1,4-Benzodioxane-2-carboxylic Acid

Base Information

• Chemical Name: 1,4-Benzodioxane-2-carboxylic Acid
• CAS No.: 3663-80-7
• Molecular Formula: C₉H₈O₄
• Molecular Weight: 180.16
• Hs Code.: 29329990
• European Community (EC) Number: 609-276-2
• UNII: T9Z56HV1B0
• DSSTox Substance ID: DTXSID30957891
• Nikkaji Number: J1.584.427B
• Wikidata: Q27289857
• Mol file: 3663-80-7.mol

Synonyms:3663-80-7;1,4-Benzodioxan-2-carboxylic acid;1,4-Benzodioxane-2-carboxylic Acid;2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid;2,3-dihydro-1,4-benzodioxine-2-carboxylic acid;34385-93-8;1,4-Benzodioxin-2-carboxylic acid, 2,3-dihydro-;rac 1,4-benzodioxane-2-carboxylic acid;Doxazosin impurity A;2,3-dihydro-1,4-benzodioxine-3-carboxylic acid;(2RS)-2,3-Dihydro-1,4-benzodioxine-2-carboxylic acid;1,4-benzodioxane 2-carboxylic acid;UNII-T9Z56HV1B0;RX 811056;RX-811056;T9Z56HV1B0;(+/-)-1,4-Benzodioxan-2-carboxylic acid;2,3-dihydro-1,4-benzodioxin-2-carboxylic acid;Doxazosin mesilate impurity A [EP];2,3-Dihydrobenzo(b)(1,4)dioxine-2-carboxylic acid;MFCD00084888;2,3-Dihydrobenzo[1,4]dioxine-2-carboxylic acid;1,4-Benzodioxin-2-carboxylic acid, 2,3-dihydro-, (A+/-)-;cholinehydroxide;CDS1_000297;Maybridge1_002585;ChemDiv2_003276;2-benzodioxanecarboxylic acid;Oprea1_073520;DivK1c_001337;SCHEMBL229498;HMS548N11;DTXSID30957891;HMBHAQMOBKLWRX-UHFFFAOYSA-N;USP Doxazosin Related Compound D;HMS1378E20;STR04611;1,4-benzodiozane-2-carboxylic acid;BBL001421;STK183543;AKOS000271138;AKOS016040108;AC-1644;AM10812;CCG-202901;CS-W002348;PB43330;SDCCGMLS-0065916.P001;PD055364;SY003328;1,4-Benzodioxan-2-carboxylic acid, 97%;1-(O-TOLYL)PIPERAZINEDIHYDROCHLORIDE;A6320;B3406;EU-0033210;FT-0606770;FT-0630207;FT-0650411;FT-0651340;EN300-00140;,3-Dihydro-benzo[1,4]dioxine-2-carboxylic Acid;2,3-Dihydro-benzo[1,4]dioxine-2-carboxylic acid;SR-01000597134;12W-0825;2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylicacid;DOXAZOSIN MESILATE IMPURITY A [EP IMPURITY];J-507002;SR-01000597134-1;2,3-dihydrobenzo [b][1,4]dioxine-2-carboxylic acid;Q27289857;Z56839652;F0913-5472;5-[5-(5-chloro-1H-indol-2-yl)-1,2,4-oxadiazol-3-yl]-1-(3-oxo-3-pyrrolidin-1-ylpropyl)-1H-benzimidazole

Chemical Property of 1,4-Benzodioxane-2-carboxylic Acid

Chemical Property:

• Appearance/Colour: white to off-white solid
• Vapor Pressure: 2.07E-05mmHg at 25°C
• Melting Point: 126-130 °C(lit.)
• Boiling Point: 347.2 °C at 760 mmHg
• PKA: 2.69±0.20(Predicted)
• Flash Point: 145.4 °C
• PSA: 55.76000
• Density: 1.379 g/cm³
• LogP: 0.91100
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 7.63g/L at 20℃
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 180.04225873
• Heavy Atom Count: 13
• Complexity: 204

Purity/Quality:

99% ^*data from raw suppliers

rac 1,4-Benzodioxane-2-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 36/37/38:
• Hazard Codes: 36/37/38:
• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC2=CC=CC=C2O1)C(=O)O

Technology Process of 1,4-Benzodioxane-2-carboxylic Acid

There total 13 articles about 1,4-Benzodioxane-2-carboxylic 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: 98.0%

2-cyano-1,4-benzodioxane (1008-92-0) → 1,4-benzodioxane-2-carboxylic acid (3663-80-7,34385-93-8,70918-53-5,70918-54-6)

Guidance literature:

With sulfuric acid; acetic acid; In water; at 110 ℃; for 15h;

DOI:10.1021/jm00128a049

Reference yield: 92.5%

2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin (3663-82-9) → 1,4-benzodioxane-2-carboxylic acid (3663-80-7,34385-93-8,70918-53-5,70918-54-6)

Guidance literature:

With potassium permanganate; potassium hydroxide; In water; at 0 ℃;

Reference yield: 91.0%

methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate (3663-79-4,650597-66-3) → 1,4-benzodioxane-2-carboxylic acid (3663-80-7,34385-93-8,70918-53-5,70918-54-6)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; for 3h;

DOI:10.1016/j.tetasy.2012.10.018

upstream raw materials:

diazoacetic acid ethyl ester

Methylenedioxybenzene

ethyl 2,3-dihydro-1,4-benzodioxin-2-carboxylate

2-cyano-1,4-benzodioxane

Downstream raw materials:

methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate

(S)‐1,4‐benzodioxane‐2‐carboxylic acid

(+)-(2R)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid

(+/-)-N-methoxy-N-methyl-2,3-dihydro-1,4-benzodioxine-2-carboxamide

Refernces

• 1、 -. "Method for synthesizing doxazosin". Paragraph 0063; 0071; 0072. . Retrieved 2017/01/12.
• 2、 Wang, Songlin,Chen, Yin,Zhao, Song,Xu, Xiangqing,Liu, Xin,Liu, Bi-Feng,Zhang, Guisen. "Synthesis and biological evaluation of a series of benzoxazole/ benzothiazole-containing 2,3-dihydrobenzo[b][1,4]dioxine derivatives as potential antidepressants". supporting information. p. 1766 - 1770. Retrieved 2014/04/17.