[ CAS No. 4313-73-9 ] {[proInfo.proName]}

Name: 4313-73-9|Z-Phe-Leu-OH|95%
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SKU: A156779
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2D 3D

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Quality Control of [ 4313-73-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4313-73-9 ]

SDS Specification

Alternatived Products of [ 4313-73-9 ]

Product Details of [ 4313-73-9 ]

CAS No. :	4313-73-9	MDL No. :	MFCD00038301
Formula :	C₂₃H₂₈N₂O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	412.48	Pubchem ID :	-
Synonyms :	NSC 334018

Calculated chemistry of [ 4313-73-9 ]

Physicochemical Properties

Num. heavy atoms :	30
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.35
Num. rotatable bonds :	13
Num. H-bond acceptors :	5.0
Num. H-bond donors :	3.0
Molar Refractivity :	113.21
TPSA :	104.73 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.56
Log Po/w (XLOGP3) :	3.24
Log Po/w (WLOGP) :	2.99
Log Po/w (MLOGP) :	2.55
Log Po/w (SILICOS-IT) :	3.25
Consensus Log Po/w :	2.92

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.88
Solubility :	0.0548 mg/ml ; 0.000133 mol/l
Class :	Soluble
Log S (Ali) :	-5.11
Solubility :	0.00318 mg/ml ; 0.00000771 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.08
Solubility :	0.000347 mg/ml ; 0.000000841 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.84

Safety of [ 4313-73-9 ]

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 [ 4313-73-9 ]

* 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.

Downstream synthetic route of [ 4313-73-9 ]

[ 4313-73-9 ] Synthesis Path-Downstream 1~86

1
[ 3850-45-1 ]
[ 4313-73-9 ]

Yield	Reaction Conditions	Operation in experiment
89.3%	With lithium hydroxide; In methanol; water;Cooling with ice;	General procedure: To a solution of compound 9 (5 mmol) in methanol (50 mL) cooledwith an ice bath was added lithium hydroxide solution (2 M, 50 mL). The mixturewas stirred for 6h, then was acidified to pH 2-3 with hydrochloric acid. Thesolution was concentrated to about halfvolume, then extracted with dichloromethane 3 times (3×50mL).The combined organic layers were dried over anhydrous Na2SO4.After filtration, the filtrate was concentrated to dryness, giving compounds 10. (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-phenylpropanoicacid (10a). Yield: 91.2%.
	With lithium hydroxide; In tetrahydrofuran; at 20℃; for 16h;	General procedure: The methyl ester (1 equiv.) was dissolved in THF (100 mM). The solution was stirred at 0 C for15 mins. 1M LiOH (5 equiv.) was added slowly to the solution. The mixture was stirred vigorouslyat room temperature for 16 hrs. The mixture was diluted with ethyl acetate and acidified to pH 7with 2M HCl. The aqueous layer was extracted with ethyl acetate (2×25 mL). The combinedorganic layer was washed with brine and dried over sodium sulphate. The solvent was removed invacuo to give the crude product. For details, see individual experiments.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3103 - 3108
[2]Journal of Organic Chemistry,2005,vol. 70,p. 8730 - 8733
[3]Tetrahedron, Supplement,1966,vol. 8,p. 321 - 340
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 740 - 743
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 740 - 743
[6]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 740 - 743
[7]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 436 - 441

2
[ 71274-25-4 ]
[ 4313-73-9 ]

Reference： [1]Chemische Berichte,1979,vol. 112,p. 2145 - 2157
[2]Liebigs Annalen der Chemie,1983,p. 1859 - 1885

3
[ 61-90-5 ]
[ 2578-84-9 ]
[ 4313-73-9 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 784 - 785
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 877 - 878

4
[ 61-90-5 ]
[ 60746-24-9 ]
[ 4313-73-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1993,vol. 66,p. 1566 - 1568

5
[ 61-90-5 ]
[ 35909-92-3 ]
[ 4313-73-9 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 3709 - 3710

6
[ 61-90-5 ]
[ 7663-85-6 ]
[ 4313-73-9 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 3709 - 3710

7
[ 61-90-5 ]
[ 84758-92-9 ]
[ 4313-73-9 ]

