Basic information
- Standard SMILES
CCOC(OCC)OCC- InChIKey
GKASDNZWUGIAMG-UHFFFAOYSA-N- Molecular formula
- C7H16O3
- Average molar mass
- 148.2 g/mol
- Monoisotopic mass
- 148.10994437
Overview
Ethyl orthoformate appears as a clear, colorless liquid with a pungent odor. Less dense than water. Vapors heavier than air. May irritate skin and eyes. Used to make other chemicals.
Names & identifiers
- Preferred name
- Ethyl orthoformate
- IUPAC
- diethoxymethoxyethane
- English name
- Triethyl orthoformate
- Molecular formula
- C7H16O3
- Molecular weight
- 148.2
Names & synonyms
Triethyl orthoformate122-51-0TriethoxymethaneETHYL ORTHOFORMATEAethonOrthoformic acid triethyl esterMethane, triethoxy-Ethyl formate(ortho)Orthomravencan ethylnatyEthane, 1,1',1''-[methylidynetris(oxy)]tris-Orthoformic acid, triethyl esterOrthoformic acid ethyl ester
Show more names
TEOForthoformateETHONEiethyl orthoforMate1,1'TEOE
108055-42-1Ethylester kyseliny orthomravenciNSC 5289Orthoformic acid, ethyl esterUN2524DTXSID8041957Orthomravencan ethylnaty [Czech]Triethylester kyseliny orthomravenci
Database identifiers
- CAS
108055-42-1、122-51-0- PubChem CID
- 31214
- DTXSID
DTXSID8041957- ChEMBL
CHEMBL1476236- UNII
- 355LRR361Q
- EC Number
- 204-550-4
- Nikkaji
- J5.533F
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 27.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 6
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 51.6
Experimental & physicochemical properties
Chemical Classes
Other Classes -> Ethers, Other
Flammable agents - 3rd degree
SpringerMaterials PropertiesBoiling point
Flavoring AgentsEU Flavoring substances
Vapor Pressure3.86 [mmHg]
Physical Description
Ethyl orthoformate appears as a clear, colorless liquid with a pungent odor. Less dense than water. Vapors heavier than air. May irritate skin and eyes. Used to make other chemicals.
Liquid
Liquid with a sweetish odor like pine needles; [Merck Index] Clear colorless liquid with a pungent odor; [CAMEO]
Physicochemical properties
- Melting point
- -76 °C · -76 °C (lit.)
- Boiling point
- 146 °C · 146 °C (lit.)
- Density
- 0.891 g/mL · 0.891 g/mL at 25 °C (lit.)
- vapor density
- 5.11 · 5.11 (vs air)
- vapor pressure
- 2.9 mm · 2.9 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.391(lit.)
- FLAVIS Number
- 6.096 · 06.096 | Triethoxymethane
- Flash point
- 86 °F · 86 °F
- storage temp.
- Flammables area
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
- form
- Liquid
- color
- Clear colorless
- Water Solubility
- 1.35 g/L · 1.35 g/L
- Sensitive
- Moisture Sensitive
- Merck
- 14 · 14,6884
- BRN
- 605384 · 605384
- Stability
- Moisture Sensitive
- InChI
- 1S/C7H16O3/c1-4-8-7(9-5-2)10-6-3/h7H,4-6H2,1-3H3
- InChIKey
- GKASDNZWUGIAMG-UHFFFAOYSA-N
- SMILES
- CCOC(OCC)OCC
- LogP
- 1.2 at · 1.2 at 20℃
- CAS DataBase Reference
- 122 · 122-51-0(CAS DataBase Reference)
- FDA UNII
- 355 LRR361Q · 355LRR361Q
- NIST Chemistry Reference
- Ethyl orthoformate(122-51-0)
- EPA Substance Registry System
- Ethyl orthoformate (122-51-0)
- UNSPSC Code
- 12352001 · 12352001
- NACRES
- 21 · NA.21
- Symbol(GHS)
- 2 · GHS02
- Signal word
- Warning
- Hazard statements
- 226 · H226
- Precautionary statements
- 501 · P501-P240-P210-P233-P243-P241-P242-P280-P370+P378-P303+P361+P353-P403+P235
- Hazard Codes
- Xi
- Risk Statements
- 10 · 10-36-36/38
- Safety Statements
- 16 · 16-26-37/39-36-45-36/39
- RIDADR
- 2524 · UN 2524
- WGK Germany
- 1 · 1
- RTECS
- 6475000 · RM6475000
- F
- 21 · 21
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- III
- HS Code
- 29159080 · 29159080
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 · Flam. Liq. 3
- Toxicity
- 50 orally · LD50 orally in rats: 7.06 g/kg (Smyth)
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.3% (7 of 540) of reports.
