[ CAS No. 76-09-5 ] {[proInfo.proName]}

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2D 3D

Structure of 76-09-5 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 76-09-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 76-09-5 ]

SDS Specification

Alternatived Products of [ 76-09-5 ]

Product Details of [ 76-09-5 ]

CAS No. :	76-09-5	MDL No. :	MFCD00004462
Formula :	C₆H₁₄O₂	Boiling Point :	-
Linear Structure Formula :	((CH₃)₂(OH)C)₂	InChI Key :	IVDFJHOHABJVEH-UHFFFAOYSA-N
M.W :	118.17	Pubchem ID :	6425
Synonyms :

Calculated chemistry of [ 76-09-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	33.36
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.64
Log Po/w (XLOGP3) :	0.09
Log Po/w (WLOGP) :	0.53
Log Po/w (MLOGP) :	0.61
Log Po/w (SILICOS-IT) :	0.13
Consensus Log Po/w :	0.6

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.56
Solubility :	32.3 mg/ml ; 0.273 mol/l
Class :	Very soluble
Log S (Ali) :	-0.49
Solubility :	37.9 mg/ml ; 0.32 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.33
Solubility :	55.9 mg/ml ; 0.473 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 76-09-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330	UN#:	N/A
Hazard Statements:	H302-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 76-09-5 ]

* 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 [ 76-09-5 ]
Downstream synthetic route of [ 76-09-5 ]

[ 76-09-5 ] Synthesis Path-Upstream 1~5

1
[ 76-09-5 ]
[ 374790-93-9 ]

Reference： [1] Journal of the American Chemical Society, 2016, vol. 138, # 30, p. 9521 - 9532

2
[ 76-09-5 ]
[ 1993-03-9 ]
[ 18107-18-1 ]
[ 517920-60-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: at 60℃; for 4 h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; 1,4-dioxane; water at 60℃; for 4 h;	To a 10 mL reaction tube equipped with a magnet was added 56 mg (0.4 mmol) of 2-fluorobenzeneboronic acid, 0.6 mL (1.2 mmol) of trimethylsilyl diazomethane (2 M n-hexane solution), 1 mL of toluene was added to the system, The rubber stopper was stoppered and reacted on an electromagnetic heating stirrer at 60 ° C for 4 hours.(0.4 mmol) of tetramethylammonium fluoride (1 M tetrahydrofuran solution) and 200 uL of water were added to an electromagnetic heating stirrer at 60 ° C On the reaction for 4 hours.After completion of the reaction, the organic solvent was removed by a rotary evaporator and purified by column chromatography2-fluorobenzyl boronic acid pinacol ester, its structure is as follows:The compound was a colorless liquid in a yield of 81percent and its NMR data was as follows:

Reference： [1] Patent: CN105884808, 2016, A, . Location in patent: Paragraph 0148; 0149; 0150; 0151; 0152; 0153

3
[ 76-09-5 ]
[ 179117-44-3 ]

Reference： [1] Tetrahedron Letters, 2013, vol. 54, # 2, p. 166 - 169

4
[ 76-09-5 ]
[ 1003845-06-4 ]
[ 1003845-08-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With magnesium sulfate In toluene at 20℃; for 15 h;	34). Synthesis of 2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidine; To a solution of 5-bromo-2-chloro-pyrimidine (10 mmol, 1.93 g) and triisopropyl borate (12 mmol, 2.8 ml.) in toluene (16 ml) and THF (4 mi_) is added n-buty. lithium \\r, hexane (1.58 M, 12 mmol, 7.6 mL) dropwise at -78 ⁰C over 45 min and stirred at -78 ⁰C for 1 hour. The mixture is warmed to -20 ⁰C, then added aq. hydrogen chloride (1M, 20 mL). The mixture is warmed to room temperature. The precipitate is collected and washed with hexane to give a colorless powder (808 mg, 51percent). A mixture of the powder (3.63 mmol, 575 mg), pinacol (3.81 mmol, 450 mg) and MgSO₄ (18.15 mmol, 2.2 g) in toluene (10 mL) is <n="192"/>stirred at room temperature for 15 hour. The mixture is filtrated and the solution is concentrated under reduced pressure. The resultant solid is washed with water to give 2- chloro-5-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-pyrimidine (875 mg, quant); ESI-MS m/z: 159 [M+1-pinacol]\\ Retention time 1.75 min (condition A).
100%	With magnesium sulfate In toluene at 20℃; for 15 h;	Example 14; 1) Synthesis of 2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidine To a solution of 5-bromo-2-chloro-pyrimidine (10 mmol, 1.93 g) and triisopropyl borate (12 mmol, 2.8 mL) in toluene (16 mL) and THF (4 mL) is added n-butyl lithium in hexane (1.58 M, 12 mmol, 7.6 mL) dropwise at -78° C. over 45 min and stirred at -78° C. for 1 hour. The mixture is warmed to -20° C., then added aqueous 1 M HCl (20 mL). The mixture is warmed to room temperature. The precipitate is collected and washed with hexane to give a colorless powder (808 mg, 51percent). A mixture of the powder (3.63 mmol, 575 mg), pinacol (3.81 mmol, 450 mg) and MgSO4 (18.15 mmol, 2.2 g) in toluene (10 mL) is stirred at room temperature for 15 hour. The mixture is filtrated and the solution is concentrated under reduced pressure. The resultant solid is washed with water to give 2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidine (875 mg, quant); ESI-MS m/z: 159 [M+1-pinacol]+, Retention time 1.75 min (condition A).

