5470-11-1

Basic information

• Product Name: Hydroxylamine hydrochloride
• Synonyms: OXAMMONIUM HCL;OXAMMONIUM HYDROCHLORIDE;hydroxyaminehydrochloride;hydroxylaminechloride;hydroxylaminechloride(1:1);Oxammionium;HYDROXYAMMONIUM CHLORIDE;HYDROXYLAMINE/HCL SOLUTION
• CAS NO: 5470-11-1
• Molecular Formula: Cl*H₄NO
• Molecular Weight: 69.49
• EINECS: 226-798-2
• Product Categories: Pharmaceutical Intermediates;Anilines, Aromatic Amines and Nitro Compounds;Inorganics;Amination;Hydroxylamines;Hydroxylamines (Unsubstituted);Synthetic Organic Chemistry;Pharma material
• Mol File: 5470-11-1.mol

Chemical Properties

• Melting Point: 155-157 °C (dec.)(lit.)
• Boiling Point: 56.5 °C at 760 mmHg
• Appearance: White to off-white/Liquid
• Density: 1.67 g/mL at 25 °C(lit.)
• Vapor Pressure: 179mmHg at 25°C
• Storage Temp.: Store at RT.
• Solubility: 470g/l
• Water Solubility: 560 g/L (20 ºC)
• Sensitive: Hygroscopic
• Stability: Substances to be avoided include strong oxidizing agents. Heating above 115 C may cause explosion; do not store above 65C. Moist
• Merck: 14,4828
• BRN: 3539763
• CAS DataBase Reference: Hydroxylamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Hydroxylamine hydrochloride(5470-11-1)
• EPA Substance Registry System: Hydroxylamine hydrochloride(5470-11-1)

Safety Data

• Hazard Codes: Xn,N,E
• Statements: 22-36/38-43-48/22-50-40-21/22-2
• Safety Statements: 22-24-37-61-36/37
• RIDADR: UN 2923 8/PG 2
• WGK Germany: 3
• RTECS: NC3675000
• F: 21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 5470-11-1(Hazardous Substances Data)

Usage

Description

Hydroxylamine hydrochloride is a reducing agent that is routinely used for the deacetylation of SATA to form free sulfhydryls (Figure 1), for cleavage of protein cross‐linkers that contain carbonyl groups (i.e. EGS) and for mutagenesis of plasmid DNA.Hydroxylamine converts aldehydes and ketones (carbonyls) to their oxime derivative in weak bases, therefore cross‐linkers and other compounds with carbonyl groups are cleavable with Hydroxylamine hydrochloride.SATA and SATP are modification reagents that add a sulfhydryl group to primary amines on biomolecules. The initial modification results in the addition of an acetyl‐protected sulfur enabling storage of the biomolecule. To generate a free sulfhydryl the biomolecule is treated with hydroxylamine to remove the protecting acetyl group (see figure).EGS and sulfo‐EGS are homobifunctional, succinimidyl ester, amine reactive crosslinkers that are resistant to cleavage by denaturants used in SDS‐PAGE conditions, but may be cleaved with hydroxylamine.

Description

Hydroxylamine hydrochloride is an inorganic substance, a colorless crystalline, easily deliquescence, white chemical substance, mainly used as a reducing agent and an imaging agent, used in the preparation of oximes in organic synthesis, and also used in the synthesis of anticancer drugs (hydroxylamine hydrochloride). urea), sulfonamides (trimoxazole) and pesticides (methomyl). It has strong hygroscopicity and will decompose when it is damped above 151℃. At 17°C, 83.8g can be dissolved in 100g of water. This product is highly toxic and irritating to the skin. The production equipment should be sealed to prevent running, running, dripping and leaking, and operators should wear protective equipment. When splashed on the skin, rinse with plenty of water.

Chemical Properties

White crystals

Physical properties

Colorless monoclinic crystals; hygroscopic; decomposes slowly in moist air;density 1.67 g/cm3at 17°C; melts at 151°C (decomposes); highly soluble inwater (84g/100g at 20°C); soluble in lower alcohols and glycols; pH of 0.1molar solution 3.4.

