[ CAS No. 2921-14-4 ] {[proInfo.proName]}

Name: 2921-14-4|O-(Carboxymethyl)hydroxylamine hemihydrochloride|95%
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SKU: A709258
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2D 3D

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Quality Control of [ 2921-14-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2921-14-4 ]

SDS Specification

Alternatived Products of [ 2921-14-4 ]

Product Details of [ 2921-14-4 ]

CAS No. :	2921-14-4	MDL No. :	MFCD00012955
Formula :	C₄H₁₁ClN₂O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KBXIJIPYZKPDRU-UHFFFAOYSA-N
M.W :	218.59	Pubchem ID :	2723609
Synonyms :	Carboxymethoxylamine hemihydrochloride;Aminooxyacetate hemihydrochloride;Aminooxyacetate;Aminooxyacetic Acid (hydrochloride);AOAA hemihydrochloride;AOA hemihydrochloride	Chemical Name :	O-(Carboxymethyl)hydroxylamine hemihydrochloride

Calculated chemistry of [ 2921-14-4 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	4
Num. H-bond acceptors :	8.0
Num. H-bond donors :	4.0
Molar Refractivity :	41.55
TPSA :	145.1 Å²

Pharmacokinetics

GI absorption :	Low
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) :	-11.83 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-5.91
Log Po/w (WLOGP) :	-1.28
Log Po/w (MLOGP) :	-1.74
Log Po/w (SILICOS-IT) :	-1.22
Consensus Log Po/w :	-2.03

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	2.79
Solubility :	135000.0 mg/ml ; 619.0 mol/l
Class :	Highly soluble
Log S (Ali) :	3.53
Solubility :	748000.0 mg/ml ; 3420.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	1.05
Solubility :	2480.0 mg/ml ; 11.4 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.3

Safety of [ 2921-14-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2921-14-4 ]

* 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 [ 2921-14-4 ]
Downstream synthetic route of [ 2921-14-4 ]

[ 2921-14-4 ] Synthesis Path-Upstream 1~2

1
[ 5382-89-8 ]
[ 2921-14-4 ]

Reference： [1] Org.Synth.Coll.Vol.III<1955>172,
[2] Journal of the American Chemical Society, 1948, vol. 70, p. 1972
[3] Journal of the American Chemical Society, 1936, vol. 58, p. 2020

2
[ 24424-99-5 ]
[ 2921-14-4 ]
[ 42989-85-5 ]

Reference： [1] Tetrahedron Letters, 2003, vol. 44, # 46, p. 8379 - 8382
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 9, p. 1255 - 1261
[3] Tetrahedron Letters, 1993, vol. 34, # 52, p. 8419 - 8422
[4] Patent: US2010/144726, 2010, A1, . Location in patent: Page/Page column 49

[ 2921-14-4 ] Synthesis Path-Downstream 1~88

1
[ 5382-89-8 ]
[ 2921-14-4 ]

Reference： [1]Organic Syntheses, Collective,

2
[ 112-53-8 ]
[ 2921-14-4 ]
Aminooxyesssigsaeure-dodecylester [ No CAS ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1962,vol. 5,p. 464 - 477

3
[ 1198-34-1 ]
[ 2921-14-4 ]
[ 1214-56-8 ]

Reference： [1]Journal of medicinal chemistry,1964,vol. 7,p. 824 - 826

4
[ 590-28-3 ]
[ 2921-14-4 ]
[ 5820-99-5 ]

Reference： [1]Tetrahedron,1966,vol. 22,p. 1445 - 1451

5
[ 108-24-7 ]
[ 2921-14-4 ]
[ 5382-88-7 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1962,vol. 5,p. 464 - 477

6
[ 66-77-3 ]
[ 2921-14-4 ]
[ 1144-17-8 ]

Reference： [1]Journal of medicinal chemistry,1964,vol. 7,p. 824 - 826

7
[ 555-16-8 ]
[ 2921-14-4 ]
[ 1141-97-5 ]

Reference： [1]Monatshefte fur Chemie,1961,vol. 92,p. 725 - 739
[2]Journal of medicinal chemistry,1964,vol. 7,p. 824 - 826

8
[ 122-85-0 ]
[ 2921-14-4 ]
[ 34063-66-6 ]

Reference： [1]Monatshefte fur Chemie,1961,vol. 92,p. 725 - 739

9
[ 2921-14-4 ]
[ 100-52-7 ]
[ 141891-22-7 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1962,vol. 5,p. 464 - 477

10
[ 2921-14-4 ]
[ 123-08-0 ]
[ 90564-13-9 ]

