645-88-5

Basic information

• Product Name: Hydroxylamine, O-(carboxymethyl)-
• Synonyms: Hydroxylamine, O-(carboxymethyl)-;Aminooxyacetic Acid;2-(Aminooxy)acetic acid;AOAA;O-(Carboxymethyl)hydroxylamine;U-7524;(Carboxymethoxy)amine;Aminoxyacetic acid
• CAS NO: 645-88-5
• Molecular Formula: C₂H₅NO₃
• Molecular Weight: 91.08
• Mol File: 645-88-5.mol

Chemical Properties

• Melting Point: 138℃
• Boiling Point: 327℃
• Flash Point: 151℃
• Appearance: /
• Density: 1.375
• Refractive Index: 1.4264 (estimate)
• PKA: 1.92±0.10(Predicted)
• CAS DataBase Reference: Hydroxylamine, O-(carboxymethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Hydroxylamine, O-(carboxymethyl)-(645-88-5)
• EPA Substance Registry System: Hydroxylamine, O-(carboxymethyl)-(645-88-5)

Safety Data

• Safety Statements: x." target="_blank">Poison by subcutaneous and intraperitoneal routes. Mutation data reported. When heated to decomposition it e
• Hazardous Substances Data: 645-88-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Hydroxylamine, O-(carboxymethyl)is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique functional groups enable the formation of diverse chemical structures, contributing to the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical industry, Hydroxylamine, O-(carboxymethyl)serves as a key intermediate in the production of various agrochemicals, such as pesticides and herbicides. Its reactivity and functional group compatibility allow for the creation of effective and targeted agrochemicals to protect crops and enhance agricultural productivity.
Used in Chemical Synthesis:
Hydroxylamine, O-(carboxymethyl)is utilized in the synthesis of a wide range of chemicals and materials due to its reactive functional groups. Its ability to form various chemical bonds and participate in different reaction pathways makes it a valuable building block in the chemical industry.
Used in Research and Development:
In research and development, Hydroxylamine, O-(carboxymethyl)is employed as a reagent or starting material for exploring new chemical reactions and developing innovative compounds. Its unique properties and functional groups provide opportunities for scientists to investigate novel chemical transformations and applications.

Synthetic route

ethyl N-(ethoxycarbonyl)aminooxyacetate (68871-49-8) → aminooxyacetic acid (645-88-5)

Conditions	Yield
With hydrogenchloride

Benzylidenaminooxy-essigsaeure (141891-22-7, 5382-90-1) → aminooxyacetic acid (645-88-5)

Conditions	Yield
With water; phenylhydrazine hydrochloride

N-benzoylaminooxyacetic acid (5251-93-4) → aminooxyacetic acid (645-88-5)

Conditions	Yield
With hydrogenchloride Heating;

chloroacetic acid (79-11-8) + acetone oxime (127-06-0) → aminooxyacetic acid (645-88-5)

Conditions	Yield
(i) aq. NaOH, (ii) AcOH; Multistep reaction;

(3-Bromo-5-chloro-benzoylaminooxy)-acetic acid → aminooxyacetic acid (645-88-5)

Conditions	Yield
With hydrogenchloride Heating;

ethyl 2-(aminooxy)-acetate (5740-47-6) → aminooxyacetic acid (645-88-5)

Conditions	Yield
With potassium hydroxide; bromoacetic acid,potassium salt

chloroacetic acid (79-11-8) + dipotassium-salt of/the/ hydroxylamine-N,N-disulfonic acid → aminooxyacetic acid (645-88-5)

Conditions	Yield
With potassium hydroxide Erhitzen des Reaktionsprodukts mit wss.Salzsaeure;

ethylbenzhydroximacetic acid → aminooxyacetic acid (645-88-5)

Conditions	Yield
With hydrogenchloride

ethyl bromoacetate (105-36-2) + potassium-salt of/the/ benzohydroxamic acid → aminooxyacetic acid (645-88-5)

Conditions	Yield
With potassium hydroxide Erhitzen des Reaktionsprodukts mit wss.Salzsaeure;

hydrogenchloride (7647-01-0) + (α-ethoxy-benzylidenaminooxy)-acetic acid → benzoic acid ethyl ester (93-89-0) + aminooxyacetic acid (645-88-5)