Reference： [1]Tetrahedron Letters,1982,vol. 23,p. 3831 - 3834

8
[ 4313-73-9 ]
[ 2462-32-0 ]
[ 80174-69-2 ]
[ 80174-70-5 ]

Reference： [1]Tetrahedron,1983,vol. 39,p. 61 - 66

9
[ 4313-73-9 ]
[ 71989-43-0 ]
[ 115141-39-4 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1891 - 1897

10
[ 69193-13-1 ]
[ 4313-73-9 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 740 - 743
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 740 - 743

11
[ 4313-73-9 ]
[ 541-41-3 ]
C₂₆H₃₂N₂O₇ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 86 - 93
[2]Journal of Medicinal Chemistry,1993,vol. 36,p. 1084 - 1089
[3]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3520 - 3526

12
[ 71274-31-2 ]
[ 4313-73-9 ]

Reference： [1]Liebigs Annalen der Chemie,1983,p. 1859 - 1885

13
[ 70363-50-7 ]
[ 4313-73-9 ]

Reference： [1]Tetrahedron,1983,vol. 39,p. 61 - 66

14
[ 4313-73-9 ]
[ 109-78-4 ]
[ 125816-02-6 ]

Reference： [1]Tetrahedron Letters,1989,vol. 30,p. 3569 - 3572

15
[ 4313-73-9 ]
N^G-carbobenzoxy-[1-13C]-L-arginal semicarbazone trifluoroacetate [ No CAS ]
carbobenzoxy-L-phenylalanyl-L-leucyl-N^G-carbobenzoxy-[1-13C]-L-arginal semicarbazone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 5648 - 5655

16
4-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-4-methyl-pentanoyloxy]-benzoic acid methyl ester [ No CAS ]
[ 4313-73-9 ]
[ 20269-55-0 ]

Reference： [1]Chemistry Letters,1999,p. 73 - 74

17
[ 3397-32-8 ]
[ 61-90-5 ]
[ 4313-73-9 ]

Reference： [1]Russian Journal of Bioorganic Chemistry,1999,vol. 25,p. 283 - 287
Bioorganicheskaya Khimiya,1999,vol. 25,p. 323 - 328

19
[ 4313-73-9 ]
[ 3303-55-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2003,vol. 345,p. 830 - 834

20
[ 60641-89-6 ]
[ 4313-73-9 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 8730 - 8733

21
[ 4313-73-9 ]
acetyl-L-phenylalanyl-L-leucyl-[1-13C]-L-arginal hydrochloride [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 5648 - 5655

22
[ 4313-73-9 ]
C₂₁⁽¹³⁾CH₃₇N₉O₃*2ClH [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 5648 - 5655

23
[ 4313-73-9 ]
acetyl-L-phenylalanyl-L-leucyl-[1-13C]-L-arginal semicarbazone hydrochloride [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 5648 - 5655

24
[ 4313-73-9 ]
[ 114414-64-1 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1891 - 1897

25
[ 4313-73-9 ]
[ 115141-40-7 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1891 - 1897

26
[ 4313-73-9 ]
[ 115141-26-9 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1891 - 1897

27
[ 4313-73-9 ]
Tyr-D-Thr-Gly-Phe-Leu-Thr(O-t-Bu) [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1891 - 1897

28
[ 4313-73-9 ]
Tyr-D-Ser(O-t-Bu)-Gly-Phe-Leu-Thr(O-t-Bu) [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1891 - 1897

29
[ 4313-73-9 ]
[ 115141-41-8 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1891 - 1897

30
[ 4313-73-9 ]
[ 115141-46-3 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1891 - 1897

31
[ 4313-73-9 ]
[ 114442-56-7 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1891 - 1897

32
[ 1161-13-3 ]
[ 4313-73-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1993,vol. 66,p. 1566 - 1568
[2]Tetrahedron Letters,1982,vol. 23,p. 3831 - 3834
[3]Tetrahedron, Supplement,1966,vol. 8,p. 321 - 340
[4]Journal of Peptide Science,2013,vol. 19,p. 315 - 324
[5]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3103 - 3108
[6]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 436 - 441

33
[ 4313-73-9 ]
[ 122314-23-2 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 1084 - 1089
[2]Journal of Medicinal Chemistry,1990,vol. 33,p. 86 - 93

34
[ 4313-73-9 ]
C₂₄H₃₉N₉O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 1084 - 1089