Reference： [1]Monatshefte fur Chemie,1961,vol. 92,p. 725 - 739

11
[ 2921-14-4 ]
[ 90-02-8 ]
[ 62713-03-5 ]

Reference： [1]Monatshefte fur Chemie,1961,vol. 92,p. 725 - 739

12
[ 2921-14-4 ]
[ 98-88-4 ]
[ 5251-93-4 ]

Reference： [1]Monatshefte fur Chemie,1961,vol. 92,p. 725 - 739

13
[ 2921-14-4 ]
[ 103-71-9 ]
[ 6169-23-9 ]

Reference： [1]Tetrahedron,1966,vol. 22,p. 1445 - 1451

14
[ 2921-14-4 ]
[ 75-07-0 ]
[ 89124-73-2 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1962,vol. 5,p. 464 - 477

15
[ 2921-14-4 ]
[ 501-53-1 ]
[ 42989-82-2 ]

Yield	Reaction Conditions	Operation in experiment
2.62 g	With sodium hydroxide; In water; at 0 - 5℃; for 0.25h;	a) (Z-amineoxy)-acetic acid Maintaining the reaction temperature around 0-5C by external cooling, benzylchloroformate (1.41 mL, 10 mmol) and aqueous 4N NaOH (2.23 mL) are, dropwise and alternately, added to a solution in aqueous 2N NaOH (5 mL) of 2.18 g (10 mmol) of <strong>[2921-14-4]carboxymethoxylamine hemihydrochloride</strong> [(commercial reagent) also named (amineoxy)acetic acidhydrochloride]. Stirring is continued for 15 min before removal of any organic impurities with Et2O (2x15 mL); then addition of crushed ice and acidification until pH=2 with 37% HCl yields a solid that is filtered, washed with cold water and dried under vacuum at T=40C to give 2.62 g (8.2 mmol) of (Z-amineoxy)-acetic acid.

Reference： [1]Journal of the Chemical Society,1964,p. 3931 - 3940
[2]Patent: EP1366018,2016,B1 .Location in patent: Paragraph 0099

16
[ 2921-14-4 ]
[ 4707-71-5 ]
[ 1157-06-8 ]

Reference： [1]Journal of medicinal chemistry,1964,vol. 7,p. 824 - 826

17
[ 2921-14-4 ]
[ 79-04-9 ]
[ 83660-15-5 ]

Reference： [1]Monatshefte fur Chemie,1961,vol. 92,p. 725 - 739

18
[ 2921-14-4 ]
[ 120-92-3 ]
[ 1197-59-7 ]

Reference： [1]Journal of medicinal chemistry,1964,vol. 7,p. 824 - 826

19
[ 75-44-5 ]
[ 2921-14-4 ]
[ 62-53-3 ]
[ 6169-23-9 ]

Reference： [1]Tetrahedron,1966,vol. 22,p. 1445 - 1451

20
[ 2921-14-4 ]
[ 98-86-2 ]
[ 1205-09-0 ]

Reference： [1]Journal of medicinal chemistry,1964,vol. 7,p. 824 - 826

21
[ 2921-14-4 ]
[ 93-55-0 ]
[ 1208-09-9 ]

Reference： [1]Journal of medicinal chemistry,1964,vol. 7,p. 824 - 826

22
[ 2921-14-4 ]
[ 98-09-9 ]
[ 90222-94-9 ]

Reference： [1]Monatshefte fur Chemie,1961,vol. 92,p. 725 - 739

23
[ 2921-14-4 ]
[ 86-84-0 ]
ε-Naphthylureido-oxyessigsaeure [ No CAS ]

Reference： [1]Tetrahedron,1966,vol. 22,p. 1445 - 1451

24
[ 593-56-6 ]
[ 2921-14-4 ]
[ 106-51-4 ]
[ 90868-41-0 ]

Reference： [1]Monatshefte fur Chemie,1961,vol. 92,p. 725 - 739

25
[ 2921-14-4 ]
[ 106-51-4 ]
[ 90085-07-7 ]

Reference： [1]Monatshefte fur Chemie,1961,vol. 92,p. 725 - 739

26
[ 2921-14-4 ]
[ 106-51-4 ]
[ 94216-79-2 ]

Reference： [1]Monatshefte fur Chemie,1961,vol. 92,p. 725 - 739

27
[ 2921-14-4 ]
[ 71-36-3 ]
[ 89584-40-7 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1962,vol. 5,p. 464 - 477

28
[ 2921-14-4 ]
[ 502-42-1 ]
[ 1202-45-5 ]

