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138-56-7

Basic Information
CAS No.: 138-56-7
Name: Trimethobenzamide
Article Data: 9
Molecular Structure:
Molecular Structure of 138-56-7 (Trimethobenzamide)
Formula: C21H28N2O5
Molecular Weight: 388.464
Synonyms: Benzamide,N-[p-[2-(dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxy- (6CI,7CI,8CI);4-(2-Dimethylaminoethoxy)-N-(3,4,5-trimethoxybenzoyl)benzylamine;Emedur;N-[p-[2-(Dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxybenzamide;Trimethobenzamide;
EINECS: 205-332-1
Density: 1.131 g/cm3
Boiling Point: 506.9 °C at 760 mmHg
Flash Point: 260.4 °C
PSA: 69.26000
LogP: 2.97370
Synthetic route
25245-29-8

5-iodo-1,2,3-trimethoxybenzene

201230-82-2

carbon monoxide

20059-73-8

4-<2-(dimethylamino)ethoxy>benzylamine

138-56-7

Trimethobenzamide

Conditions
ConditionsYield
With triethylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 80℃; for 18h; Glovebox; Sealed tube; Inert atmosphere;99%
20059-73-8

4-<2-(dimethylamino)ethoxy>benzylamine

tert-butyl phenyl(3,4,5-trimethoxybenzoyl)carbamate

138-56-7

Trimethobenzamide

Conditions
ConditionsYield
In acetonitrile at 20℃; for 15h; Schlenk technique; Inert atmosphere;94%
3840-31-1

(3,4,5-trimethoxyphenyl)methanol

20059-73-8

4-<2-(dimethylamino)ethoxy>benzylamine

138-56-7

Trimethobenzamide

Conditions
ConditionsYield
With potassium tert-butylate; [Ru(PtBuNNHBn)H(CO)Cl] In tert-butyl methyl ether at 70℃; under 760.051 Torr; for 60h; Inert atmosphere;94%
3086-62-2

3,4,5-trimethoxybenzamide

131028-54-1

(4-(2-(dimethylamino)ethoxy)phenyl)methanol

138-56-7

Trimethobenzamide

Conditions
ConditionsYield
With 1,10-Phenanthroline; nickel dibromide; sodium t-butanolate In toluene at 130℃; for 48h; Schlenk technique; Inert atmosphere;80%
20059-73-8

4-<2-(dimethylamino)ethoxy>benzylamine

118-41-2

Eudesmic acid

138-56-7

Trimethobenzamide

Conditions
ConditionsYield
With 6,6'-diselanediylbis(N-(2-(dimethylamino)ethyl)-3-nitrobenzamide); oxygen; triethyl phosphite In acetonitrile at 30℃; for 18h; Molecular sieve;73%
20059-73-8

4-<2-(dimethylamino)ethoxy>benzylamine

118-41-2

Eudesmic acid

A

138-56-7

Trimethobenzamide

B

1445977-41-2

C30H36N2O9

C

1445977-42-3

trimethobenzamide

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide Reagent/catalyst;A n/a
B 0.5%
C 4%
20059-73-8

4-<2-(dimethylamino)ethoxy>benzylamine

4521-61-3

3,4,5-Trimethoxybenzoyl chloride

138-56-7

Trimethobenzamide

118-41-2

Eudesmic acid

2-oxy-4.6.ω-trimethoxy-acetophenone

2-oxy-4.6.ω-trimethoxy-acetophenone

138-56-7

Trimethobenzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / 0.5 h / Heating
2: Et3N / CHCl3 / 2 h / Ambient temperature
View Scheme
15182-92-0, 87330-48-1

4-(2-dimethylaminoethoxy)benzaldehyde

138-56-7

Trimethobenzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Raney nickel; ethanol; NH3 / 80 °C / 51485.6 Torr / Hydrogenation
View Scheme
Multi-step reaction with 2 steps
1: ammonia / methanol / 8 h / 50 - 55 °C / 6000.6 - 7500.75 Torr / Large scale
2: potassium carbonate / ethyl acetate / 2.5 h / 10 °C / Inert atmosphere; Large scale
View Scheme
123-08-0

4-hydroxy-benzaldehyde

138-56-7

Trimethobenzamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium methylate; chlorobenzene
2: Raney nickel; ethanol; NH3 / 80 °C / 51485.6 Torr / Hydrogenation
View Scheme
Multi-step reaction with 3 steps
1: sodium carbonate / butanone / 18 h / 25 - 80 °C / Large scale
2: ammonia / methanol / 8 h / 50 - 55 °C / 6000.6 - 7500.75 Torr / Large scale
3: potassium carbonate / ethyl acetate / 2.5 h / 10 °C / Inert atmosphere; Large scale
View Scheme
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Specification

The Trimethobenzamide, with the CAS registry number 138-56-7, is also known as 4-(2-Dimethylaminoethoxy)-N-(3,4,5-trimethoxybenzoyl)benzylamine. Its EINECS registry number is 205-332-1. This chemical's molecular formula is C21H28N2O5 and molecular weight is 388.46. Its IUPAC name is called N-[[4-(2-dimethylaminoethyloxy)phenyl]methyl]-3,4,5-trimethoxybenzamide. This chemical's classification codes are Antiemetics; Autonomic Agents; Central Nervous System Agents; Gastrointestinal Agents; Peripheral Nervous System Agents. This chemical is an antiemetic used to prevent nausea and vomiting. Trimethobenzamide is generally considered the most potent antiemetic that does not have effects on the serotonergic, dopaminergic, or histaminergic systems, so it has a lower likelihood of causing undesired side effects.

Physical properties of Trimethobenzamide: (1)ACD/LogP: 1.85; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.96; (4)ACD/LogD (pH 7.4): 0.6; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 13.58; (9)#H bond acceptors: 7; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 10; (12)Index of Refraction: 1.546; (13)Molar Refractivity: 108.69 cm3; (14)Molar Volume: 343.2 cm3; (15)Surface Tension: 40.1 dyne/cm; (16)Density: 1.131 g/cm3; (17)Flash Point: 260.4 °C; (18)Enthalpy of Vaporization: 77.69 kJ/mol; (19)Boiling Point: 506.9 °C at 760 mmHg; (20)Vapour Pressure: 2.13E-10 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CN(C)CCOC1=CC=C(C=C1)CNC(=O)C2=CC(=C(C(=C2)OC)OC)OC
(2)InChI: InChI=1S/C21H28N2O5/c1-23(2)10-11-28-17-8-6-15(7-9-17)14-22-21(24)16-12-18(25-3)20(27-5)19(13-16)26-4/h6-9,12-13H,10-11,14H2,1-5H3,(H,22,24)
(3)InChIKey: FEZBIKUBAYAZIU-UHFFFAOYSA-N