Product Name

  • Name

    DexmedetomidineHclC13H16N2.Hcl

  • EINECS 601-281-8
  • CAS No. 113775-47-6
  • Article Data16
  • CAS DataBase
  • Density 1.053 g/cm3
  • Solubility
  • Melting Point 146-149°C
  • Formula C13H16N2
  • Boiling Point 381.9 °C at 760 mmHg
  • Molecular Weight 200.283
  • Flash Point 191.3 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 113775-47-6 (DexmedetomidineHclC13H16N2.Hcl)
  • Hazard Symbols
  • Synonyms 1H-Imidazole,4-[(1S)-1-(2,3-dimethylphenyl)ethyl]- (9CI);1H-Imidazole,4-[1-(2,3-dimethylphenyl)ethyl]-, (S)-;(+)-Medetomidine;(S)-Medetomidine;MPV 1440;d-Medetomidine;
  • PSA 28.68000
  • LogP 3.17830

Synthetic route

medetomidine
86347-14-0

medetomidine

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
Stage #1: medetomidine With L-Lysine ethyl ester In ethanol at 75℃; for 3h;
Stage #2: With sodium hydroxide In water at 100℃; Temperature; enantioselective reaction;		94.2%
Stage #1: medetomidine With sodium carbonate In dichloromethane at 20 - 25℃; for 0.25h;
Stage #2: With L-Tartaric acid In ethanol; water at 10℃; for 1.5h; Reflux;
Stage #3: With ammonium hydroxide In ethanol; water at 30 - 40℃; for 1h;		45.3%
Multi-step reaction with 2 steps
1: water; acetone / 0.5 h / 45 - 55 °C
2: water; ethanol; isopropyl alcohol / 0.2 h / 30 - 70 °C
View Scheme
4-<1-(2,3-dimethylphenyl)-1-hydroxyethyl>-1-(triphenylmethyl)imidazole
176721-03-2

4-<1-(2,3-dimethylphenyl)-1-hydroxyethyl>-1-(triphenylmethyl)imidazole

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In dichloromethane at -10 - 20℃;89%
With formic acid; palladium 10% on activated carbon; ammonium formate at 120℃; for 10h;82.8%
With triethylsilane; hydrogen; trifluoroacetic acid; palladium on activated charcoal 1.) r.t., CH2Cl2, 2.) r.t., 1 bar, 2 h, H2O; Yield given. Multistep reaction;
1H-imidazole
288-32-4

1H-imidazole

1-(1-chloroethyl)-2,3-dimethylbenzene

1-(1-chloroethyl)-2,3-dimethylbenzene

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
With iron(III) chloride at 75℃; for 0.5h; Reagent/catalyst; Temperature;84.8%
(S)-4-(1-(2,3-dimethylphenyl)ethyl)-1-trityl-1H-imidazole

(S)-4-(1-(2,3-dimethylphenyl)ethyl)-1-trityl-1H-imidazole

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
With hydrogenchloride In water; toluene at 80 - 84℃; for 4h;78.6%
C13H16N2*C6H10O4

C13H16N2*C6H10O4

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
In ethanol; water; isopropyl alcohol at 30 - 70℃; for 0.2h;65%
2,3-dimethylbromobenzene
576-23-8

2,3-dimethylbromobenzene

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) magnesium, iodine / 1.) THF, reflux, 1 h, 2.) r.t., THF, 1.5 h
2: 90 percent / MnO2 / dioxane / 5 h / Heating
3: 95 percent / tetrahydrofuran / 2 h / Ambient temperature
4: 1.) trifluoroacetic acid, triethylsilane, 2.) H2 / Pd/C / 1.) r.t., CH2Cl2, 2.) r.t., 1 bar, 2 h, H2O
View Scheme
Multi-step reaction with 3 steps
1.1: magnesium; iodine / tetrahydrofuran / 1 h / 65 - 70 °C
1.2: 1 h / 0 - 40 °C
2.1: methylmagnesium bromide / tetrahydrofuran; 2-methyltetrahydrofuran / 2 h / 0 - 20 °C
3.1: formic acid; ammonium formate; palladium 10% on activated carbon / 10 h / 120 °C
View Scheme
Multi-step reaction with 4 steps
1.1: ethylene dibromide; magnesium / tetrahydrofuran / 1 h / 40 - 65 °C
1.2: 2 h / -5 - 0 °C
1.3: 3 h / 30 °C
2.1: tetrahydrofuran / 2 h / 0.4 - 65 °C
3.1: toluene-4-sulfonic acid / toluene / 2 h / 0.11 °C / Dean-Stark
4.1: (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; bis(norbornadiene)rhodium(l)tetrafluoroborate; hydrogen / methanol / 5 h / 40 - 45 °C / 2250.23 - 7500.75 Torr
View Scheme
4-<(2,3-dimethylphenyl)carbonyl>-1-(triphenylmethyl)imidazole
176721-02-1

