Product Name

  • Name

    O-(TRIMETHYLSILYL)HYDROXYLAMINE

  • EINECS
  • CAS No. 22737-36-6
  • Article Data10
  • CAS DataBase
  • Density 0.86
  • Solubility
  • Melting Point
  • Formula C3H11 N O Si
  • Boiling Point 98-100 °C(lit.)
  • Molecular Weight 105.212
  • Flash Point 48 °F
  • Transport Information UN 2733
  • Appearance clear colorless liquid
  • Safety
    Hazard Codes F,C
    Risk Statements 11-34
    Safety Statements 16-26-36/37/39-45
    RIDADR UN 2733 3/PG 2
    WGK Germany 3
    F 10-21
    TSCA No
    HazardClass 3.1
    PackingGroup II
  • Risk Codes R11;R34   
  • Molecular Structure Molecular Structure of 22737-36-6 (O-(TRIMETHYLSILYL)HYDROXYLAMINE)
  • Hazard Symbols
  • Synonyms O-(Trimethylsilyl)hydroxylamine;Trimethylsiloxyamine
  • PSA 35.25000
  • LogP 1.41190

Synthetic route

trimethylsilyl N-[(chloromethyl)dimethylsilyl]-N-(trimethylsiloxy)carbamate

trimethylsilyl N-[(chloromethyl)dimethylsilyl]-N-(trimethylsiloxy)carbamate

A

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

B

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

C

1,3-Bis(chloromethyl)-1,1,3,3-tetramethyldisiloxane
2362-10-9

1,3-Bis(chloromethyl)-1,1,3,3-tetramethyldisiloxane

Conditions
ConditionsYield
In water; acetone at 60℃;A n/a
B 91%
C n/a
...Expand
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

Conditions
ConditionsYield
With hydroxylamine hydrochloride In dichloromethane; ethylenediamine for 24h;80%
With hydroxylamine hydrochloride; ethylenediamine 1.) CH2Cl2, RT, 6 h, 2.) CH2Cl2, RT, 24 h; Yield given. Multistep reaction;
With pyridine; hydroxylamine hydrochloride at 20℃;
trimethylsilyl amine
7379-79-5

trimethylsilyl amine

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

Conditions
ConditionsYield
With hydroxylamine hydrochloride In diethyl ether; ammonia
1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

Conditions
ConditionsYield
With hydroxylamine hydrochloride; triethylamine In pentane
With tri-n-propylamine; hydroxylamine hydrochloride
1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

A

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

B

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

Conditions
ConditionsYield
With tri-n-propylamine; hydroxylamine hydrochloride for 24h; Ambient temperature; Yield given;
oxalyl dichloride
79-37-8

oxalyl dichloride

2-[(3,4-dimethoxyphenyl)sulfonyl]-6-phenylhexanoic acid

2-[(3,4-dimethoxyphenyl)sulfonyl]-6-phenylhexanoic acid

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

N-hydroxy-2-[(3,4-dimethoxyphenyl)sulfonyl]-6-phenylhexanamide

N-hydroxy-2-[(3,4-dimethoxyphenyl)sulfonyl]-6-phenylhexanamide

Conditions
ConditionsYield
In dichloromethane; ethyl acetate100%
...Expand
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

C9H21NO3Si

C9H21NO3Si

Conditions
ConditionsYield
With lithium perchlorate In diethyl ether at 20℃; for 0.5h;98%
O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

acetyl chloride
75-36-5

acetyl chloride

N-acetoxyacetamide
7340-09-2

N-acetoxyacetamide

Conditions
ConditionsYield
In pentane at 20℃; for 12h;96%
O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

Phenyl glycidyl ether
122-60-1

Phenyl glycidyl ether

C12H21NO3Si

C12H21NO3Si

Conditions
ConditionsYield
With lithium perchlorate In diethyl ether at 20℃; for 0.5h;96%
indole
120-72-9

indole

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

pivalaldehyde
630-19-3

pivalaldehyde

C16H26N2OSi

C16H26N2OSi

Conditions
ConditionsYield
With chloro-trimethyl-silane; lithium perchlorate In diethyl ether at 20℃; for 2h; Friedel-Crafts reaction;96%
...Expand
indole
120-72-9

