[ CAS No. 2419-56-9 ] {[proInfo.proName]}

Name: 2419-56-9|H-Glu(OtBu)-OH|98%
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2D 3D

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Quality Control of [ 2419-56-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2419-56-9 ]

SDS Specification

Alternatived Products of [ 2419-56-9 ]

Product Details of [ 2419-56-9 ]

CAS No. :	2419-56-9	MDL No. :	MFCD00038580
Formula :	C₉H₁₇NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OIOAKXPMBIZAHL-LURJTMIESA-N
M.W :	203.24	Pubchem ID :	7010573
Synonyms :	(S)-2-Amino-5-(tert-butoxy)-5-oxopentanoic acid	Chemical Name :	H-Glu(OtBu)-OH

Calculated chemistry of [ 2419-56-9 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.78
Num. rotatable bonds :	6
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	51.18
TPSA :	89.62 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) :	-9.23 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	-2.38
Log Po/w (WLOGP) :	0.52
Log Po/w (MLOGP) :	-1.79
Log Po/w (SILICOS-IT) :	0.17
Consensus Log Po/w :	-0.38

Druglikeness

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

Water Solubility

Log S (ESOL) :	0.8
Solubility :	1270.0 mg/ml ; 6.24 mol/l
Class :	Highly soluble
Log S (Ali) :	1.04
Solubility :	2210.0 mg/ml ; 10.9 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.66
Solubility :	44.7 mg/ml ; 0.22 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.42

Safety of [ 2419-56-9 ]

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 [ 2419-56-9 ]

* 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 [ 2419-56-9 ]
Downstream synthetic route of [ 2419-56-9 ]

[ 2419-56-9 ] Synthesis Path-Upstream 1~19

1
[ 3886-08-6 ]
[ 2419-56-9 ]

Reference： [1] Helvetica Chimica Acta, 2002, vol. 85, # 5, p. 1210 - 1245
[2] Justus Liebigs Annalen der Chemie, 1964, vol. 673, p. 196 - 207

2
[ 71989-18-9 ]
[ 2419-56-9 ]

Reference： [1] Patent: WO2011/19942, 2011, A2, . Location in patent: Page/Page column 31-32
[2] Chemical Communications, 2015, vol. 51, # 78, p. 14624 - 14627

3
[ 16874-06-9 ]
[ 2419-56-9 ]

Reference： [1] Organic Process Research and Development, 2004, vol. 8, # 1, p. 72 - 85

4
[ 71989-18-9 ]
[ 56-86-0 ]
[ 2419-56-9 ]

Reference： [1] Amino Acids, 2014, vol. 46, # 2, p. 367 - 374

5
[ 3967-18-8 ]
[ 2419-56-9 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1964, vol. 673, p. 196 - 207
[2] Journal of the American Chemical Society, 1965, vol. 87, p. 99 - 104

6
[ 62188-74-3 ]
[ 2419-56-9 ]

Reference： [1] Journal of Organic Chemistry, 1963, vol. 28, p. 1251 - 1253

7
[ 13030-09-6 ]
[ 2419-56-9 ]

Reference： [1] Journal of Organic Chemistry, 1963, vol. 28, p. 1251 - 1253

8
[ 16874-06-9 ]
[ 56-86-0 ]
[ 2419-56-9 ]
[ 45120-30-7 ]

Reference： [1] Patent: US2004/30177, 2004, A1, . Location in patent: Page 3
[2] Patent: US2004/30177, 2004, A1, . Location in patent: Page 4-5
[3] Patent: US2004/30177, 2004, A1, . Location in patent: Page 3
[4] Patent: US2004/30177, 2004, A1, . Location in patent: Page 4
[5] Patent: US2004/30177, 2004, A1, . Location in patent: Page 4-5
[6] Patent: US2004/30177, 2004, A1, . Location in patent: Page 3-4
[7] Patent: US2004/30177, 2004, A1, . Location in patent: Page 4
[8] Patent: US2004/30177, 2004, A1, . Location in patent: Page 4
[9] Patent: US2004/30177, 2004, A1, . Location in patent: Page 4
[10] Patent: US2004/30177, 2004, A1, . Location in patent: Page 4
[11] Patent: US2004/30177, 2004, A1, . Location in patent: Page 3-4

9
[ 32677-01-3 ]
[ 56-86-0 ]
[ 2419-56-9 ]
[ 45120-30-7 ]

Reference： [1] Patent: US2004/30177, 2004, A1, . Location in patent: Page 3

10
[ 56877-41-9 ]
[ 2419-56-9 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1964, vol. 673, p. 196 - 207

11
[ 115-11-7 ]
[ 2419-56-9 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 11, p. 2189 - 2191

12
[ 3705-42-8 ]
[ 2419-56-9 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1964, vol. 673, p. 196 - 207

13
[ 47709-87-5 ]
[ 2419-56-9 ]

Reference： [1] Helvetica chimica acta, 1968, vol. 51, # 4, p. 622 - 632

14
[ 24424-99-5 ]
[ 2419-56-9 ]
[ 13726-84-6 ]

Reference： [1] Patent: US2008/26017, 2008, A1, . Location in patent: Page/Page column 9

