40138-16-7|(2-Formylphenyl)boronic acid| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 40138-16-7 ] Purity: 98% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Citations

STUDIES IN THREE-COMPONENT MODIFICATION OF LYSINE, INVESTIGATING REVERSIBLE POTENTIAL OF AN INTRICATE BICYCLO [3.3.1] NONANE SCAFFOLD

Bartlett, Ryan ;

Abstract: Synthesis of small-molecule conjugates capable of selective attachment to a peptide/protein backbone paves way for new therapeutic applications of protein modification. Sufficient inhibition or installation of function requires extensive design so the compound may identify and attach to the intended site. The utility of such an approach has prompted a number of applicable strategies and has rendered the development of new modification scaffolds less necessary. On the other hand, covalent modification to the biologics with ability to remove the conjugate via stimulus is underdeveloped, amplifying a current need to investigate the reversible potential for conjugation and deconjugation techniques in regard to molecular scaffolds. The investigation reported therein involves a small molecule design capable of conjugation and facile deconjugation from peptide/protein structure. Taking advantage of special reactivity between aldehyde and thiol, we utilize a number of readily available mercapto-benzaldehyde derivatives that have been synthesized by simple procedure and characterized by NMR. These compounds chemoselectively bind to backbone amino by institution of distinctive [3.3.1] and [2.2.1] bicyclic scaffolds. This protocol enables amino modification in a multi-component fashion in aqueous buffer and mild conditions, characterized by combination of HPLC and LC-MS methods. The various bicyclic modification derivatives were investigated for progression of the reversed reaction under mild condition, utilizing a commercially available amine reagent. In restoring the original protein motif, a full investigation of a heterocyclic derivative for reversible attachment to several linear peptides was subsequently performed. Upon completion, the effectiveness of this approach was demonstrated in the modification and quantifiable regeneration of insulin protein.

Purchased from AmBeed: 40138-16-7 ; 115290-70-5

Product Details of [ 40138-16-7 ]

CAS No. :	40138-16-7
Formula :	C₇H₇BO₃
M.W :	149.94
SMILES Code :	O=CC1=CC=CC=C1B(O)O
MDL No. :	MFCD00151822
InChI Key :	DGUWACLYDSWXRZ-UHFFFAOYSA-N
Pubchem ID :	292189

Safety of [ 40138-16-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 40138-16-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	41.66
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	57.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.29
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.82
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.36
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.6
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.3

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.22
Solubility	8.95 mg/ml ; 0.0597 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.06
Solubility	13.1 mg/ml ; 0.087 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.22
Solubility	9.08 mg/ml ; 0.0605 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.01 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.23

Application In Synthesis of [ 40138-16-7 ]

* 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.

Upstream synthesis route of [ 40138-16-7 ]
Downstream synthetic route of [ 40138-16-7 ]

[ 40138-16-7 ] Synthesis Path-Upstream 1~1

1
[ 40138-16-7 ]
[ 124-40-3 ]
[ 85107-53-5 ]

References: [1] Journal of the American Chemical Society, 2015, vol. 137, # 20, p. 6492 - 6495.

[ 40138-16-7 ] Synthesis Path-Downstream 1~35

1
[ 40138-16-7 ]
[ 131818-17-2 ]
[ 870703-82-5 ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 5563 - 5566.

2
[ 3032-81-3 ]
[ 40138-16-7 ]
[ 656305-96-3 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 355 - 374.

3
[ 21906-31-0 ]
[ 40138-16-7 ]
[ 2039-77-2 ]

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 495 - 501.
[2]Advanced Synthesis and Catalysis,2018,vol. 360,p. 1711 - 1718.

4
[ 40138-16-7 ]
[ 18531-99-2 ]
[ 180683-64-1 ]
tert-butyl (E,1S,2S)-2-((2-((Sa)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaborepin-4-yl)phenyl)methylideneamino)cyclohexylcarbamate [ No CAS ]

References: [1]Tetrahedron Asymmetry,2008,vol. 19,p. 489 - 494.

