Methyl 2,3-dihydro-1,4-benzodioxine-2-carboxylate

Base Information

• Chemical Name: Methyl 2,3-dihydro-1,4-benzodioxine-2-carboxylate
• CAS No.: 3663-79-4
• Molecular Formula: C10H10 O4
• Molecular Weight: 194.187
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID50389175
• Nikkaji Number: J1.109.030C
• Mol file: 3663-79-4.mol

Synonyms:3663-79-4;methyl 2,3-dihydro-1,4-benzodioxine-2-carboxylate;Methyl 1,4-Benzodioxane-2-carboxylate;methyl 1,4-benzodioxan-2-carboxylate;methyl 2,3-dihydro-1,4-benzodioxine-3-carboxylate;2,3-Dihydro-benzo[1,4]dioxine-2-carboxylic acid methyl ester;MFCD00297092;1,4-Benzodioxin-2-carboxylic acid, 2,3-dihydro-, methyl ester;2,3-dihydro-benzo[1,4]dioxine-2-carboxylic acidmethyl ester;Methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate;Methyl1,4-Benzodioxane-2-carboxylate;BAS 00258350;Enamine_004749;SCHEMBL7491132;DTXSID50389175;SNLAAGHHNZECPE-UHFFFAOYSA-N;HMS1407H19;1,4-Benzodioxin-2-carboxylicacid, 2,3-dihydro-, methyl ester;AC2382;BBL020130;STK182756;AKOS000301547;AKOS016313895;CS-11285;SY014175;BB 0218192;CS-0150727;FT-0678666;EN300-15475;Methyl (2RS)-1,4-Benzodioxane-2-carboxylate;1,4-Benzodioxane-2-carboxylic acid methyl ester;A823320;AO-365/40129133;Z19517075;2,3-Dihydrobenzo[1,4]dioxine-2-carboxylic acid, methyl ester

Chemical Property of Methyl 2,3-dihydro-1,4-benzodioxine-2-carboxylate

Chemical Property:

• PSA: 44.76000
• LogP: 0.99940
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 216

Purity/Quality:

97% ^*data from raw suppliers

Methyl1,4-Benzodioxan-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1COC2=CC=CC=C2O1
• Uses: Methyl 1,4-Benzodioxan-2-carboxylate is an intermediate used to prepare 2,3-dihydrobenzo[b|[1,4|dioxin- and indolealkylamine derivatives as potential antidepressants.

Technology Process of Methyl 2,3-dihydro-1,4-benzodioxine-2-carboxylate

There total 8 articles about Methyl 2,3-dihydro-1,4-benzodioxine-2-carboxylate 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: 97.0%

methanol (67-56-1) + 1,4-benzodioxane-2-carboxylic acid (3663-80-7,34385-93-8,70918-53-5,70918-54-6) → methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate (3663-79-4,650597-66-3)

Guidance literature:

With sulfuric acid; for 1h; Heating;

DOI:10.1021/jm00128a049

Reference yield: 92.0%

Methyl 2,3-dibromopropionate (1729-67-5) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate (3663-79-4,650597-66-3)

Guidance literature:

With potassium carbonate; In acetone; for 18h; Reflux;

DOI:10.1021/acs.orglett.8b01469

Reference yield:

2-cyano-1,4-benzodioxane (1008-92-0) → methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate (3663-79-4,650597-66-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / HOAc, conc. H₂SO₄ / H₂O / 15 h / 110 °C

2: 97 percent / conc. H₂SO₄ / 1 h / Heating

With sulfuric acid; acetic acid; In water;

DOI:10.1021/jm00128a049

upstream raw materials:

methanol

1,4-benzodioxane-2-carboxylic acid

2-cyano-1,4-benzodioxane

benzene-1,2-diol

Downstream raw materials:

(S)-doxazosin

(R)-doxazosin

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

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