4-<(2,3-dimethylphenyl)carbonyl>-1-(triphenylmethyl)imidazole

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / tetrahydrofuran / 2 h / Ambient temperature
2: 1.) trifluoroacetic acid, triethylsilane, 2.) H2 / Pd/C / 1.) r.t., CH2Cl2, 2.) r.t., 1 bar, 2 h, H2O
View Scheme
4-<(2,3-dimethylphenyl)hydroxymethyl>-1-(triphenylmethyl)imidazole
176721-01-0

4-<(2,3-dimethylphenyl)hydroxymethyl>-1-(triphenylmethyl)imidazole

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / MnO2 / dioxane / 5 h / Heating
2: 95 percent / tetrahydrofuran / 2 h / Ambient temperature
3: 1.) trifluoroacetic acid, triethylsilane, 2.) H2 / Pd/C / 1.) r.t., CH2Cl2, 2.) r.t., 1 bar, 2 h, H2O
View Scheme
(S)-dexmedetomidine-L-(+)-tartrate
176721-04-3

(S)-dexmedetomidine-L-(+)-tartrate

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
With sodium hydrogencarbonate12.16 g
C4H6O5*C13H16N2

C4H6O5*C13H16N2

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane pH=> 12;65 g
1-(1-chloroethyl)-2,3-dimethylbenzene

1-(1-chloroethyl)-2,3-dimethylbenzene

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: titanium tetrachloride; triethylamine / dichloromethane / 5 h / -3 - 20 °C
2.1: sodium carbonate / dichloromethane / 0.25 h / 20 - 25 °C
2.2: 1.5 h / 10 °C / Reflux
2.3: 1 h / 30 - 40 °C
View Scheme
1-(2,3-dimethyl-phenyl)-ethanone
2142-71-4

1-(2,3-dimethyl-phenyl)-ethanone

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tetrabutyl-ammonium chloride; lanthanum(III) chloride; SeCl3 / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C / Schlenk technique; Inert atmosphere
1.2: 3 h / 0 - 20 °C
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / -10 - 20 °C
View Scheme
medetomidine
86347-14-0

medetomidine

A

dexmedetomidine
113775-47-6

dexmedetomidine

B

levomedetomidine

levomedetomidine

Conditions
ConditionsYield
Stage #1: medetomidine With L-lysine In ethanol at 75℃; for 12h;
Stage #2: With sodium hydroxide In water at 100℃; Overall yield = 61.7 %; Overall yield = 13.3 g; enantioselective reaction;		A n/a
B n/a
With Chiralcel OJ-3R In acetonitrile at 25℃; pH=8; Reagent/catalyst; Resolution of racemate;
1H-imidazole
288-32-4

1H-imidazole

1-(1-chloroethyl)-2,3-dimethylbenzene

1-(1-chloroethyl)-2,3-dimethylbenzene

A

dexmedetomidine
113775-47-6

dexmedetomidine

B

levomedetomidine

levomedetomidine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; 1-butyl-3-methylimidazolium Tetrafluoroborate at 90℃; for 0.5h; Temperature; Reagent/catalyst; Inert atmosphere; Overall yield = 81.1 %; Overall yield = 16.9 g;A n/a
B n/a
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; potassium carbonate; zinc In N,N-dimethyl-formamide at 70℃; for 5h; Reagent/catalyst; Temperature; Inert atmosphere; Overall yield = 89.5 %; Overall yield = 17.9 g; Optical yield = 90.61 %ee;
...Expand
C20H19ClN2O

C20H19ClN2O

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
With phosphoric acid at 23℃; for 48h; pH=6.5; Enzymatic reaction;18.2 g
1H-imidazole
288-32-4

