622-30-0

Basic information

• Product Name: N-BENZYLHYDROXYLAMINE HYDROCHLORIDE
• Synonyms: N-Benzylhydroxylamine;N-Hydroxybenzenemethanamine;N-Hydroxybenzylamine
• CAS NO: 622-30-0
• Molecular Formula: C₇H₉NO
• Molecular Weight: 123.15246
• Product Categories: Polyamines
• Mol File: 622-30-0.mol
• Article Data: 57

Chemical Properties

• Melting Point: ~105 °C
• Boiling Point: 253.9 °C at 760 mmHg
• Flash Point: 135.2 °C
• Appearance: /
• Density: 1.098g/cm³
• Vapor Pressure: 0.00923mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 13.19±0.30(Predicted)
• CAS DataBase Reference: N-BENZYLHYDROXYLAMINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYLHYDROXYLAMINE HYDROCHLORIDE(622-30-0)
• EPA Substance Registry System: N-BENZYLHYDROXYLAMINE HYDROCHLORIDE(622-30-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 622-30-0(Hazardous Substances Data)

Usage

Preparation

(a) Preparation of a-phenyl-N-benzylnitrone. To a flask equipped with a stirrer and condenser and containing 17.6 gm (0.0827 mole) of N,N-dibenzylhydroxylamine is added 36.8 gm (0.17 mole) of yellow mer-curic oxide and 100 ml of ether. The mixture is stirred and the resulting exothermic reaction causes the ether to reflux for 1 hr. After a total of 3 hr reaction time the reaction mixture is filtered and concentrated to afford 15.7 gm (90%), m.p. 81.5-83.5°C (recrystallized from acetone-ligroin). Jones and Sneed [12a] earlier reported that air-KOH can also be used to effect this oxidation. (b) Hydrolysis of a-phenyl-N-benzylnitrone to N-benzylhydroxylamine [12a]. To a flask containing 17.0 gm (0.0806 mole) of the above nitrone is added 34 ml of concentrated hydrochloric acid solution. Then the mixture is steam-distilled to remove the formed benzaldehyde. After the benzal-dehyde is removed the hydrochloric acid is removed by heating over a low flame. To the cool residue is added a cold solution of sodium carbonate to neutralize the mixture. The mixture is filtered, and the filtrate, after being cooled to 0°C, is made alkaline. After 1 hr N-benzylhydroxylamine pre-cipitates from the cold filtrate and is filtered to afford 6.0 gm (61%), m.p. 57°C (recrystallized from benzene-petroleum ether). Yields as high as 88% have been reported for this preparation.

InChI:InChI=1/C7H9NO/c9-8-6-7-4-2-1-3-5-7/h1-5,8-9H,6H2

Synthetic route

Benzaldoxime (932-90-1) → N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With K12(Ga4(1,5-bis(2,3-dihydroxybenzamido)naphthalene))6; potassium phosphate; borane pyridine In water-d2 at 20℃; for 22h; Reagent/catalyst; Inert atmosphere; Sealed tube;	100%
With Benzyltriethylammonium borohydride for 0.133333h; solid-phase conditions;	95%
With sodium cyanoborohydride at 20℃;	80%

N-benzylhydroxylamine hydrochloride (29601-98-7) → N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With sodium hydrogencarbonate In water	100%
With sodium hydrogencarbonate In methanol for 0.25h;
With 4-methyl-morpholine In dichloromethane Schlenk technique; Inert atmosphere;

syn-benzaldehyde oxime (932-90-1, 622-31-1, 140461-24-1, 140461-25-2, 622-32-2) → N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With sodium cyanoborohydride; acetyl chloride In methanol at 0℃;	94%
With hydrogenchloride; sodium cyanoborohydride In methanol at 25℃; for 4h;	87%
With hydrogenchloride; sodium cyanoborohydride In methanol pH=3;	61%
With hydrogenchloride; sodium cyanoborohydride In methanol at 20℃; for 3h;	49%

(Z)-benzaldehyde oxime (622-32-2) → N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With hydrogenchloride; sodium cyanoborohydride In methanol at 25℃; for 3.5h; Reduction;	94%

benzylamine (100-46-9) → N-benzyl hydroxylalmine (622-30-0) + Benzaldoxime (932-90-1)

