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
A
hydroxylamine hydrochloride
B
ammonia
C
tin(IV) chloride
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]
ethylenediamine hydrochloride
B
hydroxylamine hydrochloride
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 |
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% |
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 |
hydrogen sulfide
nitrosylchloride
A
hydroxylamine hydrochloride
B
sulfur
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 |
hydroxylamine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride byproducts: HCO2H; under cooling; | |
With HCl byproducts: HCO2H; under cooling; |
B
hydroxylamine hydrochloride
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
hydroxylamine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride with cooled,concd. HCl; evapn.,dissolving in water,removing of the Hg with H2S,evapn.,crystn.; |
Conditions | Yield |
---|---|
With hydrogenchloride heating in closed tube,130-150°C; |
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; |
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; |
Conditions | Yield |
---|---|
With hydrogenchloride In water byproducts: acetic acid; diluting with water,distn.,filtering,pptg. of tin with H2S,evapn.,washing with ether; |
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
2,2-dinitropropane
A
hydroxylamine hydrochloride
B
dinitrogen monoxide
Conditions | Yield |
---|---|
With hydrogenchloride byproducts: acetone; with dild. HCl,cooling; pptg. of Sn with H2S,filtering,evapn.,washing with ether-alcohol; |
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.; |
Conditions | Yield |
---|---|
With hydrogenchloride with dild. HCl; |
Conditions | Yield |
---|---|
With tin | |
With Sn |
Conditions | Yield |
---|---|
In not given boiling the dild. soln.; | |
In not given boiling the dild. soln.; |
ethyl Bromopyruvate
hydroxylamine hydrochloride
ethyl (2Z)-3-bromo-2-(hydroxyimino)propanoate
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
hydroxylamine hydrochloride
4-[1-(2,2-dimethyl-propionyl)-5-(hydroxyimino-methyl)-1H-indol-6-yloxy]-but-2-enoic acid ethyl ester
Conditions | Yield |
---|---|
With sodium acetate In ethanol at 0℃; for 1h; | 100% |
hydroxylamine hydrochloride
Conditions | Yield |
---|---|
With sodium acetate In methanol at 20℃; for 24h; | 100% |
(RS)-2,3,3a,4,5,6-hexahydro-phenalen-1-one
hydroxylamine hydrochloride
2,3,3a,4,5,6-hexahydro-phenalen-1-one oxime
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% |
Conditions | Yield |
---|---|
With pyridine at 20 - 116℃; for 22h; | 100% |
Methyl 4-(3,4-dichlorobenzyl)-2-formylfuro[3,2-b ]pyrrole-5-carboxylate
hydroxylamine hydrochloride
Methyl 2-cyano-4-(3,4-dichlorobenzyl)furo[3,2-b ]pyrrole-5-carboxylate
Conditions | Yield |
---|---|
With acetic anhydride In pyridine | 100% |
With acetic anhydride In pyridine | 100% |
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
hydroxylamine hydrochloride
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
hydroxylamine hydrochloride
2,3-dihydro-2-hexyl-6-hydroxy-2,5,7,8-tetramethyl-4H-1-benzopyran-4-one-oxime
Conditions | Yield |
---|---|
In pyridine at 70℃; | 100% |
3,4-dihydro-2,2,5,7,8-pentamethyl-6-hydroxy-2H-1-benzopyran-4-one
hydroxylamine hydrochloride
2,3-dihydro-6-hydroxy-2,2,5,7,8-pentamethyl-4H-1-benzopyran-4-one-oxime
Conditions | Yield |
---|---|
In pyridine at 70℃; | 100% |
hydroxylamine hydrochloride
N-(bis(1,2,3,5,6,7-hexahydropyrido(3,2,1-ij)quinolin-9-yl)methyl)-hydroxylamine
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% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 20℃; for 1h; Cooling with ice; | 100% |
2,3-dihydro-4H-1-benzopyran-4-one
hydroxylamine hydrochloride
(4E)-2,3-dihydro-4H-chromen-4-one oxime
Conditions | Yield |
---|---|
With sodium acetate In ethanol; water | 99% |
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% |
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
hydroxylamine hydrochloride
(C5H5)Fe(C5H4C(C6H4CF3)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% |
hydroxylamine hydrochloride
1-allyl-1H-benzo[d]imidazole-2-carboxaldehyde
Conditions | Yield |
---|---|
With triethylamine In ethanol at 80℃; for 0.5h; Microwave irradiation; | 99% |
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
tetra(n-butyl)ammonium hydroxide
4-nitrobenzaldehdye
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
hydroxylamine hydrochloride
tert-Butyl N-hydroxycarbamate
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 |
Conditions | Yield |
---|---|
With sodium acetate In ethanol at 0℃; for 3h; | 98% |
2',4'-dihydroxy-4-acetophenone
