Product Name

  • Name

    Hydroxylamine, O-(carboxymethyl)-

  • EINECS
  • CAS No. 645-88-5
  • Density 1.375
  • Solubility
  • Melting Point 138℃
  • Formula C2H5 N O3
  • Boiling Point 327℃
  • Molecular Weight 91.0666
  • Flash Point 151℃
  • Transport Information
  • Appearance
  • Safety Poison by subcutaneous and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
  • Risk Codes
  • Molecular Structure Molecular Structure of 645-88-5 (Hydroxylamine, O-(carboxymethyl)-)
  • Hazard Symbols
  • Synonyms Aceticacid, (aminooxy)- (6CI,8CI,9CI); (Aminooxy)acetic acid; (Carboxymethoxy)amine;(O-Carboxymethyl)hydroxylamine; AOA; AOAA; Aminoxyacetic acid; Hydroxylamine,O-(carboxymethyl)-; Methoxyamine, 1-carboxy-; O-(Carboxymethyl)hydroxyamine; U7524; a-Aminooxyacetic acid
  • PSA 75.38000
  • LogP -1.67310

Synthetic route

ethyl N-(ethoxycarbonyl)aminooxyacetate
68871-49-8

ethyl N-(ethoxycarbonyl)aminooxyacetate

aminooxyacetic acid
645-88-5

aminooxyacetic acid

Conditions
ConditionsYield
With hydrogenchloride
Benzylidenaminooxy-essigsaeure
141891-22-7, 5382-90-1

Benzylidenaminooxy-essigsaeure

aminooxyacetic acid
645-88-5

aminooxyacetic acid

Conditions
ConditionsYield
With water; phenylhydrazine hydrochloride
N-benzoylaminooxyacetic acid
5251-93-4

N-benzoylaminooxyacetic acid

aminooxyacetic acid
645-88-5

aminooxyacetic acid

Conditions
ConditionsYield
With hydrogenchloride Heating;
chloroacetic acid
79-11-8

chloroacetic acid

acetone oxime
127-06-0

acetone oxime

aminooxyacetic acid
645-88-5

aminooxyacetic acid

Conditions
ConditionsYield
(i) aq. NaOH, (ii) AcOH; Multistep reaction;
(3-Bromo-5-chloro-benzoylaminooxy)-acetic acid

(3-Bromo-5-chloro-benzoylaminooxy)-acetic acid

aminooxyacetic acid
645-88-5

aminooxyacetic acid

Conditions
ConditionsYield
With hydrogenchloride Heating;
ethyl 2-(aminooxy)-acetate
5740-47-6

ethyl 2-(aminooxy)-acetate

aminooxyacetic acid
645-88-5

aminooxyacetic acid

Conditions
ConditionsYield
With potassium hydroxide; bromoacetic acid,potassium salt
chloroacetic acid
79-11-8

chloroacetic acid

dipotassium-salt of/the/ hydroxylamine-N,N-disulfonic acid

dipotassium-salt of/the/ hydroxylamine-N,N-disulfonic acid

aminooxyacetic acid
645-88-5

aminooxyacetic acid

Conditions
ConditionsYield
With potassium hydroxide Erhitzen des Reaktionsprodukts mit wss.Salzsaeure;
ethylbenzhydroximacetic acid

ethylbenzhydroximacetic acid

aminooxyacetic acid
645-88-5

aminooxyacetic acid

Conditions
ConditionsYield
With hydrogenchloride
ethyl bromoacetate
105-36-2

ethyl bromoacetate

potassium-salt of/the/ benzohydroxamic acid

potassium-salt of/the/ benzohydroxamic acid

aminooxyacetic acid
645-88-5

aminooxyacetic acid

Conditions
ConditionsYield
With potassium hydroxide Erhitzen des Reaktionsprodukts mit wss.Salzsaeure;
hydrogenchloride
7647-01-0

