4229-44-1

Basic information

• Product Name: N-Methylhydroxylamine hydrochloride
• Synonyms: N-Methylhydroxyaminehydrochloride;HYDROXYLAMINOMETHANE HYDROCHLORIDE;N-METHYLHYDROXYLAMINE HCL;N-METHYLHYDROXYLAMINE HYDROCHLORIDE;N-METHYLHYDROXYLAMMONIUM CHLORIDE;N-Methylhydroxylaminehydrochloride,98%;N-METHYLHYDROXYAMINEHCL;Methyl hydroxylamine .HCL
• CAS NO: 4229-44-1
• Molecular Formula: CH₆NO*Cl
• Molecular Weight: 83.52
• EINECS: 224-181-2
• Product Categories: Hydroxylamines;Hydroxylamines (N-Substituted);Nitrogen Compounds;Organic Building Blocks
• Mol File: 4229-44-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 86-88 °C(lit.)
• Boiling Point: 69.4 °C at 760 mmHg
• Flash Point: 41.9 °C
• Appearance: White to almost white crystals or cryst. powder
• Density: 1.36 g/cm3
• Vapor Pressure: 96.6mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: H2O: 0.1 g/mL, clear, very faintly yellow
• Water Solubility: soluble
• Sensitive: Hygroscopic
• BRN: 3541409
• CAS DataBase Reference: N-Methylhydroxylamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylhydroxylamine hydrochloride(4229-44-1)
• EPA Substance Registry System: N-Methylhydroxylamine hydrochloride(4229-44-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• RIDADR: 1759
• WGK Germany: 3
• F: 3-10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 4229-44-1(Hazardous Substances Data)

Usage

Chemical Properties

WHITE TO ALMOST WHITE CRYSTALS OR CRYST. POWDER

Uses

Different sources of media describe the Uses of 4229-44-1 differently. You can refer to the following data:
1. N-Methylhydroxylamine is used as an inorganic catalyst used in the transamidation of primary amides with amines.
2. N-Methylhydroxylamine hydrochloride is used as an inorganic catalyst used in the transamidation of primary amides with amines. It is employed in constructing hydroxamates, important functional groups for the complexation of iron.

InChI:InChI=1/CH5NO.ClH/c1-2-3;/h2-3H,1H3;1H

Synthetic route

C-(2-nitrophenyl)-N-methyl-nitrone (41106-02-9) → N-methylhydroxyamine hydrochloride (4229-44-1) + 2-nitrobenzaldehyde oxime (3717-25-7, 4836-00-4, 6635-41-2)

Conditions	Yield
With hydroxylamine hydrochloride In methanol; diethyl ether at 20℃; for 4h;	A 98% B n/a

4-(N-methylnitrono)-2,2,5,5-tetramethyltetrahydrofuran-3-one E-isomer (67036-74-2, 67036-80-0) → 2,2,5,5-Tetramethyl-furan-3,4-dione (14744-18-4) + N-methylhydroxyamine hydrochloride (4229-44-1)

Conditions	Yield
With hydrogenchloride Heating;	A 46% B 94%
With hydrogenchloride Heating;	A 43% B 94%
With hydrogenchloride Product distribution; Heating;	A 43% B 94%

nitromethane (75-52-5) → N-methylhydroxyamine hydrochloride (4229-44-1)

Conditions	Yield
With ammonium chloride; zinc In water for 0.5h;
With ammonium chloride; zinc In water at 0 - 15℃;

hydrogenchloride (7647-01-0) + N-methyl-diphenyl-nitrone (7500-79-0) → benzophenone (119-61-9) + N-methylhydroxyamine hydrochloride (4229-44-1)

Conditions	Yield
Hydrolysis;

N,O-Dimesyl-N-methylhydroxylamin (80653-57-2) → 1,3,5-Trioxan (110-88-3) + formaldehyd (50-00-0) + N-Methylhydroxylamine (593-77-1) + N-methylhydroxyamine hydrochloride (4229-44-1) + methanesulfonic acid sodium salt (2386-57-4) + NH3