hydroxylamine hydrochloride
(1Z)-1-(2,4-dihydroxyphenyl)ethanone oxime
Conditions | Yield |
---|---|
In pyridine at 20℃; | 98% |
hydroxylamine hydrochloride
Conditions | Yield |
---|---|
In ethanol at 70℃; for 1h; | 98% |
5-(N-ethyl-N-ferrocenylmethylamino)pentan-2-one
hydroxylamine hydrochloride
5-(N-ethyl-N-ferrocenylmethylamino)pentan-2-one-oxime
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
hydroxylamine hydrochloride
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% |
hydroxylamine hydrochloride
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]
hydroxylamine hydrochloride
fac-[iridium(III)(2-(4'-methoxy-5'-(CHNOH)phenyl)pyridine)3]
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
4-(4-(N,N-bis(2-chloroethyl)amino)phenyl)butanal
N-hydroxy-4-(4-N',N'-bis(2-chloroethyl)amino)phenylbutylimine
Conditions | Yield |
---|---|
With triethylamine In ethanol for 0.416667h; | 98% |
4-acetyl[2.2]paracyclophane
hydroxylamine hydrochloride
4-acetyl[2.2]paracyclophane-O-methyloxime
Conditions | Yield |
---|---|
With pyridine In methanol Molecular sieve; Reflux; | 98% |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 50℃; for 12h; pH=6 - 7; | 97.17% |
Molecular Structure of Hydroxylamine hydrochloride (CAS NO.5470-11-1):
IUPAC Name: Hydroxylamine hydrochloride
Molecular Formula: H3NO.HCl
Molecular Weight: 69.49
EINECS: 226-798-2
H-Bond Donor: 3
H-Bond Acceptor: 2
storage temp.: Store at RT.
Water Solubility :560 g/L (20 °C)
Sensitive: Hygroscopic
Density: 1.67 g/mL at 25 °C(lit.)
Melting Point: 155-157 °C (dec.)(lit.)
Enthalpy of Vaporization: 34.9 kJ/mol
Boiling Point: 56.5 °C at 760 mmHg
Vapour Pressure: 179 mmHg at 25 °C
Appearance: Colorless or off-white crystalline solid
Classification Code: Mutation data
Canonical SMILES: NO.Cl
InChI: InChI=1S/ClH.H3NO/c;1-2/h1H;2H,1H2
InChIKey: WTDHULULXKLSOZ-UHFFFAOYSA-N
Stability: Substances to be avoided include strong oxidizing agents. Heating above 115 C may cause explosion; do not store above 65C. Moisture and air sensitive.
Hydroxylamine hydrochloride (CAS NO.5470-11-1) is used in organic synthesis for preparation of oximes and hydroxamic acids from carboxylic acids, N- and O- substituted hydroxyamines, and addition reactions of carbon-carbon double bond. It is also used as a fixative for textile dyes, auxiliary in some dyeing processes, as a metal extraction and flotation aid, as an antioxidant in fatty acids and soaps, and as a color stabilizer and emulsion additive in color films. Hydroxylamine hydrochloride can be used to remove bromine and polybromide from the solution.
In surface treatments, Hydroxylamine hydrochloride is used in the preparation of anti-skinning agents, corrosion inhibitors, and cleaner additives. It is also a starting material for pharmaceuticals and agrochemicals manufacturing. In the rubber and plastics industries, it is an antioxidant, vulcanization accelerator, and radical scavenger.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LDLo | subcutaneous | 70mg/kg (70mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935. | |
mouse | LD50 | intraperitoneal | 10mg/kg (10mg/kg) | National Technical Information Service. Vol. AD277-689, | |
mouse | LD50 | oral | 408mg/kg (408mg/kg) | Acta Pharmacologica et Toxicologica. Vol. 6, Pg. 285, 1950. | |
mouse | LD50 | subcutaneous | 125mg/kg (125mg/kg) | Acta Biologica et Medica Germanica. Vol. 21, Pg. 635, 1968. | |
rat | LD50 | oral | 141mg/kg (141mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | National Technical Information Service. Vol. OTS0555279, |
Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
Poison by intraperitoneal and subcutaneous routes. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits very toxic fumes of HCl and NOx.
Safety Information of Hydroxylamine hydrochloride (CAS NO.5470-11-1):
Hazard Codes: Xn,N
Risk Statements: 22-36/38-43-48/22-50
R22:Harmful if swallowed.
R36/38:Irritating to eyes and skin.
R43:May cause sensitization by skin contact.
R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed.
R50:Very toxic to aquatic organisms.
Safety Statements: 22-24-37-61
S22:Do not breathe dust.
S24:Avoid contact with skin.
S37:Wear suitable gloves.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 2923 8/PG 2
WGK Germany: 3
RTECS: NC3675000
F: 21
HazardClass: 8
PackingGroup: III
Hydroxylamine hydrochloride (CAS NO.5470-11-1), its Synonyms are Hydroxyamine hydrochloride ; Hydroxyammonium chloride ; Hydroxylamine chloride ; Hydroxylamine chloride (1:1) ; Hydroxylamine-1-hydrochloride ; Hydroxylammonium chloride ; Oxammonium hydrochloride .
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