O-methoxycarbonylmethylhydroxylamine (25184-48-9) → aminooxyacetic acid (645-88-5)

Conditions	Yield
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 → aminooxyacetic acid (645-88-5)

Conditions	Yield
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) + aminooxyacetic acid (645-88-5) → (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	Yield
In pyridine at 20℃; for 17h;	100%

Estrone (53-16-7) + aminooxyacetic acid (645-88-5) → 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)

Conditions	Yield
With pyridine at 20℃; for 17h;	100%

Virginiamycin S1 (668-72-4, 23152-29-6, 117603-96-0) + aminooxyacetic acid (645-88-5) → [(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	Yield
With pyridine Condensation;	96%

3-(1H-benzotriazol-1-ylcarbonyl)-7-(diethylamino)-2H-chromen-2-one (1286276-78-5) + aminooxyacetic acid (645-88-5) → C16H18N2O6 (1286277-09-5)

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃; for 1h;	92%

Fmoc-L-Phe-Bt + aminooxyacetic acid (645-88-5) → C26H24N2O6 (1296207-17-4)

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃; for 1h;	92%

Fmoc-L-Met-Bt + aminooxyacetic acid (645-88-5) → C22H24N2O6S (1286329-68-7)

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃; for 1h;	92%

[1-(4-carbaldehydephenyl)-1,2,2-triphenyl]ethylene (1289218-74-1) + aminooxyacetic acid (645-88-5) → C29H23NO3

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water for 2.5h; Reflux;	92%

Dehydroabientinal (10181-17-6, 10181-28-9, 13601-88-2, 24035-50-5, 62319-06-6) + aminooxyacetic acid (645-88-5) → C22H31NO3

Conditions	Yield
In tetrahydrofuran; 1,4-dioxane at 20℃; for 4h;	91%

Cbz-AzaAla-Phe-Bt (1429433-35-1) + aminooxyacetic acid (645-88-5) → Cbz-AzaAla-Phe-AOGly-OH (1429433-51-1)

Conditions	Yield
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) + aminooxyacetic acid (645-88-5) → [4-(5-p-methylphenyl-3-trifluoromethyl-pyrazol-1-yl)-henzenesulfonylaminooxy]-acetic acid

Conditions	Yield
With sodium acetate In 1,4-dioxane; dichloromethane; water	88%

7-methoxy-3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromene-2-one (1286276-26-3) + aminooxyacetic acid (645-88-5) → C13H11NO7 (1286277-86-8)

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃; for 1h;	87%

3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromene-2-one (312929-01-4) + aminooxyacetic acid (645-88-5) → C12H9NO6 (1286277-87-9)

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃; for 1h;	83%

di-tert-butyl dicarbonate (24424-99-5) + aminooxyacetic acid (645-88-5) → [({[(2-methyl-2-propanyl)oxy]carbonyl}amino)oxy]acetic acid (42989-85-5)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1.5h;	83%

N-(coumarin-3-ylcarbonyl)-Gly-Bt (1290610-17-1) + aminooxyacetic acid (645-88-5) → C14H12N2O7 (1286329-87-0)

Conditions	Yield
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) + aminooxyacetic acid (645-88-5) → 5-[4-(carboxymethoxyimino-methyl)-5-hydroxy-6-methyl-pyrazolo[3,4-b]pyridin-2-yl]-isophthalic acid

Conditions	Yield
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) + aminooxyacetic acid (645-88-5) + Et3N → (N-tritylaminooxy)acetic acid (112257-05-3)

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide for 2h; Heating;	77%

N-(7-methoxycoumarin-3ylcarbonyl)-Gly-Bt (1286276-59-2) + aminooxyacetic acid (645-88-5) → C15H14N2O8 (1286320-43-1)

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃; for 1h;	75%

trityl chloride (76-83-5) + aminooxyacetic acid (645-88-5) → (N-tritylaminooxy)acetic acid (112257-05-3)

Conditions	Yield
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 + aminooxyacetic acid (645-88-5) → ({[(6E)-14-hydroxy-3-methoxy-17-methyl-4,5-epoxymorphinan-6-ylidene]amino}oxy)acetic acid