15
[ 16874-06-9 ]
[ 56-86-0 ]
[ 2419-56-9 ]
[ 45120-30-7 ]

16
[ 32677-01-3 ]
[ 56-86-0 ]
[ 2419-56-9 ]
[ 45120-30-7 ]

Reference： [1] Patent: US2004/30177, 2004, A1, . Location in patent: Page 3

17
[ 2419-56-9 ]
[ 82911-69-1 ]
[ 71989-18-9 ]

Reference： [1] Synthetic Communications, 2009, vol. 39, # 11, p. 2022 - 2031
[2] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 11, p. 2189 - 2191
[3] European Journal of Organic Chemistry, 2015, vol. 2015, # 17, p. 3767 - 3770

18
[ 2419-56-9 ]
[ 88744-04-1 ]
[ 71989-18-9 ]

Reference： [1] Synthesis, 1986, # 4, p. 303 - 305

19
[ 2419-56-9 ]
[ 102774-86-7 ]
[ 71989-18-9 ]

Reference： [1] Liebigs Annalen der Chemie, 1988, p. 1095 - 1098

[ 2419-56-9 ] Synthesis Path-Downstream 1~88

1
[ 18701-36-5 ]
[ 2419-56-9 ]
[ 47709-87-5 ]

Reference： [1]Helvetica chimica acta,1968,vol. 51,p. 622 - 632

2
[ 2188-18-3 ]
[ 2419-56-9 ]
N^α-tert.-Butyloxycarbonylnitroarginyl-γ-tert.-butyl-glutaminsaeure [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1965,vol. 87,p. 620 - 631

3
[ 2419-56-9 ]
[ 32886-55-8 ]
[ 45309-25-9 ]

Reference： [1]Journal of general chemistry of the USSR,1971,vol. 41,p. 425 - 427
Zhurnal Obshchei Khimii,1971,vol. 41,p. 433 - 436

4
[ 2419-56-9 ]
[ 4666-16-4 ]
[ 47793-84-0 ]

Reference： [1]Journal of general chemistry of the USSR,1971,vol. 41,p. 425 - 427
Zhurnal Obshchei Khimii,1971,vol. 41,p. 433 - 436

5
[ 2419-56-9 ]
[ 25474-85-5 ]
p-Methoxy-(-)-carbobenzoxy-Glu-γ-OBut [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1964,vol. 673,p. 196 - 207

6
[ 3886-08-6 ]
[ 2419-56-9 ]

Reference： [1]Helvetica Chimica Acta,2002,vol. 85,p. 1210 - 1245
[2]Justus Liebigs Annalen der Chemie,1964,vol. 673,p. 196 - 207

7
[ 62188-74-3 ]
[ 2419-56-9 ]

Reference： [1]Journal of Organic Chemistry,1963,vol. 28,p. 1251 - 1253

8
[ 2419-56-9 ]
[ 7669-54-7 ]
[ 13155-43-6 ]

Reference： [1]Journal of the American Chemical Society,1965,vol. 87,p. 99 - 104

9
[ 47709-87-5 ]
[ 2419-56-9 ]

Reference： [1]Helvetica chimica acta,1968,vol. 51,p. 622 - 632

10
[ 3967-18-8 ]
[ 2419-56-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1964,vol. 673,p. 196 - 207
[2]Journal of the American Chemical Society,1965,vol. 87,p. 99 - 104

11
(S)-2-(2-Nitro-phenylsulfanylamino)-pentanedioic acid 5-tert-butyl ester; compound with dicyclohexyl-amine [ No CAS ]
[ 2419-56-9 ]

Reference： [1]Journal of the American Chemical Society,1965,vol. 87,p. 99 - 104

12
[ 7763-16-8 ]
[ 2419-56-9 ]
[ 110484-40-7 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 361 - 370
[2]Liebigs Annalen der Chemie,1990,p. 249 - 252
[3]Zeitschrift fur Naturforschung, B: Chemical Sciences,1993,vol. 48,p. 1000 - 1008

13
[ 2419-56-9 ]
[ 59938-06-6 ]
[ 133992-77-5 ]

Reference： [1]Synthesis,1991,p. 207 - 209

14
[ 2419-56-9 ]
[ 10068-65-2 ]
[ 138541-09-0 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 361 - 370

15
[ 2419-56-9 ]
[ 102774-86-7 ]
[ 71989-18-9 ]

Reference： [1]Liebigs Annalen der Chemie,1988,p. 1095 - 1098

16
[ 2419-56-9 ]
[ 88744-04-1 ]
[ 71989-18-9 ]

Reference： [1]Synthesis,1986,p. 303 - 305

17
[ 2419-56-9 ]
[ 86061-00-9 ]
[ 143038-31-7 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062

18
[ 2419-56-9 ]
[ 116869-01-3 ]
[ 138296-33-0 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 8001 - 8024

19
[ 2419-56-9 ]
[ 109636-25-1 ]
[ 143038-25-9 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062

20
[ 2419-56-9 ]
[ 53666-01-6 ]
[ 5868-49-5 ]