Uses

Organic synthesis, photographic developer, medicine, controlled reduction reactions, nondiscoloring short-stopper for synthetic rubbers, antioxidant for fatty acids.

Uses

Hydroxylamine hydrochloride is a monomoamine oxidase inhibitor. It is used to prepare oximes and hydroxmic acids in organic synthesis. It acts as a copolymerization inhibitor. It can be used to remove bromine and polybromide from a solution during extraction of lignin from lignocellulosic biomass. It is key starting material for the preparation of pharmaceuticals and agrochemicals. It plays a vital role in rubber and plastic industries as an antioxidant, a vulcanization accelerator and a radical scavenger. It is also used as a color stabilizer and emulsion additive in color films.

Uses

Hydroxylammonium-chloride is a reducing agent in photography; in synthetic and analytical chemistry; as an antioxidant for fatty acids and soaps; in textiles; in medicine; controlled reduction reactions; non-discoloring short stoppers for synthetic rubbers; reagent for enzyme reactivation; powerful reducing agent; converts aldehydes and ketones to oximes and acid chlorides to hydroxamic acids; catalyst, swelling agent, and copolymerization inhibitor in polymerization processes; in floor lacquers and as an antioxidant for fatty acids and soaps.

Preparation

Sodium nitrite synthesis method (oximation method) Add water to the reaction kettle, add sodium nitrite under stirring, add sodium metabisulfite in stages, and then acidify with sulfuric acid. The acidified material is sent to the hydrolysis kettle, acetone is added, neutralized with liquid caustic soda, and the neutralized liquid is distilled to obtain acetone oxime. Acetone oxime and hydrochloric acid are added to the salt-forming kettle for reaction to generate hydroxylamine hydrochloride and acetone. Acetone is recovered and used; hydroxylamine hydrochloride is concentrated, crystallized by cooling, centrifuged and dried to obtain the finished product. Raw material consumption quota: sodium nitrite (95%) 1970kg/t, sodium metabisulfite (64% as SO2) 5418kg/t, acetone (98%) 1175kg/t. 2. Nitromethane method Nitromethane reacts with hydrochloric acid and water to obtain hydroxylamine hydrochloride. According to HGB3044-76, the hydroxylamine hydrochloride product is white crystal, the content of the second-grade product is ≥98.5, and the content of the third-grade product is ≥97%. Raw material consumption quota: nitromethane 1200kg/t, hydrochloric acid (30%) 1500kg/t. Or by the action of nitromethane with hydrochloric acid and water to obtain hydroxylamine hydrochloride.

Preparation

Hydroxylamine hydrochloride is prepared by electrolytic reduction ofammonium chloride.

Biotechnological Applications

Hydroxylamine hydrochloride is a strong reducing agent that is useful in biochemical crosslinking applications, including the deacetylation of SATA and chemical cleavage of EGS and Sulfo-EGS. Hydroxylamine converts carbonyl compounds (aldehydes and ketones) to their oxime derivatives in the presence of a weak base. Therefore, crosslinkers and other compounds that contain a carbonyl within their structure are cleavable with hydroxylamine?HCl. EGS? and its water-soluble analog, Sulfo-EGS, are homobifunctional, succinimidyl ester, amine-reactive crosslinkers useful for covalent stabilization of polypeptide multimers and protein:protein interactions. Unlike disulfidecontaining crosslinkers, EGS and Sulfo-EGS will not cleave by reducing SDS-PAGE conditions but may be cleaved when necessary with hydroxylamine. SATA? and SATP are modification reagents for addition of sulfhydryl groups to proteins and other molecules containing primary amines. Such sulfhydryl addition is an important step in one popular method for preparing protein conjugates such as antibodies with horseradish peroxidase enzyme. The initial modification results in addition of an acetyl-protected sulfur, enabling storage of the modified protein; to make the sulfur available as a sulhydryl group (-SH) for the final conjugation reaction, hydroxylamine is used to remove the protecting acetyl group. Hydroxylamine?HCl is more stable to oxidation than the free base form of hydroxylamine; nevertheless, always prepare hydroxylamine solutions immediately before use and store the product desiccated. Hydroxylamine?HCl is soluble in polar solvents such as water, ethanol, methanol, glycerol and propylene glycol.

