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164534

Sigma-Aldrich

Trimethyl orthobenzoate

98%

Linear Formula:
C6H5C(OCH3)3
CAS Number:
Molecular Weight:
182.22
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

liquid

refractive index

n20/D 1.489 (lit.)

bp

87-88 °C/7 mmHg (lit.)

density

1.061 g/mL at 25 °C (lit.)

SMILES string

COC(OC)(OC)c1ccccc1

InChI

1S/C10H14O3/c1-11-10(12-2,13-3)9-7-5-4-6-8-9/h4-8H,1-3H3

InChI key

IECKAVQTURBPON-UHFFFAOYSA-N

Related Categories

General description

Trimethyl orthobenzoate reacts with P-dimethylaminophosphonic acid bis(1-methylhydrazide) to yield 1,2,5,6-tetrahydro-1,5-dimethyl-6-(N,N-dimethylamino)-6-phenyl-1,2,4,5,6-tetrazaphosphorine-6-oxide.

Application

Trimethyl orthobenzoate was used in the preparation of 5-phenyl-4,6-dipyrrin and 2,3-orthoester derivatives of ethyl-1-thio-α-L-rhamnopyranoside.

Packaging

10, 50 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

179.6 °F - closed cup

Flash Point(C)

82 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

Reactions between pyrrole and orthoesters: preparation of tri-(pyrrol-2-yl) alkanes.
Reese CB and Yan H.
Tetrahedron Letters, 43(32), 5545-5547 (2001)
R G Hicks et al.
Inorganic chemistry, 40(8), 1865-1870 (2001-04-21)
Reaction of P-dimethylaminophosphonic acid bis(1-methylhydrazide) (6) with trimethyl orthobenzoate gave 1,2,5,6-tetrahydro-1,5-dimethyl-6-(N,N-dimethylamino)-6-phenyl-1,2,4,5,6-tetrazaphosphorine-6-oxide (7), which was subsequently oxidized to the corresponding P-diemthylamino-6-phosphaverdazyl (5) as a persistent radical. Analysis of the electron paramagnetic resonance spectrum of 5 revealed significant spin density on the
Incidence and avoidance of stereospecific 1, 2-ethylthio group migration during the synthesis of ethyl 1-thio-a-l-rhamnopyranoside 2, 3-orthoester.
Auzanneau F-I and Bundle DR.
Carbohydrate Research, 212, 13-24 (1991)

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