[ CAS No. 38588-64-6 ] {[proInfo.proName]}

Name: 38588-64-6|3,5-Bis(methoxycarbonyl)benzoic acid|97%
Brand: Ambeed
SKU: A149416
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3d Animation Molecule Structure of 38588-64-6

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Quality Control of [ 38588-64-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 38588-64-6 ]

CAS No. :	38588-64-6	MDL No. :	MFCD06797584
Formula :	C₁₁H₁₀O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OGZWRRQXMPHWIZ-UHFFFAOYSA-N
M.W :	238.19	Pubchem ID :	12411418
Synonyms :

Calculated chemistry of [ 38588-64-6 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.18
Num. rotatable bonds :	5
Num. H-bond acceptors :	6.0
Num. H-bond donors :	1.0
Molar Refractivity :	55.96
TPSA :	89.9 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.7
Log Po/w (XLOGP3) :	1.15
Log Po/w (WLOGP) :	0.96
Log Po/w (MLOGP) :	1.46
Log Po/w (SILICOS-IT) :	1.1
Consensus Log Po/w :	1.27

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.97
Solubility :	2.54 mg/ml ; 0.0107 mol/l
Class :	Very soluble
Log S (Ali) :	-2.63
Solubility :	0.555 mg/ml ; 0.00233 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.93
Solubility :	2.79 mg/ml ; 0.0117 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.61

Safety of [ 38588-64-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 38588-64-6 ]

* 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 [ 38588-64-6 ]
Downstream synthetic route of [ 38588-64-6 ]

[ 38588-64-6 ] Synthesis Path-Upstream 1~5

1
[ 2672-58-4 ]
[ 38588-64-6 ]

Reference： [1] Chemical Communications, 2017, vol. 53, # 12, p. 1945 - 1948
[2] RSC Advances, 2018, vol. 8, # 39, p. 22250 - 22258
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 19, p. 5950 - 5966
[4] Patent: WO2011/103321, 2011, A1, . Location in patent: Page/Page column 20-21
[5] Chemistry - A European Journal, 2013, vol. 19, # 2, p. 685 - 690
[6] Journal of the American Chemical Society, 1999, vol. 121, # 44, p. 10286 - 10296
[7] European Journal of Organic Chemistry, 2018, vol. 2018, # 37, p. 5180 - 5192
[8] Journal of Medicinal Chemistry, 2017, vol. 60, # 8, p. 3314 - 3334
[9] Crystal Growth and Design, 2017, vol. 17, # 12, p. 6653 - 6659
[10] Tetrahedron, 1999, vol. 55, # 10, p. 2835 - 2846
[11] Inorganic Chemistry, 2014, vol. 53, # 22, p. 12199 - 12204
[12] Journal of the American Chemical Society, 2003, vol. 125, # 51, p. 15935 - 15940
[13] Journal of the American Chemical Society, 2008, vol. 130, # 4, p. 1120 - 1121
[14] Tetrahedron Letters, 2004, vol. 45, # 6, p. 1151 - 1153
[15] Dyes and Pigments, 2015, vol. 121, p. 1 - 6
[16] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4188 - 4201
[17] CrystEngComm, 2018, vol. 20, # 13, p. 1874 - 1881
[18] Tetrahedron, 1993, vol. 49, # 39, p. 8761 - 8770
[19] Tetrahedron, 1997, vol. 53, # 37, p. 12497 - 12504
[20] European Journal of Organic Chemistry, 2009, # 10, p. 1570 - 1577
[21] Tetrahedron, 2015, vol. 71, # 46, p. 8758 - 8765
[22] Chemistry - A European Journal, 2015, vol. 21, # 43, p. 15388 - 15394
[23] Patent: CN108409599, 2018, A, . Location in patent: Paragraph 0046-0048; 0061-0062; 0069-0070