Reference： [1]Journal of medicinal chemistry,1964,vol. 7,p. 824 - 826

29
[ 4863-69-8 ]
[ 2921-14-4 ]
[2-(4-Chloro-phenyl)-1-methyl-3-phenyl-prop-(Z)-ylideneaminooxy]-acetic acid [ No CAS ]
[2-(4-Chloro-phenyl)-1-methyl-3-phenyl-prop-(E)-ylideneaminooxy]-acetic acid [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1980,vol. 57,p. 1244 - 1247

30
[ 24424-99-5 ]
[ 2921-14-4 ]
[ 42989-85-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In 1,4-dioxane;	M. Kurono, M. Isobe Chem. Lett. 2004, 33, 452-453; M. Kurono, A. Shimomura, N. Chikusa Tetrahedron 2004, 60, 1773-1780 and S. Deroo, E. Defrancq, C. Moucheron, A. Kirsch-De Mesmaecker, P. Dumy Tetrahedron Lett. 2003, 44, 8379-8382, by protection of commercial of O-carboxymethyl-hydroxylamine hemihydrochloride ((H2NOCH2COOH)2. HCl) with di-t-butyl dicarbonate (Boc2O) in dioxane in a basic medium (NaOH) (80%) followed by reaction of the acid obtained as an intermediate product (BocNHOCH2COOH) with N-hydroxysuccinimide in the presence of dicyclohexylcarbodiimide (DCC) in CH2Cl2 (yield: 90%);

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 8379 - 8382
[2]Journal of Medicinal Chemistry,1993,vol. 36,p. 1255 - 1261
[3]Tetrahedron Letters,1993,vol. 34,p. 8419 - 8422
[4]Patent: US2010/144726,2010,A1 .Location in patent: Page/Page column 49

31
[ 4038-15-7 ]
[ 2921-14-4 ]
[1-(2,4-Dimethoxy-phenyl)-1-(4-methoxy-phenyl)-meth-(Z)-ylideneaminooxy]-acetic acid [ No CAS ]
[1-(2,4-Dimethoxy-phenyl)-1-(4-methoxy-phenyl)-meth-(E)-ylideneaminooxy]-acetic acid [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1980,vol. 57,p. 1244 - 1247

32
[ 82-66-6 ]
[ 2921-14-4 ]
O-carboxymetheyl oxime [ No CAS ]

Reference： [1]Tetrahedron Letters,1985,vol. 26,p. 4883 - 4886

33
[ 78141-21-6 ]
[ 2921-14-4 ]
[1-Methyl-2-phenyl-3-p-tolyl-prop-(Z)-ylideneaminooxy]-acetic acid [ No CAS ]
[1-Methyl-2-phenyl-3-p-tolyl-prop-(E)-ylideneaminooxy]-acetic acid [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1980,vol. 57,p. 1244 - 1247

34
[ 54635-92-6 ]
[ 2921-14-4 ]
[3-(2-Chloro-phenyl)-1-methyl-2-phenyl-prop-(Z)-ylideneaminooxy]-acetic acid [ No CAS ]
[3-(2-Chloro-phenyl)-1-methyl-2-phenyl-prop-(E)-ylideneaminooxy]-acetic acid [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1980,vol. 57,p. 1244 - 1247

35
[ 152-58-9 ]
[ 2921-14-4 ]
anti-11-deoxycortisol-3-carboxymethyloxime [ No CAS ]
[ 110013-88-2 ]

Reference： [1]Steroids,1982,vol. 39,p. 115 - 128

36
[ 16429-03-1 ]
[ 2921-14-4 ]
[ 73331-15-4 ]

Reference： [1]Journal of Chemical and Engineering Data,1980,vol. 25,p. 176 - 183

37
[ 112117-75-6 ]
[ 2921-14-4 ]
[ 73331-18-7 ]

Reference： [1]Journal of Chemical and Engineering Data,1980,vol. 25,p. 176 - 183

38
[ 7323-86-6 ]
[ 2921-14-4 ]
[ 37654-41-4 ]

Reference： [1]Steroids,1983,vol. 42,p. 123 - 136

39
[ 24852-69-5 ]
[ 2921-14-4 ]
[1-(2-Benzylselanyl-phenyl)-meth-(E)-ylideneaminooxy]-acetic acid [ No CAS ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 4347 - 4348

40
[ 127-31-1 ]
[ 2921-14-4 ]
[(8S,9R,10S,11S,13S,14S,17R)-9-Fluoro-11,17-dihydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylideneaminooxy]-acetic acid [ No CAS ]

