(R)-1,4-Benzodioxane-2-carboxylic acid

Base Information

• Chemical Name: (R)-1,4-Benzodioxane-2-carboxylic acid
• CAS No.: 70918-53-5
• Molecular Formula: C9H8 O4
• Molecular Weight: 180.16
• Hs Code.: 2932999099
• European Community (EC) Number: 634-729-6
• DSSTox Substance ID: DTXSID80350737
• Nikkaji Number: J1.995.249E
• Wikidata: Q27451705
• Mol file: 70918-53-5.mol

Synonyms:70918-53-5;(R)-1,4-Benzodioxane-2-carboxylic acid;(R)-2,3-Dihydro-benzo[1,4]dioxine-2-carboxylic acid;(3R)-2,3-dihydro-1,4-benzodioxine-3-carboxylic acid;(R)-2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylic acid;(2r)-2,3-Dihydro-1,4-Benzodioxine-2-Carboxylic Acid;1,4-Benzodioxin-2-carboxylic acid, 2,3-dihydro-, (2R)-;(R)-2,3-Dihydro-1,4-benzodioxin-2-carboxylic acid;MFCD00239407;(R)-2,3-dihydrobenzo[1,4]dioxine-2-carboxylic acid;(R)-1,4-Benzodioxan-2-CarboxylicAcid;SCHEMBL566636;DTXSID80350737;HMBHAQMOBKLWRX-MRVPVSSYSA-N;AMY21352;BCP15476;AKOS016842394;CS-W016009;(R)-1,4-Benzodioxane-2-carboxylicacid;(r)-1,4-benzodioxane 2-carboxylic acid;AC-30247;AS-37657;A9322;(2R)-2,3-dihydro-1,4-benzodioxin-2-carboxylic acid;Q27451705;(R)-2 pound not3-Dihydro-benzo[1 pound not4]dioxine-2-carboxylic acid;(R)-1,4-Benzodioxane-2-carboxylic acid, >=97.0% (sum of enantiomers, GC)

Chemical Property of (R)-1,4-Benzodioxane-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 2.07E-05mmHg at 25°C
• Melting Point: 96-99 ºC
• 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.: 2-8°C
• 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

(R)-2,3-Dihydrobenzo[1,4]dioxine-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC2=CC=CC=C2O1)C(=O)O
• Isomeric SMILES: C1[C@@H](OC2=CC=CC=C2O1)C(=O)O
• Uses: (R)-1,4-Benzodioxane-2-carboxylic acid is a chiral synthon mostly used in the preparation of doxazosin mesylate, a drug treating benign prostatic hyperplasia.

Technology Process of (R)-1,4-Benzodioxane-2-carboxylic acid

There total 30 articles about (R)-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: 100.0%

(R)-N-((R)-1-phenylethyl)-2,3-dihydrobenzo [b][1,4]dioxine-2-carboxamide → (R)-1-phenyl-ethyl-amine (3886-69-9) + (+)-(2R)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid (70918-53-5)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 90 ℃;

DOI:10.1016/j.tetlet.2016.03.100

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: 98.0%

1,4-benzodioxin-2-carboxylic acid (67471-01-6) → (+)-(2R)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid (70918-53-5)

Guidance literature:

With bis(norbornadiene)rhodium(l)tetrafluoroborate; C₄₆H₃₈F₆FeN₂P₂S; hydrogen; In dichloromethane; at 25 ℃; for 12h; under 7600.51 Torr; Reagent/catalyst; enantioselective reaction; Catalytic behavior; Autoclave;

DOI:10.1021/acs.orglett.8b01469

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:

1,4-benzodioxane-2-carboxyamide

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

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

(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(piperazin-1-yl)methanone

Refernces

• 1、 Campbell,Davey,Hardstone,Lewis,Palmer. "2,4-Diamino-6,7-dimethoxyquinazolines. 1. 2-[4-(1,4-benzodioxan-2-ylcarbonyl)piperazin-1-yl] derivatives as α1-adrenoceptor antagonists and antihypertensive agents". . p. 49 - 57. Retrieved 1987.
• 2、 Yin, Xuguang,Huang, Yi,Chen, Ziyi,Hu, Yang,Tao, Lin,Zhao, Qingyang,Dong, Xiu-Qin,Zhang, Xumu. "Enantioselective Access to Chiral 2-Substituted 2,3-Dihydrobenzo[1,4]dioxane Derivatives through Rh-Catalyzed Asymmetric Hydrogenation". . p. 4173 - 4177. Retrieved 2018/07/29.
• 3、 -. "Method for synthesizing doxazosin". Paragraph 0063; 0071; 0072. . Retrieved 2017/01/12.