Conditions	Yield
With sodium hydroxide In water Mechanism; Product distribution; hydrolysis with basic, neutral and acidic aqu. solutions;	A 5 % Spectr. B n/a C 1 % Spectr. D n/a E 33 % Spectr. F n/a

(Z)-C-(3,4-dimethoxyphenyl)-N-methyl-nitrone (314768-38-2, 919112-42-8) → 3,4-Dimethoxy-benzaldehyde oxime (2169-98-4, 39627-82-2) + N-methylhydroxyamine hydrochloride (4229-44-1)

Conditions	Yield
With hydroxylamine hydrochloride In methanol; diethyl ether at 20℃; for 4h;

N-Methylhydroxylamine (593-77-1) → N-methylhydroxyamine hydrochloride (4229-44-1)

Conditions	Yield
With hydrogenchloride In water at 25℃; Cooling with ice;	333.4 g

N-methylhydroxyamine hydrochloride (4229-44-1) + 4-nitrobenzaldehdye (555-16-8) → N-(p-nitrobenzylidene)methylamine N-oxide (16089-71-7, 57414-31-0, 97792-07-9)

Conditions	Yield
With 3 A molecular sieve at 20℃; for 0.25h;	100%
With sodium hydroxide; silica gel at 20℃; for 0.166667h;	96%
With sodium hydrogencarbonate In dichloromethane for 0.1h; microwave irradiation;	95%

N-methylhydroxyamine hydrochloride (4229-44-1) + 2-nitro-benzaldehyde (552-89-6) → α-(2-nitrophenyl)-N-methylnitrone (41106-02-9)

Conditions	Yield
With 3 A molecular sieve at 20℃; for 0.25h;	100%
With sodium hydroxide; silica gel at 20℃; for 0.166667h;	98%
With potassium carbonate In methanol Reflux;	96.5%
With ethanol; potassium acetate

N-methylhydroxyamine hydrochloride (4229-44-1) + 3a-(3,4-dimethoxyphenyl)-5,5-(ethylenedioxy)-3,3a,4,5,6,7-hexahydro-2H-inden-2-one (88176-86-7) → 3a-(3,4-dimethoxyphenyl)-5,5-(ethylenedioxy)-3,3a,4,5,6,7-hexahydro-2H-inden-2-one N-methylnitrone (91713-15-4)

Conditions	Yield
With sodium acetate In ethanol for 40h; Heating;	100%

N-methylhydroxyamine hydrochloride (4229-44-1) + benzaldehyde (100-52-7) → N-methyl-α-phenylnitrone (3376-23-6)

Conditions	Yield
With benzophenone Product distribution; Further Variations:; Reagents;	100%
With sodium hydrogencarbonate In dichloromethane at 50℃; for 4.5h;	100%
With magnesium oxide at 20℃; for 0.0416667h; Grinding; Neat (no solvent);	98%

N-methylhydroxyamine hydrochloride (4229-44-1) + 5,6,7-trideoxy-2,3-O-isopropylidene-α,β-D-lyxo-hept-6-enofuranose → C11H19NO4 (158227-57-7)

Conditions	Yield
With pyridine for 20h; Ambient temperature;	100%

N-methylhydroxyamine hydrochloride (4229-44-1) + (2R*,3R*)-1-(4-methoxyphenyl)-3-methyl-4-oxoazetidine-2-carbaldehyde (133505-00-7) → C13H16N2O3

Conditions	Yield
With triethylamine In benzene at 20℃; for 16h;	100%

N-methylhydroxyamine hydrochloride (4229-44-1) + 5,11,17,23-Tetraformyl-25,26,27,28-tetrapropoxycalix[4]arene (159910-49-3, 638199-75-4, 154497-06-0) → p-propyloxycalix[4]arenenitrone

Conditions	Yield
With sodium hydroxide In ethanol at 20℃;	100%

C7H5N3O2 (1256824-45-9) + N-methylhydroxyamine hydrochloride (4229-44-1) → 1-(4-fluorobenzyl)-N-hydroxy-N-methyl-1H-pyrazolo[3,4-c]pyridine-5-carboxamide