Reference： [1]Steroids,1994,vol. 59,p. 555 - 558

41
[ 379-68-0 ]
[ 2921-14-4 ]
18-hydroxy-11-deoxycorticosterone-3-(O-carboxymethyl)-oxime [ No CAS ]

Reference： [1]Steroids,1980,vol. 35,p. 427 - 438

42
[ 379-68-0 ]
[ 2921-14-4 ]
18-hydroxy-11-deoxycorticosterone-3-(O-carboxymethyl)-oxime [ No CAS ]
[1-{(8R,9S,10R,13R,14S,17S)-3-[(E)-Carboxymethoxyimino]-13-hydroxymethyl-10-methyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl}-2-hydroxy-eth-(Z)-ylideneaminooxy]-acetic acid [ No CAS ]

Reference： [1]Steroids,1980,vol. 35,p. 427 - 438

43
[ 378-44-9 ]
[ 2921-14-4 ]
[ 61600-49-5 ]

Reference： [1]Steroids,1981,vol. 37,p. 303 - 314

44
[ 2862-62-6 ]
[ 2921-14-4 ]
[ 114894-95-0 ]

Reference： [1]Chemical and pharmaceutical bulletin,1988,vol. 36,p. 994 - 999

45
[ 4072-13-3 ]
[ 2921-14-4 ]
[1-(2-Methoxy-5-methyl-phenyl)-1-phenyl-meth-(Z)-ylideneaminooxy]-acetic acid [ No CAS ]
[1-(2-Methoxy-5-methyl-phenyl)-1-phenyl-meth-(E)-ylideneaminooxy]-acetic acid [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1980,vol. 57,p. 1244 - 1247

46
[ 78141-14-7 ]
[ 2921-14-4 ]
[1-Ethyl-2,3-diphenyl-prop-(Z)-ylideneaminooxy]-acetic acid [ No CAS ]
[1-Ethyl-2,3-diphenyl-prop-(E)-ylideneaminooxy]-acetic acid [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1980,vol. 57,p. 1244 - 1247

47
[ 13609-67-1 ]
[ 2921-14-4 ]
anti-cortisol 17-butyrate-3-(O-carboxymethyl)-oxime [ No CAS ]
syn-cortisol 17-butyrate-3-(O-carboxymethyl)-oxime [ No CAS ]

Reference： [1]Steroids,1983,vol. 42,p. 23 - 36

48
[ 2921-14-4 ]
[ 76596-53-7 ]
[ 138116-86-6 ]

Reference： [1]Il Farmaco,1991,vol. 46,p. 887 - 897

49
[ 2921-14-4 ]
[ 105175-10-8 ]
[ 138116-87-7 ]

Reference： [1]Il Farmaco,1991,vol. 46,p. 887 - 897

50
[ 2921-14-4 ]
[ 151112-37-7 ]
[ 109527-48-2 ]

Reference： [1]Steroids,1991,vol. 56,p. 17 - 21

51
[ 2921-14-4 ]
[ 85302-16-5 ]
[ 144528-22-3 ]

Reference： [1]Il Farmaco,1992,vol. 47,p. 567 - 584

52
[ 2921-14-4 ]
[ 93599-28-1 ]
[ 93599-19-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1984,vol. 23,p. 692 - 694

53
[ 2921-14-4 ]
[ 93599-30-5 ]
[ 93599-27-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1984,vol. 23,p. 692 - 694

54
[ 2921-14-4 ]
[ 91119-39-0 ]
[ 91119-64-1 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 1236 - 1242

55
[ 2921-14-4 ]
[ 52253-18-6 ]
[ 79550-56-4 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1981,vol. 46,p. 1413 - 1424

56
[ 2921-14-4 ]
[ 75226-95-8 ]
[1-(4-Allyloxy-phenyl)-1-(2,4-dimethoxy-phenyl)-meth-(Z)-ylideneaminooxy]-acetic acid [ No CAS ]
[1-(4-Allyloxy-phenyl)-1-(2,4-dimethoxy-phenyl)-meth-(E)-ylideneaminooxy]-acetic acid [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1980,vol. 57,p. 1244 - 1247

57
[ 2921-14-4 ]
[ 80721-93-3 ]
[ 80721-96-6 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 1385 - 1391

58
[ 2921-14-4 ]
[ 37087-78-8 ]
[ 79727-65-4 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1981,vol. 46,p. 1614 - 1624

59
[ 2921-14-4 ]
[ 69662-36-8 ]
[ 79550-57-5 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1981,vol. 46,p. 1413 - 1424

