1072960-66-7|4-Formylphenylboronic acid MIDA ester| Ambeed

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Quality Control of [ 1072960-66-7 ] Purity: 95% SDS Specification

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Product Details of [ 1072960-66-7 ]

CAS No. :	1072960-66-7
Formula :	C₁₂H₁₂BNO₅
M.W :	261.04
SMILES Code :	CN12CC([O-][B+3]1([C-]1=CC=C(C=C1)C=O)[O-]C(C2)=O)=O
MDL No. :	MFCD11215233
InChI Key :	ATAFRFKGTAHILE-UHFFFAOYSA-N
Pubchem ID :	71310647

Safety of [ 1072960-66-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 1072960-66-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1072960-66-7 ]

[ 1072960-66-7 ] Synthesis Path-Downstream 1~31

1
[ 1072960-66-7 ]
(3R)-3-propionyl-4-benzyloxazolidin-2-one [ No CAS ]
(C₆H₅CH₂C₃H₃O₂NCOCHCH₃CHOHC₆H₄)BN(CH₃)(CH₂CO₂)2 [ No CAS ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14084 - 14085.

2
[ 110-91-8 ]
[ 1072960-66-7 ]
[ 1072960-75-8 ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14084 - 14085.

3
[ 16940-66-2 ]
[ 1072960-66-7 ]
[ 1072960-82-7 ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14084 - 14085.

4
[ 75-47-8 ]
[ 1072960-66-7 ]
[ 1072960-73-6 ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14084 - 14085.

5
[ 867-13-0 ]
[ 1072960-66-7 ]
[ 1072960-72-5 ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14084 - 14085.
[2]Journal of the American Chemical Society,2008,vol. 130,p. 14084 - 14085.

6
[ 1072960-82-7 ]
[ 1072960-66-7 ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14084 - 14085.
[2]Journal of the American Chemical Society,2008,vol. 130,p. 14084 - 14085.

7
[ 1072960-66-7 ]
C₁₃H₁₃BINO₄ [ No CAS ]
C₁₃H₁₃BINO₄ [ No CAS ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14084 - 14085.

8
[ 1072960-66-7 ]
[ 1072960-82-7 ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14084 - 14085.

9
[ 1072960-66-7 ]
(3R)-3-propionyl-4-benzyloxazolidin-2-one [ No CAS ]
C₂₅H₂₇BN₂O₈ [ No CAS ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14084 - 14085.

10
[ 4408-64-4 ]
[ 87199-17-5 ]
[ 1072960-66-7 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 80℃;Molecular sieve; Inert atmosphere;	0.4 mmol of 4-formylphenylboronic acid, 0.5 mmol of N-methyliminodiacetic acid, 4Å molecular sieve (40 mg)After dissolving in N, N-dimethylformamide,Under an argon atmosphereStir at 130 C.The amount of 4-formyl phenyl bromic acid consumed was checked to complete the reaction, and the mixture was cooled to 80 C to produce a compound represented by formula (32).
	In N,N-dimethyl-formamide; at 130℃;Molecular sieve; Inert atmosphere;	Formyl phenylboronic acid (0.5 mmol), N-methyliminodiacetic acid (1.5 mmol) and 4A molycularis (200 mg) were dissolved in 4 mL of N, N-dimethylformamide (DMF).The reaction mixture was stirred in an argon atmosphereThe reaction mixture was heated to 130 C and stirred.Respectively. After completion of the reaction, the reaction mixture was cooled to room temperature.[0228](I). Without filtration or separation, (a) into the cooled mixtureA mixture of 1,2-phenylenediamine (1, 0.55 mmol; 1.1 eq) and a catalytic amount of KI (0.1 mmol, 0.2 eq)And the inner wall was washed with 1 mL of DMFAnd the mixture was stirred in an atmosphere exposed to air at 80 C.When the mixture prepared in (A) was exhausted, the reaction was terminated and the reaction mixture was cooled to room temperature and the solvent was distilled off under reduced pressure. The mixtureAnd purified by solid column chromatography to prepare a benzimidazole derivative substituted with a boronic acid.

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14084 - 14085.
[2]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.
[3]Patent: KR2015/140978,2015,A .Location in patent: Paragraph 0214.
[4]Patent: KR101653532,2016,B1 .Location in patent: Paragraph 0226-0028.