1H-imidazole

1-(2,3-dimethylphenyl)ethyl trifluoromethanesulfonate

1-(2,3-dimethylphenyl)ethyl trifluoromethanesulfonate

A

dexmedetomidine
113775-47-6

dexmedetomidine

B

levomedetomidine

levomedetomidine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; N-butylpyridinium tetrafluoroborate at 70℃; for 0.5h; Temperature; Reagent/catalyst; Inert atmosphere; Overall yield = 84.7 %; Overall yield = 17.6 g; Optical yield = 79.89 %ee;
...Expand
1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene
1021949-47-2

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / chloroform / 2 h / 20 - 26 °C / Inert atmosphere
2: bis(norbornadiene)rhodium(l)tetrafluoroborate; hydrogen; (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-[bis[4-(trifluoromethyl)phenyl]phosphino]ferrocene / dichloromethane / 24 h / 25 °C / 6000.6 Torr
3: hydrogenchloride / toluene; water / 4 h / 80 - 84 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / chloroform / 2 h / 20 - 26 °C / Inert atmosphere
2: bis(norbornadiene)rhodium(l)tetrafluoroborate; hydrogen; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene / dichloromethane / 3 h / 25 °C / 6000.6 Torr
3: hydrogenchloride / toluene; water / 4 h / 80 - 84 °C
View Scheme
4-(1-(2,3-dimethylphenyl)vinyl)-1-trityl-1H-imidazole

4-(1-(2,3-dimethylphenyl)vinyl)-1-trityl-1H-imidazole

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bis(norbornadiene)rhodium(l)tetrafluoroborate; hydrogen; (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-[bis[4-(trifluoromethyl)phenyl]phosphino]ferrocene / dichloromethane / 24 h / 25 °C / 6000.6 Torr
2: hydrogenchloride / toluene; water / 4 h / 80 - 84 °C
View Scheme
Multi-step reaction with 2 steps
1: bis(norbornadiene)rhodium(l)tetrafluoroborate; hydrogen; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene / dichloromethane / 3 h / 25 °C / 6000.6 Torr
2: hydrogenchloride / toluene; water / 4 h / 80 - 84 °C
View Scheme
4-(2,3-dimethylbenzoyl)-1H-imidazole

4-(2,3-dimethylbenzoyl)-1H-imidazole

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran / 2 h / 0.4 - 65 °C
2: toluene-4-sulfonic acid / toluene / 2 h / 0.11 °C / Dean-Stark
3: (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; bis(norbornadiene)rhodium(l)tetrafluoroborate; hydrogen / methanol / 5 h / 40 - 45 °C / 2250.23 - 7500.75 Torr
View Scheme
1-(2,3-dimethylphenyl)-1-(1H-imidazol-4-yl)ethanol

1-(2,3-dimethylphenyl)-1-(1H-imidazol-4-yl)ethanol

dexmedetomidine
113775-47-6

dexmedetomidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid / toluene / 2 h / 0.11 °C / Dean-Stark
2: (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; bis(norbornadiene)rhodium(l)tetrafluoroborate; hydrogen / methanol / 5 h / 40 - 45 °C / 2250.23 - 7500.75 Torr
View Scheme
1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene
1021949-47-2

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene

A

dexmedetomidine
113775-47-6

dexmedetomidine

B

levomedetomidine

levomedetomidine

Conditions
ConditionsYield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; hydrogen In methanol at 40 - 45℃; under 2250.23 - 7500.75 Torr; for 5h; Optical yield = 79.3 percent ee;
dexmedetomidine
113775-47-6

dexmedetomidine

dexmedetomidine hydrochloride

dexmedetomidine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; ethyl acetate at 20℃; for 1h;92.5%
With hydrogenchloride In ethanol; water; isopropyl alcohol at 35 - 50℃;90%
L-Tartaric acid
87-69-4

L-Tartaric acid

dexmedetomidine
113775-47-6

dexmedetomidine

(S)-dexmedetomidine-L-(+)-tartaric acid salt

(S)-dexmedetomidine-L-(+)-tartaric acid salt

Conditions
ConditionsYield
In ethanol; isopropyl alcohol at 20℃; Reflux;77.1%
dexmedetomidine
113775-47-6

dexmedetomidine

Rezatomidine
847829-38-3

Rezatomidine

Conditions
ConditionsYield
With sodium hydrogencarbonate; phenylcarbonochloridothioate In tetrahydrofuran; water at 20℃; for 4h;53%
With sodium hydrogencarbonate; phenylcarbonochloridothioate In tetrahydrofuran; water at 20℃; for 4h;53%
L-Tartaric acid
87-69-4