35
[ 4313-73-9 ]
Ac-FLR-CHO [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 1084 - 1089

36
[ 4313-73-9 ]
C₂₂H₃₇N₉O₃*2ClH [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 1084 - 1089

37
[ 4313-73-9 ]
[ 119866-68-1 ]

Reference： [1]Tetrahedron Letters,1989,vol. 30,p. 3569 - 3572

38
[ 84758-90-7 ]
[ 4313-73-9 ]

Reference： [1]Tetrahedron Letters,1982,vol. 23,p. 3831 - 3834

39
[ 84758-88-3 ]
[ 4313-73-9 ]

Reference： [1]Tetrahedron Letters,1982,vol. 23,p. 3831 - 3834

40
[ 4313-73-9 ]
[ 122314-33-4 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 86 - 93

41
[ 4313-73-9 ]
[ 122314-30-1 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 86 - 93

42
[ 4313-73-9 ]
C₂₂H₃₇N₉O₃*ClH [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 86 - 93

43
[ 4313-73-9 ]
[ 122314-41-4 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 86 - 93

44
[ 4313-73-9 ]
[ 122314-37-8 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 86 - 93

45
[ 4313-73-9 ]
[ 122406-12-6 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 86 - 93

46
[ 4313-73-9 ]
C₃₀H₄₃N₉O₅*ClH [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 86 - 93

47
[ 7517-19-3 ]
[ 4313-73-9 ]

Reference： [1]Tetrahedron, Supplement,1966,vol. 8,p. 321 - 340
[2]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3103 - 3108

48
[ 6163-66-2 ]
[ 4313-73-9 ]
[ 92176-52-8 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid;palladium; In ethanol;	(a) L-Phenylalanyl-L-leucine, 1,1-dimethylethyl ester, p-toluenesulfonic acid salt p-Toluenesulfonic acid (8.12 g., 42.7 mmole) is added to an ice-chilled solution of <strong>[4313-73-9]N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-L-leucine</strong>, 1,1-dimethylethyl ester (20 g., 42.68 mmole) in 95% ethanol (325 ml.). The reaction vessel is purged with argon, and 10% palladium on carbon catalyst (2.0 g.) is added. The mixture is placed under 1 atmosphere of hydrogen and stirred for 20 hours. Filtering off the catalyst and concentrating the filtrate produces a sticky white solid which is triturated with ethyl ether and dried in vacuo to give 18.75 g. of L-phenylalanyl-L-leucine, 1,1-dimethylethyl ester, p-toluenesulfonic acid salt; m.p. (softens at 145) 157-159.5.
	With toluene-4-sulfonic acid;palladium; In ethanol;	(b) L-Phenylalanyl-L-leucine, 1,1-dimethylethyl ester, p-toluenesulfonic acid salt p-Toluenesulfonic acid (8.12 g., 42.7 mmole) is added to an ice-chilled solution of <strong>[4313-73-9]N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-L-leucine</strong>, 1,1-dimethylethyl ester (20 g., 42.68 mmole) in 95% ethanol (325 ml.). The reaction vessel is purged with argon, and 10% palladium on carbon catalyst (2.0 g.) is added. The mixture is placed under 1 atmosphere of hydrogen and stirred for 20 hours. Filtering off the catalyst and concentrating the filtrate produces a sticky white solid which is triturated with ethyl ether and dried in vacuo to give 18.75 g. of L-phenylalanyl-L-leucine, 1,1-dimethylethyl ester, p-toluenesulfonic acid salt; m.p. (softens at 145) 157-159.5.

Reference： [1]Patent: US4499079,1985,A
[2]Patent: US4560506,1985,A

49
[ 6163-66-2 ]
[ 4313-73-9 ]
[ 102124-00-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride;palladium; In phosphorus pentaoxide; ethanol; hexane;	(b) L-Phenylalanyl-L-leucine,1,1-dimethylethyl ester, hydrochloride A solution of <strong>[4313-73-9]N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-L-leucine</strong>, 1,1-dimethylethyl ester (93.72 g., 200.0 mmole) in 95% ethanol (1.5 l.) is hydrogenated under atmospheric pressure hydrogen using a 10% palladium on carbon (6.0 g.) catalyst. After stirring overnight, the mixture is filtered through Celite, concentrated to about 1/2 volume, filtered again, and concentrated to a viscous yellow oil. This oil is taken up in hexane (1.2 l.) and treated, with vigorous stirring, with 200 ml. of 1N hydrogen chloride in ether. The resulting thick, white suspension is diluted with hexane (1 l.), filtered, and washed with additional hexane. Drying overnight in vacuo over phosphorus pentoxide yields 71.80 g. of L-phenylalanyl-L-leucine, 1,1-dimethylethyl ester, hydrochloride as a white solid; m.p. 152.5-154 with bubbling.