11
[ 1072960-66-7 ]
(2S,3R,4S,5R)-4-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-5-(hydroxymethyl)-2-neopentylpyrrolidine-3-carbonitrile [ No CAS ]
(2S,3R,4S,5R)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-2-(2,2-dimethyl-propyl)-5-hydroxymethyl-1-[4-(6-methyl-4,8-dioxo-[1,3,6,2]dioxazaborocan-2-yl)-benzyl]-pyrrolidine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃;	In a 25 mL round-bottomed flask, 4-Formyl Phenyl MIDA Boronic ester (44.9 mg, 172 μmol, Eq: 1.5), chiral(2S,3R,4S,5R)-4-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-5-(hydroxymethyl)-2-neopentylpyrrolidine-3-carbonitrile (52 mg, 115 μmol, Eq: 1.00), acetic acid (100 μL) and sodium triacetoxyborohydride (36.5 mg, 172 μmol, Eq: 1.5) were combined with DCE (5 ml) to give a light yellow solution. Reaction stirred 4 h at rt. Not complete, added more 4-Formyl Phenyl MIDA Boronic ester (60 mg, 230 μmol, 230 eq), triacetoxyborohydride (48.7 mg, 230 μmol, 2 eq) and acetic acid (1 mL) allowed to stir overnight. The reaction was diluted with ethyl acetate and 0.1N NaOH, organic separated and washed with water (3*). Organic layer was concentrated under reduced pressure and purified with column chromatography (8 g Analogix column, 0-100% Ethyl acetate/heptane) to afford chiral(2S,3R,4S,5R)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-2-(2,2-dimethyl-propyl)-5-hydroxymethyl-1-[4-(6-methyl-4,8-dioxo-[1,3,6,2]dioxazaborocan-2-yl)-benzyl]-pyrrolidine-3-carbonitrile (12 mg, 15%) as an off-white solid. HRMS (ES+) m/z Calcd for C35H36BCl2F2N3O5[(M+)1+]: LCMS (7 min-C18-PosNeg50-100-Grad-LC RT=4.61, [(M+)1+]: 698.1

References: [1]Patent: US2012/149660,2012,A1 .Location in patent: Page/Page column 16.

12
[ 1072960-66-7 ]
tert-butyl 3-amino-4-((tributylstannyl)methoxy)pyrrolidine-1-carboxylate [ No CAS ]
C₃₄H₅₆BN₃O₇Sn [ No CAS ]

References: [1]Organic Letters,2015,vol. 17,p. 1934 - 1937.

13
[ 1072960-66-7 ]
tert-butyl 4-amino-4-(((tributylstannyl)methoxy)methyl)piperidine-1-carboxylate [ No CAS ]
C₃₆H₆₀BN₃O₇Sn [ No CAS ]

References: [1]Organic Letters,2015,vol. 17,p. 1934 - 1937.

14
[ 1072960-66-7 ]
[ 3171-45-7 ]
(4-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid MIDA ester [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.

15
[ 1072960-66-7 ]
[ 95-83-0 ]
(4-(6-chloro-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid MIDA ester [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.

16
[ 5348-42-5 ]
[ 1072960-66-7 ]
(4-(5,6-dichloro-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid MIDA ester [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.

17
[ 1072960-66-7 ]
[ 534-85-0 ]
(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid MIDA ester [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.

18
[ 1072960-66-7 ]
[ 95-54-5 ]
(4-(1H-benzo[d]imidazol-2-yl)phenyl)boronic acid [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.

19
[ 1072960-66-7 ]
[ 95-54-5 ]
C₁₃H₁₁BN₂O [ No CAS ]
(4-(1H-benzo[d]imidazol-2-yl)phenyl)boronic acid MIDA ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%; 60%	With water; potassium iodide; In N,N-dimethyl-formamide; at 80℃; for 24h;Molecular sieve;	In the case where water is contained in the reaction, as shown in the following reaction formula, it is confirmed that benzimidazole having a functional group of boronic acid protected by a protecting group is produced in less than 70% and side reaction is proceeded by 30% or more, This is because in the presence of water, the protective group-protected moiety is hydrolyzed to boronic acid, so that the boronic acid reacts directly with the amine.

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.
[2]Patent: KR101653532,2016,B1 .Location in patent: Paragraph 0391-0394.