General Description

Colorless or off-white crystalline solid. pH (0.1 molar aqueous solution) 3.4. pH (0.2 molar aqueous solution) 3.2.

Air & Water Reactions

Hygroscopic. Sensitive to prolonged exposure to air. Water soluble. Reacts slowly with water.

Reactivity Profile

A powerful reducing agent. Reacts with bases and oxidizing agents.

Hazard

Toxic by ingestion, strong irritant to tissue.

Fire Hazard

Flash point data for Hydroxylamine hydrochloride are not available; however, Hydroxylamine hydrochloride is probably combustible.

Biochem/physiol Actions

MAO inhibitor; inhibits platelet aggregation.

Contact allergens

Hydroxylamine and its salts are used in various branches of industry, as reducing agents in color film developers or as reagents in laboratories.

Purification Methods

Crystallise the salt from aqueous75% ethanol or boiling methanol, and dry it under vacuum over CaSO4 or P2O5. It has also been dissolved in a minimum of water and saturated with HCl; after three such crystallisations, it is dried under a vacuum over CaCl2 and NaOH. Its solubility at 20o is 85% in H2O, 6% in EtOH and 12% in MeOH. [Hurd Inorg Synth I 87 1939, Semon in Org Synth Coll Vol I 318 1941.]

InChI:InChI=1/ClH.H3NO/c;1-2/h1H;2H,1H2

Synthetic route

Mo(NO)(NH2O)(C6H4S2C2H4S2C6H4)*C4H8O → {Mo(NO)(Cl)(dttd)} + hydroxylamine hydrochloride (5470-11-1)

Conditions	Yield
With hydrogenchloride In methanol byproducts: NH4Cl, N2H5Cl; (N2); HCl bubbled through a soln. of the Mo-complex at 0°C for 15 min; soln. stirred for 1.5 h at room temp.; N2 bubbled through the suspn. for 15 min; ppt. filtered, washed with methanol and diethyl ether; recrystd. from hot THF;	A 93% B n/a

ethyl nitrate (625-58-1) + tin(ll) chloride → hydroxylamine hydrochloride (5470-11-1) + ammonia (7664-41-7) + tin(IV) chloride (7646-78-8)

Conditions	Yield
With hydrogenchloride In hydrogenchloride byproducts: C2H5OH, H2O; in concd. HCl soln.; evapn. of the alcohol,diluting with water,pptg. of the Sn with H2S,evapn. and crystn. from alcohol;	A 90% B <1 C n/a

[Ni(II)(salicylaldehyde oximate)2] (54515-04-7, 50897-08-0, 14363-30-5) + ethylenediamine hydrochloride (18299-54-2) → Ni(C6H4(O)CHNC2H4NH2)2 + hydroxylamine hydrochloride (5470-11-1)

Conditions	Yield
In methanol stirring the soln. for 30 min between room temp. and 60°C, pptn.; filtration, washing with water, recrystn. from acetone;	A 90% B n/a

potassium nitrite (7758-09-0) → hydroxylamine hydrochloride (5470-11-1)

Conditions	Yield
With hydrogenchloride; sulfur dioxide In water byproducts: H2SO4; react. in water contg. ice and K-acetate leading SO2 into it,mixing,at 0°C;filtering,washing with 0.5 n HCl,hydrolysis at 100°C,for 2h; pptg. of H2SO4 with BaCl2,filtering,evapn.;	85%

hydrogenchloride (7647-01-0) + nitric acid (7697-37-2) → hydroxylamine hydrochloride (5470-11-1) + ammonium chloride

Conditions	Yield
In sulfuric acid Electrolysis; mixing dild. HCl with dild. HNO3 in an amalgated lead cell as cathode under applying lead anode (anode liquid: dild. H2SO4), 15°C, current: 50 A and 25 V; evapn., then cooling, removing of NH4Cl by treating with cold abs. alc., recrystn. from alcohol;	A 80% B n/a
In sulfuric acid aq. H2SO4; Electrolysis; mixing dild. HCl with dild. HNO3 in an amalgated lead cell as cathode under applying lead anode (anode liquid: dild. H2SO4), 15°C, current: 50 A and 25 V; evapn., then cooling, removing of NH4Cl by treating with cold abs. alc., recrystn. from alcohol;	A 80% B n/a