Conditions	Yield
With 4a-FlEt-OOH In 1,4-dioxane at 30℃; Rate constant;	A n/a B 90%

ethyl 2-benzyl-2,5-dihydro-3-methyl-5-oxoisoxazole-4-carboxylate (113768-51-7) → N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With hydrogenchloride; acetic acid In water	81%

N-Benzylidenebenzylamine N-oxide (3376-26-9) → N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With hydrogenchloride steam destillation;	79%
With sulfuric acid In water for 4h; Heating;	71%
With hydrogenchloride In water for 1h; Reflux;

benzyl bromide (100-39-0) → N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With hydroxylamine monohydrate In methanol at 100℃; under 18100.7 Torr; for 0.166667h; Flow reactor; chemoselective reaction;	76%

benzyl chloride (100-44-7) → N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With hydroxylamine monohydrate In methanol at 100℃; under 18100.7 Torr; for 0.166667h; Flow reactor; chemoselective reaction;	65%
With hydroxylamine hydrochloride; triethylamine In water; dimethyl sulfoxide at 100℃; for 1h;	38%

(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal (104701-87-3) → N-benzyl hydroxylalmine (622-30-0) + (R)-(-)-N-(3-t-butyldimethylsilyloxy-2-methylpropylidene)benzylamine N-oxide (112057-68-8, 299179-53-6)

Conditions	Yield
With calcium chloride In argon	A n/a B 64%

trans-Dihydro-3-phenyl-5-(phenylmethyl)-6-heptyl-1,2,4,5-trioxazine (122744-71-2) → Octanal (124-13-0) + 3,6-diphenyl-1,2,4,5-tetraoxane (16204-37-8) + α-Heptyl-N-benzylnitrone (72552-76-2) + benzaldehyde (100-52-7) + N-benzyl hydroxylalmine (622-30-0) + benzoic acid (65-85-0)

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 15h; Product distribution; Ambient temperature;	A 26% B 11% C 25% D 30% E 25% F 16%

N,O-dibenzylhydroxylamine (4383-24-8) → benzyl chloride (100-44-7) + N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With hydrogenchloride at 130℃; im geschlossenen Rohr;

N-benzyl-O-benzoylhydroxylamine (38636-02-1) + sodium ethanolate (141-52-6) → N-benzyl hydroxylalmine (622-30-0) + benzoic acid (65-85-0)

N-Benzylidenebenzylamine N-oxide (3376-26-9) → N-benzyl hydroxylalmine (622-30-0) + benzaldehyde phenylhydrazone (588-64-7)

Conditions	Yield
With phenylhydrazine at 80℃;

N-benzyl-1,1-diphenylmethanimine oxide (3376-29-2) → N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With hydrogenchloride

N-benzyl-1,1-diphenylmethanimine oxide (3376-29-2) → benzophenone (119-61-9) + N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
Hydrolyse;

N,N,O-tribenzylhydroxylamine (112408-47-6) → N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
bei der Destillation im Vakuum;

benzyl chloride (100-44-7) + acetic acid (64-19-7) + acetone oxime (127-06-0) → N-benzyl hydroxylalmine (622-30-0)

benzyl chloride (100-44-7) + N,N-dibenzylhydroxylamine (621-07-8) → tribenzylamine (620-40-6) + N-benzyl hydroxylalmine (622-30-0) + benzylamine (100-46-9) + dibenzylamine (103-49-1)

N-Benzylidenebenzylamine N-oxide (3376-26-9) + phenylhydrazine (100-63-0) → N-benzyl hydroxylalmine (622-30-0) + benzaldehyde phenylhydrazone (588-64-7)

N-benzyl-O-benzoylhydroxylamine (38636-02-1) → N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With sodium hydroxide In methanol

N-Benzyl-4-methyl-N-(2,4,6-trimethyl-benzyloxy)-benzenesulfonamide (52245-12-2) → N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With hydrogen bromide In acetic acid

N,N-Dibenzyl-O-ethyl-hydroxylamin (5815-55-4) → N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With peracetic acid In acetonitrile

benzyl bromide (100-39-0) → N-benzyloxyamine (622-33-3) + N-benzyl hydroxylalmine (622-30-0) + N,N-dibenzylhydroxylamine (621-07-8)

Conditions	Yield
With hydroxylamine hydrochloride; potassium tert-butylate In tert-butyl alcohol for 1.33333h; Ambient temperature; Yield given. Yields of byproduct given;