5
[ 3034-53-5 ]
[ 40138-16-7 ]
[ 223575-69-7 ]

Yield	Reaction Conditions	Operation in experiment
38%	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile; at 160℃; for 0.0833333h;Microwave irradiation;	6.21. Synthesis of (S)-2-Amino-3-(4-{2-amino-6-[2,2,2-trifluoro-1-(2-thiazol-2-yl-phenyl)-ethoxy]-pyrimidin-4-yl}-phenyl)-propionic acid To a 40 ml microwave reactor, was added 1.04 g of 2-formyl phenylboronic acid (6.9 mmoles), 1.14 g of 2-bromo thiazole (6.9 mmoles), 240 mg of palladium bistriphenyl-phosphine dichloride (Pd(PPh3)2Cl2, 0.34 mmoles). Then, 13.8 ml of 1M Na2CO3 (13.8 mmoles) and 10 ml of CH3CN were added to the mixture. The reactor was sealed, and the reaction was run under microwave at 160 C. for 5 minutes. LCMS shows completion of the reaction with desired product. The reaction mixture was then poured into a separation funnel. Then 200 ml of methylene chloride and 100 ml of water were added for extraction. The methylene chloride layer was dried over MgSO4. Removal of solvent gave a crude product, which was purified by silica gel column chromatography eluding with hexanes/ethyl acetate mixture (5/1 to 2/1) to give pure 2-thiazol-2-yl-benzaldehyde (0.5 g, yield: 38%).
38%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In acetonitrile; at 160℃; for 0.0833333h;Sealed tube; Microwave irradiation;	To a 40 ml microwave reactor was added 1.04 g of 2-formylphenylboronic acid (6.9 mmol) of 1.14 g of 2-bromothiazole(6.9 mmol), 240 mg of bistriphenyl-phosphine palladium dichloride (Pd (PPh3) 2Cl2, 0.34 mmol). then,To the mixture was added 13.8 ml of 1 M Na2CO3 (13.8 mmol) and 10 ml of CH3CN. Sealed reactor,The reaction was run under microwave at 160 C for 5 minutes.LCMS shows the desired reaction of the desired product. The reaction mixture was then poured into a separation funnel. Add 200 ml of dichloromethaneAlkane and 100 ml of water for extraction. The dichloromethane layer was dried over MgSO4. The solvent was removed to give the crude product, which was passed through siliconThe column chromatography was eluted with a hexane / ethyl acetate mixture (5/1 to 2/1)To give pure 2-thiazol-2-yl-benzaldehyde (0.5 g, yield: 38%).
	With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; for 6h;Reflux;	Example 4 1-phenyl-8-[[2-(2-thiazolyl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one (Compound 24) Step A: To a mixture of 2-bromothiazole (826 mg, 4.99 mmol) and tetrakis(triphenylphosphine) palladium (0) (175 mg, 0.151 mmol) in 1,2-dimethoxyethane (20 mL) was added 2-formylbenzeneboronic acid (0.9017 g, 6.01 mmol) and 1 N aqueous NaHCO3 (8 mL). The resultant mixture was heated at reflux for 6 hrs. The reaction mixture was diluted with water and extracted with EtOAc (2 X 50 mL). The organic solution was dried over Na2SO4, filtered and concentrated. The crude product was purified by gradient flash chromatography (10% to 25% EtOAc in hexane) to yield 2-(2-thiazolyl)benzaldehyde as a white solid. MS (loop pos) MH+ = 190.1 1 H NMR (300 MHz, CDCl3) 7.50 (m, 1 H), 7.55-7.60 (m, 1 H), 7.65-7.70 (m, 1 H), 7.75-7.80 (m, 1 H), 7.95-7.97 (m, 1 H), 8.00-8.05 (m, 1 H), 10.5 (s, 1 H)

References: [1]Patent: US2008/153852,2008,A1 .Location in patent: Page/Page column 20.
[2]Patent: CN104045626,2017,B .Location in patent: Paragraph 0240.
[3]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 8607 - 8618.
[4]Patent: EP1392687,2017,B1 .Location in patent: Paragraph 0133-0136.

6
[ 3034-53-5 ]
palladium bistriphenyl-phosphine dichloride [ No CAS ]
[ 40138-16-7 ]
[ 223575-69-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In dichloromethane; water; acetonitrile;	6.54. Synthesis of (S)-2-Amino-3-(4-{2-amino-6-[2,2,2-trifluoro-1-(2-thiazol-2-yl-phenyl)-ethoxyl-pyrimidin-4-yl}-phenyl)-propionic acid To a 40 ml microwave reactor, was added 1.04 g of 2-formyl phenylboronic acid (6.9 mmoles), 1.14 g of 2-bromo thiazole (6.9 mmoles), 240 mg of palladium bistriphenyl-phosphine dichloride (Pd(PPh3)2Cl2, 0.34 mmoles). Then, 13.8 ml of 1M Na2CO3 (13.8 mmoles) and 10 ml of CH3CN were added to the mixture. The reactor was sealed, and the reaction was run under microwave at 160 C. for 5 minutes. LCMS shows completion of the reaction with desired product. The reaction mixture was then poured into a separation funnel. Then 200 ml of methylene chloride and 100 ml of water were added for extraction. The methylene chloride layer was dried over MgSO4. Removal of solvent gave a crude product, which was purified by silica gel column chromatography eluding with hexanes/ethyl acetate mixture (5/1 to 2/1) to give pure 2-thiazol-2-yl-benzaldehyde (0.5 g, yield: 38%).