20
[ 1072960-66-7 ]
[ 95-54-5 ]
(4-(1H-benzo[d]imidazol-2-yl)phenyl)boronic acid MIDA ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium iodide; In N,N-dimethyl-formamide; at 100℃; for 24h;Molecular sieve;	Test Example 2. Effect according to reaction temperatureIn order to confirm the effect on the reaction temperature, the reaction was carried out under DMF solvent, KI catalyst and anhydrous condition,The results are shown in Table 2 belowThe results are shown in Table 2 belowAs shown in Table 2, it was confirmed that the reaction proceeded by 97% or more within 2 hours even at a low reaction temperature of 60 C, And when the reaction temperature was set to 80 C or higher, the reaction was completed within 30 minutes
	With potassium iodide; In N,N-dimethyl-formamide; at 80℃;Molecular sieve; Inert atmosphere;	0.4 mmol of 2-phenylenediamine and 0.4 mmol of KI were added to the reaction mixture, and the inlet of the reaction vessel was opened to prepare an atmosphere for exposure to air, followed by stirring at 80 C. The resulting compound represented by the formula (32) The reaction was terminated, and after cooling to room temperature, the solvent was removed under reduced pressure.

References: [1]Patent: KR101653532,2016,B1 .Location in patent: Paragraph 0381-0385.
[2]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.
[3]Patent: KR2015/140978,2015,A .Location in patent: Paragraph 0213; 0215.

21
[ 1072960-66-7 ]
(4-(1H-benzo[d]imidazol-2-yl)phenyl)boronic acid [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.
[2]Patent: KR101653532,2016,B1 .

22
[ 1072960-66-7 ]
(4-(6-methyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.

23
[ 1072960-66-7 ]
(4-(6-chloro-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.

24
[ 1072960-66-7 ]
(4-(5,6-dichloro-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.

25
[ 1072960-66-7 ]
[ 952514-79-3 ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.

26
[ 1072960-66-7 ]
[ 1259883-01-6 ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.

27
[ 1072960-66-7 ]
[ 496-72-0 ]
(4-(6-methyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid MIDA ester [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2951 - 2956.

28
[ 1072960-66-7 ]
2,3,6,7-tetrakis(4-bromophenyl)-4,8-didecylbenzo[1,2-b:4,5-b']difuran [ No CAS ]
4',4‴,4‴",4‴⁗-(4,8-didecylbenzo[1,2-b:4,5-b']difuran-2,3,6,7-tetrayl)tetrakis([1,1'-biphenyl]-4-carbaldehyde) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%		General procedure: To a stirred solution of 2,3,6,7-tetrakis(4-bromophenyl)-4,8-didecylbenzo[1,2-b:4,5-b′]difuran (7) (0.318g, 0.3mmol), an appropriate boronic acid MIDA ester (1.8mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.066g, 0.09mmol), an argon degassed 1,4-dioxane (6mL) was added. The resulting mixture was stirred at room temperature for 5min under argon atmosphere. Tripotassium phosphate (3M aqueous solution, 1.2mL) was added and the mixture was stirred at 80C for 22h. Reaction mixture was cooled to rt and transferred into a separatory funnel. Chloroform (50mL) and 10% sodium hydroxide (10mL) were added and the layers were separated. Aqueous layer was extracted with chloroform (3×50mL). Combined organic layers were dried over anhydrous magnesium sulfate and concentrated. The crude product was crystallized from chloroform/methanol or p-xylene.

References: [1]Dyes and Pigments,2016,vol. 129,p. 199 - 208.

29
[ 1072960-66-7 ]
3-bromo-5-(1-methyl-1H-pyrazol-4-yl)furo[3,2-b]pyridine [ No CAS ]
4-(5-(1-methyl-1H-pyrazol-4-yl)furo[3,2-b]pyridin-3-yl)benzaldehyde [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 1062 - 1066.
Angew. Chem.,2019,vol. 131,p. 1074 - 1078,5.

30
[ 87199-17-5 ]
[ 13480-36-9 ]
[ 1072960-66-7 ]

References: [1]Organic Letters,2020,vol. 22,p. 9408 - 9414.

31
[ 4408-64-4 ]
[ 1072960-66-7 ]

References: [1]Organic Letters,2020,vol. 22,p. 9408 - 9414.

Historical Records

Technical Information

• Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Friedel-Crafts Reaction • Hydrogenolysis of Benzyl Ether • Preparation of Alkylbenzene • Reactions of Benzene and Substituted Benzenes • Vilsmeier-Haack Reaction

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H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 1072960-66-7

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CAS No.: 1072960-66-7

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[ 1072960-66-7 ] Synthesis Path-Downstream 1~31

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