[ CAS No. 99-14-9 ] {[proInfo.proName]}

Name: 99-14-9|Propane-1,2,3-tricarboxylic acid|97%
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3d Animation Molecule Structure of 99-14-9

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COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 99-14-9 ]

Product Details of [ 99-14-9 ]

CAS No. :	99-14-9	MDL No. :	MFCD00002723
Formula :	C₆H₈O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KQTIIICEAUMSDG-UHFFFAOYSA-N
M.W :	176.12	Pubchem ID :	14925
Synonyms :		Chemical Name :	Propane-1,2,3-tricarboxylic acid

Calculated chemistry of [ 99-14-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	5
Num. H-bond acceptors :	6.0
Num. H-bond donors :	3.0
Molar Refractivity :	36.27
TPSA :	111.9 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) :	-8.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-0.26
Log Po/w (XLOGP3) :	-1.25
Log Po/w (WLOGP) :	-0.36
Log Po/w (MLOGP) :	-0.68
Log Po/w (SILICOS-IT) :	-0.94
Consensus Log Po/w :	-0.7

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	0.19
Solubility :	270.0 mg/ml ; 1.53 mol/l
Class :	Highly soluble
Log S (Ali) :	-0.6
Solubility :	43.8 mg/ml ; 0.249 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	1.14
Solubility :	2450.0 mg/ml ; 13.9 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.82

Safety of [ 99-14-9 ]

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

Application In Synthesis of [ 99-14-9 ]

* 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 [ 99-14-9 ]
Downstream synthetic route of [ 99-14-9 ]

[ 99-14-9 ] Synthesis Path-Upstream 1~3

1
[ 67-56-1 ]
[ 99-14-9 ]
[ 6138-26-7 ]

Reference： [1] Journal of the Chemical Society, 1902, vol. 81, p. 35
[2] Chemische Berichte, 1889, vol. 22, p. 2922

2
[ 99-14-9 ]
[ 77-76-9 ]
[ 6138-26-7 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1975, p. 1400 - 1401

3
[ 186581-53-3 ]
[ 99-14-9 ]
[ 6138-26-7 ]

Reference： [1] South African Journal of Chemistry, 1996, vol. 49, # 1-2, p. 31 - 34

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Yield	Reaction Conditions	Operation in experiment
61%		Comparative Example 1 [Synthesis of Thickening/stabilizing Agent (3) (1,2,3-propanetricarboxylic acid tris(2-methylcyclohexylamide))] (0087) A 100 mL four-necked separable flask equipped with a Dimroth condenser, a nitrogen inlet, a dropping funnel and a thermocouple was charged with 20 mL of pyridine, 2.97 g (0.017 mol) of 1,2,3-propanetricarboxylic acid, and 7.0 g (0.056 mol) of diisopropylcarbodiimide, and the resultant was aged for 3 hours with a temperature within the system set to 50 C. (0088) Thereafter, 5.7 g (0.051 mol) of 2-methylcyclohexylamine was added thereto, and the resultant was aged for another 8 hours. (0089) Then, a low-boiling component of the thus obtained crude liquid was removed with an evaporator, and the resultant was washed with methanol to obtain a pale yellow wet powder. The thus obtained wet powder was washed with acetone to obtain 4.7 g of 1,2,3-propanetricarboxylic acid tris(2-methylcyclohexylamide) (yield: 61%).
61%		In a 100 mL four-neck separable flask equipped with a Dimroth condenser, a nitrogen inlet, a dropping funnel and a thermocouple, 20 mL of pyridine, 2.97 g (0.017 mol) of 1, 2, 3-propane tricarboxylic acid, 7.0 g of diisopropyl carbo diimide (0.056 mol) were charged, and the temperature in the system was set at 50 C and aged for 3 hours. Further, 5.7 g (0.051 mol) of 2-methyl cyclohexyl amine was charged and aged for 8 hours. Thereafter, the low boiling fraction of the resulting crude liquid was removed by an evaporator and washed with methanol to obtain light yellow wet powder. Further, the obtained wet powder was washed with acetone to obtain 4.7 g of 1, 2, 3-propane tricarboxylic acid tris (2-methyl cyclohexyl amide) (yield: 61%).

Yield	Reaction Conditions	Operation in experiment
72%		After 7.3 mL (100 mmol) of thionyl chloride was dropped into a 0.2 ml dimethylformamide solution of 3.5 g (20 mmol) of 1 , 2 , 3-propanetricarboxylic acid, agitation was performed at 90 C for 2 hours. Subsequently, concentration was performed under reduced pressure, and dilution was performed with 40 mL of dichloromethane. The resulting solution was dropped into a 100 mL dichloromethane solution of 10 mL of triethylamine and 12.2 mL (72 mmol) ofdibutylamine, and agitation was performed for 5 days. After the reaction was completed, dilution was performed with 400 mL of dichloromethane. Subsequently, washing was performed with water, 1 mol/L hydrochloric acid, saturated sodium hydrogen carbonate aqueous solution, and saturated saline solution. After an organic layer was concentrated under reduced pressure, refining was performed with silica gel column chromatography, so as to obtain 7.37 g (yield 72%) of Compound ( 11 ) . ·Analytical result of Compound (11)[1] XH NMR (400 MHz, CDC13, room temperature): delta [ppm] = 0.99 to 0.84 (m, 18H) , 1.69 to 1.23 (m, 24H) , 2.53 to 2.45 (m, 2H) , 2.63 to 2.55 (m, 2H) , 3.31 to 3.12 (m, 10H) , 3.46 (t, 2H, J = 8.01 Hz), 3.75 to 3.68 (m, 1H)[2] Mass analysis (ESI-TOF) : m/z = 510.4699 (M+H)+
72%		7.3 mL (100 mmol) of thionyl chloride was dropped into 0.2 mL of dimethylformamide solution of 3.5 g (20 mmol) of 1,2,3-propanetricarboxylic acid, then the solution was stirred at 90 C. for 2 hours. After concentrating under reduced pressure, the solution was diluted with 40 mL of dichloromethane. The solution was dropped into 100 mL of dichloromethane solution of 10 mL of triethylamine and 12.2 mL (72 mmol) of dibutylamine, then the mixed solution was stirred for 5 days. After the reaction, the mixture solution was diluted with 400 mL of dichloromethane and washed with water, 1 mol/L hydrochloric acid solution, saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride solution. The organic layer was concentrated under reduced pressure, then the residue was purified with silica gel chromatography to obtain 7.37 g (in 72% yield) of compound.