indole

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

hexanal
66-25-1

hexanal

C17H28N2OSi

C17H28N2OSi

Conditions
ConditionsYield
With chloro-trimethyl-silane; lithium perchlorate In diethyl ether at 20℃; for 2h; Friedel-Crafts reaction;95%
...Expand
indole
120-72-9

indole

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

isobutyraldehyde
78-84-2

isobutyraldehyde

C15H24N2OSi

C15H24N2OSi

Conditions
ConditionsYield
With chloro-trimethyl-silane; lithium perchlorate In diethyl ether at 20℃; for 2h; Friedel-Crafts reaction;95%
...Expand
oxalyl dichloride
79-37-8

oxalyl dichloride

(-)-2-(2-Benzenesulfonyl-ethyl)-3-(3,4-dimethoxy-phenylsulfanyl)-7-phenyl-heptanoic acid
193549-76-7

(-)-2-(2-Benzenesulfonyl-ethyl)-3-(3,4-dimethoxy-phenylsulfanyl)-7-phenyl-heptanoic acid

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

(-)-N-hydroxy-2-(2-benzenesulfonylethyl)-3-(3,4-dimethoxyphenylsulfanyl)-7-phenylheptanamide

(-)-N-hydroxy-2-(2-benzenesulfonylethyl)-3-(3,4-dimethoxyphenylsulfanyl)-7-phenylheptanamide

Conditions
ConditionsYield
In dichloromethane; N,N-dimethyl-formamide95%
...Expand
carbon monoxide
201230-82-2

carbon monoxide

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

17-iodo-androsta-16-ene
26313-26-8

17-iodo-androsta-16-ene

17-(N-(trimethylsilyloxy)carbamoyl)androst-16-ene

17-(N-(trimethylsilyloxy)carbamoyl)androst-16-ene

Conditions
ConditionsYield
With triethylamine; triphenylphosphine; palladium diacetate at 60℃; Carbonylation;94%
...Expand
indole
120-72-9

indole

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

butyraldehyde
123-72-8

butyraldehyde

C15H24N2OSi

C15H24N2OSi

Conditions
ConditionsYield
With chloro-trimethyl-silane; lithium perchlorate In diethyl ether at 20℃; for 2h; Friedel-Crafts reaction;94%
...Expand
indole
120-72-9

indole

pentanal
110-62-3

pentanal

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

C16H26N2OSi

C16H26N2OSi

Conditions
ConditionsYield
With chloro-trimethyl-silane; lithium perchlorate In diethyl ether at 20℃; for 2h; Friedel-Crafts reaction;93%
...Expand
2-methyl-1,2-epoxypropane
558-30-5

2-methyl-1,2-epoxypropane

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

C7H19NO2Si

C7H19NO2Si

Conditions
ConditionsYield
With lithium perchlorate In diethyl ether at 20℃; for 0.5h;92%
carbon monoxide
201230-82-2

carbon monoxide

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

17-iodo-4-aza-4-methyl-androst-16-en-3-one
204317-14-6

17-iodo-4-aza-4-methyl-androst-16-en-3-one

17-(N-(trimethylsilyloxy)carbamoyl)-4-aza-4-methylandrost-16-en-3-one

17-(N-(trimethylsilyloxy)carbamoyl)-4-aza-4-methylandrost-16-en-3-one

Conditions
ConditionsYield
With triethylamine; triphenylphosphine; palladium diacetate at 60℃; Carbonylation;91%
...Expand
indole
120-72-9

indole

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

C18H28N2OSi

C18H28N2OSi

Conditions
ConditionsYield
With chloro-trimethyl-silane; lithium perchlorate In diethyl ether at 20℃; for 2h; Friedel-Crafts reaction;90%
...Expand
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

N-trimethylsiloxy O-tert-butyl carbamate

N-trimethylsiloxy O-tert-butyl carbamate

Conditions
ConditionsYield
With thioglycoluril In ethanol at 30 - 40℃; for 0.166667h; chemoselective reaction;90%
With lithium perchlorate In dichloromethane at 20℃; for 5h;76%
oxalyl dichloride
79-37-8

oxalyl dichloride

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

(+/-)-3-(4-Methoxyphenylsulfanyl)-2-methyl-7-phenylheptanoic acid
193550-75-3

(+/-)-3-(4-Methoxyphenylsulfanyl)-2-methyl-7-phenylheptanoic acid

(+/-)-3-(4-methoxyphenylsulfanyl)-2-methyl-7-phenylheptanoic acid hydroxyamide
193547-71-6