Reference： [1]Patent: US4560506,1985,A

50
[ 67-56-1 ]
[ 4313-73-9 ]
[ 3850-45-1 ]

Reference： [1]Synthesis,2009,p. 809 - 814

51
[ 4313-73-9 ]
[ 100-51-6 ]
[ 60641-89-6 ]

Reference： [1]Synthesis,2009,p. 809 - 814

52
[ 4313-73-9 ]
[ 75-65-0 ]
[ 29842-94-2 ]

Reference： [1]Synthesis,2009,p. 809 - 814

53
[ 26093-31-2 ]
[ 4313-73-9 ]
[ 1170322-50-5 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5145 - 5150

54
[ 4313-73-9 ]
[ 100-01-6 ]
[ 83799-04-6 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5145 - 5150

55
[ 4313-73-9 ]
[ 62-53-3 ]
Z-L-Phe-L-Leu-NHPh [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5145 - 5150

56
[ 29842-94-2 ]
[ 4313-73-9 ]

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2011,vol. 71,p. 79 - 84
[2]Journal of Organic Chemistry,2009,vol. 74,p. 5145 - 5150

57
[ 21691-53-2 ]
[ 4816-89-1 ]
[ 4313-73-9 ]

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2011,vol. 71,p. 79 - 84

58
[ 61-90-5 ]
[ 41518-17-6 ]
[ 4313-73-9 ]

Reference： [1]Journal of Peptide Science,2013,vol. 19,p. 315 - 324

59
[ 4313-73-9 ]
[ 693-02-7 ]
[ 1449018-00-1 ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1799 - 1807

60
[ 4313-73-9 ]
[ 21233-94-3 ]
[ 1449018-01-2 ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1799 - 1807

61
[ 4313-73-9 ]
[ 1493792-59-8 ]

Reference： [1]Synthesis,2013,vol. 45,p. 2727 - 2736

62
[ 4313-73-9 ]
[ 1493792-72-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium sulfide; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In acetonitrile; at 0℃;	General procedure: To a soln of the appropriate carboxylic acid (1.0 mmol) and T3P (2.2 mmol) in anhyd MeCN (8.0 mL) was added Et3N (1.5 mmol)at 0 C, followed by finely ground Na2S (3.0 mmol). The resulting mixture was stirred for 2-3 h until the reaction was complete (TLC monitoring), concentrated and then diluted with H2O. The mixture was acidified with aq citric acid soln (10%) and the product was extracted with EtOAc (10 mL). The organic layer was washed with H2O (2 × 10 mL) and brine (10 mL), and then dried over anhyd Na2SO4. The solvent was evaporated in vacuo to afford the corresponding amino thioacid in quant. yield.

Reference： [1]Synthesis,2013,vol. 45,p. 2727 - 2736

63
[ 4313-73-9 ]
[ 95-51-2 ]
[ 1493792-59-8 ]

Reference： [1]International Journal of Peptide Research and Therapeutics,2014,vol. 20,p. 353 - 363

64
2-(aminomethyl)-5-(benzyloxy)pyridin-4(1H)-one [ No CAS ]
[ 4313-73-9 ]
benzyl ((S)-1-(((S)-1-(((5-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)amino)-4-methyl-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78.1%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;Cooling with ice;	General procedure: To a solution of compounds 10 (4 mmol), compound 7(4.4 mmol) and HCTU (4.4 mmol) in dry DMF (24 mL) cooled on an ice-bath was addedDIPEA (21 mmol). The mixture was stirred for 18 h. After removal of DMF, theresidue was dissolved in dichloromethane (50 mL), washed with saturated NaHCO3solution (2×40mL) and brine (40mL) successively, dried overanhydrous Na2SO4. After filtration, the filtrate wasconcentrated, the residue was purified by silica gel column chromatography (CH3OH/CH2Cl21:15),providing compounds 11.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3103 - 3108

