43083-12-1

Basic information

• Product Name: Trimethyl orthobutyrate
• Synonyms: Butane, 1,1,1-trimethoxy-;ORTHO-N-BUTYRIC ACID TRIMETHYL ESTER;ORTHOBUTYRIC ACID TRIMETHYL ESTER;TRIMETHYL ORTHOBUTYRATE;1,1,1-TRIMETHOXYBUTANE;Trimethyl orthobutylate;RimethylOrthobutyrate;o-Trimethyl butyrate
• CAS NO: 43083-12-1
• Molecular Formula: C₇H₁₆O₃
• Molecular Weight: 148.2
• EINECS: 256-079-9
• Product Categories: Intermediates of Dyes and Pigments;Orthoesters;Organic synthesis
• Mol File: 43083-12-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 140-144 °C
• Flash Point: 50 °C
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.926 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.98mmHg at 25°C
• Refractive Index: 1.402-1.404
• Storage Temp.: Flammables area
• Solubility: Chloroform, Ethyl Acetate
• BRN: 1737319
• CAS DataBase Reference: Trimethyl orthobutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: Trimethyl orthobutyrate(43083-12-1)
• EPA Substance Registry System: Trimethyl orthobutyrate(43083-12-1)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/38-10-36/37/38
• Safety Statements: 37/39-26-16-36
• RIDADR: UN 3272
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 43083-12-1(Hazardous Substances Data)

Usage

Description

Trimethyl orthobutyrate is an organic compound that serves as an acetylating agent in various chemical reactions and processes.

Uses

Trimethyl orthobutyrate is used as an acetylating agent for the preparation of:
1. 5-acetamido-9-O-butyroyl-3,5-dideoxy-D-glycero-2-nonulo pyranosonic acid
2. 9-O-butyroyl-3,5-dideoxy-5-glycoloylamido-D-glycero-2-nonulo pyranosonic acid
Trimethyl orthobutyrate is also used for:
1. Acylation at OH-9 of N-acetylneuraminic acid and N-glycoloylneuraminic acid to give the corresponding 9-O-acylated derivatives.
2. Conversion of 2-amino-N-(1-H-benzimidazol-2-yl)benzamide to 2-propyl-3-benzimidazolyl-4(3H)-quinazolinone.
3. Preparation of 2-propyl substituted benzimidazoles from 1,2-benzenediamines.
Additionally, Trimethyl orthobutyrate can be used in the total synthesis of:
1. dl-camptothecin
2. Olmesartan Medoxomil
3. DE and CDE ring analogs of camptothecin
4. Homologs of 1,25-dihydroxyvitamin D3.

InChI:InChI=1/C7H16O3/c1-5-6-7(8-2,9-3)10-4/h5-6H2,1-4H3

Upstream product

• 57583-92-3 methyl imini ester hydrochloride of butyric acid 

Downstream Products

• 51802-42-7 2-propylimidazole-4,5-dicarbonitrile 
• 377752-77-7 Butyric acid (1R,2S,3S,4S,5S,6S)-2,3-bis-(bis-benzyloxy-phosphoryloxy)-4,6-bis-butyryloxy-5-hydroxy-cyclohexyl ester 
• 1088610-82-5 methyl N-(5-chloro-2-cyanophenyl)butanimidate 
• 1088610-88-1 methyl N-(4-chloro-2-cyanophenyl)butanimidate 
• 1088610-94-9 methyl N-(4,5-dimethoxy-2-cyanophenyl)butanimidate 
• 197163-61-4 methyl N-(2-cyanophenyl)butanimidate 
• 1616086-47-5 4-(5-propyl-1,3,4-oxadiazole-2-yl)benzene-1,2-diol 
• 139592-86-2 methyl 2-benzylbut-3-enoate 
• 1293363-13-9 3-(phenylamino)-2-propylquinazolin-4(3H)-one 

Relevant articles and documents

Process for preparation of adjacently disubstituted ketones

A novel 7-hydroxyprostaglandin E1, or a stereoisomer thereof, or a protected derivative thereof, having the following formula: STR1 wherein R8 represents H, CH3 or C2 H5, R9 represents H or CH3, R10 and R11 are identical or different, and each represents H, tetrahydropyranyl or t-butyldimethylsilyl. Also provided is a process for producing an adjacently disubstituted ketone including the above compounds, i.e. 7-oxoprostaglandin, etc. which comprises reacting an α,β-unsaturated carbonyl compound with a cuprous salt and an organolithium compound in an aprotic inert organic medium in the presence of trialkylphosphine, the amounts of said cuprous salt and said organolithium compound being substantially equimolar, and reacting the product with a protected acetal derivative of an organic carbonyl compound or an aldehyde in the presence of a Lewis acid, if necessary, followed by reacting the product with a proton donor.