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
• Article Data: 4

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

General Description

Hydroxylamine, O-(carboxymethyl)- is a chemical compound with the molecular formula C3H7NO3. It is an organic compound that contains both a hydroxylamine functional group and a carboxymethyl functional group. Hydroxylamine is a derivative of ammonia and is utilized in various industrial processes, including the production of pharmaceuticals and agrochemicals. The carboxymethyl group contains a carboxyl group bonded to a methyl group and is often used in the synthesis of various chemicals and materials. The combination of these two functional groups in the compound hydroxylamine, O-(carboxymethyl)- makes it useful for a wide range of applications in the chemical industry.

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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