Conditions	Yield
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) + aminooxyacetic acid (645-88-5) → 2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylaminooxy)acetic acid (473433-22-6)

Conditions	Yield
In N,N-dimethyl-formamide for 15h;	68%

4-formylphenylboronic acid, (87199-17-5) + aminooxyacetic acid (645-88-5) → C9H10BNO5

Conditions	Yield
In methanol at 25℃; Inert atmosphere;	68%

salutaridine (4090-18-0, 23979-21-7, 1936-18-1) + aminooxyacetic acid (645-88-5) → salutaridine-7-(O-carboxymethyl)oxime

Conditions	Yield
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 + aminooxyacetic acid (645-88-5) → 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	Yield
With sodium acetate; acetic acid In ethanol at 20℃; for 18h; Inert atmosphere;	67%

2-bromoisobutyric acid bromide (20769-85-1) + allyl alcohol (107-18-6) + aminooxyacetic acid (645-88-5) → C9H14BrNO4

Conditions	Yield
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) + aminooxyacetic acid (645-88-5) → Aloc-Aoa-OH

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;	55%

4-[(1,4,4-trimethyl-pyrrolidin-2-ylidene)-acetyl]-benzaldehyde + aminooxyacetic acid (645-88-5) → [1-(4-{2-[1,4,4-Trimethyl-pyrrolidin-(2E)-ylidene]-acetyl}-phenyl)-meth-(E)-ylideneaminooxy]-acetic acid

Conditions	Yield
With barium carbonate In ethanol for 3h; Heating;	53%

[(3R,4R)-3-acetyloxy-4-methyl-6-oxo-N-MeNle]-1-cyclosporin (121584-52-9) + aminooxyacetic acid (645-88-5) → C62H110N12O15 (122547-79-9)

Conditions	Yield
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) + aminooxyacetic acid (645-88-5) → 2-(3-benzylureidooxy)acetic acid (1198777-83-1)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;	33%

tylosin (1401-69-0) + aminooxyacetic acid (645-88-5) → C48H80N2O19 (1235514-45-0)

Conditions	Yield
In dimethyl sulfoxide at 50℃; for 12h; pH=4.7; sodium acetate buffer;	28%

methanol (67-56-1) + aminooxyacetic acid (645-88-5) → O-methoxycarbonylmethylhydroxylamine (25184-48-9)

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

Upstream product

• 68871-49-8 ethyl N-(ethoxycarbonyl)aminooxyacetate 
• 141891-22-7 Benzylidenaminooxy-essigsaeure 
• 5251-93-4 N-benzoylaminooxyacetic acid 
• 79-11-8 chloroacetic acid 
• 127-06-0 acetone oxime 
• 5740-47-6 ethyl 2-(aminooxy)-acetate 
• 105-36-2 ethyl bromoacetate 
• 7647-01-0 hydrogenchloride 
• 25184-48-9 O-methoxycarbonylmethylhydroxylamine 
• 5251-81-0 N-(ethoxy carbonyl methoxy)-phthalimide 

Downstream Products

• 141891-22-7 benzaldehyde imino-oxy acetic acid 
• 1205-09-0 (1-phenyl-ethylidenaminooxy)-acetic acid 
• 5382-89-8 [(propan-2-ylideneamino)oxy]acetic acid 
• 71103-67-8 {[((E)-4-phenylbut-3-en-2-ylidene)amino]oxy}acetic acid 
• 10190-93-9 testosterone 3-(O-carboxymethyl)oxime 
• 6169-23-9 ε-Phenylureido-oxyessigsaeure 
• 5740-47-6 ethyl 2-(aminooxy)-acetate 
• 27091-81-2 Guanidinooxyacetic-acid 
• 46230-31-3 benzyl 2-(aminooxy)acetate 
• 37654-41-4 6-oxoestriol-6-(O-carboxymethyl)oxime 
• 35048-47-6 6-keto-1,3,5(10)estratriene-3,17β-diol 6-carboxymethyloxime 
• 14962-35-7 N-carboxymethoxy-4-toluenesulfonamide 
• 188175-95-3 Benzoic acid (3S,8R,9S,10S,13S,14S,17S)-17-acetoxy-10-(carboxymethoxyimino-methyl)-13-methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 112257-05-3 (N-tritylaminooxy)acetic acid 

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