Reference： [1]Zeitschrift fur Chemie,1980,vol. 20,p. 415 - 416

21
[ 2419-56-9 ]
[ 95485-01-1 ]
[ 95485-00-0 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 660 - 667

22
[ 2419-56-9 ]
Z-Lys(Z)-OSu [ No CAS ]
[ 78075-55-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 819 - 830

23
[ 2419-56-9 ]
[ 143038-34-0 ]
[ 53665-58-0 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062

24
[ 2419-56-9 ]
[ 3391-99-9 ]
[ 78346-78-8 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 2953 - 2968

25
3,5-dioxopiperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester [ No CAS ]
[ 2419-56-9 ]
[ 811450-62-1 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4483 - 4485

26
[ 2419-56-9 ]
[ 78269-85-9 ]
Teoc-Glu(O^δ-t-Bu)OH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In 1,4-dioxane; water; at 20℃;	To a stirred solution of G1 - tBa)~OH (2.089 g, 0.28 tmxoi) and trie&yl amine (0.2,15 mL, 15.43 ramol) in J : 1 .Dioxane:water (v v) (31 mL) Teoc-OSa (3,2 g, 12.34 tnmo) vvss added in one portion. The mixture i. stirred at room .temperature overnight, then diluted with water (15 mL), acidified "with 4 HQ and 1 N HCJ, nd extracted vvfth ethyl acetate (3 40 mL). The combined organic layers are washed with brine (60 mL), dried with magnesium sulfate, filtered and evaporated to gi ve a erode oil (3,451 g, 96.6% yield) and dried overnight

Reference： [1]Organic Letters,2004,vol. 6,p. 4483 - 4485
[2]Patent: WO2018/31809,2018,A1 .Location in patent: Paragraph 0130-0131

27
[ 2419-56-9 ]
[ 81-30-1 ]
(S)-2-[7-((S)-3-tert-butoxycarbonyl-1-carboxy-propyl)-1,3,6,8-tetraoxo-3,6,7,8-tetrahydro-1H-benzo[lmn][3,8]phenanthrolin-2-yl]-pentanedioic acid 5-tert-butyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 7063 - 7066

28
[ 2419-56-9 ]
[ 873201-21-9 ]

Yield	Reaction Conditions	Operation in experiment
20%	With hydrogen bromide; potassium bromide; sodium nitrite; In water; at 0℃; for 3h;	A solution Of NaNO2 (1.35 g; 19.6 mmol) in water (15 mL) was added dropwise over 30 min to a mixture of L-glutamic acid 5-utyl ester 1 (commercial product) (2.0 g; 9.8 mmol) and KBr (4.31 g; 36.0 mmol) in 1 N HBr (45 mL) cooled to O0C. After 3 h at O0C the solution was extracted with EtOAc (3 x 100 mL). The combined organic phases were washed with brine (80 mL), dried (Na2SO4) and evaporated under reduced pressure. The crude product was purified by column chromatography to give (0.53 g) 2 as a colourless oil. Yield 20%.

Reference： [1]Patent: WO2006/2873,2006,A2 .Location in patent: Page/Page column 82

29
[ 24424-99-5 ]
[ 2419-56-9 ]
[ 13726-84-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In 1,4-dioxane; at 20℃; for 20h;	To a solution of Glu (O-t-Bu) in saturated sodium bicarbonate solution was added a solution of di-t-butyl pyrocarbonate in dioxane and the mixture was stirred at room temperature for about 20 hrs. Dioxane was removed from the reaction mixture. The aqueous solution was acidified with 10% KHSO4 solution and the liberated Boc-Glu (O-t-Bu) was extracted into ethyl acetate. The ethyl acetate solution was washed with water, dried and concentrated. Precipitation was done using petroleum ether (60-800).

Reference： [1]Patent: US2008/26017,2008,A1 .Location in patent: Page/Page column 9

30
[ 2419-56-9 ]
[ 83896-44-0 ]
C₆₀H₉₂N₂O₂₂ [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2006,vol. 32,p. 595 - 601

31
[ 186581-53-3 ]
[ 2419-56-9 ]
[ 53838-27-0 ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2006,vol. 32,p. 595 - 601

32
[ 36653-82-4 ]
[ 2419-56-9 ]
[ 929697-37-0 ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2006,vol. 32,p. 407 - 412

33
[ 2419-56-9 ]
[ 929697-44-9 ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2006,vol. 32,p. 407 - 412

34
[ 2419-56-9 ]
5-hexadecyl N-(ornithyl)glutamate trifluoroacetate [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2006,vol. 32,p. 407 - 412

35
[ 2419-56-9 ]
C₅₄H₈₀N₂O₂₂ [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2006,vol. 32,p. 595 - 601

36
[ 2419-56-9 ]
[ 948913-76-6 ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2006,vol. 32,p. 595 - 601

37
[ 2419-56-9 ]
C₅₂H₇₆N₂O₂₂ [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2006,vol. 32,p. 595 - 601

38
[ 2419-56-9 ]
5-[5-(1-methoxycarbonyl-2-phenyl-ethylamino)-3-oxo-3,6-dihydro-2<i>H</i>-pyridin-1-yl]-5-oxo-4-(2-trimethylsilanyl-ethoxycarbonylamino)-pentanoic acid <i>tert</i>-butyl ester [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4483 - 4485