2
[ 2672-58-4 ]
[ 38588-64-6 ]
[ 18263-95-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With water; sodium hydroxide In methanol for 8 h;	The trimethyl benzene-1,3,5-tricarboxylate (62 g, 246 mmol) was dissolved in MeOH (800 mL), aq. sodium hydroxide (221 mL, 221 mmol)-(1N) was slowly added. The suspension was stirred vigorously and slowly dissolved during 8 hours. The reaction was left stirred at room temperature for 18 hours, then the solvent was removed in vacuo. (1044) DCM (600 mL) was added to the solid and the organic phase was washed with sat. NaHCO₃(3×500 mL) 3 layers in the separation funnel—solution was filtered and solid on the funnel was rinsed with DCM. The LC-MS of the crude confirmed that MW was of the desired product (MW:238; 48.8 g; yield 83percent). The LC-MS analysis of material from the organic layer showed a mixture of the desired product as well as over-hydrolyzed product (MW: 224; 9 g), and analysis of material from the aqueous layer showed start material.

Reference： [1] Patent: US2016/24159, 2016, A1, . Location in patent: Paragraph 1043-1044
[2] Chemical Communications, 2006, # 42, p. 4404 - 4406

3
[ 554-95-0 ]
[ 38588-64-6 ]

Reference： [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4188 - 4201
[2] Journal of the American Chemical Society, 1999, vol. 121, # 44, p. 10286 - 10296
[3] Tetrahedron, 1997, vol. 53, # 37, p. 12497 - 12504
[4] Tetrahedron, 1993, vol. 49, # 39, p. 8761 - 8770
[5] European Journal of Organic Chemistry, 2018, vol. 2018, # 37, p. 5180 - 5192

4
[ 569-51-7 ]
[ 38588-64-6 ]

Reference： [1] Chemistry - A European Journal, 2013, vol. 19, # 2, p. 685 - 690

5
[ 67-56-1 ]
[ 554-95-0 ]
[ 2672-58-4 ]
[ 38588-64-6 ]
[ 18263-95-1 ]

Reference： [1] Inorganic Chemistry, 2015, vol. 54, # 4, p. 1785 - 1790

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Yield	Reaction Conditions	Operation in experiment
83%	With sodium hydroxide In methanol; water at 50℃; for 0.25h; Microwave irradiation;
81%	With sodium hydroxide In methanol for 12h; Reflux;
80%	With sodium hydroxide In methanol for 12h; Reflux;

79%	Stage #1: 1,3,5-tris-(methoxycarbonyl)benzene With water; sodium hydroxide In methanol for 18h; Stage #2: With hydrogenchloride In water
79%	Stage #1: 1,3,5-tris-(methoxycarbonyl)benzene With sodium hydroxide Stage #2: With hydrogenchloride	5 The acid chloride (43) was prepared as follows. Trimethyl-1 ,3,5-benzenetricarboxylate (46) was converted to the mono-acid diester (47) according to literature procedures (Dimick, et al. "On the Meaning of Affinity: Cluster Glycoside Effects and Concanavalin A" J. Am. Chem. Soc. 1999, 121 , 10286- 10296), and compound 47 was refluxed in excess thionyl chloride to give acid chloride 43 (Scheme 5).
79%	With water; sodium hydroxide In methanol at 20℃; for 22h;	Synthesis of 17 To a solution of Trimethyl 1,3,5-Benzenetricarboxylate (1.1 g, 4.36 mmol) in MeOH (100 mL) wasadded 1 M NaOH aq. (3.95 mL, 3.95 mmol). The solution was stirred for 22 h at rt. After removal ofthe solvent by evaporation, the mixture was washed with CH2Cl2. The aqueous layer was acidified with 6 M HCl to pH 2 and then extracted with AcOEt. The organic layer was dried over Na2SO4 andthe solution was concentrated by evaporation to give 17 (849 mg, 79%) as a white solid.
78%	With sodium hydroxide In methanol for 12h; Reflux;
76%	With sodium hydroxide In methanol for 18h;
76%	With sodium hydroxide In methanol; water at 20℃;
75%	With sodium hydroxide In methanol; water at 20℃; for 18h;
73%	With sodium hydroxide In methanol; water for 16h; Reflux;
70%	With sodium hydroxide
70%	Stage #1: 1,3,5-tris-(methoxycarbonyl)benzene With sodium hydroxide In methanol; water for 36h; Stage #2: With sodium hydrogencarbonate In water at 50℃; for 2h; Stage #3: With hydrogenchloride In water
70%	With sodium hydroxide In methanol at 85℃;
69%	With sodium hydroxide In methanol for 12h; Heating;
60%	With sodium hydroxide In ethanol; water
55%	With sodium hydroxide In methanol
49%	With lithium hydroxide In tetrahydrofuran; water at 20℃; for 2.5h;
49.6%	With sodium hydroxide In methanol at 20℃; for 48h;
	With hydrogenchloride; sodium hydroxide 1.) MeOH, rt., 1 h, 2.) pH=7-8, 16 h; Yield given. Multistep reaction;
	With sodium hydroxide In methanol; water
	With sodium hydroxide
	With water; sodium hydroxide
	With sodium hydroxide
	With sodium hydroxide In methanol for 12h; Reflux;	1 Synthesis of product 1 3.7515 g of trimethyl 1,3,5-benzenetrihydroxy acid ester and 0.5798 g of NaOH were dissolved in 110 ml of methanol, and the temperature was slowly raised to reflux temperature for 12 hours, and the solvent was removed by rotary evaporation.The product was dissolved in dichloromethane and the product was extracted with saturated sodium bicarbonate. The extracted aqueous phase was washed twice with dichloromethane, then HCl was adjusted to pH = 1 and a precipitate was produced.The precipitate was washed with water until neutral and the product was dried in a vacuum oven to give product 1.