65
2-(aminomethyl)-5-(benzyloxy)pyridin-4(1H)-one [ No CAS ]
[ 4313-73-9 ]
(S)-2-((S)-2-amino-3-phenylpropanamido)-N-((5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl)-4-methylpentanamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3103 - 3108

66
[ 4313-73-9 ]
[ 4818-02-4 ]
Cbz-L-Phe-L-Leu-L-Ile-L-Val-OMe [ No CAS ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 4263 - 4267

67
[ 4313-73-9 ]
[ 75927-49-0 ]
benzyl ((2S)-1-((5-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexan-3-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 2155 - 2159
Angew. Chem.,2018,vol. 130,p. 2177 - 2181,5

68
[ 24828-96-4 ]
[ 4313-73-9 ]
[ 36261-83-3 ]

Yield	Reaction Conditions	Operation in experiment
61%	With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 18h;	[000222] To a solution of <strong>[4313-73-9]Z-Phe-Leu-OH</strong> (206 mg, 0.5 mmol) and Lys(Boc)- H2 (212 mg, 0.75 mmol) in 5 mL DCM, HBTU (569 mg, 1.5 mmol), HOBt (67 mg. 0.5 mmol) and DIEA (323 mg, 2.5 mmol) were added. The mixture was stirred at rt. for 18 hrs. The mixture was washed with 1 N NaHS04, saturated NaHC0 and brine. After drying over anhydrous Na2S04, the solution was concentrated and purified with silica gel column (Hexane/EtOAc=10/l to 7/1) to obtain ZL0142 (196 mg, 61%) as a light yellow solid. 1H NMR (300 MHz, DMSO) delta 8.14 (d, J = 8.0 Hz, 0.40H), 7.77 (d, J = 8.0 Hz, 0.41H), 7.51 (d, J = 8.5 Hz, 0.44H), 7.39 - 7.28 (m, 5H), 7.27 - 7.15 (m, 5H), 7.02 (s, 0.59H), 6.74 (t, J = 5.3 Hz, 0.51H), 4.94 (s, 2H), 4.41 - 4.22 (m, 2H), 4.15 (dd, J = 7.9, 5.2 Hz, 1H), 3.02 (0357) (dd, J = 13.8, 3.4 Hz, 1H), 2.87 (m, 2H), 2.73 (m, 1H), 1.62 (m, 2H), 1.56 - 1.42 (m, 3H), 1.36 (s, 11H), 1.22 (m, 1H), 0.88 (dd, J = 13.4, 6.4 Hz, 6H). 1 C NMR (75 MHz, MeOD + CDC1 ) delta 175.35, 173.10, 172.98, 157.11, 157.03, 136.99, 136.65, 129.00, 128.07, 127.59, 127.32, 126.38, 66.29, 56.45, 52.93, 52.09, 40.09, 37.43, 31.38, 29.12, 27.45, 24.37, 22.80, 22.14, 20.63. ESI-MS (M + H)+ m/z 640.4. HR ESI-MS (M + H)+ m/z = 640.3713 (0358) (calcd for C34H5oN507: 640.3710).

Reference： [1]Patent: WO2018/94335,2018,A1 .Location in patent: Paragraph 000221-000222

69
[ 4313-73-9 ]
Z-Phe-Leu-Pro-Lys(Boc)-NH2 [ No CAS ]

Reference： [1]Patent: WO2018/94335,2018,A1

70
[ 4313-73-9 ]
Z-Phe-Leu-Pro-OH [ No CAS ]

Reference： [1]Patent: WO2018/94335,2018,A1

71
[ 4313-73-9 ]
H-Phe-Leu-Pro-Lys(Boc)-NH2 [ No CAS ]

Reference： [1]Patent: WO2018/94335,2018,A1

72
[ 4313-73-9 ]
Bz-Phe-Leu-Pro-Lys(Boc)-NH2 [ No CAS ]

Reference： [1]Patent: WO2018/94335,2018,A1

73
[ 4313-73-9 ]
tert-butyl ((S)-6-amino-5-((S)-2-((S)-2-amino-3-phenylpropanamido)-4-methylpentanamido)-6-oxohexyl)carbamate [ No CAS ]