hydrogenchloride

(α-ethoxy-benzylidenaminooxy)-acetic acid

(α-ethoxy-benzylidenaminooxy)-acetic acid

A

benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

B

aminooxyacetic acid
645-88-5

aminooxyacetic acid

O-methoxycarbonylmethylhydroxylamine
25184-48-9

O-methoxycarbonylmethylhydroxylamine

aminooxyacetic acid
645-88-5

aminooxyacetic acid

Conditions
ConditionsYield
Stage #1: O-methoxycarbonylmethylhydroxylamine With water; sodium hydroxide In methanol at 70℃; for 2h;
Stage #2: With hydrogenchloride In water pH=1;
2-(aminooxy)acetic acid hemihydrochloride

2-(aminooxy)acetic acid hemihydrochloride

aminooxyacetic acid
645-88-5

aminooxyacetic acid

Conditions
ConditionsYield
With sodium carbonate In water pH=5;
(2E,4E,6E,8E)-2-cyanoethyl 3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-enyl)nona-2,4,6,8-tetraenoate
1225383-35-6

(2E,4E,6E,8E)-2-cyanoethyl 3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-enyl)nona-2,4,6,8-tetraenoate

aminooxyacetic acid
645-88-5

aminooxyacetic acid

(2E,4E,6E,8E)-2-cyanoethyl 9-((E)-3-(2-hydroxy-2-oxoethoxyimino)-2,6,6-trimethylcyclohex-1-enyl)-3,7-dimethylnona-2,4,6,8-tetraenoate

(2E,4E,6E,8E)-2-cyanoethyl 9-((E)-3-(2-hydroxy-2-oxoethoxyimino)-2,6,6-trimethylcyclohex-1-enyl)-3,7-dimethylnona-2,4,6,8-tetraenoate

Conditions
ConditionsYield
In pyridine at 20℃; for 17h;100%
Estrone
53-16-7

Estrone

aminooxyacetic acid
645-88-5

aminooxyacetic acid

2-({(E)-[(8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-ylidene]amino}oxy)acetic acid
16218-61-4

2-({(E)-[(8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-ylidene]amino}oxy)acetic acid

Conditions
ConditionsYield
With pyridine at 20℃; for 17h;100%
aminooxyacetic acid
645-88-5

aminooxyacetic acid

[(3S,6S,12R,15S,16R,19S)-3-Benzyl-12-ethyl-15-[(3-hydroxy-pyridine-2-carbonyl)-amino]-4,16-dimethyl-2,5,11,14,18,21-hexaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.06,10]hexacos-(24Z)-ylideneaminooxy]-acetic acid

[(3S,6S,12R,15S,16R,19S)-3-Benzyl-12-ethyl-15-[(3-hydroxy-pyridine-2-carbonyl)-amino]-4,16-dimethyl-2,5,11,14,18,21-hexaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.06,10]hexacos-(24Z)-ylideneaminooxy]-acetic acid

Conditions
ConditionsYield
With pyridine Condensation;96%
3-(1H-benzotriazol-1-ylcarbonyl)-7-(diethylamino)-2H-chromen-2-one
1286276-78-5

3-(1H-benzotriazol-1-ylcarbonyl)-7-(diethylamino)-2H-chromen-2-one

aminooxyacetic acid
645-88-5

aminooxyacetic acid

C16H18N2O6
1286277-09-5

C16H18N2O6

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 1h;92%
Fmoc-L-Phe-Bt

Fmoc-L-Phe-Bt

aminooxyacetic acid
645-88-5

aminooxyacetic acid

C26H24N2O6
1296207-17-4

C26H24N2O6

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 1h;92%
Fmoc-L-Met-Bt

Fmoc-L-Met-Bt

aminooxyacetic acid
645-88-5

aminooxyacetic acid

C22H24N2O6S
1286329-68-7

C22H24N2O6S

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 1h;92%
[1-(4-carbaldehydephenyl)-1,2,2-triphenyl]ethylene
1289218-74-1

