| Identification | More | [Name]
Trimethoxymethane | [CAS]
149-73-5 | [Synonyms]
METHYL ORTHOFORMATE
ORTHOFORMIC ACID TRIMETHYL ESTER
TMOF
TRIMETHOXYMETHANE
TRIMETHYL-O-FORMATE
TRIMETHYL ORTHOFORMATE
CH(OCH3)3
Methane,trimethoxy-
Methoxymethylal
Methylester kyseliny orthomravenci
methylesterkyselinyorthomravenci
methylesterkyselinyorthomravenci(czech)
Orthoformic acid methyl ester
orthoformicacidmethylester
Orthomravencan methylnaty
orthomravencanmethylnaty
orthomravencanmethylnaty(czech)
trimethoxy-methan
Trimethylester kyseliny orthomravenci
trimethylesterkyselinyorthomravenci | [EINECS(EC#)]
205-745-7 | [Molecular Formula]
C4H10O3 | [MDL Number]
MFCD00008483 | [Molecular Weight]
106.12 | [MOL File]
149-73-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless liquid | [Melting point ]
-53 °C
| [Boiling point ]
101-102 °C(lit.)
| [density ]
0.97 g/mL at 25 °C(lit.)
| [vapor density ]
3.67 (vs air)
| [vapor pressure ]
23.5 mm Hg ( 20 °C)
| [refractive index ]
n20/D 1.379(lit.)
| [Fp ]
60 °F
| [storage temp. ]
Store at RT. | [solubility ]
Miscible with ether, alcohol and benzene. | [form ]
Liquid | [color ]
Clear colorless | [explosive limit]
1.4-44.6%(V) | [Water Solubility ]
10 g/L (hydrolysis) | [Sensitive ]
Moisture Sensitive | [Merck ]
14,6884 | [BRN ]
969215 | [InChIKey]
PYOKUURKVVELLB-UHFFFAOYSA-N | [LogP]
-0.03-0.09 at 20℃ | [CAS DataBase Reference]
149-73-5(CAS DataBase Reference) | [NIST Chemistry Reference]
Methane, trimethoxy-(149-73-5) | [EPA Substance Registry System]
149-73-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
F,Xi | [Risk Statements ]
R11:Highly Flammable.
R36:Irritating to the eyes. | [Safety Statements ]
S9:Keep container in a well-ventilated place .
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S29:Do not empty into drains . | [RIDADR ]
UN 3272 3/PG 2
| [WGK Germany ]
1
| [RTECS ]
RM6650000
| [Autoignition Temperature]
255 °C | [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29159080 | [Safety Profile]
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. | [Hazardous Substances Data]
149-73-5(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 3130 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Sodium hydroxide-->Sodium-->Chloroform | [Preparation Products]
N-METHYL-P-ANISIDINE-->N-Boc-5,6,7,8-tetrahydro-3-methoxy-[1,2,4]triazolo[4,3-A]pyrazine ,98%-->6-BROMO-4-CHLOROQUINOLINE-->5,6-DIHYDRO-4-METHOXY-2H-PYRAN-->4,7-DIMETHOXY-1,10-PHENANTHROLINE, 97%-->4-TRIFLUOROMETHYL-N-METHYLANILINE 97-->3-METHOXY-N-METHYLANILINE-->6-bromoquinolin-4(3H)-one-->Pipemidic acid-->Methyl trifluoroacetate-->Methyl methanesulfonate-->Tetramethoxyethylene-->ETHYL 5-AMINO-1-PYRIDIN-2-YL-1H-PYRAZOLE-4-CARBOXYLATE-->Bromoform-->THEBAINE-->2-Methylundecanal dimethylacetal-->(-)-Dimethyl D-tartrate-->P-ANISALDEHYDE DIMETHYL ACETAL-->6,7-DIHYDRO-2-PHENYL-5H-PYRROLO[2,1-C]-1,2,4-TRIAZOLIUM CHLORIDE-->BASIC RED 12 |
| Hazard Information | Back Directory | [Description]
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. | [Chemical Properties]
Colorless liquid | [Uses]
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. | [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 | [General Description]
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]
Highlyflammable | [Synthesis]
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. | [Toxics Screening Level]
The initial threshold screening level (ITSL) for trimethyl orthoformate is 800 μg/m3 based on an annual averaging time. | [Precautions]
Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with acids and strong oxidizing agents.? | [References]
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. |
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