39
[ 2419-56-9 ]
[ 890660-21-6 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 2953 - 2968

40
[ 2419-56-9 ]
[ 890660-20-5 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 2953 - 2968

41
[ 2419-56-9 ]
(S)-4-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-4-{(S)-1-[(S)-1-((E)-2-methanesulfonyl-vinyl)-3-methyl-butylcarbamoyl]-ethylcarbamoyl}-butyric acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 2953 - 2968

42
[ 2419-56-9 ]
2-(4-nitrophenylsulfonyl)ethoxycarbonyl-Glu(Ot-Bu)-OH (Nsc-Glu(Ot-Bu)-OH) [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 7821 - 7824

43
[ 2419-56-9 ]
[ 110484-41-8 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062
[2]Liebigs Annalen der Chemie,1992,p. 361 - 370
[3]Liebigs Annalen der Chemie,1990,p. 249 - 252

44
[ 2419-56-9 ]
[ 50715-11-2 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062

45
[ 2419-56-9 ]
[ 143038-33-9 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062

46
[ 2419-56-9 ]
[ 143063-36-9 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062

47
[ 2419-56-9 ]
[ 143063-35-8 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062

48
[ 2419-56-9 ]
[ 143038-35-1 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062

49
[ 2419-56-9 ]
[ 143038-32-8 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062

50
[ 2419-56-9 ]
[ 143063-31-4 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062

51
[ 2419-56-9 ]
[ 143038-19-1 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062

52
[ 2419-56-9 ]
[ 143038-29-3 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062

53
[ 2419-56-9 ]
[ 143038-18-0 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062

54
[ 2419-56-9 ]
[ 143038-30-6 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1055 - 1062

55
[ 2419-56-9 ]
[ 77753-37-8 ]

Reference： [1]Zeitschrift fur Chemie,1980,vol. 20,p. 415 - 416

56
[ 2419-56-9 ]
[ 52799-42-5 ]

Reference： [1]Zeitschrift fur Chemie,1980,vol. 20,p. 415 - 416

57
[ 2419-56-9 ]
[ 14485-95-1 ]

Reference： [1]Zeitschrift fur Chemie,1980,vol. 20,p. 415 - 416

58
[ 2419-56-9 ]
[ 52799-43-6 ]

Reference： [1]Zeitschrift fur Chemie,1980,vol. 20,p. 415 - 416

59
[ 2419-56-9 ]
[ 78075-56-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 819 - 830

60
[ 2419-56-9 ]
[ 78075-57-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 819 - 830

61
[ 2419-56-9 ]
(S)-4-Azidocarbonyl-4-((S)-2,6-bis-benzyloxycarbonylamino-hexanoylamino)-butyric acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 819 - 830

62
[ 2419-56-9 ]
[ 52799-45-8 ]

Reference： [1]Zeitschrift fur Chemie,1980,vol. 20,p. 415 - 416

63
[ 2419-56-9 ]
[ 77753-38-9 ]

Reference： [1]Zeitschrift fur Chemie,1980,vol. 20,p. 415 - 416

64
[ 2419-56-9 ]
[ 73809-01-5 ]

Reference： [1]Zeitschrift fur Chemie,1980,vol. 20,p. 415 - 416
[2]Zeitschrift fur Chemie,1980,vol. 20,p. 415 - 416

65
[ 2419-56-9 ]
[ 138541-11-4 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 361 - 370
[2]Liebigs Annalen der Chemie,1992,p. 361 - 370

66
[ 2419-56-9 ]
Z-L-Thr(tBu)-L-Glu(OtBu)-OSu [ No CAS ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 361 - 370

67
[ 2419-56-9 ]
[ 110484-31-6 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 361 - 370

68
[ 2419-56-9 ]
[ 138541-07-8 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 361 - 370

69
[ 2419-56-9 ]
H-L-Gln-L-Glu(OtBu)-L-Lys(Boc)-OPh*HCl [ No CAS ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 361 - 370

70
[ 2419-56-9 ]
[ 138541-08-9 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 361 - 370
[2]Liebigs Annalen der Chemie,1992,p. 361 - 370

71
[ 2419-56-9 ]
[ 138541-28-3 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 361 - 370
[2]Liebigs Annalen der Chemie,1992,p. 361 - 370

72
[ 2419-56-9 ]
[ 138541-12-5 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 361 - 370
[2]Liebigs Annalen der Chemie,1992,p. 361 - 370

73
[ 2419-56-9 ]
[ 133992-83-3 ]

Reference： [1]Synthesis,1991,p. 207 - 209

74
[ 2419-56-9 ]
[ 86061-04-3 ]

Reference： [1]Synthesis,1986,p. 303 - 305

75
[ 2419-56-9 ]
[ 110484-43-0 ]

Reference： [1]Liebigs Annalen der Chemie,1990,p. 249 - 252

76
[ 2419-56-9 ]
[ 110484-45-2 ]