Conditions	Yield
With triethylamine; HATU In DMF (N,N-dimethyl-formamide)	100%

2-iodobenzaldehyde (26260-02-6) + N-methylhydroxyamine hydrochloride (4229-44-1) → (Z)-N-(2-iodobenzylidene)methylamine N-oxide (1037396-94-3)

Conditions	Yield
With sodium hydrogencarbonate at 20℃; for 2h;	100%

2-formylbenzo[b]furan (4265-16-1) + N-methylhydroxyamine hydrochloride (4229-44-1) → (Z)-N-(benzofuran-2-ylmethylidene)methylamine N-oxide (1037397-11-7)

Conditions	Yield
With sodium hydrogencarbonate at 20℃; for 0.5h;	100%

N-methylhydroxyamine hydrochloride (4229-44-1) + p-(iodophenyl)carboxaldehyde (15164-44-0) → (Z)-1-(4-iodo phenyl)-N-methylmethanimine oxide (1037396-90-9, 33499-28-4)

Conditions	Yield
With sodium hydrogencarbonate at 20℃; for 1h;	100%
With magnesium sulfate; triethylamine In dichloromethane at 0 - 20℃; for 48h;	91%

pentanal (110-62-3) + N-methylhydroxyamine hydrochloride (4229-44-1) → N-methylpentan-1-imine oxide

Conditions	Yield
With sodium hydrogencarbonate; calcium chloride In diethyl ether; water for 1h;	100%

N-methylhydroxyamine hydrochloride (4229-44-1) + 2-phenoxybenzoic acid (2243-42-7) → C14H13NO3

Conditions	Yield
Stage #1: 2-phenoxybenzoic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 23℃; Stage #2: N-methylhydroxyamine hydrochloride With triethylamine In tetrahydrofuran; dichloromethane; water at 23℃;	100%

di-tert-butyl dicarbonate (24424-99-5) + N-methylhydroxyamine hydrochloride (4229-44-1) → N-(tert-butoxycarbonyl)-N-methylhydroxylamine (19689-97-5)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃;	99%
With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 5h;	97%
With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 5h;	97%

N-methylhydroxyamine hydrochloride (4229-44-1) + 3a-(2,3-dimethoxyphenyl)-5,5-(ethylenedioxy)-3,3a,4,5,6,7-hexahydro-2H-inden-2-one (91712-97-9) → 3a-(2,3-dimethoxyphenyl)-5,5-(ethylenedioxy)-3,3a,4,5,6,7-hexahydro-2H-inden-2-one N-methylnitrone (91712-99-1)

Conditions	Yield
With sodium acetate In ethanol Heating;	99%

(E)-1-acetoxy-1-phenyl-2-butene (51801-01-5, 87246-94-4, 97996-32-2, 100017-27-4, 100017-28-5, 108033-84-7, 146566-19-0, 146566-20-3, 79594-08-4) + N-methylhydroxyamine hydrochloride (4229-44-1) → N-Methyl-N-((E)-1-methyl-3-phenyl-allyl)-hydroxylamine (118149-83-0)

Conditions	Yield
With sodium hydroxide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran	99%

N-methylhydroxyamine hydrochloride (4229-44-1) + hydrocinnamic acid chloride (645-45-4) → N-hydroxy-N-methyl-3-phenylpropanamide (111750-23-3)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	99%
With triethylamine In dichloromethane for 1h; Ambient temperature;	88%
With sodium hydrogencarbonate In dichloromethane at 0 - 20℃; Inert atmosphere;	75%

N-methylhydroxyamine hydrochloride (4229-44-1) + benzyl chloroformate (501-53-1) → benzyl hydroxy(methyl)carbamate (15058-52-3)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃;	99%
With sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 15.5h;	3%

N-methylhydroxyamine hydrochloride (4229-44-1) + 2-nitro-benzaldehyde (552-89-6) → C-(2-nitrophenyl)-N-methyl-nitrone (41106-02-9)

