Trimethobenzamide supplier

Name
Trimethobenzamide
EINECS 205-332-1
CAS No. 138-56-7
Article Data9
CAS DataBase
Density 1.131 g/cm³
Solubility
Melting Point
Formula C₂₁H₂₈N₂O₅
Boiling Point 506.9 °C at 760 mmHg
Molecular Weight 388.464
Flash Point 260.4 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
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

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

...Expand

: 20059-73-8
4-<2-(dimethylamino)ethoxy>benzylamine

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

: 138-56-7
Trimethobenzamide

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

: 123-08-0
4-hydroxy-benzaldehyde

A: 138-56-7
Trimethobenzamide

B: 1445977-41-2
C30H36N2O9

C: 1445977-42-3
trimethobenzamide

Conditions

Conditions	Yield
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: thionyl chloride; N,N-dimethyl-formamide View Scheme

...Expand

: 15182-92-0, 87330-48-1
4-(2-dimethylaminoethoxy)benzaldehyde

A: 138-56-7
Trimethobenzamide

B: 1445977-41-2
C30H36N2O9

C: 1445977-42-3
trimethobenzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia / methanol / 8 h / 50 - 55 °C / 6000.6 - 7500.75 Torr / Large scale 2: thionyl chloride; N,N-dimethyl-formamide View Scheme

...Expand

: 20059-73-8
4-<2-(dimethylamino)ethoxy>benzylamine

: N-(3,4,5-trimethoxybenzoyl)imidazole

: 138-56-7
Trimethobenzamide

Conditions

Conditions	Yield
With potassium carbonate In ethyl acetate at 10℃; for 2.5h; Concentration; Inert atmosphere; Large scale;

: 118-41-2
Eudesmic acid

: 138-56-7
Trimethobenzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ethyl acetate / 2 h / 50 - 55 °C / Large scale 2: potassium carbonate / ethyl acetate / 2.5 h / 10 °C / Inert atmosphere; Large scale View Scheme

: 3940-75-8
3,4,5-trimethoxy-N-phenylbenzamide

: 138-56-7
Trimethobenzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 15 h / 20 °C / Schlenk technique; Inert atmosphere 2: acetonitrile / 15 h / 20 °C / Schlenk technique; Inert atmosphere View Scheme

: 138-56-7
Trimethobenzamide

: 73183-34-3
bis(pinacol)diborane

: (S)-N-((4-(2-(dimethylamino)ethoxy)phenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)-3,4,5-trimethoxybenzamide

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; [Rh(OH)(cod)]2; (11bR)-4-(((R)-2'-((triisopropylsilyl)oxy)-[1,1'-binaphthalen]-2-yl)oxy)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine In acetonitrile at 60℃; for 15h; Inert atmosphere; Sealed tube; enantioselective reaction;	63%

: 80-43-3
bis(1-methyl-1-phenylethyl)peroxide

: 138-56-7
Trimethobenzamide

: 76-05-1
trifluoroacetic acid

: C22H30N2O5*C2HF3O2

Conditions

Conditions	Yield
With (1,2-dimethoxyethane)dichloronickel(II); [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 25℃; for 16h; Irradiation; chemoselective reaction;	44%

...Expand

: 138-56-7
Trimethobenzamide

: 554-92-7
N-[p-[(2-dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxybenzamide hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water; acetone Large scale;	103 kg

: 138-56-7
Trimethobenzamide

: 73183-34-3
bis(pinacol)diborane

: N-((4-(2-(dimethylamino)ethoxy)phenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)-3,4,5-trimethoxybenzamide

Conditions

Conditions	Yield
With [Rh(OH)(cod)]2 at 60℃; for 15h; Inert atmosphere; Sealed tube;

Trimethobenzamide 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

Product Name

Trimethobenzamide

Synthetic route

Trimethobenzamide Specification

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