Yield	Reaction Conditions	Operation in experiment
20%	With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; at 20℃; for 72h;	After 12.6 mL (80 mmol) of N, -diethyl-1, 3- diaminopropane and 22.1 g (80 mmol) of 4- (4 , 6-dimethoxy- 1, 3, 5-triazin-2-yl ) -4-methylmorpholinium chloride ( DMT-MM) were added to a 80 ml methanol solution of 3.5 g (20 mmol) of 1 , 2 , 3-propanetricarboxylic acid, agitation was performed at room temperature for 3 days. The reaction solution was concentrated under reduced pressure and, thereafter,refining was performed with silica gel column chromatography, so as to obtain 2.1 g (yield 20%) of Compound (13).Analytical result of Compound (13)[1] XH NMR (400 MHz, CDC13, room temperature): delta [ppm] = 1.02 (tt, 18H, J = 15.57, 6.49 Hz), 1.62 (dt, 6H, J = 17.71, 5.38Hz), 2.17 (s, 2H) , 2.35 (dd, 2H, J = 14.65, 5.04 Hz), 2.54 to 2.44 (m, 18H) , 3.14 to 3.10 (m, 1H) , 3.28 (dq, 6H, J = .25.87, 6.56 Hz), 7.56 (3H, t, J = 5.27 Hz)[2] Mass analysis (ESI-TOF) : m/z = 513.4603 (M+H)+
20%	With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; at 20℃; for 72h;	12.6 mL (80 mmol) of N,N-diethyl-1,3-diaminopropane and 22.1 g (80 mmol) of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) were added into 80 mL of methanol solution of 3.5 g (20 mmol) of 1,2,3-propanetricarboxylic acid, and then the solution was stirred for 3 days at room temperature.The reaction solution was concentrated under reduced pressure, then the residue was purified with silica gel chromatography to obtain 2.1 g (in 20% yield) of compound (13).

Yield	Reaction Conditions	Operation in experiment
37%	With boron trioxide; In xylene; for 6h;Reflux;	Addition of 44.5 g (240 mmol) of n-dodecylamine to a 150 ml xylene solution of 13.0 g (120 mmol) of cresol, 7.0 g (40 mmol) of 1 , 2 , 3-propanetricarboxylic acid, and 1.0 g (14.4 mmol) of boric oxide was performed, and heat-refluxing was performed for 6 hours to effect dehydration. After the reaction was completed, concentration was performed under reduced pressure and, then, suspension cleaning wasperformed with 150 mL of acetonitrile through agitation at 50C for 1 hour. Solids were filtrated, so as to obtain 10.0 g (yield 37%) of Compound (4).Analytical result of Compound (4)[1] XH NMR (400 MHz, DMSO-d6, room temperature): delta [ppm] = 0.85 (t, 9H, J = 6.64 Hz), 1.17 (m, 60H) , 2.50 (t, 11H, J = 1.83 Hz), 7.64 (s, 1H) , 8.03 (s, 1H) , 10.8 (s, 1H)[2] Mass analysis (ESI-TOF) : m/z = 676.6414 (M-H) ~
37%	With boron trioxide; In 5,5-dimethyl-1,3-cyclohexadiene; for 6h;Reflux;	Cresol 13.0g (120mmol),1,2,3-propane tricarboxylic acid 7.0g (40mmol),It was added to the xylene 150mL solution of boron oxide 1.0g (14.4mmol) n- dodecylamine 44.5g (240mmol),6 hours under heating to reflux after completion of the reaction obtained by dehydration,After concentration under reduced pressure,Acetonitrile 150 mL, was suspended and washed by stirring for 1 hour at 50 C.. The solid was filtered,Compound (4) was obtained 10.0 g (37% yield). Analysis results for compound (4)]
37%	With boron trioxide; In 5,5-dimethyl-1,3-cyclohexadiene; for 6h;Reflux;	13.0 g of cresol (120 mmol), 7.0 g of 1,2,3-propanetricarboxylic acid (40 mmol), and 1.0 g of diboron trioxide (14.4 mmol) were dissolved in 150 ml xylene, and 44.5 g of n-dodecyl amine (240 mmol) was added to the xylene solution. The xylene solution was heated and refluxed for 6 hours for dehydration. After the reaction, the solution was concentrated, and then stirred at 50 C. for 1 hour for suspension washing in 150 ml of acetonitrile. The resultant solid was filtered to obtain 10.0 g of compound (4) (in 37% yield).

[ CAS No. 99-14-9 ] {[proInfo.proName]}

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