(E,Z)-(4-chlorophenyl)(cyclopropyl)methanone oxime → 4-chlorophenyl cyclopropyl ketone (6640-25-1) + hydroxylamine hydrochloride (5470-11-1)

hydrogen sulfide (7783-06-4) + nitrosylchloride (2696-92-6) → hydroxylamine hydrochloride (5470-11-1) + sulfur (7704-34-9)

Conditions	Yield
In neat (no solvent) byproducts: sulfur chloride, HCl, NO; further by-products: N2, NH4Cl;;	A 0% B n/a
In neat (no solvent) byproducts: sulfur chloride, HCl, NO; further by-products: N2, NH4Cl;;	A 0% B n/a

mercury(II) fulminate → hydroxylamine hydrochloride (5470-11-1)

Conditions	Yield
With hydrogenchloride byproducts: HCO2H; under cooling;
With HCl byproducts: HCO2H; under cooling;

hydroxyammonium sulfate + barium(II) chloride → barium sulfate + hydroxylamine hydrochloride (5470-11-1)

Conditions	Yield
In water excess of BaCl2; evapn., residue extrd. in a Soxhlet apparate with abs. alcohol, crystn.;
In water excess of BaCl2; evapn., residue extrd. in a Soxhlet apparate with abs. alcohol, crystn.;

mercury fulminate (3021-39-4, 34460-67-8, 72044-14-5) → hydroxylamine hydrochloride (5470-11-1)

Conditions	Yield
With hydrogenchloride with cooled,concd. HCl; evapn.,dissolving in water,removing of the Hg with H2S,evapn.,crystn.;

1-Nitropropane (108-03-2) → hydroxylamine hydrochloride (5470-11-1) + propionic acid (802294-64-0)

Conditions	Yield
With hydrogenchloride heating in closed tube,130-150°C;

hydrogenchloride (7647-01-0) + 1-Nitropropane (108-03-2) → hydroxylamine hydrochloride (5470-11-1)

Conditions	Yield
In water decompn. of nitro compound with a double volume of aq. HCl in a sealed tube at 130-150°C;
In water decompn. of nitro compound with a double volume of aq. HCl in a sealed tube at 130-150°C;

hydrogenchloride (7647-01-0) + 2-nitropropane (79-46-9) → hydroxylamine hydrochloride (5470-11-1)

Conditions	Yield
In water decompn. of nitro compound with a double volume of aq. HCl in a sealed tube at 130-150°C;
In water decompn. of nitro compound with a double volume of aq. HCl in a sealed tube at 130-150°C;

tin (7440-31-5) + ethylnitrolic acid (600-26-0) → hydroxylamine hydrochloride (5470-11-1)

Conditions	Yield
With hydrogenchloride In water byproducts: acetic acid; diluting with water,distn.,filtering,pptg. of tin with H2S,evapn.,washing with ether;

hydrogenchloride (7647-01-0) + ethylnitrolic acid (600-26-0) → hydroxylamine hydrochloride (5470-11-1)

Conditions	Yield
With tin In water heating, removing of Sn with H2S, diln. with water; evapn.;
With Sn In water heating, removing of Sn with H2S, diln. with water; evapn.;

tin (7440-31-5) + 2,2-dinitropropane (595-49-3) → hydroxylamine hydrochloride (5470-11-1) + dinitrogen monoxide (10024-97-2)

Conditions	Yield
With hydrogenchloride byproducts: acetone; with dild. HCl,cooling; pptg. of Sn with H2S,filtering,evapn.,washing with ether-alcohol;

hydrogenchloride (7647-01-0) + 2,2-dinitropropane (595-49-3) → hydroxylamine hydrochloride (5470-11-1)

Conditions	Yield
With tin In water heating, removing of Sn with H2S, diln. with water; evapn.;
With Sn In water heating, removing of Sn with H2S, diln. with water; evapn.;

tin (7440-31-5) + trinitromethane (517-25-9) → hydroxylamine hydrochloride (5470-11-1)

Conditions	Yield
With hydrogenchloride with dild. HCl;

hydrogenchloride (7647-01-0) + trinitromethane (517-25-9) → hydroxylamine hydrochloride (5470-11-1)