N-benzyl-O-(p-methylbenzyl)hydroxylamine (146085-62-3) → benzaldehyde (100-52-7) + 4-Methylbenzyl chloride (104-82-5) + N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With hydrogenchloride for 5h; Heating;	A 0.3 mmol B 2.4 mmol C 0.2 g

N-benzylbenzohydroxamic acid (7339-99-3) → N-benzyl hydroxylalmine (622-30-0) + benzoic acid (65-85-0)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 55℃; Rate constant; Thermodynamic data; Mechanism; var. conc. HCl; ΔH(excit.), ΔS(excit.), ΔG(excit.);
With hydrogenchloride; cetyltrimethylammonim bromide In 1,4-dioxane Kinetics; Activation energy; Further Variations:; Reagents; Hydrolysis;

N-Benzyl-p-fluorobenzohydroxamic acid (85407-77-8) → 4-Fluorobenzoic acid (456-22-4) + N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 55℃; Rate constant; Thermodynamic data; Mechanism; var. conc. HCl; ΔH(excit.), ΔS(excit.), ΔG(excit.);

N-Benzyl-N-hydroxy-4-methyl-benzamide → p-Toluic acid (99-94-5) + N-benzyl hydroxylalmine (622-30-0)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 55℃; Rate constant; Thermodynamic data; Mechanism; var. conc. HCl; ΔH(excit.), ΔS(excit.), ΔG(excit.);

acetaldehyde (75-07-0) + N-benzyl hydroxylalmine (622-30-0) → 5(Z)-N-ethylidene-1-phenylmethanamine N-oxide (243140-08-1)

Conditions	Yield
In dichloromethane at 20℃; for 1h;	100%
With sodium sulfate In dichloromethane Ambient temperature;	55%

acetaldehyde (75-07-0) + N-benzyl hydroxylalmine (622-30-0) → N-ethylidenebenzylamine N-oxide (20135-15-3, 243140-08-1, 139189-66-5)

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 1h; Inert atmosphere;	100%
With magnesium sulfate In dichloromethane at 20℃; for 1h; Inert atmosphere;	100%
With magnesium sulfate In dichloromethane at 20℃; for 1h; Inert atmosphere;	100%

3-allylcyclohexanone (20498-05-9) + N-benzyl hydroxylalmine (622-30-0) → (1S,5R,7R)-2-Benzyl-3-oxa-2-aza-tricyclo[5.3.1.01,5]undecane (86437-24-3, 104265-41-0)

Conditions	Yield
at 80℃; for 3h; aromatic solvent;	100%
In methanol; benzene for 3h; Heating; azeotropic water removal;	100%

N-benzyl hydroxylalmine (622-30-0) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4, 111058-38-9, 1165677-00-8)

Conditions	Yield
With sodium sulfate In dichloromethane at 20℃; for 16.5h; Inert atmosphere;	100%
With magnesium sulfate In dichloromethane for 2h;	95%
With magnesium sulfate In dichloromethane at 20℃; Condensation;	94%

N-benzyl hydroxylalmine (622-30-0) + acrylonitrile (107-13-1) → 3-(benzyl(hydroxy)amino)propanenitrile

Conditions	Yield
In chloroform-d1 at 20℃; for 0.166667h;	100%

N-benzyl hydroxylalmine (622-30-0) + isobutyraldehyde (78-84-2) → (Z)-N-(2-methylpropylidene)benzylamine N-oxide (105623-17-4, 115869-93-7)

Conditions	Yield
In diethyl ether at 20℃; for 1h;	99%
With magnesium sulfate In diethyl ether for 15h;	84%
With magnesium sulfate In dichloromethane for 4h; Ambient temperature;	83%
With magnesium sulfate In diethyl ether for 15h; Addition;	78%
With magnesium sulfate In diethyl ether at 20℃; for 15h; Inert atmosphere;	65%

ethylmagnesium chloride (2386-64-3) + N-benzyl hydroxylalmine (622-30-0) → (4S,5S)-(Z)-N-(2,2,5-trimethyl-1,3-dioxolan-4-yl)methylenebenzylamine N-oxide (111612-92-1, 138515-69-2)

Conditions	Yield
for 20h;	99%

benzyloxyacetoaldehyde (60656-87-3) + N-benzyl hydroxylalmine (622-30-0) → (Z)-N-[2-(benzyloxy)ethylidene]benzylamine N-oxide (192220-12-5, 199463-78-0)