Reference： [1]Liebigs Annalen der Chemie,1990,p. 249 - 252

77
[ 2419-56-9 ]
[ 110484-42-9 ]

Reference： [1]Liebigs Annalen der Chemie,1990,p. 249 - 252

78
[ 2419-56-9 ]
[ 110484-44-1 ]

Reference： [1]Liebigs Annalen der Chemie,1990,p. 249 - 252

79
[ 2419-56-9 ]
[ 110484-34-9 ]

Reference： [1]Liebigs Annalen der Chemie,1990,p. 249 - 252

80
[ 2419-56-9 ]
[ 32886-58-1 ]

Reference： [1]Journal of general chemistry of the USSR,1971,vol. 41,p. 425 - 427
Zhurnal Obshchei Khimii,1971,vol. 41,p. 433 - 436

81
[ 13030-09-6 ]
[ 2419-56-9 ]

Reference： [1]Journal of Organic Chemistry,1963,vol. 28,p. 1251 - 1253

82
[ 3705-42-8 ]
[ 2419-56-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1964,vol. 673,p. 196 - 207

83
[ 56877-41-9 ]
[ 2419-56-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1964,vol. 673,p. 196 - 207

84
[ 32677-01-3 ]
[ 56-86-0 ]
[ 2419-56-9 ]
[ 45120-30-7 ]

Yield	Reaction Conditions	Operation in experiment
	With water; sodium acetate; at 50℃; for 25h;pH 4.9;Conversion of starting material;	[0036] A reaction mixture containing 670 mM of L-glu-di-tert-butyl ester HCl and 2 mole equivalents of sodium acetate, pH 4.9, was stirred in a round bottomed flask fitted with a condenser and Therm-o-watch [12R, Cheltenhana, Pa.], at 50 C. Samples were taken over time intervals and analyzed by HPLC for L-glu-alpha-tert-butyl ester alpha-monoester), L-glu-gamma-tert-butyl ester (gamma-monoester), L-glu-di-tert-butyl esters (diester) and L-glutamic acid (diacid). [0037] The results which are present in TABLE I show that under the reaction condition set forth above, approximately half of the substrate (diester) was hydrolyzed within 25 hours. The product of the hydrolytic reaction included alpha-monoester, gamma-monoester, and diacid. However, gamma-monoester was predominant, indicating that the hydrolysis was selective for the alpha-ester group.

Reference： [1]Patent: US2004/30177,2004,A1 .Location in patent: Page 3

85
[ 16874-06-9 ]
[ 56-86-0 ]
[ 2419-56-9 ]
[ 45120-30-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; sodium acetate; for 20 - 24h;pH 4.7 - 5.0;Conversion of starting material;	[0038] Two reaction mixtures were prepared by adding 2.0 mL of 200 g/L of L-glu-di-tert-butyl ester free base as substrate, to a reaction vessel. Then 2.10 g of solid sodium acetate (NaOAc.3H2O) was added with about 5.0 mL of water. The pH of the first reaction mixture was adjusted to a pH of about 4.7 to about 5.0 using concentrated hydrochloric acid (HCl). The pH of the second reaction mixture was adjusted to a pH of about 4.8 with concentrated sulfuric acid (H2SO4). The volume of each mixture was adjusted to 10 mL. At about 20 to 24 hours, the samples of the reaction mixture were analyzed. The results shown in TABLE II indicate that L-glu-di-tert-butyl ester free base could be used as the substrate for the non-enzyme hydrolysis method. Although at 20 to 24 hours, the conversion of the diester was not complete, the conversion resulted mainly in gamma-monoester. The percent conversion to gamma-monoester reached 42.32% for the first reaction mixture and 42.55% for the second mixture.
	With potassium phosphate; water; at 40℃; for 46h;pH 5.5 - 6.5;Conversion of starting material;	[0042] Four sets of reactions were initiated by mixing 30 mM of L-glu-di-tert-butyl ester with 100 mM of potassium phosphate (3 sets) or sodium acetate (1 set). The pH of the first 3 sets of the reaction was adjusted to 6.5, 6.0, and 5.5, while the pH of the last set was adjusted to 5.5. The reactions were run at a temperature of 40 C. for about 46 hours. Samples were taken at various intervals and analyzed. The results which are presented in TABLE VI, generally indicate that under the specified reaction condition, L-glu-di-tert-butyl ester was converted to mainly gamma-monoester and a small amount of alpha-monoester, and L-glu (diacid). The data further indicates that in the presence of potassium phosphate, the percent conversion of the diester to gamma-monoester increased from 48.56% to 92.45% with the increased pH from pH 5.5 to 6.5. However, when sodium acetate was used in place of potassium phosphate, the percent conversion was high (93.53%) at a lower pH (5.5).
	With sulfuric acid; water; sodium acetate; for 20 - 24h;pH 4.8;Conversion of starting material;	[0038] Two reaction mixtures were prepared by adding 2.0 mL of 200 g/L of L-glu-di-tert-butyl ester free base as substrate, to a reaction vessel. Then 2.10 g of solid sodium acetate (NaOAc.3H2O) was added with about 5.0 mL of water. The pH of the first reaction mixture was adjusted to a pH of about 4.7 to about 5.0 using concentrated hydrochloric acid (HCl). The pH of the second reaction mixture was adjusted to a pH of about 4.8 with concentrated sulfuric acid (H2SO4). The volume of each mixture was adjusted to 10 mL. At about 20 to 24 hours, the samples of the reaction mixture were analyzed. The results shown in TABLE II indicate that L-glu-di-tert-butyl ester free base could be used as the substrate for the non-enzyme hydrolysis method. Although at 20 to 24 hours, the conversion of the diester was not complete, the conversion resulted mainly in gamma-monoester. The percent conversion to gamma-monoester reached 42.32% for the first reaction mixture and 42.55% for the second mixture.