Conditions	Yield
With tin
With Sn

dihydrogen hexachloroplatinate + hydroxyl ammonium hydroxide → Pt(2+)*4NH2OH*2OH(1-)={Pt(NH2OH)4}(OH)2 + nitrogen (7727-37-9) + hydroxylamine hydrochloride (5470-11-1)

Conditions	Yield
In not given boiling the dild. soln.;
In not given boiling the dild. soln.;

ethyl Bromopyruvate (70-23-5) + hydroxylamine hydrochloride (5470-11-1) → ethyl (2Z)-3-bromo-2-(hydroxyimino)propanoate (127033-04-9)

Conditions	Yield
In methanol; chloroform for 16h; Ambient temperature;	100%

4-[1-(2,2-dimethyl-propionyl)-5-formyl-1H-indol-6-yloxy]-but-2-enoic acid ethyl ester (666234-08-8) + hydroxylamine hydrochloride (5470-11-1) → 4-[1-(2,2-dimethyl-propionyl)-5-(hydroxyimino-methyl)-1H-indol-6-yloxy]-but-2-enoic acid ethyl ester (666234-09-9)

Conditions	Yield
With sodium acetate In ethanol at 0℃; for 1h;	100%

hydroxylamine hydrochloride (5470-11-1) + (3Z/E)-3-(chloromethylene)-2,3-dihydro-1-benzoxepine-7-carbaldehyde → 1-[3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-yl]ethanone oxime

Conditions	Yield
With sodium acetate In methanol at 20℃; for 24h;	100%

(RS)-2,3,3a,4,5,6-hexahydro-phenalen-1-one (62715-22-4) + hydroxylamine hydrochloride (5470-11-1) → 2,3,3a,4,5,6-hexahydro-phenalen-1-one oxime (100371-82-2)

Conditions	Yield
Stage #1: (RS)-2,3,3a,4,5,6-hexahydro-phenalen-1-one; hydroxylamine hydrochloride With sodium acetate In ethanol at 20 - 80℃; for 20h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water	100%

C27H27ClN4O2 + hydroxylamine hydrochloride (5470-11-1) → C27H27N5O2

Conditions	Yield
With pyridine at 20 - 116℃; for 22h;	100%

Methyl 4-(3,4-dichlorobenzyl)-2-formylfuro[3,2-b ]pyrrole-5-carboxylate (238749-16-1) + hydroxylamine hydrochloride (5470-11-1) → Methyl 2-cyano-4-(3,4-dichlorobenzyl)furo[3,2-b ]pyrrole-5-carboxylate (238749-19-4)

Conditions	Yield
With acetic anhydride In pyridine	100%
With acetic anhydride In pyridine	100%

ferrocenecarboxaldehyde (12093-10-6) + hydroxylamine hydrochloride (5470-11-1) → ferrocenecarboxaldoxime

Conditions	Yield
With sodium hydroxide In ethanol for 16h; Inert atmosphere; Schlenk technique; Reflux;	100%
With sodium acetate In ethanol; water under N2; H2NOH*HCl (2 equiv.) in water added to Fe complex in EtOH; AcONa (3 equiv.) added; refluxed for 3 h; cooled; concd. in vac.; CHCl3 added dropwise; stirred for 0.5 h; according to K. Schoegl, et al., Monatsh. Chem. 97 (1966) 150; filtered; filtrate concd. under vac.;	95.8%
With sodium hydroxide In ethanol for 3h; Reflux;	92%

HIrCl2(tricyclohexylphosphine)2 (70876-21-0) + hydroxylamine hydrochloride (5470-11-1) → Ir(3+)*2Cl(1-)*H(1-)*NH2OH*2P(C6H11)3=IrCl2(NH2OH)(H)(P(C6H11)3)2

Conditions	Yield
With KOH In toluene Ar-atmosphere; stirring for 24 h (pptn.); collection (filtration), washing (MeOH), drying (vac.); elem. anal.;	100%