Warning
H226 (98.7%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P264+P265, P280, P303+P361+P353, P305+P351+P338, P337+P317, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 540 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
Hazard information
Regulatory Information
Chemical: Ethane, 1,1',1''-[methylidynetris(oxy)]tris-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Ethane, 1,1',1''-[methylidynetris(oxy)]tris- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethane, 1,1',1''-[methylidynetris(oxy)]tris- 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: 27-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15861
Triethyl orthoformate: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
DOT LabelFlammable Liquid
Fire Hazards
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Health Hazards
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
· May cause toxic effects if inhaled or absorbed through skin.
Hazards Summary
A mild skin and moderate eye irritant; Dermal LD50 (rabbit) = 20 mL/kg; [RTECS] Not a skin sensitizer in guinea pig maximization study; No sensitization reactions observed in maximization test of 26 volunteers at 4% in petrolatum; [IUCLID] Safe when used as a flavoring agent in food; [EFSA] A mild skin irritant; [Sigma-Aldrich MSDS] See 1,1-Dimethoxyethane.
DOT ID and Guide2524 129
Reactive GroupEthers
Reactivity AlertsHighly Flammable
Reactivity Profile
ETHYL ORTHOFORMATE is an ether. Ethers can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.
DOT Hazard Classification
Ethyl orthoformate
UN2524
Class 3 Flammable and combustible liquid (49 eCFR § 173.120)
PG III: the degree of danger presented by the material is minor
Air and Water ReactionsHighly flammable. Slightly soluble in water.
Hazard Classes and Categories
Flam. Liq. 3 (98.7%)
Flammable liquids - Category 3
Flammable agents - 3rd degree
Safety & protection
Fire FightingExcerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
General First Aid:
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Nonfire Spill ResponseExcerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Isolation and Evacuation
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Immediate precautionary measure
Personal Protective Equipment (PPE)Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Emergency Response Planning GuidelinesCAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient.
Toxicology
Toxicity DataLCLo (rat) = 4,000 ppm/8hr
Safety data
- F
- 21
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- RM6475000
- ridadr
- UN 2524
- hs_code
- 29159080
- Toxicity
- LD50 orally in rats: 7.06 g/kg (Smyth)
- risk_code
- 10-36-36/38
- Signal word
- Warning
- Symbol(GHS)
- GHS02
- hazard_code
- Xi
- safety_code
- 16-26-37/39-36-45-36/39
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- Hazard statements
- H226
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Flam. Liq. 3
- Precautionary statements
- P501-P240-P210-P233-P243-P241-P242-P280-P370+P378-P303+P361+P353-P403+P235
Chemistry & industry
Uses & manufacturing
Uses
Used in chemical manufacture; [CAMEO] Used in chemical synthesis, in the paints-lacquers-varnishes industry, and as a stabilizer; [IUCLID] Used to make large scale and fine chemicals; [ECHA REACH Registrations] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]
Painting (Solvents) [Category: Paint]
U.S. Production2023: 100,000 - <250,000 lb
Consumer UsesDrier
Industry UsesDrier
General Manufacturing Information
All Other Chemical Product and Preparation Manufacturing
Ethane, 1,1',1''-[methylidynetris(oxy)]tris-: ACTIVE
Applications
UsesTriethyl orthoformate is used in Bodroux-Chichibabin aldehyde synthesis to prepare an aldehyde with one carbon higher by reacting with Grignard reagent. It is also used in the electrophilic formylation of activated aromatic species such as phenol.
General DescriptionTriethyl orthoformate is a clear, colorless liquid with a pungent odor. Less dense than water. Flash point 86°F. Vapors heavier than air. May irritate skin and eyes. Used to make other chemicals.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers2 total
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
Hefei TNJ Chemical Industry Co.,Ltd.+86-0551-65418684 +86-18949823763 · [email protected]
Related reactions
2,292 records
Linked notes
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