(+/-)-3-(4-methoxyphenylsulfanyl)-2-methyl-7-phenylheptanoic acid hydroxyamide

Conditions
ConditionsYield
In dichloromethane90%
...Expand
O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

Diisopropyl chlorophosphate
2574-25-6

Diisopropyl chlorophosphate

C9H24NO4PSi

C9H24NO4PSi

Conditions
ConditionsYield
With triethylamine In hexane for 24h; Ambient temperature;89%
O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

C10H16ClNOSi

C10H16ClNOSi

Conditions
ConditionsYield
With chloro-trimethyl-silane; zirconium borohydride-piperazine; lithium perchlorate In dichloromethane for 3h;89%
O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

4-bromobenzyl mercaptan
19552-10-4

4-bromobenzyl mercaptan

3-(chloromethyl)-1H-1,2,4-triazol-5(4H)-one
252742-72-6

3-(chloromethyl)-1H-1,2,4-triazol-5(4H)-one

5-({[(4-bromophenyl)methyl]thio}methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
935760-75-1

5-({[(4-bromophenyl)methyl]thio}methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 12h;88%
...Expand
O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

dipropyl chlorophosphate
2510-89-6

dipropyl chlorophosphate

C9H24NO4PSi

C9H24NO4PSi

Conditions
ConditionsYield
With triethylamine In hexane for 24h; Ambient temperature;87%
O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

diethyl chlorophosphate
814-49-3

diethyl chlorophosphate

N-(diethoxyphosphoroyl)-O-trimethylsilylhydroxylamine
151452-12-9

N-(diethoxyphosphoroyl)-O-trimethylsilylhydroxylamine

Conditions
ConditionsYield
With triethylamine In hexane for 24h; Ambient temperature;86%
O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

4-(4-methoxyphenyl)-2-methyl-2-(methylsulfonyl)butanoic acid
1354546-78-3

4-(4-methoxyphenyl)-2-methyl-2-(methylsulfonyl)butanoic acid

N-hydroxy-4-(4-methoxyphenyl)-2-methyl-2-(methylsulfonyl)butanamide
1289622-76-9

N-hydroxy-4-(4-methoxyphenyl)-2-methyl-2-(methylsulfonyl)butanamide

Conditions
ConditionsYield
Stage #1: 4-(4-methoxyphenyl)-2-methyl-2-(methylsulfonyl)butanoic acid With oxalyl dichloride In dichloromethane for 1h;
Stage #2: O-Trimethylsilylhydroxylamine In dichloromethane for 1h;		85%
oxalyl dichloride
79-37-8

oxalyl dichloride

(+/-)-(2R*,3R*)-3-(4-methoxybenzenesulfonyl)-7-phenyl-2-(2-phenoxyethyl)heptanoic acid

(+/-)-(2R*,3R*)-3-(4-methoxybenzenesulfonyl)-7-phenyl-2-(2-phenoxyethyl)heptanoic acid

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

acetonitrile
75-05-8

acetonitrile

(+/-)-(2R*,3R*)-3-(4-Methoxybenzenesulfonyl)-7-phenyl-2-(2-phenoxyethyl)heptanoic acid hydroxyamide

(+/-)-(2R*,3R*)-3-(4-Methoxybenzenesulfonyl)-7-phenyl-2-(2-phenoxyethyl)heptanoic acid hydroxyamide

Conditions
ConditionsYield
In dichloromethane; water; trifluoroacetic acid69%
...Expand
O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

1-methyl-1-<4-(benzyloxy)phenyl>ethanol
94571-13-8

1-methyl-1-<4-(benzyloxy)phenyl>ethanol

N-<1-methyl-1-<4-(benzyloxy)phenyl>ethyl>hydroxylamine
118684-95-0

N-<1-methyl-1-<4-(benzyloxy)phenyl>ethyl>hydroxylamine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 0℃; for 1h;68%
O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

di(4-isocyanatophenyl)methane
101-68-8

di(4-isocyanatophenyl)methane

(isocyanatooxy)trimethylsilane
86672-45-9

(isocyanatooxy)trimethylsilane

Conditions
ConditionsYield
at 200℃;67%
(3R)-6-cyclohexyl-3-(3-{[(3-pyridinylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoic acid
438629-24-4