Yield	Reaction Conditions	Operation in experiment
88%	With dimethylsulfide borane complex In tetrahydrofuran at 27℃; for 24h;
87%	With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 24h;
65%	With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 25h; Inert atmosphere;	Synthesis of 18 To an ice-cooled solution of 17 (500 mg, 2.10 mmol) in dry THF (3.5 mL) was added dropwise 2M BH3-Me2S in THF (2.1 mL, 4.20 mmol) under N2 atmosphere. The solution was stirred for 25 h atrt. After addition of MeOH (7.5 mL) on ice-cooling, the solution was stirred for 30 min at rt. Afterremoval of the solvent by evaporation, the residue was dissolved with AcOEt. The mixture waswashed with water, sat. NaHC3 aq. and brine followed by drying over Na2SO4. After removal of thesolvent by evaporation, the residue was purified by column chromatography on SiO2 (Hexane :AcOEt = 1 : 1) to give 18 (306 mg, 65%) as a white solid.

45%	With dimethyl sulfide borane In tetrahydrofuran at 20℃;
38.5%	With borane-THF In tetrahydrofuran at 20℃; for 24h; Cooling with ice;	3 3,5-bis(methoxycarbonyl)benzoic acid (10 g, 42.0 mmol) was dissolved in dry THF (80 mL). The flask was placed in ice-bath and bh3.thf (84 mL, 84 mmol) was added slowly (some bubbling occurred). The reaction mixture was left stirring at room temperature for 24 hours. After 14 hours reaction did not progress, another 3 eq. of bh3.thf (42.0 mL, 42.0 mmol) were slowly added and the reaction mixture was stirred at room temperature for hours. The reaction was completed (95% by LC-MS). (1046) The reaction mixture was quenched with MeOH (added slowly 80 mL) and left stirred for 1 hour at RT. The solvent was removed in vacuo. The product was re-dissolved in EtOAc (white solution 1000 mL) and the organic layer was washed with water (2×800 mL), sat. NaHCO3 (800 mL) and brine (800 mL). The EtOAc was dried with MgSO4, filtered and concentrated in vacuo (3.62 g; yield 38.5%).
	With dimethylsulfide borane complex
	With dimethylsulfide borane complex

[ CAS No. 38588-64-6 ] {[proInfo.proName]}

Quality Control of [ 38588-64-6 ]

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Product Details of [ 38588-64-6 ]