Conditions	Yield
In tetrahydrofuran at 20℃; for 4h;	99%

N-methylhydroxyamine hydrochloride (4229-44-1) + benzaldehyde (100-52-7) → N-(benzylidene)methylamine N-oxide (3376-23-6, 7372-59-0, 59862-60-1)

Conditions	Yield
In sodium hydroxide at 20℃; for 0.5h;	99%
With sodium hydrogencarbonate In ethanol at 60℃; for 18h;	71%

2-formylbenzene boronic acid (40138-16-7) + N-methylhydroxyamine hydrochloride (4229-44-1) → 1,2-dihydro-1,1-dihydroxy-3-methyl-1H-2,3,1,-benzoxazaborine

Conditions	Yield
With aq. NaOH In ethanol; water standing (pH=7, room temp., 12 h); evapn. (50°C), dissolution (MeOH), filtration, evapn., dissolution (water), evapn., washing (Me2CO), drying;	99%

N-methylhydroxyamine hydrochloride (4229-44-1) + Allyl chloroformate (2937-50-0) → allyl hydroxy(methyl)carbamate (15151-43-6)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃;	99%

N-methylhydroxyamine hydrochloride (4229-44-1) + chloroformic acid ethyl ester (541-41-3) → ethyl hydroxyl(methyl)carbamate (3016-84-0)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃;	99%
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃;

C25H26O4 + N-methylhydroxyamine hydrochloride (4229-44-1) → C26H29NO4

Conditions	Yield
Stage #1: C25H26O4 With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide Stage #2: N-methylhydroxyamine hydrochloride With triethylamine In tetrahydrofuran; dichloromethane; water at 23℃;	99%

(E)-3-(m-tolyl)acrylaldehyde (66223-54-9, 93614-80-3) + N-methylhydroxyamine hydrochloride (4229-44-1) → (Z)-N-((E)-3-(m-tolyl)allylidene)methanamine oxide

Conditions	Yield
With sodium sulfate; triethylamine In dichloromethane at 0℃;	99%

5-(tertbutyldiphenylsilyloxymethyl)furfural (1528764-16-0) + N-methylhydroxyamine hydrochloride (4229-44-1) → (Z)-1-(5-(((tert-butyldiphenylsilyl)oxy)methyl)furan-2-yl)-N-methylmethanimine oxide

Conditions	Yield
With sodium hydrogencarbonate; magnesium sulfate In isopropyl alcohol at 20℃; for 16h;	99%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) + N-methylhydroxyamine hydrochloride (4229-44-1) → (Z)-1-(5-(hydroxymethyl)furan-2-yl)-N-methylmethanimine oxide

Conditions	Yield
With sodium hydrogencarbonate; magnesium sulfate In isopropyl alcohol at 20℃; for 16h;	99%

N-methylhydroxyamine hydrochloride (4229-44-1) + 3-nitro-benzaldehyde (99-61-6) → α-(3-nitrophenyl)-N-methylnitrone (16089-77-3, 54420-44-9, 54420-46-1)

Conditions	Yield
With 3 A molecular sieve at 20℃; for 0.25h;	98%
With sodium hydrogencarbonate In dichloromethane for 0.1h; microwave irradiation;	96%
With sodium hydroxide; silica gel at 20℃; for 0.166667h;	96%

N-methylhydroxyamine hydrochloride (4229-44-1) + ortho-anisaldehyde (135-02-4) → N-(2-methoxybenzylidene)methanamine N-oxide (33499-30-8)

Conditions	Yield
With triethylamine In chloroform for 22h;	98%
With magnesium oxide at 20℃; for 0.05h; Grinding; Neat (no solvent);	95%
With sodium hydrogencarbonate In dichloromethane for 0.25h; microwave irradiation;	88%

furfural (98-01-1) + N-methylhydroxyamine hydrochloride (4229-44-1) → N-[2-furylmethylene]methanamine N-oxide (41106-11-0, 91328-46-0, 925933-52-4)

