3-Methoxycarbonyl-5-nitrophenylboronic acid

Base Information

• Chemical Name: 3-Methoxycarbonyl-5-nitrophenylboronic acid
• CAS No.: 117342-20-8
• Molecular Formula: C8H8BNO6
• Molecular Weight: 224.966
• Hs Code.: 29319090
• European Community (EC) Number: 833-747-3
• DSSTox Substance ID: DTXSID00378493
• Nikkaji Number: J2.040.763H
• Wikidata: Q72489494
• ChEMBL ID: CHEMBL88902
• Mol file: 117342-20-8.mol

Synonyms:3-Methoxycarbonyl-5-nitrophenylboronic acid;117342-20-8;(3-(Methoxycarbonyl)-5-nitrophenyl)boronic acid;3-(methoxycarbonyl)-5-nitrophenylboronic acid;(3-methoxycarbonyl-5-nitrophenyl)boronic acid;METHYL 3-BORONO-5-NITROBENZOATE;[3-(methoxycarbonyl)-5-nitrophenyl]boronic acid;MFCD02179469;methyl 3-(dihydroxyboranyl)-5-nitrobenzoate;3-(Methoxycarbonyl)-5-nitrobenzeneboronic acid;Benzoic acid, 3-borono-5-nitro-, 1-methyl ester;CHEMBL88902;SCHEMBL1462874;BDBM92723;DTXSID00378493;CDGIRLKQNJXHBJ-UHFFFAOYSA-N;AMY29200;ETHYL2-AZEPAN-2-YLIDENACETATE;AKOS015852173;AB11194;CS-W014221;3-carbomethoxy-5-nitrophenylboronic acid;AS-14925;3-Nitro-5-methoxycarbonylphenylboronic acid;FT-0642871;M2808;3-methoxy-carbonyl-5-nitro-phenylboronic acid;(3-(Methoxycarbonyl)-5-nitrophenyl)boronicacid;EN300-106812;F11297;A803755;3-(Dihydroxyboryl)-5-nitrobenzoic acid methyl ester;J-522099;3-Methoxycarbonyl-5-nitrophenylboronic acid, AldrichCPR;Z1407840915;(3-methoxycarbonyl-5-nitro-phenyl)boronic acid;3-(Methoxycarbonyl)-5-nitrophenylboronic Acid (contains varying amounts of Anhydride)

Chemical Property of 3-Methoxycarbonyl-5-nitrophenylboronic acid

Chemical Property:

• Vapor Pressure: 9.85E-09mmHg at 25°C
• Melting Point: 250-255 °C
• Refractive Index: 1.564
• Boiling Point: 445.879 °C at 760 mmHg
• PKA: 6.13±0.10(Predicted)
• Flash Point: 223.46 °C
• PSA: 112.58000
• Density: 1.452 g/cm³
• LogP: -0.41560
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 225.0444671
• Heavy Atom Count: 16
• Complexity: 278

Purity/Quality:

99% ^*data from raw suppliers

3-Methoxycarbonyl-5-nitrophenylboronic acid 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39-36-60-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC(=C1)[N+](=O)[O-])C(=O)OC)(O)O
• Uses: suzuki reaction

Technology Process of 3-Methoxycarbonyl-5-nitrophenylboronic acid

There total 2 articles about 3-Methoxycarbonyl-5-nitrophenylboronic 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: 92.0%

3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (377780-80-8) + methylamine (74-89-5) → (3-(methoxycarbonyl)-5-nitrophenyl)boronic acid (117342-20-8)

Guidance literature:

3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid; methylamine; With propane-1,3-diyl dinitrite; In tetrahydrofuran; at 90 ℃; for 0.333333h; under 12929 Torr; Flow reactor;

With sodium periodate; ammonium acetate; In water; acetone; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b02231

Reference yield:

methanol (67-56-1) + (3-carboxy-5-nitrophenyl)boronic acid (101084-81-5) → (3-(methoxycarbonyl)-5-nitrophenyl)boronic acid (117342-20-8)

Guidance literature:

With thionyl chloride; at 20 ℃; Cooling with ice;

DOI:10.1021/acschemneuro.0c00003

Reference yield: 100.0%

(3-(methoxycarbonyl)-5-nitrophenyl)boronic acid (117342-20-8) → methyl 3-hydroxy-5-nitrobenzoate (55076-32-9)

Guidance literature:

With Oxone; sodium hydrogencarbonate; sodium hydroxide; In water; acetone; at 8 ℃; for 0.0833333h;

upstream raw materials:

3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

methylamine

methanol

(3-carboxy-5-nitrophenyl)boronic acid

Downstream raw materials:

3-methoxycarbonyl-5-nitro-phenylmercury ⁽¹⁺⁾; chloride

(3-amino-5-(methoxycarbonyl)phenyl)boronic acid

methyl 3-[((7S)-7-{(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}-5,6,7,8-tetrahydro-2-naphthalenyl)oxy]-5-nitrobenzoate

methyl 3-methyl-5-nitrobenzoate

Refernces

• 1、 Audubert, Clément,Lebel, Hélène. "Mild Esterification of Carboxylic Acids via Continuous Flow Diazotization of Amines". supporting information. p. 4407 - 4410. Retrieved 2017/08/23.