3,4-Methylenedioxyphenylboronic acid

Base Information

• Chemical Name: 3,4-Methylenedioxyphenylboronic acid
• CAS No.: 94839-07-3
• Molecular Formula: C7H7BO4
• Molecular Weight: 165.941
• Hs Code.: 29163990
• European Community (EC) Number: 672-307-3
• DSSTox Substance ID: DTXSID10370261
• Nikkaji Number: J1.478.154D
• Wikidata: Q72490465
• ChEMBL ID: CHEMBL141313
• Mol file: 94839-07-3.mol

Synonyms:94839-07-3;3,4-METHYLENEDIOXYPHENYLBORONIC ACID;Benzo[d][1,3]dioxol-5-ylboronic acid;3,4-(Methylenedioxy)phenylboronic acid;1,3-benzodioxol-5-ylboronic acid;3,4-(Methylenedioxy)benzeneboronic acid;3,4-Methylenedioxyphenyl boronic acid;1,3-Benzodioxole-5-boronic acid;3,4-Methylenedioxybenzeneboronic acid;MFCD01009695;Boronic acid, 1,3-benzodioxol-5-yl-;CHEMBL141313;(2H-1,3-BENZODIOXOL-5-YL)BORONIC ACID;5-benzo[d][1,3]dioxole boronic acid;3,4-METHYLENEDIOXYPHENYLBORONICACID;SCHEMBL30231;4-methylenedioxyphenylboronic acid;DTXSID10370261;CMHPUBKZZPSUIQ-UHFFFAOYSA-N;5-benzo[1,3]dioxolylboronic acid;1,3-benzodioxol-5-yl boronic acid;1,3-Benzodioxole-5-ylboranic acid;(1,3-dioxaindan-5-yl)boronic acid;BDBM50067897;(1,3-benzodioxol-5-yl)boronic acid;3,4-methylene dioxyphenylboronic acid;3,4-methylenedioxyphenyl-boronic acid;benzo[1,3]dioxol-5-yl-boronic acid;3,4-methylenedioxybenzene boronic acid;AKOS009159266;Benzo[d][1,3]dioxol-5-ylboronicacid;(3,4-methylenedioxyphenyl)boronic acid;3,4-methylenedioxy-phenyl boronic acid;AB07960;CS-W003981;GS-6344;(3,4-methylenedioxy)benzeneboronic acid;(3,4-methylenedioxyphenyl)-boronic acid;3,4-(methylenedioxy) phenylboronic acid;AM808125;Boronic acid, B-1,3-benzodioxol-5-yl-;BP-11813;SY014778;BENZO[1,3]DIOXOLE-5-BORONIC ACID;FT-0614106;M2035;A22896;EN300-212504;Q-102220;Z381540928

Chemical Property of 3,4-Methylenedioxyphenylboronic acid

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: 224-229 °C(lit.)
• Boiling Point: 347.342 °C at 760 mmHg
• PKA: 8.48±0.20(Predicted)
• Flash Point: 163.867 °C
• PSA: 58.92000
• Density: 1.423 g/cm³
• LogP: -0.90490
• Storage Temp.: 0-6°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 166.0437389
• Heavy Atom Count: 12
• Complexity: 164

Purity/Quality:

99% ^*data from raw suppliers

3,4-(Methylenedioxy)phenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=C(C=C1)OCO2)(O)O
• Uses: Reactant involved in:? ;Petasis reaction between glyoxylic acid, α-amino phosphonates, and organylboronic acids1? ;Mannich-type multicomponent assembly and 1,3-dipolar cycloaddition for synthesis of tetrahydroisoquinoline fused isoxazolidine scafford2? ;Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides3,4? ;Oxidative Heck reaction for synthesis of functionalized cinnamaldehyde derivatives5? ;Intramolecular Alder-ene and Pictet-Spengler reactions for synthesis of crinine6 suzuki reaction Reactant involved in:Petasis reaction between glyoxylic acid, α-amino phosphonates, and organylboronic acidsMannich-type multicomponent assembly and 1,3-dipolar cycloaddition for synthesis of tetrahydroisoquinoline fused isoxazolidine scaffordSuzuki-Miyaura cross-coupling of aryl and heteroaryl halidesOxidative Heck reaction for synthesis of functionalized cinnamaldehyde derivativesIntramolecular Alder-ene and Pictet-Spengler reactions for synthesis of crinine

Technology Process of 3,4-Methylenedioxyphenylboronic acid

There total 10 articles about 3,4-Methylenedioxyphenylboronic 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%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + boric acid tributyl ester (688-74-4) → 3,4-(methylenedioxy)-benzeneboronic acid (94839-07-3)

Guidance literature:

With hydrogenchloride; magnesium; In tetrahydrofuran; treatment of Grignard reagent (prepd. from bromoderivative) with B(OBu)3 (-78°C), hydrolysis of ester with aq. HCl;

DOI:10.1039/c39940000061

Reference yield: 79.0%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + tetrahydroxydiboron (13675-18-8) → 3,4-(methylenedioxy)-benzeneboronic acid (94839-07-3)

Guidance literature:

In methanol; at 15 ℃; for 3h; Microwave irradiation;

DOI:10.1021/jacs.6b01376

Reference yield: 73.0%

tetrahydroxydiboron (13675-18-8) + benzo[1,3]dioxolo-5-ylamine (14268-66-7) → 3,4-(methylenedioxy)-benzeneboronic acid (94839-07-3)

Guidance literature:

benzo[1,3]dioxolo-5-ylamine; With hydrogenchloride; sodium nitrite; In water; at 0 ℃; for 0.25h;

tetrahydroxydiboron; With sodium acetate; In water; at 20 ℃; for 0.333333h;

DOI:10.1002/chem.201402487

upstream raw materials:

1,2-(methylenedioxy)-4-bromobenzene

Trimethyl borate

boric acid tributyl ester

Methylenedioxybenzene

Downstream raw materials:

Dubamine

methyl 2-(3',4'-methylenedioxyphenyl)cyclohex-2-enylcarbamate

(1R,1'S,2S,5R)-5-methyl-2-methylethylcyclohexyl 2'-(3'',4''-methylenedioxyphenyl)cyclohex-2'-enylcarbamate

(1R,1'R,2S,5R)-5-methyl-2-methylethylcyclohexyl 2'-(3'',4''-methylenedioxyphenyl)cyclohex-2'-enylcarbamate

Refernces

• 1、 Fan, Chenrui,Wu, Qixu,Zhu, Chengfeng,Wu, Xiang,Li, Yougui,Luo, Yunfei,He, Jian-Bo. "Enantioselective Conjugate Addition of Aryl Halides and Triflates to Electron-Deficient Olefins via Nickel- And Rhodium-Catalyzed Sequential Relay Reactions". supporting information. p. 8888 - 8892. Retrieved 2019/10/14.
• 2、 Mfuh, Adelphe M.,Doyle, John D.,Chhetri, Bhuwan,Arman, Hadi D.,Larionov, Oleg V.. "Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts". supporting information. p. 2985 - 2988. Retrieved 2016/03/19.