Basic information
- Standard SMILES
COC(OC)OC- InChIKey
PYOKUURKVVELLB-UHFFFAOYSA-N- Molecular formula
- C4H10O3
- Average molar mass
- 106.12 g/mol
- Monoisotopic mass
- 106.06299418
Names & identifiers
- Preferred name
- Trimethyl orthoformate
- IUPAC
- trimethoxymethane
- English name
- Trimethoxymethane
- Molecular formula
- C4H10O3
- Molecular weight
- 106.12
Names & synonyms
TrimethoxymethaneTRIMETHYL ORTHOFORMATE149-73-5Methyl orthoformateMethane, trimethoxy-MethoxymethylalOrthoformic acid methyl esterOrthoformic acid, trimethyl esterOrthomravencan methylnatyOrthoformic acid trimethyl esterMethylester kyseliny orthomravenciNSC 147479
Show more names
TMOFCH(OCH3)3ch(ome)3Trimethyl esterThrimethyl orthoformateorthoformicacidmethylesterTrimethylorthoformiatTrimethyl orthoformate,99%
DTXSID7027122HSDB 1006Orthomravencan methylnaty [Czech]Trimethylester kyseliny orthomravenciEINECS 205-745-7BRN 0969215XAM28819YJMethylester kyseliny orthomravenci [Czech]
Database identifiers
- CAS
149-73-5- PubChem CID
- 9005
- DTXSID
DTXSID7027122- ChEMBL
CHEMBL3187679- UNII
- XAM28819YJ
- EC Number
- 205-745-7
- Nikkaji
- J8.664I
Properties
Computed structural properties
- XLogP
- 0.2
- Topological polar surface area
- 27.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 28.4
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Ethers, Other
SpringerMaterials PropertiesSchoenflies notation
OdorPUNGENT ODOR
Density
0.9676 @ 20 °C/4 °C
0.9676 @ 20°C
Color/FormCOLORLESS LIQUID
SolubilitySOL IN ETHANOL, IN ETHER
Boiling Point
100.6 °C @ 760 MM HG
100.6 °C @760 [mm Hg]
Vapor Density3.67 (AIR= 1)
Vapor Pressure81.4 [mmHg]
Refractive IndexINDEX OF REFRACTION: 1.3773 @ 25 °C/D
Physical Description
Liquid
Colorless liquid with a pungent odor; [HSDB]
Physicochemical properties
- Melting point
- -53 °C · -53 °C
- Boiling point
- 101 · 101-102 °C(lit.)
- Density
- 0.97 g/mL · 0.97 g/mL at 25 °C(lit.)
- vapor density
- 3.67 · 3.67 (vs air)
- vapor pressure
- 23.5 mm · 23.5 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.379(lit.)
- Flash point
- 60 °F · 60 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Miscible with ether, alcohol and benzene.
- form
- Liquid
- color
- Clear colorless
- explosive limit
- 1.4 · 1.4-44.6%(V)
- Water Solubility
- 10 g/L · 10 g/L (hydrolysis)
- Sensitive
- Moisture Sensitive
- Merck
- 14 · 14,6884
- BRN
- 969215 · 969215
- Henry's Law Constant
- 6.9 · 6.9×10-1 mol/(m3Pa) at 25℃, Guthrie (1973)
- InChI
- 1S/C4H10O3/c1-5-4(6-2)7-3/h4H,1-3H3
- InChIKey
- PYOKUURKVVELLB-UHFFFAOYSA-N
- SMILES
- COC(OC)OC
- LogP
- -0.03 · -0.03-0.09 at 20℃
- CAS DataBase Reference
- 149 · 149-73-5(CAS DataBase Reference)
- FDA UNII
- 28819 YJ · XAM28819YJ
- NIST Chemistry Reference
- Methane, trimethoxy-(149-73-5)
- EPA Substance Registry System
- Trimethoxymethane (149-73-5)
- UNSPSC Code
- 12352112 · 12352112
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 316 · H316-H319-H225
- Precautionary statements
- 501 · P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P303+P361+P353-P332+P313-P403+P235
- target organs
- Respiratory system
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- F,Xi
- Risk Statements
- 11 · 11-36
- Safety Statements
- 9 · 9-16-26-29
- RIDADR
- 3272 · UN 3272 3/PG 2
- WGK Germany
- 1 · 1
- RTECS
- 6650000 · RM6650000
- Autoignition Temperature
- 255 °C · 255 °C
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29159080 · 29159080
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 2 Flam · Eye Irrit. 2Flam. Liq. 2STOT SE 3
- Hazardous Substances Data
- 149 · 149-73-5(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in Rabbit: 3130 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.7% (2 of 294) of reports.
Danger
H225 (99.3%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P319, P337+P317, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 294 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
Hazard information
Regulatory Information
Chemical: Methane, trimethoxy-
Methane, trimethoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methane, trimethoxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 08-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/12626
Trimethyl orthoformate: Does not have an individual approval but may be used under an appropriate group standard
Fire PotentialSLIGHT, WHEN EXPOSED TO HEAT OR FLAME; CAN REACT WITH OXIDIZING MATERIALS.
Hazards Summary
A skin, eye, and mucous membrane irritant; [HSDB] Findings in lethal dose animal experiments include cyanosis, loss of muscle tone, and unresponsiveness. [ToxPlanet: IUCLID] Hydrolyzed by water producing methanol; An irritant; [MSDSonline] See Methyl alcohol.
Hazard Classes and Categories
Flam. Liq. 2 (99.3%)
Flammable liquids - Category 2
Explosive Limits and PotentialSEE CHLOROFORM: UNPUBLISHED INFORMATION (1948). DURING ATTEMPTED PREPN OF TRIMETHYL ORTHOFORMATE, ADDITION OF SODIUM TO AN INADEQUATELY COOLED CHLOROFORM-METHANOL MIXTURE CAUSED VIOLENT EXPLOSION.
Safety & protection
Protective Action Criteria (PAC)
12 [mg/m3]
130 [mg/m3]
790 [mg/m3]
Toxicology
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Human Toxicity ExcerptsAN IRRITANT TO SKIN, EYES, & MUCOUS MEMBRANES.
Toxicity DataLC50 (rat) = 40,000 mg/m3
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- RM6650000
- ridadr
- UN 3272 3/PG 2
- hs_code
- 29159080
- Toxicity
- LD50 orally in Rabbit: 3130 mg/kg
- risk_code
- 11-36
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xi
- safety_code
- 9-16-26-29
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- target organs
- Respiratory system
- Hazard statements
- H316-H319-H225
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Flam. Liq. 2STOT SE 3
- Autoignition Temperature
- 255 °C
- Precautionary statements
- P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P303+P361+P353-P332+P313-P403+P235
- Hazardous Substances Data
- 149-73-5(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
U.S. Production2023: 1,323 lb
Consumer UsesOther
Industry UsesIntermediate
Methods of Manufacturing/IT IS/ PREPARED FROM CHLOROFORM AND METHANOL IN PRESENCE OF SODIUM: SAH, MA, J AM CHEM SOC 54, 2965 (1932).
General Manufacturing Information
Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing
Methane, trimethoxy-: ACTIVE
Applications
DescriptionTrimethyl 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.
UsesTrimethyl 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.
UsesTrimethyl 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.
UsesTrimethyl 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.
General DescriptionTrimethyl 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.
Upstream & downstream products
Upstream raw materials
Downstream products
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