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

Name: 99-14-9|Propane-1,2,3-tricarboxylic acid|97%
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Quality Control of [ 99-14-9 ]

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 :	(HO₂CCH₂)₂CHCO₂H	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 ] Expand+

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

[ 99-14-9 ] Synthesis Path-Downstream 1~109

1
[ 108-73-6 ]
[ 99-14-9 ]
(1',3',6',8'-tetrahydroxy-5-oxo-4,5-dihydro-3H-spiro[furan-2,9'-xanthen]-4-yl)-acetic acid [ No CAS ]

Reference： [1]Journal of the Chemical Society,1931,p. 2511,2512

2
[ 78-88-6 ]
[ 64-17-5 ]
[ 151-50-8 ]
[ 99-14-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1873,vol. 170,p. 126

3
[ 78-88-6 ]
[ 151-50-8 ]
[ 99-14-9 ]

Reference： [1]Chemische Berichte,1872,vol. 5,p. 360
Justus Liebigs Annalen der Chemie,1873,vol. 170,p. 127

4
[ 99-67-2 ]
[ 99-14-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1880,vol. 201,p. 53

5
[ 6127-93-1 ]
[ 151-50-8 ]
[ 99-14-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1878,vol. 191,p. 69,72,74

6
[ 499-12-7 ]
[ 110-15-6 ]
[ 99-14-9 ]

Reference： [1]Nippon Nogeikagaku Kaishi,1940,vol. 16,p. 663
Chem.Abstr.,1941,p. 769

7
[ 499-12-7 ]
[ 99-14-9 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1862,vol. 55,p. 510
Justus Liebigs Annalen der Chemie,1862,vol. Suppl.2,p. 188
[2]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1903,vol. 136,p. 1331
[3]Justus Liebigs Annalen der Chemie,1864,vol. 132,p. 62
[4]Helvetica Chimica Acta,1935,vol. 18,p. 1206,1210
[5]Journal of the American Chemical Society,1939,vol. 61,p. 845
[6]Zeitschrift fur Elektrochemie und angewandte physikalische Chemie,1938,vol. 44,p. 768
[7]Zhurnal Obshchei Khimii,1948,vol. 18,p. 1237,1241
Chem.Abstr.,1949,p. 955
[8]Justus Liebigs Annalen der Chemie,1901,vol. 314,p. 15
[9]Patent: US10280287,2019,B2 .Location in patent: Page/Page column 2

8
[ 585-84-2 ]
[ 99-14-9 ]

Reference： [1]Bulletin International de l'Academie Polonaise des Sciences et des Lettres, Classe des Sciences Mathematiques et Naturelles, Serie A: Sciences Mathematiques,1929,p. 271
Chemisches Zentralblatt,1929,vol. 100,p. 2176

9
[ 4023-65-8 ]
[ 99-14-9 ]

Reference： [1]Nippon Nogeikagaku Kaishi,1940,vol. 16,p. 663
Chem.Abstr.,1941,p. 769
[2]Bulletin International de l'Academie Polonaise des Sciences et des Lettres, Classe des Sciences Mathematiques et Naturelles, Serie A: Sciences Mathematiques,1929,p. 271
Chemisches Zentralblatt,1929,vol. 100,p. 2176

10
[ 96-23-1 ]
[ 151-50-8 ]
[ 99-14-9 ]

Reference： [1]Bulletin de la Societe Chimique de France,1923,vol. <4>33,p. 731,732

11
[ 36653-82-4 ]
[ 99-14-9 ]
[ 4964-56-1 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1933,vol. <2>136,p. 309

12
[ 355-80-6 ]
[ 99-14-9 ]
[ 376-85-2 ]

Reference： [1]Industrial and Engineering Chemistry,1956,vol. 48,p. 445,447

13
[ 99-14-9 ]
[ 188290-36-0 ]

Reference： [1]Chemische Berichte,1886,vol. 19,p. 2445

14
[ 99-14-9 ]
[ 250-84-0 ]

Reference： [1]Chemische Berichte,1886,vol. 19,p. 2445

15
[ 99-14-9 ]
[ 4756-10-9 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 2861 - 2867
[2]Molecules,2000,vol. 5,p. 665 - 673
[3]Chemische Berichte,1891,vol. 24,p. 600
[4]Journal of Chemical and Engineering Data,1959,vol. 4,p. 79,80
[5]Journal of the Chemical Society,1902,vol. 81,p. 35
[6]Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques,1929,p. 269
Chemisches Zentralblatt,1929,vol. 100,p. 2176
[7]Journal of the Chemical Society. Perkin transactions II,1991,p. 1531 - 1540
[8]Tetrahedron Letters,2000,vol. 41,p. 2289 - 2293

