3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-7-yl)propanoic acid

Base Information

• Chemical Name: 3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-7-yl)propanoic acid
• CAS No.: 1268335-33-6
• Molecular Formula: C₁₀H₁₁BO₄
• Molecular Weight: 206.006
• Mol file: 1268335-33-6.mol

Synonyms:3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-7-yl)propanoic acid

Chemical Property of 3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-7-yl)propanoic acid

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

3-(1-Hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-7-yl)propanoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-7-yl)propanoic acid

There total 20 articles about 3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-7-yl)propanoic 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: 92.9%

[3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)]propionic acid ethyl ester (1195621-88-5) → 3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-7-yl)propanoic acid (1268335-33-6)

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃;

Reference yield: 46.8%

cycl-isopropylidene malonate (2033-24-1) + 1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-7-carbaldehyde (1195621-75-0) → 3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-7-yl)propanoic acid (1268335-33-6)

Guidance literature:

With formic acid/triethylamine complex 5:2; at 110 ℃; for 15h;

DOI:10.1016/j.tetlet.2011.05.088

Reference yield:

2,6-bis(hydroxymethyl)bromobenzene (59346-22-4) → 3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-7-yl)propanoic acid (1268335-33-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: silica gel; pyridinium chlorochromate / dichloromethane / 20 - 25 °C

2.1: toluene-4-sulfonic acid / toluene / Reflux

2.2: 2 h / Reflux

3.1: sodium tetrahydroborate / methanol / 1 h / 20 - 25 °C

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 7 h / 20 - 25 °C

5.1: n-butyllithium / hexane; tetrahydrofuran / 0.33 h / -78 °C

5.2: -78 - 25 °C

6.1: sodium hydride / tetrahydrofuran; mineral oil / 20 h / 20 - 25 °C

7.1: hydrogen / platinum(IV) oxide trihydrate / methanol / 20 - 25 °C

8.1: sodium hydroxide; water / methanol / 1 h / Reflux

8.2: pH 2 / Acidic conditions

With sodium tetrahydroborate; n-butyllithium; water; hydrogen; silica gel; sodium hydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; sodium hydroxide; platinum(IV) oxide trihydrate; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; mineral oil;

upstream raw materials:

2-bromo-3-(bromomethyl)benzonitrile

cycl-isopropylidene malonate

1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-7-carbaldehyde

2-bromo-3-cyanobenzyl acetate

Downstream raw materials:

N-phenyl-3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]borazole-7-yl)propanamide

3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-methoxylphenyl)propanamide

3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-((tert-butoxycarbonyl)aminomethyl)phenyl)propanamide

7-{2'-[4''-(aminoethyl)phenylcarbamoyl]ethyl}-1,3-dihydro-1-hydroxy-2,1-benzoxaborole

Refernces

• 1、 -. "A NEW TYPE OF ANTITUMOR COMPOUNDS: DERIVATIVES OF 7-PROPANAMIDE SUBSTITUTED BENZOXABOROLE". . . Retrieved 2020/10/09.
• 2、 Zhang, Jiong,Zhang, Jinyi,Hao, Guiyun,Xin, Weixiang,Yang, Fei,Zhu, Mingyan,Zhou, Huchen. "Design, synthesis, and structure-activity relationship of 7-propanamide benzoxaboroles as potent anticancer agents". . p. 6765 - 6784. Retrieved 2019/08/20.