60
[ 2921-14-4 ]
[ 135604-84-1 ]
[1-[(3S,8S,9S,10S,13S,14S,17S)-3-Acetoxy-17-((R)-1-acetoxy-ethyl)-13-methyl-1,2,3,4,7,8,9,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-10-yl]-meth-(E)-ylideneaminooxy]-acetic acid [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1991,vol. 56,p. 1087 - 1092

61
[ 2921-14-4 ]
[ 58994-85-7 ]
C₄₅H₆₈N₂O₁₈ [ No CAS ]

Reference： [1]Steroids,1994,vol. 59,p. 472 - 478

62
[ 2921-14-4 ]
[ 141210-22-2 ]
[ 141210-17-5 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 1407 - 1416

63
[ 2921-14-4 ]
[ 78414-77-4 ]
[ 78414-85-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 1712 - 1720

64
[ 2921-14-4 ]
[ 73407-66-6 ]
[ 139183-20-3 ]

Reference： [1]Steroids,1992,vol. 57,p. 32 - 36

65
[ 2921-14-4 ]
[ 139173-66-3 ]
[ 139173-61-8 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1991,vol. 56,p. 2884 - 2891

66
[ 2921-14-4 ]
[ 139173-58-3 ]
[ 139173-61-8 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1991,vol. 56,p. 2884 - 2891

67
[ 2921-14-4 ]
6-oxo-2-hydroxyestriol [ No CAS ]
6-oxo-2-hydroxyestriol 6-(O-carboxymethyl)oxime [ No CAS ]

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 1189 - 1194

68
[ 2921-14-4 ]
[ 561-65-9 ]
[ 74418-17-0 ]

Reference： [1]Steroids,1984,vol. 43,p. 509 - 516
[2]Steroids,1980,vol. 35,p. 427 - 438

69
[ 2921-14-4 ]
[ 561-65-9 ]
[ 74418-17-0 ]
C₂₅H₃₆N₂O₉ [ No CAS ]

Reference： [1]Steroids,1980,vol. 35,p. 427 - 438

70
[ 2921-14-4 ]
[ 88477-91-2 ]
[ 88477-92-3 ]

Reference： [1]Steroids,1983,vol. 41,p. 155 - 164

71
[ 2921-14-4 ]
[ 84573-10-4 ]
[ 84573-11-5 ]

Reference： [1]Steroids,1983,vol. 41,p. 165 - 172

72
[ 2921-14-4 ]
[ 93800-94-3 ]
[ 93800-95-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 3088 - 3092

73
[ 2921-14-4 ]
[ 85698-93-7 ]
[ 87085-08-3 ]

Reference： [1]Chemical and pharmaceutical bulletin,1983,vol. 31,p. 3583 - 3588

74
[ 186581-53-3 ]
[ 928047-10-3 ]
[ 2921-14-4 ]
[ 928047-11-4 ]

Reference： [1]Steroids,2006,vol. 71,p. 120 - 128

75
[ 928047-23-8 ]
[ 2921-14-4 ]
[ 928047-24-9 ]

Reference： [1]Steroids,2006,vol. 71,p. 120 - 128

76
[ 476372-97-1 ]
[ 2921-14-4 ]
C₁₈H₂₅NO₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6368 - 6382

77
[ 2921-14-4 ]
bis-[4-(quinolin-2-ylmethoxy)-phenyl]-acetaldehyde [ No CAS ]
[2,2-Bis-[4-(quinolin-2-ylmethoxy)-phenyl]-eth-(E)-ylideneaminooxy]-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3322 - 3334

78
C₂₀H₁₆F₃NO₂ [ No CAS ]
[ 2921-14-4 ]
((((1E)-(1-allyl-5-((4-(trifluoromethyl)benzyl)oxy)-1H-indol-3-yl)methylidene)amino)oxy)acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In ethanol; at 60℃; for 2h;	To a solution of aldehyde (0.5 mmol) dissolved in pyridine (0.5 ml) and ETOH (4.5 ml) was added <strong>[2921-14-4]carboxymethoxylamine hemihydrochloride</strong> (54.6 mg, 0.25 mmol).The reaction was heated to 60 C for 2 hours. The solvent was evaporated in vacuo. The crude product was purified by RP-HPLC to give example 224. 1H NMR (DMSO d6,300 MHz) 8 4.61 (s, 2H), 4.81 (d, J= 5.4 Hz, 2H), 5.02-5. 18 (m, 2H), 5.22-5. 27 (m, 3H), 5.94-6. 03 (m, 1H), 6.97 (dd, J= 8.9, 2.4 Hz, 1H), 7.40 (d, J=8.7 Hz, 1H), 7.69-7. 79 (m, 5H), 8.38 (s, 1H), 12.72 (s, 1H); MS: (M+H) 433.0 [0140]