	With water; sodium acetate; at 50℃; for 43 - 65h;pH 5.0;Conversion of starting material;	[0041] Three reaction mixtures were prepared with 340 mM of L-glu-di-tert-butyl ester free base as substrate. The first mixture further contained 1×(=340 mM) sodium acetate, the second mixture contained 1.5×(=510 mM) sodium acetate, and the third mixture contained 2×(=680 mM) sodium acetate. The reactions were run with the pH adjusted to 5.0 and the reaction temperature was maintained at 50 C. The reactions were run for about 43 to about 65 hours. The results shown in TABLE V indicate that the conversion of the diester to gamma-monoester depended on the concentration of sodium acetate. The addition of 1× concentration of sodium acetate resulted in the conversion of diester to mainly diacid and gamma-monoester. The amount of diacid recovered was about twice as much as the amount of gamma-monoester. The addition of 1.5× concentration of sodium acetate resulted in a higher percent conversion to gamma-monoester, and the addition of 2× concentration of sodium acetate resulted in the a highest percent conversion to gamma-monoester, (83.47%).
	With water; sodium acetate; at 40℃; for 46h;pH 5.5;Conversion of starting material;	[0042] Four sets of reactions were initiated by mixing 30 mM of L-glu-di-tert-butyl ester with 100 mM of potassium phosphate (3 sets) or sodium acetate (1 set). The pH of the first 3 sets of the reaction was adjusted to 6.5, 6.0, and 5.5, while the pH of the last set was adjusted to 5.5. The reactions were run at a temperature of 40 C. for about 46 hours. Samples were taken at various intervals and analyzed. The results which are presented in TABLE VI, generally indicate that under the specified reaction condition, L-glu-di-tert-butyl ester was converted to mainly gamma-monoester and a small amount of alpha-monoester, and L-glu (diacid). The data further indicates that in the presence of potassium phosphate, the percent conversion of the diester to gamma-monoester increased from 48.56% to 92.45% with the increased pH from pH 5.5 to 6.5. However, when sodium acetate was used in place of potassium phosphate, the percent conversion was high (93.53%) at a lower pH (5.5).
	With water; sodium acetate; at 40℃; for 46h;Conversion of starting material;	[0039] Eight reaction mixtures were prepared with different amounts of L-glu-di-tert-butyl ester free base (diester) as substrate. The mixtures were divided into two groups. Different amounts of sodium acetate were added into the mixtures in the first group. No sodium acetate was added to the mixtures in the second group. The reactions were run at 40 C. for about 46 hours. The results in TABLE III show generally that in the absence of sodium acetate, the conversion of the diester was complete in 46 hours. However, most of the conversion resulted in the diacid. The percent conversion of the diester into gamma-monoester was relatively low, but slightly increased with the decreasing concentrations of the substrate. The data in TABLE III also show that, in the presence of sodium acetate, the conversion of the diester was almost complete at 46 hours. Only relatively small amounts of the diester remained. The conversion resulted mainly in the production of gamma-monoester indicating selective hydrolysis. The increased amounts of the substrate and sodium acetate had little effect on the percent conversion of the diester to gamma-monoester.
	With water; for 24h;pH 5.5;Aqueous sodium acetate buffer;Conversion of starting material;	[0040] Four reaction mixtures were each prepared by adding 100 mg/L of L-glu-di-tert-butyl ester (diester) as substrate, to 340 mM of one of four different buffers. The substrate was first prepared by mixing 2.0 g of the diester with 10 ml of water. To each vial, 2 mL of the diester solution was added, followed by 1.36 mL of 1M buffer and 640 muL of water. The four different buffers were sodium citrate, sodium succinate, sodium formate and sodium acetate. Sodium citrate was prepared by titration of citric acid and sodium hydroxide to a pH 5.5. Sodium succinate was prepared by titration of succinic acid and sodium hydroxide to a pH 5.5. Sodium formate was prepared by titration of formic acid with sodium hydroxide to a pH of 5.5. The reaction was run for 24 hours. The results in TABLE IV indicate that all the non-enzyme additives tested had similar effects on the percent conversion of the diester gamma-monoester. The conversion to alpha-monoester was minimal when the reaction was run in the presence of sodium citrate and sodium formate. On the other hand, in the presence of sodium succinate or sodium acetate, the conversion to alpha-monoester was relatively high in this particular experiment. Nevertheless, selective hydrolysis of the alpha-ester group was evidenced by the % conversion to gamma-monoester. After 24 hours, the percent conversion ranged from 59.91% to 65.70%.