L-Tartaric acid

dexmedetomidine
113775-47-6

dexmedetomidine

(S)-dexmedetomidine-L-(+)-tartrate
176721-04-3

(S)-dexmedetomidine-L-(+)-tartrate

Conditions
ConditionsYield
In ethanol at 65℃; for 2h; Temperature;47.3%
dexmedetomidine
113775-47-6

dexmedetomidine

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(+)-(S)-4-<1-(2,3-dimethylphenyl)ethyl>-1-tosyl-1H-imidazole

(+)-(S)-4-<1-(2,3-dimethylphenyl)ethyl>-1-tosyl-1H-imidazole

Conditions
ConditionsYield
With triethylamine In dichloromethane for 2.5h; Ambient temperature;31.1%
dexmedetomidine
113775-47-6

dexmedetomidine

(S)-4-[1-(2,3-dimethylphenyl)ethyl]-3H-imidazole hydrobromide
1391972-96-5

(S)-4-[1-(2,3-dimethylphenyl)ethyl]-3H-imidazole hydrobromide

Conditions
ConditionsYield
With hydrogen bromide Dean-Stark;
dexmedetomidine
113775-47-6

dexmedetomidine

(S)-4-[1-(2,3-dimethylphenyl)ethyl]-3H-imidazole hydroiodide

(S)-4-[1-(2,3-dimethylphenyl)ethyl]-3H-imidazole hydroiodide

Conditions
ConditionsYield
With hydrogen iodide Dean-Stark;
oxalic acid
144-62-7

oxalic acid

dexmedetomidine
113775-47-6

dexmedetomidine

(S)-4-[1-(2,3-dimethylphenyl)ethyl]-3H-imidazole oxalate

(S)-4-[1-(2,3-dimethylphenyl)ethyl]-3H-imidazole oxalate

Conditions
ConditionsYield
In ethanol
ethyl iodide
75-03-6

ethyl iodide

dexmedetomidine
113775-47-6

dexmedetomidine

A

C15H20N2

C15H20N2

B

C15H20N2

C15H20N2

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0 - 50℃; for 4h; Temperature; Solvent; Reagent/catalyst;A 200 mg
B 400 mg
...Expand

Dexmedetomidine Specification

The CAS registry number of 1H-Imidazole,5-[(1S)-1-(2,3-dimethylphenyl)ethyl]- is 113775-47-6. The IUPAC name is 5-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole. In addition, the molecular formula is C13H16N2 and the molecular weight is 200.28. What's more, it belongs to the classes of Aromatics Compounds; Aromatics; Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals. And it should be stored in a cool and dry place.

Physical properties about 1H-Imidazole,5-[(1S)-1-(2,3-dimethylphenyl)ethyl]- are: (1)ACD/LogP: 3.10; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.67; (4)ACD/LogD (pH 7.4): 2.96; (5)ACD/BCF (pH 5.5): 4.96; (6)ACD/BCF (pH 7.4): 98.09; (7)ACD/KOC (pH 5.5): 43.05; (8)ACD/KOC (pH 7.4): 851.05; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 17.82 Å2; (13)Index of Refraction: 1.569; (14)Molar Refractivity: 62.37 cm3; (15)Molar Volume: 190.1 cm3; (16)Polarizability: 24.72 ×10-24cm3; (17)Surface Tension: 42.5 dyne/cm; (18)Density: 1.053 g/cm3; (19)Flash Point: 191.3 °C; (20)Enthalpy of Vaporization: 60.55 kJ/mol; (21)Boiling Point: 381.9 °C at 760 mmHg; (22)Vapour Pressure: 1.08E-05 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: n1cc(nc1)[C@H](c2c(c(ccc2)C)C)C
(2)InChI: InChI=1/C13H16N2/c1-9-5-4-6-12(10(9)2)11(3)13-7-14-8-15-13/h4-8,11H,1-3H3,(H,14,15)/t11-/m0/s1
(3)InChIKey: CUHVIMMYOGQXCV-NSHDSACABZ

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