

6,6-dibromopenicillanic acid (205320-24-7) → penicillanic acid (87-53-6,820211-53-8)

Guidance literature:

With tetraethylammonium tosylate; In methanol; at 0 - 10 ℃; electroreduction;

DOI:10.1248/cpb.36.1976

upstream raw materials:

(S)-6-Chloro-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

(S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

6,6-dibromopenicillanic acid

6-aminopenicillanic acid

Downstream raw materials:

penicillanic acid 4-nitro-benzyl ester

sulbactum

tazobactam acid

C₈H₁₁NO₄S

Refernces

• 1、 -. "Synthetic method for tazobactam chiral isomer". Paragraph 0034; 0035. . Retrieved 2019/04/04.
• 2、 Yang, Yuanshuai,Tang, Sheng,Liu, Zhandong,Wang, Yanxiang,Pang, Jing,You, Xuefu,Song, Danqing,Li, Yinghong,Lu, Xi. "Synthesis and antibacterial evaluation of sulbactam derivatives against Acinetobacter baumannii". . p. 433 - 437. Retrieved 2018/09/10.