[1-(4-carbaldehydephenyl)-1,2,2-triphenyl]ethylene

aminooxyacetic acid
645-88-5

aminooxyacetic acid

C29H23NO3

C29H23NO3

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water for 2.5h; Reflux;92%
aminooxyacetic acid
645-88-5

aminooxyacetic acid

C22H31NO3

C22H31NO3

Conditions
ConditionsYield
In tetrahydrofuran; 1,4-dioxane at 20℃; for 4h;91%
Cbz-AzaAla-Phe-Bt
1429433-35-1

Cbz-AzaAla-Phe-Bt

aminooxyacetic acid
645-88-5

aminooxyacetic acid

Cbz-AzaAla-Phe-AOGly-OH
1429433-51-1

Cbz-AzaAla-Phe-AOGly-OH

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 2h;90%
4-[5-(4-methylphenyl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonyl chloride
190711-56-9

4-[5-(4-methylphenyl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonyl chloride

aminooxyacetic acid
645-88-5

aminooxyacetic acid

[4-(5-p-methylphenyl-3-trifluoromethyl-pyrazol-1-yl)-henzenesulfonylaminooxy]-acetic acid

[4-(5-p-methylphenyl-3-trifluoromethyl-pyrazol-1-yl)-henzenesulfonylaminooxy]-acetic acid

Conditions
ConditionsYield
With sodium acetate In 1,4-dioxane; dichloromethane; water88%
7-methoxy-3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromene-2-one
1286276-26-3

7-methoxy-3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromene-2-one

aminooxyacetic acid
645-88-5

aminooxyacetic acid

C13H11NO7
1286277-86-8

C13H11NO7

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 1h;87%
3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromene-2-one
312929-01-4

3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromene-2-one

aminooxyacetic acid
645-88-5

aminooxyacetic acid

C12H9NO6
1286277-87-9

C12H9NO6

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 1h;83%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

aminooxyacetic acid
645-88-5

aminooxyacetic acid

[({[(2-methyl-2-propanyl)oxy]carbonyl}amino)oxy]acetic acid
42989-85-5

[({[(2-methyl-2-propanyl)oxy]carbonyl}amino)oxy]acetic acid

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 1.5h;83%
N-(coumarin-3-ylcarbonyl)-Gly-Bt
1290610-17-1

N-(coumarin-3-ylcarbonyl)-Gly-Bt

aminooxyacetic acid
645-88-5

aminooxyacetic acid

C14H12N2O7
1286329-87-0

C14H12N2O7

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 1h;82%
5-(4-formyl-5-hydroxy-6-methyl-pyrazolo[3,4-b]pyridin-2-yl)-isophthalic acid
918441-01-7

5-(4-formyl-5-hydroxy-6-methyl-pyrazolo[3,4-b]pyridin-2-yl)-isophthalic acid

aminooxyacetic acid
645-88-5

aminooxyacetic acid

5-[4-(carboxymethoxyimino-methyl)-5-hydroxy-6-methyl-pyrazolo[3,4-b]pyridin-2-yl]-isophthalic acid

5-[4-(carboxymethoxyimino-methyl)-5-hydroxy-6-methyl-pyrazolo[3,4-b]pyridin-2-yl]-isophthalic acid

Conditions
ConditionsYield
Stage #1: 5-(4-formyl-5-hydroxy-6-methyl-pyrazolo[3,4-b]pyridin-2-yl)-isophthalic acid; aminooxyacetic acid In water for 0.333333h; pH=6;
Stage #2: With hydrogenchloride In water
80%
bromo-triphenyl-methane
596-43-0

bromo-triphenyl-methane

aminooxyacetic acid
645-88-5

aminooxyacetic acid

Et3N

Et3N

(N-tritylaminooxy)acetic acid
112257-05-3

(N-tritylaminooxy)acetic acid

Conditions
ConditionsYield
In dichloromethane; N,N-dimethyl-formamide for 2h; Heating;77%
N-(7-methoxycoumarin-3ylcarbonyl)-Gly-Bt
1286276-59-2

