1187190-70-0

Basic information

• Product Name: benzo[c][1,2]oxaborole-1,5(3H)-diol
• Synonyms: benzo[c][1,2]oxaborole-1,5(3H)-diol;1,3-dihydro-1-hydroxy-2,1-benzoxaborol-5-ol;1,3-dihydro-2,1-benzoxaborole-1,5-diol
• CAS NO: 1187190-70-0
• Molecular Formula: C₇H₇BO₃
• Molecular Weight: 149.93968
• Mol File: 1187190-70-0.mol

Chemical Properties

• Boiling Point: 328.6±52.0 °C(Predicted)
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.95±0.20(Predicted)
• CAS DataBase Reference: benzo[c][1,2]oxaborole-1,5(3H)-diol(CAS DataBase Reference)
• NIST Chemistry Reference: benzo[c][1,2]oxaborole-1,5(3H)-diol(1187190-70-0)
• EPA Substance Registry System: benzo[c][1,2]oxaborole-1,5(3H)-diol(1187190-70-0)

Safety Data

• Hazardous Substances Data: 1187190-70-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzo[c][1,2]oxaborole-1,5(3H)-diol is used as a reagent for the synthesis of P4-benzoxaborole-substituted macrocyclic inhibitors of HCV NS3 protease. These inhibitors play a crucial role in the development of antiviral drugs targeting Hepatitis C virus (HCV) by blocking the activity of the NS3 protease enzyme, which is essential for the virus's replication and maturation.

Upstream product

• 99-06-9 3-Carboxyphenol 
• 7781-98-8 ethyl-3-hydroxybenzoate 
• 5419-55-6 Triisopropyl borate 
• 2737-20-4 (2-bromo-5-hydroxybenzene)methanol 
• 688-74-4 boric acid tributyl ester 
• 620-24-6 3-Hydroxybenzyl alcohol 
• 906673-48-1 2-bromo-5-tert-butyldimethylsiloxybenzylalcohol 
• 351418-50-3 2-bromo-5-(tert-butyldimethylsilanyloxy)benzaldehyde 
• 138642-62-3 2-Cyanophenylboronic acid 
• 875816-94-7 1,3-dihydro-5-nitro-1-hydroxy-2,1-benzoxaborole 
• 1084897-39-1 2-bromo-5-benzyloxybenzyl alcohol 

Downstream Products

• 906673-24-3 AN₂₇₂₈ 

Relevant articles and documents

Preparation method of benzoxaborole compound

The invention discloses a preparation method of a benzoxaborole compound. The preparation method comprises the following steps: (1) reacting raw materials containing halogenated hydrocarbon and boric acid ester under an alkaline condition, acidifying and hydrolyzing to obtain an intermediate VI; and (2) reacting a raw material containing the intermediate VI with halogenated cyanophenyl to obtain the benzoxaborole compound. The raw materials are low in price, the preparation cost of the benzoxaborole compound is reduced, the steps of protection and de-protection of organic groups are not needed in the preparation process, the reaction process is simplified, and yield reduction caused by group protection is avoided; and meanwhile, the method is mild in reaction condition, low in equipment requirement and easy for large-scale industrial production.

Preparation method of crisaborole

The invention discloses a preparation method of crisaborole, which comprises the following steps: S1, reacting 2-bromo-5-hydroxybenzaldehyde with a hydroxyl protecting reagent in a solvent in the presence of alkali to obtain a compound I; S2, reducing the compound I in a solvent in the presence of a reducing agent to obtain a compound I I; S3, reacting the compound I with a hydroxyl protection reagent in a solvent in the presence of alkali to obtain a compound IV; S4, reacting the compound IV with boric acid ester in a solvent in the presence of alkali to obtain a compound V; S5, removing a hydroxyl protecting group from the compound V to obtain a compound VI; and S6, reacting the compound IV with p-fluorobenzonitrile to obtain crisaborole. A hydroxyl protecting group which is more beneficial to removal is adopted in the route, synthesis of boric acid ester is facilitated, side reactions are reduced, the yield is obviously increased, and the method is easy to operate, low in cost and beneficial to industrial production.

Method for synthesizing crisaborole intermediate by using microchannel reactor

The invention discloses a method for synthesizing a crisaborole intermediate by using a microchannel reactor. The method comprises the following steps: dissolving an intermediate a in an organic solution b, uniformly mixing to obtain a material 1, and conveying the material 1 to a pre-cooling module in the microchannel reactor through a plunger pump for mixing and pre-cooling. According to the present invention, the crisaborole intermediate is synthesized by using the microchannel reactor, the continuous online mixing, pre-cooling and reaction of the reaction material liquid can be achieved due to the unique microstructure design of the microchannel reactor, and the mixing reaction can be completed in the short time even if the two-phase or the three-phase is not dissolved, compared with the traditional stirring hydrogenation reaction kettle, the mixing efficiency is improved by more than 100 times, the whole reaction time can be shortened from several hours to about 30 seconds, the impurity content of the product can be greatly reduced due to overhigh local concentration in the process, the purity and the yield of the product are improved, and the safety is also greatly improved.

