93921-83-6

Basic information

• Product Name: 3-C-methylerythritol
• Synonyms: 3-C-methylerythritol;2-methylerythritol
• CAS NO: 93921-83-6
• Molecular Formula: C₅H₁₂O₄
• Molecular Weight: 136.14638
• Mol File: 93921-83-6.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 368.1°Cat760mmHg
• Flash Point: 193°C
• Appearance: /
• Density: 1.341g/cm³
• Vapor Pressure: 6.46E-07mmHg at 25°C
• Refractive Index: 1.528
• CAS DataBase Reference: 3-C-methylerythritol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-C-methylerythritol(93921-83-6)
• EPA Substance Registry System: 3-C-methylerythritol(93921-83-6)

Safety Data

• Hazardous Substances Data: 93921-83-6(Hazardous Substances Data)

Usage

Definition

ChEBI: A tetritol that is erythritol substituted by a methyl group at position 2.

InChI:InChI=1/C5H12O4/c1-5(9,3-7)4(8)2-6/h4,6-9H,2-3H2,1H3/t4-,5+/m0/s1

Upstream product

• 93836-32-9 3-C-methyl-L-threo-tetrofuranose 
• 78-79-5 isoprene 
• 617-54-9 citraconic acid dimethyl ester 
• 498-23-7 citraconic acid 
• 58698-41-2 (2RS,3SR)-dimethyl 2,3-dihydroxy-2-methylbutanedioate 
• 652979-96-9 1,3-O-benzylidene-2-C-methyl-D-erythritol 4-(t-butyldimethylsilyl) ether 
• 1375148-72-3 (Z)-ethyl 4-(4-methoxybenzyloxy)-3-methylbut-2-enoate 
• 1375148-86-9 (2S,3R)-4-(4-methoxybenzyloxy)-3-methylbutane-1,2,3-triol 
• 1375148-77-8 (2S,3S)-ethyl 2,3-dihydroxy-4-(4-methoxybenzyloxy)-3-methylbutanoate 
• 1092965-07-5 C₁₁H₂₀O₄ 
• 1073561-30-4 C₁₁H₁₈O₇ 
• 22122-36-7 3-methyl-5H-furan-2-one 
• 74334-76-2 (R)-2,2-Dimethyl-4-(2-methyl-oxiranyl)-[1,3]dioxolane 
• 18465-72-0 (-)-(2R,3R)-2,3-O-isopropylidene-2-C-methyl-D-erythrono-1,4-lactone 

Downstream Products

• 93836-33-0 1,2,3,4-tetra-O-benzoyl-3-C-methyl-L-threitol 

Relevant articles and documents

Synthesis of the ABCD fragment of gymnocin-B

A convergent synthesis of the ABCD fragment of gymnocin-B was accomplished. The tetracyclic ether ring system was synthesized by the construction of the BC ring system via the oxiranyl anion alkylation and ring expansion reaction, followed by the formation of the five-membered A-ring via a stereoselective radical cyclization reaction of a neopentyl-type iodide.

Development of a compound-specific carbon isotope analysis method for 2-methyltetrols, biomarkers for secondary organic aerosols from atmospheric isoprene

The stable carbon isotope compositions of 2-methyltetrols, biomarker compounds for secondary organic aerosols formed from isoprene in the atmosphere, have been determined by gas chromatography/combustion/isotope ratio mass spectrometry (GC/C/IRMS). In this work, isoprene with various δ13C values was used to produce 2-methyltetrols via an oxidation reaction with hydrogen peroxide in sulfuric acid under direct sunlight. The target compounds with different stable carbon isotope compositions were then derivatized by methylboronic acid with a known δ13C value and measured by GC/C/IRMS. With δ13C values of 2-methyltetrols and methylboronic acid predetermined, isotopic fractionation is evaluated for the derivatization process. Through reduplicate δ13C measurements, the carbon isotope analysis achieved excellent reproducibility and high accuracy with an average error of 13C values range from -0.10 to 0.29%, indicating that the derivatization process does not introduce isotopic fractionation. The δ13C values of 2-methyltetrols could be calculated on the basis of the stoichiometric mass balance equation among 2-methyltetrols, methylboronic acid, and methylboronate derivatives. Preliminary tests of 2-methyltetrols in PM2.5 aerosols at two forested sites were conducted and revealed significant differences in their isotope compositions, implying possible application of the method in helping us understand the primary emission, photochemical reaction, or removal processes of isoprene in the atmosphere.

Concise asymmetric syntheses of the (+)-2-C-methyltetritol isomers

Two brief and facile syntheses of the title compounds have been developed using the diastereocontrolled addition of organometallics to a (R)-cyclohexylideneglyceraldehyde-derived ketone as the key steps. The addition of vinylmagnesium bromide to the ketone gave a 1:1 diastereomeric mixture of separable tertiary alcohols, which were converted to the target erythri- and threitols. On the other hand, the reaction of a dithianyl anion with the ketone gave only the single stereoisomer of a tertiary alcohol, which was converted to erythritol.