2,3-dihydro-2-hexyl-6-hydroxy-2,5,7,8-tetramethyl-4H-1-benzopyran-4-one (389634-20-2) + hydroxylamine hydrochloride (5470-11-1) → 2,3-dihydro-2-hexyl-6-hydroxy-2,5,7,8-tetramethyl-4H-1-benzopyran-4-one-oxime (389634-21-3)

Conditions	Yield
In pyridine at 70℃;	100%

3,4-dihydro-2,2,5,7,8-pentamethyl-6-hydroxy-2H-1-benzopyran-4-one (19017-66-4) + hydroxylamine hydrochloride (5470-11-1) → 2,3-dihydro-6-hydroxy-2,2,5,7,8-pentamethyl-4H-1-benzopyran-4-one-oxime (24700-12-7)

Conditions	Yield
In pyridine at 70℃;	100%

hydroxylamine hydrochloride (5470-11-1) + bis(julolidin-9-yl)methylium tetrafluoroborate → N-(bis(1,2,3,5,6,7-hexahydropyrido(3,2,1-ij)quinolin-9-yl)methyl)-hydroxylamine (1397751-33-5)

Conditions	Yield
Stage #1: hydroxylamine hydrochloride With trimethylamine In ethanol at 20℃; Stage #2: bis(julolidin-9-yl)methylium tetrafluoroborate In ethanol; acetonitrile at 20℃; for 0.0833333h;	100%

hydroxylamine hydrochloride (5470-11-1) + benzaldehyde (100-52-7) → Benzaldoxime (932-90-1)

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 1h; Cooling with ice;	100%

2,3-dihydro-4H-1-benzopyran-4-one (491-37-2) + hydroxylamine hydrochloride (5470-11-1) → (4E)-2,3-dihydro-4H-chromen-4-one oxime (24541-01-3)

Conditions	Yield
With sodium acetate In ethanol; water	99%

ferrocenecarboxaldehyde (12093-10-6) + hydroxylamine hydrochloride (5470-11-1) → FeC10H9C(C6H5)NOH

Conditions	Yield
In pyridine standing of a soln. of ferrocene-compd. and hydroxylamine hydrochloridein dry pyridine at room temp. for 24 h under N2; pouring into water, pptn., recrystn. from MeOH;	99%

4-methoxybenzoylferrocene + hydroxylamine hydrochloride (5470-11-1) → FeC10H9C(C6H4OCH3)NOH

Conditions	Yield
In pyridine standing of a soln. of ferrocene-compd. and hydroxylamine hydrochloridein dry pyridine at room temp. for 24 h under N2; pouring into water, pptn., recrystn. from MeOH;	99%

(4-trifluoromethylbenzoyl)ferrocene (72848-08-9) + hydroxylamine hydrochloride (5470-11-1) → (C5H5)Fe(C5H4C(C6H4CF3)NOH) (75183-07-2)

Conditions	Yield
In pyridine standing of a soln. of ferrocene-compd. and hydroxylamine hydrochloridein dry pyridine at room temp. for 24 h under N2; pouring into water, pptn., recrystn. from MeOH;	99%

hydroxylamine hydrochloride (5470-11-1) + 1-allyl-1H-benzo[d]imidazole-2-carboxaldehyde (118482-14-7) → 1-allyl-1H-benzo[d]imidazole-2-crabaldehyde oxime

Conditions	Yield
With triethylamine In ethanol at 80℃; for 0.5h; Microwave irradiation;	99%

[3]ferrocenophane-1-one + hydroxylamine hydrochloride (5470-11-1) → [3]-ferrocenophan-1-one oxime

Conditions	Yield
With K2CO3 In ethanol (Ar); addn. of hydroxylamine hydrochloride and K2CO3 to a soln. of iron complex in ethanol, stirring overnight at room temp.; filtration, evapn. in vac.; obtained as a mixt. of isomers;	99%

hydroxylamine hydrochloride (5470-11-1) + tetra(n-butyl)ammonium hydroxide (2052-49-5) + 4-nitrobenzaldehdye (555-16-8) → C7H5N2O3(1-)*C16H36N(1+)

