2-(Benzo[d][1,3]dioxol-5-yl)-2-oxoacetic acid

Base Information

• Chemical Name: 2-(Benzo[d][1,3]dioxol-5-yl)-2-oxoacetic acid
• CAS No.: 62396-98-9
• Molecular Formula: C9H6O5
• Molecular Weight: 194.144
• DSSTox Substance ID: DTXSID90871448
• Wikidata: Q107943414
• Mol file: 62396-98-9.mol

Synonyms:62396-98-9;2-(Benzo[d][1,3]dioxol-5-yl)-2-oxoacetic acid;2-(1,3-benzodioxol-5-yl)-2-oxoacetic acid;2-(Benzo[d][1,3]dioxol-5-yl)-2-oxoaceticacid;Piperonoylcarbonsaure;[3,4-(Methylenedioxy)phenyl]glyoxylic acid;SCHEMBL11491646;DTXSID90871448;1,3-Benzodioxol-5-yl(oxo)acetic acid;|A-Oxo-1,3-benzodioxole-5-acetic Acid;F80435;2-(2H-1,3-benzodioxol-5-yl)-2-oxoacetic acid

Chemical Property of 2-(Benzo[d][1,3]dioxol-5-yl)-2-oxoacetic acid

Chemical Property:

• Boiling Point: 366.2±42.0 °C(Predicted)
• PKA: 2.15±0.54(Predicted)
• PSA: 72.83000
• Density: 1.531±0.06 g/cm3(Predicted)
• LogP: 0.68260
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 194.02152329
• Heavy Atom Count: 14
• Complexity: 262

Purity/Quality:

99% ^*data from raw suppliers

α-Oxo-1,3-benzodioxole-5-aceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)C(=O)C(=O)O
• Uses: α-Oxo-1,3-benzodioxole-5-acetic Acid is an aryl-substituted analog of oxadiazolopyrazine with potential antibacterial activity.

Technology Process of 2-(Benzo[d][1,3]dioxol-5-yl)-2-oxoacetic acid

There total 13 articles about 2-(Benzo[d][1,3]dioxol-5-yl)-2-oxoacetic 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: 70.0%

benzo[1,3]dioxol-5-ylglyoxylic acid ethyl ester (86358-30-7) → benzo[1,3]dioxol-5-yl-oxo-acetic acid (62396-98-9)

Guidance literature:

benzo[1,3]dioxol-5-ylglyoxylic acid ethyl ester; With methanol; sodium hydroxide; at 0 ℃; for 2h;

In water; pH=~ 3 - 4;

Reference yield: 39.0%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → benzo[1,3]dioxol-5-yl-oxo-acetic acid (62396-98-9)

Guidance literature:

With pyridine; selenium(IV) oxide; at 90 - 110 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b00920

Reference yield:

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) → benzo[1,3]dioxol-5-yl-oxo-acetic acid (62396-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: magnesium / tetrahydrofuran / 1 h / 20 °C

1.2: 1 h / -78 - -10 °C

2.1: sodium hydroxide; water / tetrahydrofuran / 6 h / Reflux

With water; magnesium; sodium hydroxide; In tetrahydrofuran;

DOI:10.1002/anie.201400147

upstream raw materials:

1-(benzo[d][1,3]dioxol-6-yl)ethanone

isosafrole

2-(3,4-dioxymethylenephenyl)propionaldehyde

3,4-(methylenedioxy)benzoyl chloride

Downstream raw materials:

1,3-benzodioxole-5-acetic acid

benzyl 2-(benzo[d][1,3]dioxol-5-yl)-2-oxoacetate

Refernces

• 1、 Li, Bowen,Aliyu, Muinat A.,Gao, Zhenhua,Li, Tiejun,Dong, Wei,Li, Junchen,Shi, Enxue,Tang, Wenjun. "General Synthesis of Chiral α,α-Diaryl Carboxamides by Enantioselective Palladium-Catalyzed Cross-Coupling". supporting information. p. 4974 - 4978. Retrieved 2020/07/03.
• 2、 Xie, Shasha,Li, Defang,Huang, Hanchu,Zhang, Fuyuan,Chen, Yiyun. "Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation". supporting information. p. 16237 - 16242. Retrieved 2019/10/14.