	With water; for 24h;pH 5.5;Aqueous sodium citrate buffer;Conversion of starting material;	[0040] Four reaction mixtures were each prepared by adding 100 mg/L of L-glu-di-tert-butyl ester (diester) as substrate, to 340 mM of one of four different buffers. The substrate was first prepared by mixing 2.0 g of the diester with 10 ml of water. To each vial, 2 mL of the diester solution was added, followed by 1.36 mL of 1M buffer and 640 muL of water. The four different buffers were sodium citrate, sodium succinate, sodium formate and sodium acetate. Sodium citrate was prepared by titration of citric acid and sodium hydroxide to a pH 5.5. Sodium succinate was prepared by titration of succinic acid and sodium hydroxide to a pH 5.5. Sodium formate was prepared by titration of formic acid with sodium hydroxide to a pH of 5.5. The reaction was run for 24 hours. The results in TABLE IV indicate that all the non-enzyme additives tested had similar effects on the percent conversion of the diester gamma-monoester. The conversion to alpha-monoester was minimal when the reaction was run in the presence of sodium citrate and sodium formate. On the other hand, in the presence of sodium succinate or sodium acetate, the conversion to alpha-monoester was relatively high in this particular experiment. Nevertheless, selective hydrolysis of the alpha-ester group was evidenced by the % conversion to gamma-monoester. After 24 hours, the percent conversion ranged from 59.91% to 65.70%.
	With water; for 24h;pH 5.5;Aqueous sodium formate buffer;Conversion of starting material;	[0040] Four reaction mixtures were each prepared by adding 100 mg/L of L-glu-di-tert-butyl ester (diester) as substrate, to 340 mM of one of four different buffers. The substrate was first prepared by mixing 2.0 g of the diester with 10 ml of water. To each vial, 2 mL of the diester solution was added, followed by 1.36 mL of 1M buffer and 640 muL of water. The four different buffers were sodium citrate, sodium succinate, sodium formate and sodium acetate. Sodium citrate was prepared by titration of citric acid and sodium hydroxide to a pH 5.5. Sodium succinate was prepared by titration of succinic acid and sodium hydroxide to a pH 5.5. Sodium formate was prepared by titration of formic acid with sodium hydroxide to a pH of 5.5. The reaction was run for 24 hours. The results in TABLE IV indicate that all the non-enzyme additives tested had similar effects on the percent conversion of the diester gamma-monoester. The conversion to alpha-monoester was minimal when the reaction was run in the presence of sodium citrate and sodium formate. On the other hand, in the presence of sodium succinate or sodium acetate, the conversion to alpha-monoester was relatively high in this particular experiment. Nevertheless, selective hydrolysis of the alpha-ester group was evidenced by the % conversion to gamma-monoester. After 24 hours, the percent conversion ranged from 59.91% to 65.70%.
	With water; for 24h;pH 5.5;Aqueous sodium succinate buffer;Conversion of starting material;	[0040] Four reaction mixtures were each prepared by adding 100 mg/L of L-glu-di-tert-butyl ester (diester) as substrate, to 340 mM of one of four different buffers. The substrate was first prepared by mixing 2.0 g of the diester with 10 ml of water. To each vial, 2 mL of the diester solution was added, followed by 1.36 mL of 1M buffer and 640 muL of water. The four different buffers were sodium citrate, sodium succinate, sodium formate and sodium acetate. Sodium citrate was prepared by titration of citric acid and sodium hydroxide to a pH 5.5. Sodium succinate was prepared by titration of succinic acid and sodium hydroxide to a pH 5.5. Sodium formate was prepared by titration of formic acid with sodium hydroxide to a pH of 5.5. The reaction was run for 24 hours. The results in TABLE IV indicate that all the non-enzyme additives tested had similar effects on the percent conversion of the diester gamma-monoester. The conversion to alpha-monoester was minimal when the reaction was run in the presence of sodium citrate and sodium formate. On the other hand, in the presence of sodium succinate or sodium acetate, the conversion to alpha-monoester was relatively high in this particular experiment. Nevertheless, selective hydrolysis of the alpha-ester group was evidenced by the % conversion to gamma-monoester. After 24 hours, the percent conversion ranged from 59.91% to 65.70%.
	With water; at 40℃; for 46h;Conversion of starting material;	[0039] Eight reaction mixtures were prepared with different amounts of L-glu-di-tert-butyl ester free base (diester) as substrate. The mixtures were divided into two groups. Different amounts of sodium acetate were added into the mixtures in the first group. No sodium acetate was added to the mixtures in the second group. The reactions were run at 40 C. for about 46 hours. The results in TABLE III show generally that in the absence of sodium acetate, the conversion of the diester was complete in 46 hours. However, most of the conversion resulted in the diacid. The percent conversion of the diester into gamma-monoester was relatively low, but slightly increased with the decreasing concentrations of the substrate. The data in TABLE III also show that, in the presence of sodium acetate, the conversion of the diester was almost complete at 46 hours. Only relatively small amounts of the diester remained. The conversion resulted mainly in the production of gamma-monoester indicating selective hydrolysis. The increased amounts of the substrate and sodium acetate had little effect on the percent conversion of the diester to gamma-monoester.

