Trimethylorthoformiat

Bezeichnung:Trimethylorthoformiat

CAS-Nr149-73-5

Englisch Name:Trimethoxymethane

CBNumberCB4853127

SummenformelC4H10O3

Molgewicht106.12

MOL-Datei149-73-5.mol

Synonyma

Trimethylorthoformiat

Trimethylorthoformiat physikalisch-chemischer Eigenschaften

Schmelzpunkt	-53 °C
Siedepunkt	101-102 °C(lit.)
Dichte	0.97 g/mL at 25 °C(lit.)
Dampfdichte	3.67 (vs air)
Dampfdruck	23.5 mm Hg ( 20 °C)
Brechungsindex	n20/D 1.379(lit.)
Flammpunkt	60 °F
storage temp.	Store below +30°C.
Löslichkeit	Miscible with ether, alcohol and benzene.
Aggregatzustand	Liquid
Farbe	Clear colorless
Explosionsgrenze	1.4-44.6%(V)
Wasserlöslichkeit	10 g/L (hydrolysis)
Sensitive	Moisture Sensitive
Merck	14,6884
BRN	969215
InChIKey	PYOKUURKVVELLB-UHFFFAOYSA-N
LogP	-0.03-0.09 at 20℃
CAS Datenbank	149-73-5(CAS DataBase Reference)
NIST chemische Informationen	Methane, trimethoxy-(149-73-5)
EPA chemische Informationen	Trimethoxymethane (149-73-5)

Sicherheit

Kennzeichnung gefährlicher	F,Xi
R-Sätze:	11-36
S-Sätze:	9-16-26-29
RIDADR	UN 3272 3/PG 2
WGK Germany	1
RTECS-Nr.	RM6650000
Selbstentzündungstemperatur	255 °C
TSCA	Yes
HazardClass	3
PackingGroup	II
HS Code	29159080
Giftige Stoffe Daten	149-73-5(Hazardous Substances Data)
Toxizität	LD50 orally in Rabbit: 3130 mg/kg

Gefahreninformationscode (GHS)

Trimethoxymethane Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R11:Leichtentzündlich.
R36:Reizt die Augen.
S-Sätze Betriebsanweisung:
S9:Behälter an einem gut gelüfteten Ort aufbewahren.
S16:Von Zündquellen fernhalten - Nicht rauchen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S29:Nicht in die Kanalisation gelangen lassen.
Beschreibung
Trimethyl orthoformate is an effective solvent for thallium(III) nitrate-mediated oxidations. It undergoes acid catalyzed reaction with 6-(N-D-ribitylanilino) uracils to form 8-demethyl-8-hydroxy-5-deazariboflavins.
Chemische Eigenschaften
Colorless liquid. Slightly soluble in water, miscible with alcohol and oils.
Very diffusive, ethereal, pungent or nauseating odor, pleasant in dilution, slightly wineyfruity, Brandy-like.
Sweet taste in concentrations below 100 ppm. Barely perceptible at 10 ppm.
Verwenden
Trimethyl orthoformate can be used:
- To convert sulfonic acids to methyl esters.
- To convert 2-acylcyclohexanones to the corresponding acetal derivatives.
- To mediate Pinacol reaction of various 1,2-diols with tin(IV) chloride without the formation of water.
- To synthesize 1-substituted-1H-1,2,3,4-tetrazoles via a three-component condensation with amine and sodium azide catalyzed by indium triflate under solvent-free conditions.
- For the N-methylation of amines in the presence of sulfuric acid.
Verwenden
Trimethyl Orthoformate is the most simple orthoester. Used in organic synthesis as a reagent for introducing a protecting group for aldehydes and in the creation of methoxymethylene groups and heterocyclic ring systems.
Verwenden
Trimethyl orthoformate is used as a protecting group for aldehydes in organic synthesis, as an additive in polyurethane coatings and as a dehydrating agent in the preparation of surface modified colloidal silica nanoparticles. It is also used as a chemical intermediate in the preparation of vitamin B1 and sulfa drugs. It acts as an effective solvent for thallium(III) nitrate-mediated oxidations. Furthermore. It is utilized for the synthesis of chromone from keto-hydroxy naphthol in the presence of trimethylamine.
Application
Trimethyl orthoformate was used as dehydrating agent in the preparation of surface-modified colloidal silica nanoparticles.
MOM protection of Diols using Trimethyl Orthoformate
N-Formylation of Amino Acid Esters
Allgemeine Beschreibung
Trimethyl orthoformate is an effective solvent for thallium(III) nitrate-mediated oxidations. It undergoes acid catalyzed reaction with 6-(N-D-ribitylanilino) uracils to form 8-demethyl-8-hydroxy-5-deazariboflavins.
Flammability and Explosibility
Highly flammable
Sicherheitsprofil
A skin and eye irritant. A very dangerous fire hazard when exposed to heat or flame; can react with oxidizing materials. Hazardous to prepare. To fight fire, use CO2, fog, haze. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.
Synthese
Trimethyl orthoformate is prepared on an industrial scale by the methanolysis of hydrogen cyanide:
HCN + 3 HOCH3 → HC(OCH3)3 + NH3
Trimethyl orthoformate can also be prepared from the reaction between chloroform and sodium methoxide, an example of the Williamson ether synthesis.
Vorsichtsmaßnahmen
Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with acids and strong oxidizing agents.
Einzelnachweise
Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols
P. G. M. Wuts, in Greene's Protective Groups in Organic Synthesis, 5th ed., ed. by P. G. M. Wuts, John Wiley & Sons, Inc., Hoboken, New Jersey, 2014, Chap. 2, 17.
A Facile Procedure for the Synthesis of N-Formyl Amino Acid Esters
T. Chancellor, C. Morton, Synthesis 1994, 10, 1023.

Trimethoxymethane Upstream-Materialien And Downstream Produkte

Trimethylorthoformiat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

149-73-5, Trimethoxymethane Verwandte Suche:

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