Conditions	Yield
In dichloromethane for 12h; Ambient temperature;	99%
In dichloromethane at 20℃;	97%

phenyl styryl sulfone (16212-06-9) + N-benzyl hydroxylalmine (622-30-0) → N-(2-benzenesulfonyl-1-phenyl-ethyl)-N-benzyl-hydroxylamine

Conditions	Yield
In ethanol for 12h;	99%

4-methoxy-benzaldehyde (123-11-5) + N-benzyl hydroxylalmine (622-30-0) → N-benzyl-α-(4-methoxyphenyl)nitrone (32114-41-3, 115175-98-9)

Conditions	Yield
In toluene at 20℃; for 12h; Molecular sieve;	99%
In dichloromethane for 24h; Heating;	80%
With magnesium sulfate In dichloromethane at 20℃;	55%

N-benzyl hydroxylalmine (622-30-0) + cyclohexanecarbaldehyde (2043-61-0) → (Z)-N-(cyclohexylmethylene)-1-phenylmethanamine oxide (22687-06-5, 309918-57-8)

Conditions	Yield
With magnesium sulfate In toluene at 20℃; for 16.5h; Inert atmosphere;	99%
With magnesium sulfate In diethyl ether for 18h;	88%
With magnesium sulfate In dichloromethane at 20℃;	56%
at 20℃;

benzaldehyde (100-52-7) + N-benzyl hydroxylalmine (622-30-0) → (Z)-N-benzylidenebenzylamine N-oxide (77681-22-2, 3376-26-9, 85225-56-5)

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 15h; Inert atmosphere;	99%
With magnesium sulfate In dichloromethane for 15h; Addition;	92%
With magnesium sulfate In dichloromethane for 24h;	92%

β-naphthaldehyde (66-99-9) + N-benzyl hydroxylalmine (622-30-0) → C-(2-naphthyl)-N-benzylnitrone (22661-26-3)

Conditions	Yield
for 0.0666667h; Ionic liquid; Microwave irradiation;	99%
Inert atmosphere;

benzyloxyacetoaldehyde (60656-87-3) + N-benzyl hydroxylalmine (622-30-0) → (C-benzyloxymethane-N-benzyl)nitrone (192220-12-5, 199463-78-0)

Conditions	Yield
In chloroform for 3h;	99%

4-chlorobenzaldehyde (104-88-1) + N-benzyl hydroxylalmine (622-30-0) → 4-chloro-benzaldehyde-(N-benzyl oxime ) (22687-09-8)

Conditions	Yield
With pyrrolidine In dichloromethane at 20℃; for 0.05h;	99%
Inert atmosphere;

N-benzyl hydroxylalmine (622-30-0) + phenylboronic acid (98-80-6) → N-Benzylaniline (758640-21-0)

Conditions	Yield
With trichloroacetonitrile In tert-butyl alcohol at 28℃; Solvent;	99%

4-fluoroboronic acid (1765-93-1) + N-benzyl hydroxylalmine (622-30-0) → N-benzyl-p-fluoroaniline (370-77-4)

Conditions	Yield
With trichloroacetonitrile In tert-butyl alcohol at 28℃;	99%

m-tolylboronic acid (17933-03-8) + N-benzyl hydroxylalmine (622-30-0) → N-benzyl-3-methylaniline (5405-17-4)

Conditions	Yield
With trichloroacetonitrile In tert-butyl alcohol at 28℃;	99%

4-methylphenylboronic acid (5720-05-8) + N-benzyl hydroxylalmine (622-30-0) → N-benzyl-N-(4-methylphenyl)amine (5405-15-2)

Conditions	Yield
With trichloroacetonitrile In tert-butyl alcohol at 28℃;	99%

4-dibenzofurylboronic acid (100124-06-9) + N-benzyl hydroxylalmine (622-30-0) → N-benzyldibenzo[b,d]furan-4-amine

Conditions	Yield
With trichloroacetonitrile In tert-butyl alcohol at 28℃;	99%

formaldehyd (50-00-0) + N-benzyl hydroxylalmine (622-30-0) → N-benzylmethylene nitrone (74635-18-0)

Conditions	Yield
In ethanol for 1h;	98%
With diethyl ether

N-benzyl hydroxylalmine (622-30-0) + acetone (67-64-1) → N-(1-methylethylidene)benzylamine N-oxide (159330-32-2)