Reference： [1]Patent: US2004/30177,2004,A1 .Location in patent: Page 3
[2]Patent: US2004/30177,2004,A1 .Location in patent: Page 4-5
[3]Patent: US2004/30177,2004,A1 .Location in patent: Page 3
[4]Patent: US2004/30177,2004,A1 .Location in patent: Page 4
[5]Patent: US2004/30177,2004,A1 .Location in patent: Page 4-5
[6]Patent: US2004/30177,2004,A1 .Location in patent: Page 3-4
[7]Patent: US2004/30177,2004,A1 .Location in patent: Page 4
[8]Patent: US2004/30177,2004,A1 .Location in patent: Page 4
[9]Patent: US2004/30177,2004,A1 .Location in patent: Page 4
[10]Patent: US2004/30177,2004,A1 .Location in patent: Page 4
[11]Patent: US2004/30177,2004,A1 .Location in patent: Page 3-4

86
carbobenzyloxy-L-isoleucine succinate ester [ No CAS ]
[ 2419-56-9 ]
[ 78346-78-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	With triethylamine; In tetrahydrofuran; water; at 20℃; for 16h;	Carbobenzyloxy-L-isoleucine succinate ester (2.17 g, 6.0 mmol), L-glutamic acid y-t-butyl ester (1.22 g, 6.0 mmol) and triethylamine (1.67 mL, 12.0 mmol) were stirred at ambient temperature in a mixture [OF THF] (98 mL) and water (9 mL) for 16 hr. The reaction mixture was poured into 0.2N aqueous HCl (200 mL) and extracted twice with dichloromethane. The combined organic phase was washed with water and brine, then dried over anhydrous magnesium sulfate. Filtration and solvent evaporation gave a sticky white foam that was triturated with a mixture of diethyl ether (15 mL) and n-hexane (20 mL). The white precipitate was collected and dried to give 1.84g [OF 2- (2-BENZYLOXYCARBONYLAMINO-3-METHYLPENTANOYLAMINO)-] pentanedioic acid 5-tert-butyl ester (68% yield).

Reference： [1]Patent: WO2004/14882,2004,A2 .Location in patent: Page 46-47

87
[ 108-55-4 ]
[ 6066-82-6 ]
[ 2419-56-9 ]
C₂₂H₂₉N₃O₁₁ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;dmap; In N,N-dimethyl-formamide; for 2.08333h;	L-glutamic acid gamma-t-butyl ester 12 (10.0 g, 49.2 mmol) and succinic anhydride (6.40 g, 64.0 mmol) and catalytic 4-dimethylaminopyridine (100 mg) were stirred in DMF (200 mL) for 15 hours. 1-(3-Dimethylaminopropyl)-3-ethylcardiimide hydrochloride (EDC, 25 g, 13.0 mmol) was added and continued to stir for 5 minutes, then N-hydroxysuccinimide (NHS, 15.5 g, 13.0 mmol) was added and continued to stir for 2 hours (coupling). The solvent was removed by rotary evaporation. The residue was redissolved in DCM (200 mL) and extracted two times from water. Organic phases were combined, dried with anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation. The compound 16 (13.5 g, 27.2 mmol, 55%) was obtained after silica gel column purification with ethylacetate as an eluent (TLC, Rf=0.5).

Reference： [1]Patent: US2006/263328,2006,A1 .Location in patent: Page/Page column 8

88
[ 2419-56-9 ]
4-carbamoyl-4-[4-(pyrimidin-2-ylamino)-benzoylamino]-butyric acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%		4-(Pyrimidin-2-ylamino)-benzoic acid (1.80 g, 8.4 mmol, 1 equiv.) and EDCI (2.41 g, 12.6 mmol, 1.5 equiv.) were dissolved in DMF (60 mL) under N2. The mixture was stirred at room temperature for 20 minutes, followed by the addition of H-Glu (OtBu)-NH2 (2 g, 8.4 mmol, 1 equiv), Et3N (2.92 mL, 20.9 mmol, 2.5 equiv.), and DMAP (0.512 g, 4.2 mmol, 0.5 equiv). The mixture was allowed to stir at room temperature overnight. Reaction was complete as determined by TLC. DMF was removed by rotovap and the residue was dissolved in EtOAc. The organic layer was washed with brine and dried over MgSO4. Most of the solvent was removed by rotavap and a solid was precipitated from the mixture during solvent evaporation. The solid was collected by filtration and washed with EtOAc. 823 mg of 4-Carbamoyl-4-[4-(pyrimidin-2-ylamino)-benzoylamino]-butyric acid tert-butyl ester was obtained in 25% yield. MS (ESI) m/z 400.

Reference： [1]Patent: US2007/43066,2007,A1 .Location in patent: Page/Page column 38

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H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 2419-56-9 ] {[proInfo.proName]}

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[ 2419-56-9 ] Synthesis Path-Upstream 1~19

[ 2419-56-9 ] Synthesis Path-Downstream 1~88

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Amino Acid Derivatives

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[ 2419-56-9 ]