Conditions	Yield
Stage #1: hydroxylamine hydrochloride; 4-nitrobenzaldehdye In ethanol; water Stage #2: tetra(n-butyl)ammonium hydroxide In methanol	99%

di-tert-butyl dicarbonate (24424-99-5) + hydroxylamine hydrochloride (5470-11-1) → tert-Butyl N-hydroxycarbamate (36016-38-3)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water at 0 - 20℃; for 3h; Acylation;	98%
With sodium hydrogencarbonate In tetrahydrofuran; water at 0℃; for 2.5h;	60%
With sodium hydrogencarbonate In tetrahydrofuran; water

C14H15BrO5 (663933-83-3) + hydroxylamine hydrochloride (5470-11-1) → C14H16BrNO5 (663933-84-4)

Conditions	Yield
With sodium acetate In ethanol at 0℃; for 3h;	98%

2',4'-dihydroxy-4-acetophenone (89-84-9) + hydroxylamine hydrochloride (5470-11-1) → (1Z)-1-(2,4-dihydroxyphenyl)ethanone oxime (111364-29-5)

Conditions	Yield
In pyridine at 20℃;	98%

9-(2-Oxo-3-phenyl-propyl)-2-pyridin-4-yl-3-(3-trifluoromethyl-phenyl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one + hydroxylamine hydrochloride (5470-11-1) → 9-(2-hydroxyimino-3-phenyl-propyl)-2-pyridin-4-yl-3-(3-trifluoromethyl-phenyl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

Conditions	Yield
In ethanol at 70℃; for 1h;	98%

5-(N-ethyl-N-ferrocenylmethylamino)pentan-2-one (252578-95-3) + hydroxylamine hydrochloride (5470-11-1) → 5-(N-ethyl-N-ferrocenylmethylamino)pentan-2-one-oxime (252578-96-4)

Conditions	Yield
With sodium hydroxide In ethanol; water addn. of aq. NaOH to mixt. of ferrocene derivative and NH2OH*HCl (in EtOH), stirring and refluxing for 2.5 h; water addn., extn. into CH2Cl2, drying (Na2SO4), evapn. (reduced pressure);	98%

1'-N,N-dimethylaminomethylferrocene-1-carbaldehyde (33040-02-7) + hydroxylamine hydrochloride (5470-11-1) → 1'-N,N-dimethylaminomethylferrocene-1-carbaldehyde oxime

Conditions	Yield
With NaOH In ethanol; water soln. of NaOH in water was added to stirred mixt. of Fe-complex and NH2OH*HCl in EtOH at room temp., heated under reflux for 4 h, cooled, water was added, neutralised with CO2(s); extd. with CH2Cl2, dried over Na2SO4, filtered, solvent was removed in vacuo;	98%

tricarbonyl[exo-3-[(2,3,4,5-η)-(4-methoxycyclohexa-2,4-dienyl)]propan-2-one]iron + hydroxylamine hydrochloride (5470-11-1) → tricarbonyl[exo-3-[(2,3,4,5-η)-(4-methoxycyclohexa-2,4-dienyl)]propan-2-one oxime]iron

Conditions	Yield
With pyridine In ethanol NH2OH*HCl and pyridine added to soln. of Fe complex in ethanol; mixt. stirred at room temp. for 1.5 h; evapd. (vac.); residue treated with H2O and aq. HCl; extd. twice with ethyl acetate; combined extracts washed with satd. aq. soln. of NaHCO3; dried over Na2SO4; evapd. (vac.); flash chromy. (silica gel 60N, ethyl acetate/hexane 1/7); E/Z = 6/1;	98%

fac-[iridium(III)(2-(4'-methoxy-5'-(CHO)-phenyl)pyridine)3] (1356038-03-3, 1377575-24-0) + hydroxylamine hydrochloride (5470-11-1) → fac-[iridium(III)(2-(4'-methoxy-5'-(CHNOH)phenyl)pyridine)3] (1356038-16-8)

Conditions	Yield
With NaOH In methanol under Ar; NH2OH*HCl added to soln. of Ir complex (1 equiv.), stirred at room temp. for 11 h, concd. under vac., H2O added, pH=5-6 adjusted with NaOH soln.; ppt. filtered off, washed with H2O; elem. anal.;	98%

hydroxylamine hydrochloride (5470-11-1) + 4-(4-(N,N-bis(2-chloroethyl)amino)phenyl)butanal (64977-05-5) → N-hydroxy-4-(4-N',N'-bis(2-chloroethyl)amino)phenylbutylimine (1256382-16-7)