16
[ 99-14-9 ]
[ 100953-23-9 ]

Reference： [1]Journal of the Chemical Society,1957,p. 144,149

17
[ 99-14-9 ]
[ 23666-71-9 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1933,vol. <2>136,p. 309
[2]Helvetica Chimica Acta,1980,vol. 63,p. 2271 - 2279

18
[ 99-14-9 ]
1-bromo-propane-1,2,3-tricarboxylic acid triethyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society,1932,p. 1079,1086

19
[ 52163-78-7 ]
[ 99-14-9 ]
[ 15719-64-9 ]

Reference： [1]Journal of the Chemical Society,1925,vol. 127,p. 194

20
[ 5247-13-2 ]
[ 99-14-9 ]

Reference： [1],vol. 12,p. 237
Justus Liebigs Annalen der Chemie,1863,vol. 128,p. 352;136,272

21
[ 149-91-7 ]
[ 99-14-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1875,vol. 177,p. 282

22
[ 4717-55-9 ]
[ 99-14-9 ]

Reference： [1]Journal of the Chemical Society,1926,p. 2173,2177
Journal of the Chemical Society,1927,p. 60

23
[ 98198-38-0 ]
[ 99-14-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1958,vol. 618,p. 71,78

24
[ 99-14-9 ]
[ 66711-84-0 ]

Reference： [1]Polish Journal of Chemistry,1978,vol. 52,p. 71 - 85

25
[ 14314-67-1 ]
[ 99-14-9 ]

Reference： [1]Journal of Organic Chemistry,1961,vol. 26,p. 1639 - 1640

26
3,3-Bis-<difluor-chlor-methyl>-2-aethoxycarbonyl-glutarsaeure-diaethylester [ No CAS ]
[ 99-14-9 ]

Reference： [1]Journal of the American Chemical Society,1962,vol. 84,p. 3154 - 3157

27
[ 7686-77-3 ]
[ 99-14-9 ]

Reference： [1]Journal of Organic Chemistry,1962,vol. 27,p. 2395 - 2398

28
[ 99-14-9 ]
[ 137-07-5 ]
[ 89213-01-4 ]

Reference： [1]Journal of Organic Chemistry,1961,vol. 26,p. 3434 - 3436

29
[ 99-14-9 ]
[ 77-76-9 ]
[ 6138-26-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1975,p. 1400 - 1401

30
[ 100-02-7 ]
[ 99-14-9 ]
[ 94136-73-9 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 317 - 323

31
[ 99-14-9 ]
[ 771-61-9 ]
1,2,3-propanetricarboxylic acid tris-pentafluorophenyl ester [ No CAS ]

Reference： [1]Acta Chimica Hungarica,1984,vol. 116,p. 173 - 187

32
[ 99-14-9 ]
[ 77461-97-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1991,p. 1531 - 1540
[2]Molecules,2000,vol. 5,p. 665 - 673
[3]Journal of Organic Chemistry,1981,vol. 46,p. 2861 - 2867

33
[ 59210-90-1 ]
[ 99-14-9 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1980,vol. 16,p. 2055 - 2058
Zhurnal Organicheskoi Khimii,1980,vol. 16,p. 2399 - 2403
[2]Journal of Organic Chemistry USSR (English Translation),1980,vol. 16,p. 2055 - 2058
Zhurnal Organicheskoi Khimii,1980,vol. 16,p. 2399 - 2403

34
[ 99-14-9 ]
[ 123-62-6 ]
[ 83663-22-3 ]

Yield	Reaction Conditions	Operation in experiment
42%	With pyridine; In m-xylene; at 140℃;	General procedure: Into a one-necked 25 mL flask, tricarballylic acid (518 mg, 2.95 mmol, 1.0 equiv) and the appropriate anhydride (8.83 mmol, 3 equiv) were suspended in m-xylene (5 mL, 0.6 M). Pyridine was added (47 muL, 0.59 mmol, 0.2 equiv) in one portion, then the mixture was heated to 140 C and stirred until the completion of the reaction was indicated by GC-MS (5-21 h). After cooling to r.t., CH2Cl2 (100 mL) was added and the mixture was passed through a short pad of Celite to remove insoluble side-products. The solution was washed with saturated Na2CO3 solution (2 10 mL) then with brine (10 mL). The organic phase was dried over Na2SO4, filtered, and evaporated to dryness. Purification by flash chromatography (hexanes/EtOAc) afforded the pure Fittig lactone.