Conditions	Yield
With triethylamine In chloroform for 22h;	98%
With sodium sulfate; sodium carbonate at 20℃; for 0.05h; Neat (no solvent);	94%
With magnesium oxide at 20℃; for 0.0833333h; Grinding; Neat (no solvent);	92%

Upstream product

• 80653-57-2 N,O-Dimesyl-N-methylhydroxylamin 
• 41106-11-0 N-[2-furylmethylene]methanamine N-oxide 
• 593-77-1 N-Methylhydroxylamine 
• 41106-02-9 C-(2-nitrophenyl)-N-methyl-nitrone 
• 314768-38-2 (Z)-C-(3,4-dimethoxyphenyl)-N-methyl-nitrone 
• 7647-01-0 hydrogenchloride 
• 7500-79-0 N-methyl-diphenyl-nitrone 
• 67036-74-2 4-(N-methylnitrono)-2,2,5,5-tetramethyltetrahydrofuran-3-one E-isomer 
• 75-52-5 nitromethane 

Downstream Products

• 861516-79-2 hydroxy-(hydroxy-methyl-amino)-malonic acid amide-p-toluidide 
• 203861-66-9 N-(4-chlorobenzylidene)methylamine N-oxide 
• 16089-77-3 N-methyl-α-(m-nitrophenyl)nitrone 
• 41105-99-1 α-(2-hydroxy-1-phenyl)-N-methylnitrone 
• 52045-98-4 4-cyclohexyl-2-methyl-isoxazolidine-3,5-dione 
• 101156-63-2 2-methyl-5,5-diphenyl-isoxazolidine 
• 740035-36-3 1-(2-methyl-5-phenyl-isoxazolidin-5-yl)-ethanone 
• 73174-56-8 (3aS)-7t-benzyloxy-1,5,5-trimethyl-(3ar,3bt,6at,7ac)-hexahydro-[1,3]dioxolo[4',5':3,4]cyclopenta[1,2-c]isoxazole 
• 73111-81-6 (3aS)-7c-benzyloxy-1,5,5-trimethyl-(3ar,3bc,6ac,7ac)-hexahydro-[1,3]dioxolo[4',5':3,4]cyclopenta[1,2-c]isoxazole 
• 73174-60-4 (3aS)-4t,5c,6c-tris-benzyloxy-1-methyl-(3ar,6ac)-hexahydro-cyclopenta[c]isoxazole 
• 35214-90-5 (Z)-Cyclohexylmethyldiazen-1-oxid 
• 57497-35-5 (Z)-Methylcyclohexyldiazen-1-oxid 
• 5302-16-9 4-cyclohexyl-2-methyl-[1,2,4]oxadiazolidine-3,5-dione 
• 15058-51-2 phenyl N-hydroxy-N-methylcarbamate 

Relevant articles and documents

Molybdenum(VI) complexes with N-substituted hydroxylamines

New molybdenum(VI) complexes with N-monoalkylsubstituted hydroxylamines have been synthesized and studied. The structure of [MoO2(C 2H5NHO)2] and [MoO2(i-C 3H7NHO)2], whose distinguishing feature is the bidentate chelate coordination of the ligand to molybdenum with the formation of the three-membered NMoO chelate ring, has been determined by X-ray diffraction.

PROCESS TO PRODUCE N-METHYLYDROXYLAMINE HYDROCHLORIDE

The disclosure provides improved processes for preparing N-methylhydroxylamine and N-methylhydroxylamine hydrochloride.

N-SUBSTITUTED DERIVATIVES OF (ALPHA)-MERCAPTO ALKYLAMINES, THEIR PREPARATION PROCESS AND THE INTERMEDIATES OBTAINED, THEIR USE AS MEDICAMENTS AND THE COMPOSITIONS CONTAINING THEM

Novel α-mercapto-alkylamines in all possible racemic, enantiomeric and diastereoisomeric forms of the formula STR1 wherein n, R 1, R 2, X, A, R 3A and R 4A are set forth in the claims and their non-toxic, pharmaceutically acceptable acid addition salts having excellent analgesic, psychotropic and enkephalinase inhibiting properties.