Preparation method of crisaborole

The invention relates to the technical field of crisaborole, in particular to a preparation method of crisaborole. The method comprises the following steps: carrying out nitration reaction on cyanophenylboronic acid and concentrated nitric acid to obtain 2-cyan-4-nitrobenzeneboronic acid; then carrying out reduction reaction to obtain 2-formoxyl-4-nitrobenzeneboronic acid; then carrying out reduction reaction to obtain 2-hydroxymethyl-4-nitrophenylboronic acid; carrying out condensation reaction to obtain 2-hydroxymethyl-5-nitrobenzeneboronicacidhemiester; carrying out reduction reaction and diazotization hydrolysis reaction to obtain 2-hydroxymethyl-5-hydroxy benzeneboronicacidhemiester; and finally, carrying out etherification reaction on the 2-hydroxymethyl-5-hydroxy benzeneboronicacidhemiester and fluorobenzonitrile to obtain the crisaborole. The preparation method of the crisaborole has the advantages that the purity of the prepared crisaborole is good, and the yield is high.

Preparation method of Crisaborole intermediate

The invention discloses a preparation method of a Crisaborole intermediate. The Crisaborole intermediate has a structure shown as the formula VI. The preparation method comprises the following steps:performing a contact reaction on a compound shown as the formula I and benzyl halide, so as to form a compound shown as the formula II; performing a contact reaction on the compound shown as the formula II and alkali metal borohydride, so as to obtain a compound shown as the formula III; performing a contact reaction on the compound shown as the formula III and a compound a, or performing a contact reaction on the compound shown as the formula III and dihydropyran, so as to obtain a compound shown as the formula IV, wherein the compound a is trimethylchlorosilane, tert-butyldimethylsilyl chloride and chloromethyl methyl ether; performing a contact reaction on the compound shown as the formula IV and an isopropylmagnesium chloride solution; adding an obtained solution into a compound b, performing a contact reaction on the mixture and fourth organic solvent mixed liquor and adding hydrochloric acid into the mixture for contact reaction, so as to obtain a compound shown as the formula V,wherein the compound b is 2-alkoxy-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane, triisopropyl borate or trimethyl borate; performing a hydrogenation reaction on the compound shown as the formula V toobtain a compound shown as the formula VI.

Preparation method of boracic micromolecule

The invention discloses a preparation method of a boracic micromolecule 5-(4-cyanophenoxyl)-1,3-dihydro-1-hydroxy-2,1-benzodioxole. The preparation method includes the steps of (1) subjecting 2-bromine-5-hydroxybenzaldehyde to reduction reaction in solvent with the presence of reducing agents to obtain 2-bromine-5-hydroxybenzyl alcohol; (2) subjecting 2-bromine-5-hydroxybenzyl alcohol and a hydroxyl protection reagent to reaction in solvent with the presence of alkali; (3) subjecting the previous reactant to borate reaction in solvent under an alkaline condition; (4) removing hydroxyl protecting groups from the previous reactant to obtain a benzo[c][1,2]heterocyclopentadiene-1,5(3H)-glycol body; (5) subjecting the previous reactant to reaction in solvent under an alkaline condition to obtain a target object. The preparation method has the advantages of low cost of technological raw materials, easiness in obtaining of the technological raw materials, remarkably improved reaction yield,simplicity in operation, low cost and applicability to industrial production.

Preparation method for creboro intermediate

The invention discloses a preparation method for a creboro intermediate. The preparation method for the creboro intermediate comprises the following steps that 1, 2-bromo-5-hydroxybenzaldehyde reactswith benzyl chloride or benzyl bromide in an organic solvent (i) under the existence of alkali to obtain a compound shown in a formula II; 2, the compound shown in the formula II reacts with triethylorthoformate or trimethyl orthoformate or glycol in an organic solvent (ii) under the effect of an acid catalyst to obtain a compound shown in a formula III; 3, 2-methoxyl-4, 4, 5, 5-tetramethyl-1, 3,2-boron dioxane or 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-boron dioxane or trimethyl borate or triisopropyl borate reacts with a standby solution in an organic solvent (iii) under the condition thatthe reaction temperature is 10-30 DEG C, after the reaction is completed, hydrochloric acid is added for regulating the pH value to be not larger than 3, and after a quenching reaction is performed, acompound shown in a formula IV is obtained through the reaction under the temperature of 20-100 DEG C.

Benzoxaborolane compounds and preparation method thereof

The invention relates to benzoxaborolane compounds and pharmaceutically acceptable salts or solvates thereof. The structure of the compounds is shown in the description, wherein B is boron; X is selected from oxygen, sulfur, nitrogen and hydrogen; R1 is s

BORON-CONTAINING SMALL MOLECULES

Compounds, pharmaceutical formulations, and methods of treating anti-inflammatory conditions and/or helminth-associated diseases are disclosed.

Synthesis and biological evaluations of P4-benzoxaborole-substituted macrocyclic inhibitors of HCV NS3 protease

We disclose here a series of P4-benzoxaborole-substituted macrocyclic HCV protease inhibitors. These inhibitors are potent against HCV NS3 protease, their anti-HCV replicon potencies are largely impacted by substitutions on benzoxaborole ring system and P2 groups. P2 2-thiazole-isoquinoline provides best replicon potency. The in vitro SAR studies and in vivo PK evaluations of selected compounds are described herein.