Reference： [1]Canadian Journal of Chemistry,1982,vol. 60,p. 2528 - 2530
[2]Synthesis,2019,vol. 51,p. 1263 - 1272

35
[ 2922-42-1 ]
[ 99-50-3 ]
[ 99-14-9 ]
[ 149-91-7 ]
[ 184105-29-1 ]
[ 87-66-1 ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 11587 - 11591

36
[ 186581-53-3 ]
[ 99-14-9 ]
[ 6138-26-7 ]

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

37
[ 99-14-9 ]
[ 108-93-0 ]
3-Cyclohexyloxycarbonyl-pentanedioic acid dicyclohexyl ester [ No CAS ]

Reference： [1]Journal of Molecular Structure,1997,vol. 403,p. 1 - 16

38
[ 99-14-9 ]
(1-hydroxy-2,5-dioxo-pyrrolidin-3-yl)-acetic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1451 - 1454

39
[ 99-14-9 ]
1-((R)-(α)-methylbenzylamido)formylpropane-2,3-dicarboxylic-anhydride [ No CAS ]

Reference： [1]Molecules,2000,vol. 5,p. 665 - 673
[2]Molecules,2000,vol. 5,p. 665 - 673

40
[ 99-14-9 ]
1-((R)-(α)-methylbenzylamido)formylpropane-2,3-dicarboxylic-anhydride [ No CAS ]

Reference： [1]Molecules,2000,vol. 5,p. 665 - 673
[2]Molecules,2000,vol. 5,p. 665 - 673

41
[ 99-14-9 ]
3-mono-[1-(R)-(1-phenylethyl)]amide pentane-1,5-dioic acid [ No CAS ]

Reference： [1]Molecules,2000,vol. 5,p. 665 - 673

42
[ 99-14-9 ]
(R)-2-[((R)-1-Phenyl-ethylcarbamoyl)-methyl]-succinic acid dimethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 2289 - 2293

43
[ 99-14-9 ]
(S)-2-[((R)-1-Phenyl-ethylcarbamoyl)-methyl]-succinic acid dimethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 2289 - 2293

44
[ 99-14-9 ]
(R)-2-[((R)-1-Naphthalen-1-yl-ethylcarbamoyl)-methyl]-succinic acid dimethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 2289 - 2293

45
[ 99-14-9 ]
(S)-2-[((R)-1-Naphthalen-1-yl-ethylcarbamoyl)-methyl]-succinic acid dimethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 2289 - 2293

46
[ 99-14-9 ]
3-(2-Amino-ethylcarbamoyl)-pentanedioic acid bis-[(2-amino-ethyl)-amide] [ No CAS ]

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

47
[ 99-14-9 ]
N,N,N',N',N",N"-hexabutyl-propane-1,2,3-tricarboxamide [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1980,vol. 63,p. 2271 - 2279

48
[ 99-14-9 ]
[ 94136-77-3 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 317 - 323

49
[ 99-14-9 ]
[ 137639-72-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1991,p. 1531 - 1540

50
[ 99-14-9 ]
[ 137656-90-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1991,p. 1531 - 1540

51
[ 99-14-9 ]
[ 137656-89-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1991,p. 1531 - 1540

52
[ 99-14-9 ]
[ 77461-98-4 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 2861 - 2867

53
[ 99-14-9 ]
[ 77462-02-3 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 2861 - 2867

54
[ 99-14-9 ]
[ 77462-03-4 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 2861 - 2867

55
[ 3508-77-8 ]
[ 99-14-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1880,vol. 201,p. 53

56
[ 99-14-9 ]
[1-(N-benzoyl-anilino)-2,5-dioxo-pyrrolidin-3-yl]-acetic acid-(N'-benzoyl-N'-phenyl-hydrazide) [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1899,vol. 29 II,p. 155,156

57
[ 99-14-9 ]
[ 88067-07-6 ]

Reference： [1]Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques,1929,p. 269
Chemisches Zentralblatt,1929,vol. 100,p. 2176
[2]Journal of Chemical and Engineering Data,1959,vol. 4,p. 79,80

58
[ 97-65-4 ]
sulfuric acid containing alcohol [ No CAS ]
[ 99-14-9 ]

Reference： [1]Journal of Organic Chemistry,1961,vol. 26,p. 1639 - 1640

59
[ 88326-51-6 ]
[ 99-14-9 ]

Reference： [1]Journal of Organic Chemistry,1962,vol. 27,p. 2395 - 2398

60
[ 99-14-9 ]
[ 57133-16-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1975,p. 1400 - 1401

