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144689-93-0

Basic Information
CAS No.: 144689-93-0
Name: Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate
Article Data: 10
Molecular Structure:
Molecular Structure of 144689-93-0 (Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate)
Formula: C12H20N2O3
Molecular Weight: 240.302
Synonyms: 1H-Imidazole-4-carboxylicacid, 5-(1-hydroxy-1-methylethyl)-2-propyl-, ethyl ester (9CI);2-Propyl-5-(1-hydroxy-1-methylethyl)-3H-imidazole-4-carboxylic acid ethyl ester;
EINECS: 1592732-453-0
Density: 1.131 g/cm3
Melting Point: 98-100°C
Boiling Point: 456.2 °C at 760 mmHg
Flash Point: 229.7 °C
PSA: 75.21000
LogP: 1.76630
Synthetic route
74-83-9

methyl bromide

144689-94-1

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate

144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
With iodine; magnesium In dichloromethane at 15 - 25℃; for 2h;97.5%
75-16-1

methylmagnesium bromide

144689-94-1

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate

144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
In diethyl ether; dichloromethane at 10 - 15℃; for 1h;95%
64-17-5

ethanol

849206-42-4

C10H14N2O2

144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: ethanol; C10H14N2O2 With sulfuric acid at 40 - 50℃;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate Product distribution / selectivity;
92%
676-58-4

methylmagnesium chloride

144689-94-1

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate

144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: methylmagnesium chloride; diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate In tetrahydrofuran at -10 - 0℃; for 0.166667h;
Stage #2: With water; ammonium chloride In tetrahydrofuran; dichloromethane
85%
Stage #1: methylmagnesium chloride; diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate In tetrahydrofuran; toluene for 6.5h; Inert atmosphere; Cooling with ice;
Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene pH=7;
In tetrahydrofuran at 60℃; for 2h;4.81 g
144690-04-0

4-(1-hydroxy-1-methylethyl)-2-propyl imidazole-5-carboxylic acid

64-17-5

ethanol

144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: 4-(1-hydroxy-1-methylethyl)-2-propyl imidazole-5-carboxylic acid; ethanol With thionyl chloride Reflux;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate Product distribution / selectivity;
85%
74-87-3

methylene chloride

144689-94-1

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate

144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: methylene chloride With magnesium In tetrahydrofuran for 0.5h; Reflux;
Stage #2: diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate In tetrahydrofuran at 30℃; for 2.5h; Solvent; Temperature;
80%
Stage #1: methylene chloride With magnesium at 55 - 60℃; for 1h; Inert atmosphere;
Stage #2: diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate at 0℃; for 8h;
58954-23-7

2-propyl-1H-imidazole-4,5-dicarboxylic acid

144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86 percent / HCl / Ambient temperature
2: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C
View Scheme
51802-42-7

2-propylimidazole-4,5-dicarbonitrile

144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / 6N aq. HCl / 8 h / Heating
2: 86 percent / HCl / Ambient temperature
3: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C
View Scheme
144689-94-1

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate

A

144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

B

144689-92-9

ethyl 2-butyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate

Conditions
ConditionsYield
With methylmagnesium bromide In tetrahydrofuran

diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate hydrochloride

144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide; sodium chloride / water / 1 h / Cooling with ice
2.1: toluene; tetrahydrofuran / 6.5 h / Inert atmosphere; Cooling with ice
2.2: pH 7
View Scheme
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    Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate Basic information Product Name: Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate Synonyms: 4-(1-HYDROXY-1-METHYLETHYL)-2-PROPYL-1H-IMIDAZOLE-5-CARBOXYLIC ACID

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Specification

The [5-(1-Hydroxyl-1-methylethyl)-2-propyl-imidazol-4-yl]carboxylic acid ethyl ester, with its CAS registry number 144689-93-0, has the systematic name of ethyl 5-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-4-carboxylate. As to its usage, it is usually applied in the intermediate of antihypertensive agent of Olmesartan, with its product categories including Intermediatesof; Imidazol&Benzimidazole; API intermediates. 

The physical properties of this chemical are as below: (1)ACD/LogP: 1.95; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1; (4)ACD/LogD (pH 7.4): 1; (5)ACD/BCF (pH 5.5): 2; (6)ACD/BCF (pH 7.4): 2; (7)ACD/KOC (pH 5.5): 54; (8)ACD/KOC (pH 7.4): 58; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 75.21 ; (13)Index of Refraction: 1.521; (14)Molar Refractivity: 64.655 cm3; (15)Molar Volume: 212.39 cm3; (16)Polarizability: 25.631×10-24 cm3; (17)Surface Tension: 44.004 dyne/cm; (18)Density: 1.131 g/cm3; (19)Flash Point: 229.723 °C; (20)Enthalpy of Vaporization: 75.462 kJ/mol; (21)Boiling Point: 456.234 °C at 760 mmHg. 

In addition, you could convert the following datas into the molecular structure:
(1)SMILES:O=C(OCC)c1nc(nc1C(O)(C)C)CCC
(2)InChI:InChI=1/C12H20N2O3/c1-5-7-8-13-9(11(15)17-6-2)10(14-8)12(3,4)16/h16H,5-7H2,1-4H3,(H,13,14) 
(3)InChIKey:KZBJJAFGNMRRHN-UHFFFAOYAT