Reference： [1]Patent: WO2005/30191,2005,A1 .Location in patent: Page/Page column 52

79
[ 1046152-29-7 ]
[ 2921-14-4 ]
([(1E)-(3'-[4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-3-yl)methylidene]amino}oxy)acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In ethanol; at 60℃; for 2h;	To a solution of aldehyde (0.25 mmol) from step 2 dissolved in pyridine (0.5 ml) and ETOH (4.5 ml) was added <strong>[2921-14-4]carboxymethoxylamine hemihydrochloride</strong> (54.6 mg , 0.25 mmol). The reaction was heated to 60 C for 2 hours. The solvent was evaporated in vacuo. The crude product was purified by RP-HPLC. H NMR (DMSO d6,300 MHz) 8 4.69 (s, 2H), 5.33 (s, 2H), 7.06 (dd, J= 8.1, 1.9 Hz, 1H), 7.28 (d, J= 7.8 Hz, 2H), 7. 33 (s, 1H), 7.42 (t, J=7.9 Hz, 1H), 7.54 (t, J=7.7 Hz, 1H), 7.64 (d, J= 6.8 Hz, 1H), 7.67-7. 82 (m, SH), 7.89 (s, 1H), 8.42 (s, 1H), 12.86 (s, 1H); MS: (M+H) 430.1

Reference： [1]Patent: WO2005/30191,2005,A1 .Location in patent: Page/Page column 64

80
[ 1046152-30-0 ]
[ 2921-14-4 ]
[((1E)-{3,4-bis[(4-tert-butylbenzyl)oxy]phenyl}methylidene)amino]oxy}acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; potassium carbonate; In ethanol; at 60℃; for 2h;	Step 2. To a solution of crude bisbenzyl ether (0.5 mmol) obtained from step 1 dissolved in pyridine (0.5 ml) and ETOH (4.5 ml) was added <strong>[2921-14-4]carboxymethoxylamine hemihydrochloride</strong> (109.2 mg, 0.5 MMOL). The reaction was heated to 60 C for 2 hours. The solvent was evaporated in vacuo. The crude product was purified by RP-HPLC. H NMR (DMSO d6,300 MHz) 8 1.28 (s, 18H), 4.61 (s, 2H), 5.07 (s, 2H), 5.12 (s, 2H), 7.13 (m, 2H), 7.32-7. 41 (m, 10H), 8.21 (s, 1H) ; MS: (M+H) 504.

Reference： [1]Patent: WO2005/30191,2005,A1 .Location in patent: Page/Page column 74-75

81
[ 353460-30-7 ]
[ 2921-14-4 ]
[((1E)-{2,4-bis[(4-methylbenzyl)oxy]phenyl}methylidene)amino]oxy}acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In ethanol; at 60℃; for 2h;	Step 2. To a solution of crude bisbenzyl ether (0.5 mmol) obtained from step 1 dissolved in pyridine (0.5 ml) and ETOH (4.5 ml) was added <strong>[2921-14-4]carboxymethoxylamine hemihydrochloride</strong> (109.2 mg, 0.5 MMOL). The reaction was heated to 60 C for 2 hours. The solvent was evaporated in vacuo. The crude product was purified by RP-HPLC. H NMR (DMSO D6, 300 MHz) 8 2.31 (S, 6H), 4.58 (s, 2H), 5.09 (s, 2H), 5.12 (s, 2H), 6.64 (d, 1H), 6.82 (s, 1H) 7.2 (d, 4H), 7.41 (d, 4H), 7.54 (d, 1H), 8.32 (s, 1H) ; MS: (M+H) 420.

Reference： [1]Patent: WO2005/30191,2005,A1 .Location in patent: Page/Page column 77

82
C₂₃H₂₂O₃ [ No CAS ]
[ 2921-14-4 ]
[((1E)-{2,4-bis[(4-methylbenzyl)oxy]phenyl}methylidene)amino]oxy}acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In ethanol; at 60℃; for 2h;	Step 2. To a solution of crude bisbenzyl ether (0.5 mmol) obtained from step 1 dissolved in pyridine (0.5 ml) and ETOH (4.5 ml) was added <strong>[2921-14-4]carboxymethoxylamine hemihydrochloride</strong> (109.2 mg, 0.5 mmol). The reaction was heated to 60 C for 2 hours. The solvent was evaporated in vacuo. The crude product was purified by RP-HPLC. H NMR (DMSO d6,300 MHz) 5 4.62 (s, 2H), 4.99 (s, 2H), 5.18 (s, 2H), 7.10 (m, 1H), 7.25 (m, 2H) 7.31 (d, 2H), 7.44 (d, 2H), 7.52 (d, 2H), 7. (d, 2H), 8.29 (s, 1H) ; MS: (M+H) 550.