References: [1]Patent: US2009/29993,2009,A1 .

7
[ 54044-79-0 ]
[ 40138-16-7 ]
[ 1310531-83-9 ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 20 - 100℃;	To a solution of 2-bromo-5-methyl- l,3,4-thiadiazole (150 mg, 0.84 mmol) in 1,2- dimethoxyethane (5 mL) are added 2-formylphenylboronic acid (190 mg, 1.26 mmol), Pd(PPh3)4 (97 mg, 0.08 mmol) and Na2C03 (sat., 0.10 mL) at room temperature. The solution is heated to 100 C for 18 hours then cooled and poured into water and EtOAc. Layers are separated and the aqueous phase extracted with EtOAc (lx 10 mL). The combined organics are dried (MgS04), filtered and concentrated to give the crude product which is purified via flash chromatography (12g silica gel, 5-60% EtOAc/hexanes). The product-containing fractions are combined and concentrated to give 2-(5-methyl- 1,3,4- thiadiazol-2-yl)-benzaldehyde (100 mg, 58%) which is used without further purification.

References: [1]Patent: WO2011/68821,2011,A1 .Location in patent: Page/Page column 85.

8
[ 40138-16-7 ]
[ 101335-11-9 ]
[ 1421751-51-0 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1323 - 1340.

9
[ 40138-16-7 ]
[ 101335-11-9 ]
[ 1421751-75-8 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1323 - 1340.

10
[ 16870-28-3 ]
[ 40138-16-7 ]
[ 1261953-68-7 ]

References: [1]Journal of Physical Organic Chemistry,2011,vol. 24,p. 1151 - 1156.

11
[ 16870-28-3 ]
[ 40138-16-7 ]
[ 1261945-55-4 ]

References: [1]Journal of Physical Organic Chemistry,2011,vol. 24,p. 1151 - 1156.

12
[ 40138-16-7 ]
[ 99365-48-7 ]
[ 145865-34-5 ]

References: [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 164 - 170.

13
[ 16932-45-9 ]
[ 40138-16-7 ]
[ 1256479-82-9 ]

References: [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 3558 - 3567.

14
[ 10421-85-9 ]
[ 40138-16-7 ]
[ 18741-85-0 ]
C₃₅H₂₄BClN₂O₃ [ No CAS ]
C₃₅H₂₄BClN₂O₃ [ No CAS ]

References: [1]RSC Advances,2015,vol. 5,p. 67277 - 67283.

15
[ 198544-94-4 ]
C₁₉H₁₆NO₅Pol [ No CAS ]
[ 35661-39-3 ]
[ 40138-16-7 ]
[ 92122-45-7 ]
[ 71989-14-5 ]
[ 104091-08-9 ]
H-Asp-Glu-Ala-Ala-Lys(PBA)-Ala-Ala-Lys-Asp-OH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%		General procedure: Peptides were synthesized using standard, Fmoc-based, solid-phase protocols on a Liberty Microwave Peptide Synthesizer (CEM Corporation). The peptides Fmoc-Phe-Phe-Wang resin, Fmoc-Phe-Phe-RinkAmide AM resin, and Fmoc-Asp(OtBu)-Glu(OtBu)-(Ala)2-Lys(Mtt)-(Ala)2-Lys(Boc)-Asp(OtBu)-Wangresin were assembled from C-terminus to N-terminus on 0.1 mmol or 0.25 mmol scales using Fmoc-Phe-Wang resin, RinkAmide AM resin, and Fmoc-Asp(OtBu)- , respectively. Fmoc deprotection was accomplished using a 0.1 M solution of HOBt in 20:80 (vol:vol) piperidine:DMF. The resin was treated with two cycles of deprotect solution at 75 C for 180 s. Fmoc-protected amino acids were coupled to the deprotected amine ofthe resin-bound peptide using 5 eq. amino acid, 4.5 eq. HBTU, and 10 eq. DIEA relative to the resin loading. Each coupling reaction was conducted at 75 C for 180 s. The amino acids, HBTU, and DIEA were utilized as 0.2 M solutions in DMF, a 0.5 M solution in HBTU, and a 2 M solution in NMP, respectively.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 5731 - 5734.

16
[ 766-36-9 ]
[ 40138-16-7 ]
2-ethyl-5-hydroxy-1-methylbenzo[c]pyrrolo[2,1-f ]-[1,2]azaborinin-3(5H)-one [ No CAS ]