Conditions	Yield
With triethylamine In ethanol for 0.416667h;	98%

4-acetyl[2.2]paracyclophane (10029-00-2) + hydroxylamine hydrochloride (5470-11-1) → 4-acetyl[2.2]paracyclophane-O-methyloxime (1436383-47-9)

Conditions	Yield
With pyridine In methanol Molecular sieve; Reflux;	98%

pyridine-4-carbaldehyde (872-85-5) + hydroxylamine hydrochloride (5470-11-1) → pyridine-4-aldoxime (696-54-8)

Conditions	Yield
With sodium hydroxide In water at 50℃; for 12h; pH=6 - 7;	97.17%

Upstream product

• 127-06-0 Acetone oxime 
• 77-78-1 Dimethyl sulfate 
• 7681-57-4 Sodium metabisulfite 
• 75-52-5 Nitromethane 

Downstream Products

• 24248-21-3 ETHYL 3-(2,6-DICHLORO-PHENYL)-5-METHYL-ISOXAZOLE-4-CARBOXYLATE 
• 6557-16-0 5-Chloro-3,6-dihydroxy-5-androstan-17-one 3-acetate 
• 13244-39-8 5 A-CHLORO-6 B,19-EPOXY-3 B -HYDROXY-5 A-ANDROSTAN-17-ONE 
• 55304-19-3 (2,6-DIMETHYLPHENOXY)ACETOXIME 
• 3919-76-4 3-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carboxylic acid 
• 25629-50-9 3-(2-Chlorophenyl)-5-methylisoxazole-4-carbonyl chloride 
• 1594-58-7 3-PYRIDYLAMIDOXIME 
• 1772-01-6 N'-HYDROXYPYRIDINE-2-CARBOXIMIDAMIDE 
• 18638-99-8 3,4,5-Trimethoxybenzylamine 
• 20776-60-7 2-AMINO-5,6-DICHLOROBENZOIC ACID 
• 23598-72-3 3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid 
• 23873-81-6 DIPHENYLGLYOXIME 
• 33024-60-1 4-Aminotetrahydropyran hydrochloride 
• 3717-26-8 2-CHLOROBENZALOXIME 
• 372-66-7 6-AMINO-2-METHYL-2-HEPTANOL 
• 55406-13-8 3-METHYLTHIOPHENE-2-CARBONITRILE 
• 75272-39-8 NEMONAPRIDE 
• 83171-39-5 4-(METHYLTHIO)BENZYLAMINE 
• 106627-54-7 N-Hydroxysulfosuccinimide sodium salt 
• 110035-28-4 Pyrazole-1,3-dimethyl-5-phenoxy-4-carboxaldehyde oxime 
• 1143-82-4 Ethyl 5-methyl-3-phenylisoxazole-4-carboxylate 
• 1239-31-2 Epiandrosterone acetate 
• 1594-57-6 N'-HYDROXYPYRIDINE-4-CARBOXIMIDAMIDE 
• 16883-16-2 5-Methyl-3-phenylisoxazole-4-carbonyl chloride 
• 17153-21-8 3-METHYL-5-PHENYL-4-ISOXAZOLECARBOXYLIC ACID 
• 2024-83-1 2,3-DIMETHOXYBENZONITRILE 
• 3209-72-1 ETHYL 5-METHYLISOXAZOLE-3-CARBOXYLATE 
• 321309-26-6 5-METHYL-4-ISOXAZOLESULFONYL CHLORIDE 
• 34859-64-8 5-AMINOISOXAZOLE-4-CARBOXYLIC ACID ETHYL ESTER 
• 5173-84-2 17-Ethinylandrost-5-ene-3,17-diol 
• 613-92-3 BENZAMIDOXIME HYDROCHLORIDE 
• 629-31-2 heptanal oxime 
• 6326-79-0 6-Bromoisatin 
• 63547-13-7 Adrafinil 
• 85006-31-1 Methyl 3-amino-4-methylthiophene-2-carboxylate 
• 96-29-7 2-Butanone oxime