Reference： [1]Patent: WO2005/30191,2005,A1 .Location in patent: Page/Page column 79

83
[ 1046152-32-2 ]
[ 2921-14-4 ]
C₂₃H₁₉Cl₂NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In ethanol; at 60℃; for 2h;	Step 2. To a solution of crude bisbenzyl ether (0.5 mmol) obtained from step 1 dissolved in pyridine (0.5 ml) and ETOH (4.5 ml) was added <strong>[2921-14-4]carboxymethoxylamine hemihydrochloride</strong> (109.2 mg, 0.5 mmol). The reaction was heated to 60 C for 2 hours. The solvent was evaporated in vacuo. The crude product was purified by RP-HPLC. H NMR (DMSO d6, 300 MHz) 8 4.64 (s, 2H), 5.13 (s, 4H), 6.77 (s, 1H), 6.91 (s, 2H) 7.40 (s, 6H), 7.45 (s, 2H), 8.26 (s, 1H); MS: (M+H) 460.

Reference： [1]Patent: WO2005/30191,2005,A1 .Location in patent: Page/Page column 81

84
[ 1046152-34-4 ]
[ 2921-14-4 ]
[((1E)-{4-[3-(4-tert-butylphenoxy)prop-1-ynyl]phenyl}methylidene)amino]oxy}acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In ethanol; at 60℃; for 2h;	Step 3. To a solution of the aldehyde from step 2 (0.5 mmol) dissolved in pyridine (0.5 ml) and ETOH (4.5 ml) was added <strong>[2921-14-4]carboxymethoxylamine hemihydrochloride</strong> (54.6 mg, 0.25 mmol). The reaction was heated to 60 C for 2 hours. The solvent was evaporated in vacuo. The crude product was purified by RP-HPLC.

Reference： [1]Patent: WO2005/30191,2005,A1 .Location in patent: Page/Page column 85

85
[ 2921-14-4 ]
[ 78072-60-3 ]
(4-Methyl-1-thiophen-3-yl-pentylideneaminooxy)-acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium hydroxide; In methanol; at 20℃; for 4h;	Example 28 (4-Methyl-1-thiophen-3-yl-pentylideneaminooxy)-acetic acid 4-Methyl-1-thiophen-3-yl-pentan-1-one (324 mg, 1.78 mmol) was dissolved in dry methanol (20 ml) under nitrogen atmosphere, treated with <strong>[2921-14-4]carboxymethoxylamine hemihydrochloride</strong> (194 mg, 1.78 mmol) and sodium hydroxide (35 mg, 0.89 mmol) and stirred at room temperature for 4 hours. The solvent is then removed in vacuo and the resulting oil was triturated with hexane to give the title compound as a white solid (307 mg, 67%). MS (ES+) 25. deltaH (d6 DMSO): 1.00 (6H, d), 1.45 (2H, q), 1.63 (1H, m), 2.75 (2H, t), 4.65 (2H, s), 7.39 (1H, d), 7.60 (1H, d), 7.86 (1H, s), 12.70 (1H, s).

Reference： [1]Patent: US2005/148603,2005,A1 .Location in patent: Page/Page column 109

86
C₂H₃NO₉S₂^(2-)*2Na⁽¹⁺⁾ [ No CAS ]
[ 2921-14-4 ]

Yield	Reaction Conditions	Operation in experiment
		500mL of an aqueous solution of hydroxylamine disulfonic acid sodium (2 mols/L) and 80g of 50% aqueous sodium hydroxide solution were put into a beaker, and stirred for 24 hours at 50C after adding 94.5g of chloroacetic acid. When the pH of the reaction liquid decreased to 9 or less and the termination of the reaction was confirmed, 9.8g of concentrated sulfuric acid were added to the reaction liquid, and the mixture was heated for 24 hours at approx. 90C under normal pressure to hydrogenate the reaction product (O-carboxyl hydroxylamine disulfonic acid sodium salt) and cleave off its sulfonic acid groups. 50% aqueous sodium hydroxide solution was gradually added to the hydrogenated solution until the pH became around 7 for neutralization, and then the obtained amino-oxy acetic acid was extracted by using 700mL of ethyl acetate. The ethyl acetate was removed from the extract under reduced pressure, and then 104g of 37% hydrochloric acid were added to the residue. The mixture was heated to 70C to dissolve the residue. The residue was recrystallized at room temperature, and a crystal in which one molecule of hydrochloric acid was coordinated to two molecules of amino-oxy acetic acid was obtained (yield: 107g (98%)).