61
cis-2-methylcyclohexylamine [ No CAS ]
trans-2-methylcyclohexylamine [ No CAS ]
[ 99-14-9 ]
1,2,3-propanetricarboxylic acid tris(cis-2-methylcyclohexylamide) [ No CAS ]
1,2,3-propanetricarboxylic acid tris(2-methylcyclohexylamide) [ No CAS ]
1,2,3-propanetricarboxylic acid tris(2-methylcyclohexylamide) [ No CAS ]
1,2,3-propanetricarboxylic acid tris(2-methylcyclohexylamide) [ No CAS ]
1,2,3-propanetricarboxylic acid tris(2-methylcyclohexylamide) [ No CAS ]
1,2,3-propanetricarboxylic acid tris(trans-2-methylcyclohexylamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; triphenyl phosphite; In 1-methyl-pyrrolidin-2-one; at 100℃; for 4h;Product distribution / selectivity;	The procedure of Example 1 was repeated except that 2-methylcyclohexylamine (trans isomer : cis isomer = 90.3 : 9.7, GLC composition %) was used in place of the 2-methylcyclohexylamine with trans isomer content of 100%. Table 1 shows the evaluation results. PTC-2MeCHA obtained by the reaction was 20.3 g (80% yield).; The procedure of Example 1 was repeated except that 2-methylcyclohexylamine (trans isomer : cis isomer = 77.2 : 22.8, GLC composition %) was used in place of the 2-methylcyclohexylamine with trans isomer content of 100%. Table 1 shows the evaluation results. PTC-2MeCHA obtained by the reaction was 20.0 g (79% yield).; The procedure of Example 1 was repeated except that 2-methylcyclohexylamine (trans isomer : cis isomer = 71.9 : 28.1, GLC composition %) was used in place of the 2-methylcyclohexylamine with trans isomer content of 100%. Table 1 shows the evaluation results. PTC-2MeCHA obtained by the reaction was 19.9 g (78% yield).; The procedure of Example 1 was repeated except that 2-methylcyclohexylamine (trans isomer : cis isomer =68.2 : 31.8, GLC composition %) was used in place of the 2-methylcyclohexylamine with trans isomer content of 100%. Table 1 shows the evaluation results. PTC-2MeCHA obtained by the reaction was 19.3 g (76% yield).; The procedure of Example 1 was repeated except that 2-methylcyclohexylamine (trans isomer : cis isomer = 58.9 : 41.1, GLC composition %) was used in place of the 2-methylcyclohexylamine with trans isomer content of 100%. Table 1 shows the evaluation results. PTC-2MeCHA obtained by the reaction was 19.3 g (76% yield).; The procedure of Example 1 was repeated except that 2-methylcyclohexylamine (trans isomer : cis isomer =50.4 : 49.6, GLC composition %) was used in place of the 2-methylcyclohexylamine with trans isomer content of 100%. Table 1 shows the evaluation results. PTC-2MeCHA obtained by the reaction was 18.0 g (71% yield).; The procedure of Example 1 was repeated except that 2-methylcyclohexylamine (trans isomer : cis isomer = 26.4. 73.6, GLC composition %) was used in place of the 2-methylcyclohexylamine with trans isomer content of 100%. Table 1 shows the evaluation results. PTC-2MeCHA obtained by the reaction was 15.5 g (61% yield).; The procedure of Example 1 was repeated except that 2-methylcyclohexylamine (trans isomer : cis isomer = 1.0 : 99.0, GLC composition %) was used in place of the 2-methylcyclohexylamine with trans isomer content of 100%. Table 1 shows the evaluation results. PTC-2MeCHA obtained by the reaction was 11.7 g (46% yield).