(3R)-6-cyclohexyl-3-(3-{[(3-pyridinylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoic acid

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran
96042-30-7

4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

(3R)-6-cyclohexyl-N-hydroxy-3-(3-{[(3-pyridinylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanamide

(3R)-6-cyclohexyl-N-hydroxy-3-(3-{[(3-pyridinylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanamide

Conditions
ConditionsYield
With CDI In methanol; ethyl acetate67%
...Expand
O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

allyltributylstanane
24850-33-7

allyltributylstanane

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

N-tributyltin-N-trimethylsilyloxy-1-(4-nitrophenyl)but-3-en-1-amine
937737-41-2

N-tributyltin-N-trimethylsilyloxy-1-(4-nitrophenyl)but-3-en-1-amine

Conditions
ConditionsYield
With lithium perchlorate In diethyl ether amine was added to soln. of LiClO4 in Et2O at room temp.; stirred for 10min; Sn compd. was added; stirred at room temp. for 4-5 h; TLC monitoring; quenched with cooled brine; extd. (CH2Cl2); org. extracts dried (MgSO4); concd.; chromd. (silica gel, hexane/EtOAc, 2/1 to 3/1);elem. anal.;67%
...Expand
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

allyltributylstanane
24850-33-7

allyltributylstanane

N-tributyltin-N-trimethylsilyloxy-1-(3-pyridinyl)but-3-en-1-amine
937737-40-1

N-tributyltin-N-trimethylsilyloxy-1-(3-pyridinyl)but-3-en-1-amine

Conditions
ConditionsYield
With lithium perchlorate In diethyl ether amine was added to soln. of LiClO4 in Et2O at room temp.; stirred for 10min; Sn compd. was added; stirred at room temp. for 4-5 h; TLC monitoring; quenched with cooled brine; extd. (CH2Cl2); org. extracts dried (MgSO4); concd.; chromd. (silica gel, hexane/EtOAc, 2/1 to 3/1);elem. anal.;64%
...Expand

O-(Trimethylsilyl)hydroxylamine Chemical Properties

Molecular Structure of O-(Trimethylsilyl)hydroxylamine (CAS NO.22737-36-6):

Systematic Name: (Aminooxy)(trimethyl)silane 
Molecular Formula: C3H11NOSi
Molecular Weight: 105.21 
storage temp.: 2-8 °C 
Index of Refraction: 1.398
Molar Refractivity: 29.94 cm3
Molar Volume: 123.8 cm3
Surface Tension: 19.2 dyne/cm
Density: 0.849 g/cm3
Flash Point: 8.9 °C
Enthalpy of Vaporization: 33.84 kJ/mol
Boiling Point: 99 °C at 760 mmHg
Vapour Pressure: 39 mmHg at 25 °C
Appearance: clear colorless liquid
SMILES: O(N)[Si](C)(C)C
InChI: InChI=1/C3H11NOSi/c1-6(2,3)5-4/h4H2,1-3H3
InChIKey: AEKHNNJSMVVESS-UHFFFAOYAT
Product Categories: Hydroxylamines; Hydroxylamines (O-Substituted); Si (Classes of Silicon Compounds); Silanols; Si-O Compounds

O-(Trimethylsilyl)hydroxylamine Safety Profile

Safety Information of O-(Trimethylsilyl)hydroxylamine (CAS NO.22737-36-6):
Hazard Codes: FlammableF,CorrosiveC
Risk Statements: 11-34 
R11:Highly flammable. 
R34:Causes burns.
Safety Statements: 16-26-36/37/39-45 
S16:Keep away from sources of ignition. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2733 3/PG 2
WGK Germany: 3
F: 10-21
TSCA: No
HazardClass: 3.1
PackingGroup: II

O-(Trimethylsilyl)hydroxylamine Specification

 O-(Trimethylsilyl)hydroxylamine (CAS NO.22737-36-6), its Synonyms are Hydroxylamine,O-(trimethylsilyl)- ; Trimethylsiloxyamine ; Aminoxytrimethylsilane .

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