N-(7-methoxycoumarin-3ylcarbonyl)-Gly-Bt

aminooxyacetic acid
645-88-5

aminooxyacetic acid

C15H14N2O8
1286320-43-1

C15H14N2O8

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 1h;75%
trityl chloride
76-83-5

trityl chloride

aminooxyacetic acid
645-88-5

aminooxyacetic acid

(N-tritylaminooxy)acetic acid
112257-05-3

(N-tritylaminooxy)acetic acid

Conditions
ConditionsYield
With pyridine at 20℃; for 22h; Inert atmosphere;74%
With pyridine; triethylamine at 20℃; for 22h;74%
14-hydroxy-3-methoxy-17-methyl-4,5-epoxymorphinan-6-one hydrochloride

14-hydroxy-3-methoxy-17-methyl-4,5-epoxymorphinan-6-one hydrochloride

aminooxyacetic acid
645-88-5

aminooxyacetic acid

({[(6E)-14-hydroxy-3-methoxy-17-methyl-4,5-epoxymorphinan-6-ylidene]amino}oxy)acetic acid

({[(6E)-14-hydroxy-3-methoxy-17-methyl-4,5-epoxymorphinan-6-ylidene]amino}oxy)acetic acid

Conditions
ConditionsYield
Stage #1: 14-hydroxy-3-methoxy-17-methyl-4,5-epoxymorphinan-6-one hydrochloride With sodium hydroxide In methanol for 0.25h;
Stage #2: aminooxyacetic acid With pyridine In methanol for 16h; Reflux;
70%
nitroveratryloxycarbonyl chloride
42855-00-5

nitroveratryloxycarbonyl chloride

aminooxyacetic acid
645-88-5

aminooxyacetic acid

2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylaminooxy)acetic acid
473433-22-6

2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylaminooxy)acetic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 15h;68%
4-formylphenylboronic acid,
87199-17-5

4-formylphenylboronic acid,

aminooxyacetic acid
645-88-5

aminooxyacetic acid

C9H10BNO5

C9H10BNO5

Conditions
ConditionsYield
In methanol at 25℃; Inert atmosphere;68%
aminooxyacetic acid
645-88-5

aminooxyacetic acid

salutaridine-7-(O-carboxymethyl)oxime

salutaridine-7-(O-carboxymethyl)oxime

Conditions
ConditionsYield
In methanol for 24h; Ambient temperature;67%
[4-((1R,3R)-(S)-9-bicyclo[3.3.1]non-3-yl-9-aza-bicyclo[3.3.1]non-3-yl)-3-oxo-3,4-dihydro-quinoxalin-2-yl]-4-oxo-butyric acid ethyl ester

[4-((1R,3R)-(S)-9-bicyclo[3.3.1]non-3-yl-9-aza-bicyclo[3.3.1]non-3-yl)-3-oxo-3,4-dihydro-quinoxalin-2-yl]-4-oxo-butyric acid ethyl ester

aminooxyacetic acid
645-88-5

aminooxyacetic acid

2-(((1-(4-((1R,1'R,3r,3'R,5S,5'S)-[3,9'-bi(9'-azabicyclo[3.3.1]nonan)]-3'-yl)-3-oxo-3,4-dihydroquinoxalin-2-yl)-4-ethoxy-4-oxobutylidene)amino)oxy)acetic acid

2-(((1-(4-((1R,1'R,3r,3'R,5S,5'S)-[3,9'-bi(9'-azabicyclo[3.3.1]nonan)]-3'-yl)-3-oxo-3,4-dihydroquinoxalin-2-yl)-4-ethoxy-4-oxobutylidene)amino)oxy)acetic acid

Conditions
ConditionsYield
With sodium acetate; acetic acid In ethanol at 20℃; for 18h; Inert atmosphere;67%
2-bromoisobutyric acid bromide
20769-85-1