Reference： [1]Patent: WO2018/94335,2018,A1

74
[ 4313-73-9 ]
Ac-Phe-Leu-Lys(Boc)-NH2 [ No CAS ]

Reference： [1]Patent: WO2018/94335,2018,A1

75
[ 4313-73-9 ]
Z-Phe-Leu-Lys(H)-NH2 [ No CAS ]

Reference： [1]Patent: WO2018/94335,2018,A1

76
[ 4313-73-9 ]
[ 7531-52-4 ]
Z-Phe-Leu-Pro-NH2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 18h;	[000232] To a solution of <strong>[4313-73-9]Z-Phe-Leu-OH</strong> (206 mg, 0.5 mmol) and Pro- H2 (86 mg, 0.75 mmol) in 5 mL DCM, HBTU (569 mg, 1.5 mmol), HOBt (67 mg. 0.5 mmol) and DIEA (323 mg, 2.5 mmol) were added. The mixture was stirred at rt. for 18 hrs. The solution was washed with 1 N NaHS04, saturated NaHC03 and brine. After drying over anhydrous Na2S04, the solution was concentrated and purified with silica gel column (Hexane/EtOAc=10/l to 7/1) to obtain ZL0141 (278 mg, quant.) as a white foam. 1H MR (300 MHz, CDC13) delta 7.65 (s, 1H), 7.33 (m, 4H), 7.15 (m, 6H), 6.87 (s, 1H), 5.57 - 5.32 (m, 2H), 5.11 - 4.96 (m, 2H), 4.86 (d, J = 4.8 Hz, 1H), 4.71 (s, 1H), 4.52 (s, 1H), 3.86 - 3.54 (m, 2H), 3.12 - 2.89 (m, 2H), 2.22 (m, 2H), 2.01 (s, 2H), 1.55 (m, 3H), 0.93 (dd, J = 17.1, 6.2 Hz, 6H). 13C NMR (75 MHz, CDC13) delta 173.74, 172.10, 170.94, 155.98, 136.48, 136.32, 129.37, 128.48, 128.09, 127.83, 126.79, 66.84, 59.53, 55.48, 49.01, 47.42, 41.63, 39.20, 38.61, 28.27, 25.03, 24.59, 23.28, 21.86. ESI-MS (M + H)+ m/z 509.3. HR ESI-MS (M + H)+ m/z = 509.2761 (calcd for C28H37N405: 509.2764)

Reference： [1]Patent: WO2018/94335,2018,A1 .Location in patent: Paragraph 000231-000232

77
[ 4313-73-9 ]
[ 2577-48-2 ]
Z-Phe-Leu-Pro-OMe [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 18h;	[000234] To a solution of <strong>[4313-73-9]Z-Phe-Leu-OH</strong> (1000 mg, 2.43 mmol) and Pro-OMe (483 mg, 2.9 mmol) in 20 mL DCM, HBTU (2700 mg, 7.29 mmol), HOBt (328 mg. 2.43 mmol) and DIEA (1567 mg, 12 mmol) were added. The mixture was stirred at rt. for 18 hrs. The solution was washed with 1 N NaHS04, saturated NaHC03 and brine. After drying over anhydrous Na2S04, the solution was concentrated and purified with silica gel column (DCM/MeOH = 100/1 to 50/1) to obtain ZL0176 (1500 mg, quant.) as a white foam. 1H NMR (300 MHz, CDC13) delta 7.39 - 7.29 (m, 5H), 7.27 - 7.22 (m, 3H), 7.16 (m, 2H), 6.70 (d, J = 8.1 Hz, 1H), 5.31 (d, J = 8.2 Hz, 1H), 5.07 (d, J = 3.3 Hz, 2H), 4.78 (td, J = 8.6, 5.2 Hz, 1H), 4.48 (m, 2H), 3.76 (m, 1H), 3.73 (s, 3H), 3.67 - 3.58 (m, 1H), 3.08 (d, J = 6.1 Hz, 2H), 2.29 - 2.15 (m, 1H), 2.12 - 1.94 (m, 3H), 1.70 - 1.41 (m, 3H), 0.98 (d, J = 6.2 Hz, 3H), 0.92 (d, J = 6.4 Hz, 3H). 1 C NMR (300 MHz, CDC13) delta 172.34, 170.74, 170.55, 136.26, 129.38, 128.55, 128.50, 128.12, 128.02, 126.94, 67.02, 58.71, 52.21, 49.07, 46.85, 41.70, 28.98, 24.88, 24.49, 23.26, 21.92. ESI-MS (M + H)+ m/z 524.3. HR ESI-MS (M + H)+ m/z = 524.2753 (calcd for C29H38N3O6: 524.2761). (0380)