Conditions	Yield
With magnesium sulfate; zinc(II) chloride In dichloromethane for 0.0833333h; Ambient temperature;	98%
for 1.5h; Heating;

(R)-(E)-but-2-enoic acid 4,4-dimethyl-2-oxotetrahydrofuran-3-yl ester (126983-27-5) + N-benzyl hydroxylalmine (622-30-0) → N-Benzyl-3-methylisoxazolidin-5-one (95503-62-1)

Conditions	Yield
In tetrahydrofuran at 22℃; for 25h;	98%

N-benzyl hydroxylalmine (622-30-0) + 4-Phenyl-3-oxahept-6-enal (158092-04-7) → C19H21NO2 (158091-86-2)

Conditions	Yield
With magnesium sulfate In diethyl ether at 0℃; for 1h; Condensation;	98%

N-benzyl hydroxylalmine (622-30-0) + (3aS,3bR,7aS,8aR)-2,2,5,5-tetramethyltetrahydro-8aH-[1,3]dioxolo[4′,5′:4,5]furo[3,2-d][1,3]dioxine-8a-carbaldehyde (55385-72-3) → N-(1-deoxo-2,3:4,6-di-O-isoprpylidene-α-L-xylo-hex-2-ul-1-ylidene)benzylamine N-oxide (315203-56-6)

Conditions	Yield
In diethyl ether at 0℃; for 1h; Condensation;	98%

(4R)-3-benzyl-2-oxo-oxazolidine-4-carbaldehyde (1111158-63-4) + N-benzyl hydroxylalmine (622-30-0) → (4S)-3-benzyl-2-oxo-1,3-oxazolidine-4-methylidenbenzylamine-N-oxide (1111158-64-5)

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 3h; Inert atmosphere;	98%

N-methyl-N-allylamine (627-37-2) + N-benzyl hydroxylalmine (622-30-0) → N2-benzyl-N2-hydroxy-N1-methylpropane-1,2-diamine

Conditions	Yield
With formaldehyd In tert-butyl alcohol at 30℃; for 24h; Reagent/catalyst; Solvent; Temperature; Time; Inert atmosphere;	98%
In neat (no solvent) at 80℃; for 6h; Inert atmosphere; regioselective reaction;	92%
With benzyloxyacetoaldehyde In benzene at 20℃; for 24h; Inert atmosphere;	72%

Upstream product

• 4383-24-8 N,O-dibenzylhydroxylamine 
• 38636-02-1 N-benzyl-O-benzoylhydroxylamine 
• 141-52-6 sodium ethanolate 
• 100-44-7 benzyl chloride 
• 64-19-7 acetic acid 
• 127-06-0 acetone oxime 
• 621-07-8 N,N-dibenzylhydroxylamine 
• 932-90-1 syn-benzaldehyde oxime 
• 100-39-0 benzyl bromide 
• 84627-39-4 N-benzyl-O-(4-methoxybenzyl)hydroxylamine 
• 100-46-9 benzylamine 
• 7664-93-9 sulfuric acid 
• 105798-17-2 heptanal-(N-benzyl oxime ) 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 22661-25-2 (Z)-N-(furan-2-ylmethylene)-1-phenylmethanamine oxide 
• 55606-41-2 4-methyl-benzaldehyde-(N-benzyl oxime ) 
• 22687-07-6 N-benzyl-C-o-chlorophenyl nitrone 
• 621-07-8 N,N-dibenzylhydroxylamine 
• 19172-64-6 N,O-dibenzoyl-N-benzylhydroxylamine 
• 1500-35-2 1-benzyl-1-hydroxy-3-phenyl-urea 
• 24423-93-6 N-benzyl-C-ethylnitrone 
• 74635-18-0 N-benzylmethylene nitrone 
• 35225-44-6 N,N'-methylenebis(N-benzylhydroxylamine) 
• 105798-17-2 heptanal-(N-benzyl oxime ) 
• 22661-24-1 N-benzyl-isozimtaldoxime 
• 55606-43-4 3-methoxy-benzaldehyde-(N-benzyl oxime ) 
• 55606-42-3 N-(2-methoxyphenylmethylene)benzylamine-N-oxide 
• 100393-83-7 N-benzyl-N-hydroxy-benzenesulfonamide 

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