Reference： [1] Patent: WO2008/9435, 2008, A1, . Location in patent: Page/Page column 189-190
[2] Patent: US2009/118287, 2009, A1, . Location in patent: Page/Page column 67-68

5
[ 76-09-5 ]
[ 100-63-0 ]
[ 1002334-12-4 ]

Reference： [1] Patent: CN105440067, 2016, A, . Location in patent: Paragraph 0018

Yield	Reaction Conditions	Operation in experiment
92%	In tetrahydrofuran; for 22h;Reflux;	A suspension of 4-(hydroxymethyl)phenylboronic acid (1.00 g, 6.6. mmol) and pinacol (0.79 g, 6.7 mmol) in tetrahydrofurane (40 mL) was refluxed over 22 h. During this time the starting materials were completely dissolved. The solvent was removed in vacuum (10 mbar), the residue redissolved in CH2Cl2 / EtOAc and purified by column chromatography on silica gel using the mixture of CH2Cl2 / EtOAc (9/1, v/v) as eluent. Yield 1.4 g (92%). Rf= 0.3 (silica, eluent - CH2Cl2 / EtOAc, 9/1, v/v). 1H NMR (200 MHz, CDCl3), delta in ppm: 1.35 (s, 12H), 4.71 (s, 2H), 7.37 (d, 2H, 3J = 8.2 Hz), 7.81 (d, 2H, 3J = 8.2 Hz).
92%	In tetrahydrofuran; for 22h;Reflux;	Synthesis4-(Hvdroxymethyl)phenylboronic acid pinacol ester:A suspension of 4-(hydroxymethyl)phenylboronic acid (1.00 g, 6.6 mmol) and pinacol (0.79 g, 6.7 mmol) in tetrahydrofurane (40 ml_) was refluxed over 22 h. During this time the starting materials were completely dissolved. The solvent was removed in vacuum (10 mbar), the residue redissolved in CH2CI2 / EtOAc and purified by column chromatography on silica gel using the mixture of CH2CI2 / EtOAc (9/1 , v/v) as eluent. Yield 1.4 g (92%). Rf= 0.3 (silica, eluent - CH2CI2 / EtOAc, 9/1 , v/v). H NMR (200 MHz, CDCI3), delta in ppm: 1.35 (s, 12H), 4.71 (s, 2H), 7.37 (d, 2H, 3J = 8.2 Hz), 7.81 (d, 2H, 3J = 8.2 Hz).
	With magnesium sulfate; In acetonitrile; for 24h;Reflux;	To a stirred solution of 4-(hydroxymethyl) phenylboronic acid (0.4 g, 2.63 mmol) in acetonitrile (15 mL), MgS04 (3 g) and pinacol (0.37 g, 3.15 mmol) are added. The reaction mixture is heated up to about 80C and allowed to reflux for about 24 hours. After completion of the reaction, solvent is evaporated under vacuum. The crude mixture is dissolved in dichloromethane and filtered. The obtained product (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl) methanol (i.e. compound 1) is used for further reaction without purification.

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Technical Information

• Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Heat of Combustion • Hydride Reductions • Jones Oxidation • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Swern Oxidation

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[ CAS No. 76-09-5 ] {[proInfo.proName]}

Quality Control of [ 76-09-5 ]

Related Doc. of [ 76-09-5 ]

Product Details of [ 76-09-5 ]

Calculated chemistry of [ 76-09-5 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 76-09-5 ]

Application In Synthesis of [ 76-09-5 ]

[ 76-09-5 ] Synthesis Path-Upstream 1~5

[ 76-09-5 ] Synthesis Path-Downstream 1~7

Technical Information

Related Functional Groups of [ 76-09-5 ]

Aliphatic Chain Hydrocarbons

Alcohols

Precautionary Statements-General

Prevention

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Health hazards

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Related Functional Groups of
[ 76-09-5 ]