Reference： [1]Patent: WO2018/94335,2018,A1 .Location in patent: Paragraph 000233-000234

78
[ 4313-73-9 ]
2-(4-chlorobut-1-en-2-yl)- 4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
benzyl ((2S)-1-((4-methyl-1-oxo-1-(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl)pentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 15430 - 15434
Angew. Chem.,2018,vol. 57,p. 15656 - 15660,5

79
[ 4313-73-9 ]
[ 3182-95-4 ]
benzyl ((S)-1-(((S)-1-(((S)-1-hydroxy-3-phenylpropan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; at 20℃; for 18h;	General procedure: To a stirred solution of the N-protected amino acid derivative (1.0 eq) in dry CH2Cl2 (50-75 mM)was added EDC (1.3 eq), HOBt·H2O (1.5 eq) and DIPEA (3.0 eq). The solution was stirred at rtovernight, diluted with CH2Cl2 and the organic layer washed twice with 1M HCl(aq), saturatedaqueous NaHCO3(aq) and brine. The organic layer was dried over MgSO4(s) and the solventremoved in vacuo. See individual experiments for details.

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 436 - 441

80
[ 7533-40-6 ]
[ 4313-73-9 ]
benzyl ((S)-1-(((S)-1-(((S)-1-hydroxy-4-methylpentan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; at 20℃; for 18h;	General procedure: To a stirred solution of the N-protected amino acid derivative (1.0 eq) in dry CH2Cl2 (50-75 mM)was added EDC (1.3 eq), HOBt·H2O (1.5 eq) and DIPEA (3.0 eq). The solution was stirred at rtovernight, diluted with CH2Cl2 and the organic layer washed twice with 1M HCl(aq), saturatedaqueous NaHCO3(aq) and brine. The organic layer was dried over MgSO4(s) and the solventremoved in vacuo. See individual experiments for details.

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 436 - 441

81
[ 4313-73-9 ]
[ 1359969-17-7 ]
C₃₅H₄₁N₃O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; at 20℃; for 18h;	General procedure: To a stirred solution of the N-protected amino acid derivative (1.0 eq) in dry CH2Cl2 (50-75 mM)was added EDC (1.3 eq), HOBt·H2O (1.5 eq) and DIPEA (3.0 eq). The solution was stirred at rtovernight, diluted with CH2Cl2 and the organic layer washed twice with 1M HCl(aq), saturatedaqueous NaHCO3(aq) and brine. The organic layer was dried over MgSO4(s) and the solventremoved in vacuo. See individual experiments for details.

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 436 - 441

82
[ 2666-93-5 ]
[ 4313-73-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 436 - 441

83
[ 4313-73-9 ]
benzyl ((S)-1-(((S)-4-methyl-1-oxo-1-(((S)-1-oxo-3-phenylpropan-2-yl)amino) pentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 436 - 441

84
[ 4313-73-9 ]
benzyl ((S)-1-(((S)-4-methyl-1-(((S)-4-methyl-1-oxopentan-2-yl)amino)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 436 - 441

85
[ 4313-73-9 ]
benzyl ((S)-1-(((S)-4-methyl-1-oxo-1-(((S)-1-oxo-3-(4-(prop-2-yn-1-yloxy)phenyl)propan-2-yl)amino)pentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 436 - 441

86
[ 4313-73-9 ]
[ 106-95-6 ]
allyl ((benzyloxy)carbonyl)-L-phenylalanyl-L-leucinate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 8829 - 8833
Angew. Chem.,2019,vol. 131,p. 8921 - 8925,5

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P337	If eye irritation persists:
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P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P362	Take off contaminated clothing and wash before reuse.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
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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. 4313-73-9 ] {[proInfo.proName]}

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[ 4313-73-9 ] Synthesis Path-Downstream 1~86

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