Reference： [1]Patent: EP1661884,2006,A1 .Location in patent: Page/Page column 4

87
[ 24424-99-5 ]
[ 2921-14-4 ]
(Boc)aminooxyacetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	(Boc)aminooxyacetic acid (9): O-(Carboxymethyl)hydroxylamine hemihydrochloride (1.16 g, 5.3 mmol) was dissolved in CH2Cl2 (40 mL) and the pH was adjusted to 9 by addition of triethylamine (3 mL). Then di-tert-butyl dicarbonate (2.36 g, 10.6 mmol, 2.0 equiv) was added and the mixture was stirred at room temperature until tlc indicated completion of reaction. The pH was lowered to 3 by addition of diluted HCl. The reaction mixture was partitioned between saturated aqueous NH4Cl (20 mL) and CH2Cl2 (30 mL). The aqueous phase was extracted with CH2Cl2 (3100 mL). The combined organic extracts were washed with H2O (2100 mL) and dried (Na2SO4). The solvent was removed in vacuo to afford 9 as a white solid. Yield (1.86 g, 97%); IR (CH2Cl2): vmax=3373, 2983, 2574, 2461, 1724, 1413, 1369, 1235; 1H NMR (270 MHz, CDCl3): delta=4.48 (s, 2H, CH2), 1.48 (s, 9H, Boc); MS (FAB+): m/z=214 [M+Na]+, 192 [M+H]+, 135, 123, 109, 69.
	In CH2CI2;	(Boc)aminooxyacetic acid (9): O-(Carboxymethyl)hydroxylamine hemihydrochloride (1.16 g, 5.3 mmol) was dissolved in CH2CI2 (40 mL) and the pH was adjusted to 9 by addition of triethylamine (3 mL). Then di-tert-butyl dicarbonate (2.36 g, 10.6 mmol, 2.0 equiv) was added and the mixture was stirred at room temperature until tic indicated completion of reaction. The pH was lowered to 3 by addition of diluted HCl. The reaction mixture was partitioned between saturated aqueous NH4Cl (20 mL) and CH2Cl2 (30 mL). The aqueous phase was extracted with CH2Cl2 (3100 mL). The combined organic extracts were washed with H2O (2100 mL) and dried (Na2SO4). The solvent was removed in vacuo to afford 9 as a white solid. Yield (1.86 g, 97%); IR (CH2Cl2): numax=3373, 2983, 2574, 2461, 1724, 1413, 1369, 1235; 1H NMR (270 MHz, CDCl3): delta=4.48 (s, 2H, CH2), 1.48 (s, 9H, Boc); MS (FAB'): m/z=214 [M+Na]+, 192 [M+H]+, 135, 123, 109, 69.

Reference： [1]Patent: US2002/188023,2002,A1
[2]Patent: US2005/287202,2005,A1

Yield	Reaction Conditions	Operation in experiment
		PREPARATIVE EXAMPLE 19 STR71 Dissolve 0.2 g (0.915 mmol) of (aminooxy)acetic acid hemihydrochloride (Aldrich) in 2 mL of 1N aqueous sodium hydroxide. Add a solution of 0.2 g (0.915 mmol) di-tert-butyldicarbonate (Aldrich) in 2 mL of methanol and stir for 24 hr. Cool to 0 C. and adjust to pH 5-6 with 1N HCl. Extract with four 20 mL portions of ethyl acetate. Dry the combined organic layers over magnesium sulfate and concentrate under vacuum to give 0.17 g of the product as a colorless oil that crystallized upon standing, mp=116-119 C.

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[ 2921-14-4 ]

Aliphatic Chain Hydrocarbons

[ 645-88-5 ]

2-(Aminooxy)acetic acid

Similarity: 0.94

Amines

[ 645-88-5 ]

2-(Aminooxy)acetic acid

Similarity: 0.94

Carboxylic Acids

[ 645-88-5 ]

2-(Aminooxy)acetic acid

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Code	Phrase
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P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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Code	Phrase
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P321
P322
P330	Rinse mouth.
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P335	Brush off loose particles from skin.
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P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
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.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
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.
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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
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. 2921-14-4 ] {[proInfo.proName]}

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[ 2921-14-4 ] Synthesis Path-Upstream 1~2

[ 2921-14-4 ] Synthesis Path-Downstream 1~88

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Aliphatic Chain Hydrocarbons

Amines

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