Reference： [1]Patent: EP1674447,2006,A1 .Location in patent: Page/Page column 18

62
trans-2-methylcyclohexylamine [ No CAS ]
[ 99-14-9 ]
1,2,3-propanetricarboxylic acid tris(trans-2-methylcyclohexylamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With pyridine; triphenyl phosphite; In 1-methyl-pyrrolidin-2-one; at 100℃; for 4h;	In a four-necked 500 ml flask equipped with a stirrer, a thermometer, a condenser and a gas inlet were placed 9.7 g of PTC (0.055 moles) and 100 g of N-methyl-2-pyrrolidone, and the PTC was completely dissolved with stirring under nitrogen atmosphere at room temperature. Subsequently, 20.5 g (0.1815 moles) of 2-methylcyclohexylamine (trans isomer : cis isomer = 100.0 : 0.0, GLC composition %), 56.3 g (0.1815 moles) of triphenyl phosphite, 14.4 g (0.1815 moles) of pyridine and 50 g of N-methyl-2-pyrrolidone were added thereto , and the reaction was carried out with stirring under nitrogen atmosphere for 4 hours at 100C. After cooling, the reaction solution was slowly pored into a mixture of 500 ml of isopropyl alcohol and 500 ml of water, and the resulting mixture was stirred at 40 to 50C for one hour, and white precipitate thus formed was then filtered off. The obtained white solid was washed twice with 500 ml of isopropyl alcohol at 40 to 50C, and dried at 100C and 133 Pa for 6 hours. The obtained dry product was pulverized in a mortar and passed through a standard sieve having openings of 106 mum (JIS Z-8801) to give 20.3g (80%yield) of 1, 2, 3-propanetricarboxylic acid tris(2-methylcyclohexylamide) (hereinafter referred to as "PTC-2MeCHA"). The melting point of the thus obtained white powder and the trans-2-methylcyclohexylamine residue absorbance proportion (Ctrans) were measured. Table 1 shows the evaluation results. Table 1 also shows the characteristic infrared absorptions of the obtained white solid (C=O stretching vibration (amide I absorption band) and N-H deformation vibration (amide II absorption band)), 10% weight reduction temperature and alkali resistance (PWR).

Reference： [1]Patent: EP1674447,2006,A1 .Location in patent: Page/Page column 17

63
[ 99-14-9 ]
[ 108-91-8 ]
1,2,3-propanetricarboxylic acid tris(cyclohexylamide) [ No CAS ]

Reference： [1]Patent: WO2006/109654,2006,A1 .Location in patent: Page/Page column 18-20

65
[ 99-14-9 ]
[ 7003-32-9 ]
1,2,3-propanetricarboxylic acid tris(2-methylcyclohexylamide) [ No CAS ]

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%).

Reference： [1]Patent: WO2006/109654,2006,A1 .Location in patent: Page/Page column 18-20
[2]Patent: US2017/158619,2017,A1 .Location in patent: Paragraph 0087; 0088; 0089
[3]Patent: JP2016/20327,2016,A .Location in patent: Paragraph 0092
[4]Patent: WO2006/109654,2006,A1 .Location in patent: Page/Page column 18-19
[5]Patent: WO2006/109654,2006,A1 .Location in patent: Page/Page column 18-19
[6]Patent: WO2006/109654,2006,A1 .Location in patent: Page/Page column 18-19; 22
[7]Patent: WO2006/109654,2006,A1 .Location in patent: Page/Page column 18-19; 22

66
[ 99-14-9 ]
platinum(II) chloride [ No CAS ]
[ 694-83-7 ]

Yield	Reaction Conditions	Operation in experiment
	With silver nitrate; In potassium hydroxide; water;	EXAMPLE 6 cis(and trans)-1,2-Cyclohexanediamine, compound with [1,2,3-propanetricarboxylato(2-)-O1,O3 ]platinum (1.1) To a suspension of 2 g of cis(and trans)-1,2-cyclohexanediamine compound with platinum chloride in 20 ml of water was added a solution of 1.8 g of silver nitrate in 20 ml of water. This suspension was stirred in the dark for 3 hours and then filtered. To the filtrate was added a solution of 933 mg of 1,2,3-propanetricarboxylic acid in 5.3 ml of 2M potassium hydroxide. This mixture was stirred 1.5 hours and 390 mg of amorphous precipitate collected by filtration. The filtrate was concentrated to 10 ml and the solid collected by filtration giving an additional 1.23 g. These solids were combined, slurried in 25 ml of water and dried giving 1.03 g of the desired product.

Reference： [1]Patent: US4665210,1987,A

Yield	Reaction Conditions	Operation in experiment
		In the same manner as in Example 5 except that propane-1,2,3-tricarboxylic acid was used in place of cyclohexene-1,4-dicarboxylic acid and crude propane-1,2,3-tricarbonyl dichloride and propane-1,2,3-tri[N-carbonyl-L-alanine] were charged in amounts of 5.0 mmol and 3.47 mmol, respectively, the entitled compound was prepared. Yielded amount: 1.34 g (1.35 mmol). Yield based on propane-1,2,3-tricarboxylic acid: 17.4 %. H-NMR (deltappm, CDCl3): 1.40-1.70 (m, 27H), 2.70-3.30 (m, 1H), 2.40-2.70 (m, 4H), 2.82 (s, 18H), 2.90-3.20 (m, 12H), 4.18 (m, 3H), 5.70-6.10 (m, 12H).

68
[ 99-14-9 ]
dysprosium⁽³⁺⁾ [ No CAS ]
Dy tricarballylate [ No CAS ]