2-bromoisobutyric acid bromide

allyl alcohol
107-18-6

allyl alcohol

aminooxyacetic acid
645-88-5

aminooxyacetic acid

C9H14BrNO4

C9H14BrNO4

Conditions
ConditionsYield
Stage #1: allyl alcohol; aminooxyacetic acid With thionyl chloride Inert atmosphere;
Stage #2: 2-bromoisobutyric acid bromide With pyridine In dichloromethane Inert atmosphere;
57%
N-(allyloxycarbonyloxy)succinimide
135544-68-2

N-(allyloxycarbonyloxy)succinimide

aminooxyacetic acid
645-88-5

aminooxyacetic acid

Aloc-Aoa-OH

Aloc-Aoa-OH

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;55%
4-[(1,4,4-trimethyl-pyrrolidin-2-ylidene)-acetyl]-benzaldehyde

4-[(1,4,4-trimethyl-pyrrolidin-2-ylidene)-acetyl]-benzaldehyde

aminooxyacetic acid
645-88-5

aminooxyacetic acid

[1-(4-{2-[1,4,4-Trimethyl-pyrrolidin-(2E)-ylidene]-acetyl}-phenyl)-meth-(E)-ylideneaminooxy]-acetic acid

[1-(4-{2-[1,4,4-Trimethyl-pyrrolidin-(2E)-ylidene]-acetyl}-phenyl)-meth-(E)-ylideneaminooxy]-acetic acid

Conditions
ConditionsYield
With barium carbonate In ethanol for 3h; Heating;53%
[(3R,4R)-3-acetyloxy-4-methyl-6-oxo-N-MeNle]-1-cyclosporin
121584-52-9

[(3R,4R)-3-acetyloxy-4-methyl-6-oxo-N-MeNle]-1-cyclosporin

aminooxyacetic acid
645-88-5

aminooxyacetic acid

C62H110N12O15
122547-79-9

C62H110N12O15

Conditions
ConditionsYield
Stage #1: [(3R,4R)-3-acetyloxy-4-methyl-6-oxo-N-MeNle]-1-cyclosporin; aminooxyacetic acid In acetonitrile at 20℃; for 0.5h; pH=4.9;
Stage #2: With sodium methylate In methanol at 20℃; for 4h;
Stage #3: With water; ammonium chloride In methanol
39%
benzyl isothiocyanate
3173-56-6

benzyl isothiocyanate

aminooxyacetic acid
645-88-5

aminooxyacetic acid

2-(3-benzylureidooxy)acetic acid
1198777-83-1

2-(3-benzylureidooxy)acetic acid

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃;33%
tylosin
1401-69-0

tylosin

aminooxyacetic acid
645-88-5

aminooxyacetic acid

C48H80N2O19
1235514-45-0

C48H80N2O19

Conditions
ConditionsYield
In dimethyl sulfoxide at 50℃; for 12h; pH=4.7; sodium acetate buffer;28%
methanol
67-56-1

methanol

aminooxyacetic acid
645-88-5

aminooxyacetic acid

O-methoxycarbonylmethylhydroxylamine
25184-48-9

O-methoxycarbonylmethylhydroxylamine

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; for 20h;26%

2-(Aminooxy)acetic acid Chemical Properties

AMINOOXYACETIC ACID's MF: C2H5NO3
AMINOOXYACETIC ACID's MW: 91.08
Synonyms: Hydroxylamine, O-(carboxymethyl)-;Aminooxyacetic Acid;2-(Aminooxy)acetic acid;AOAA;O-(Carboxymethyl)hydroxylamine;U-7524

2-(Aminooxy)acetic acid Uses

AMINOOXYACETIC ACID is mutagen.

2-(Aminooxy)acetic acid Toxicity Data With Reference

1.   

mmo-bcs 1 mol/L

   MUREAV    Mutation Research. 4 (1967),517.
2.   

ipr-mus LD50:40 mg/kg

   BCPCA6    Biochemical Pharmacology. 28 (1979),1397.
3.   

scu-mus LD50:40 mg/kg

   BCPCA6    Biochemical Pharmacology. 27 (1978),103.

2-(Aminooxy)acetic acid Safety Profile

Poison by subcutaneous and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
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