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Trimethyl orthoformate

Trimethyl orthoformate structure

CAS No:
149-73-5
Formula:
C4H10O3
Chemical Name:
Trimethyl orthoformate
Synonyms:
Methane,trimethoxy-;Orthoformic acid,trimethyl ester;Trimethoxymethane;Methyl orthoformate;Trimethyl orthoformate;Orthoformic acid methyl ester;Methoxymethylal;NSC 147479;Perma-Flo OF;OFM;TMOF;251301-35-6
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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Description

Colorless liquid

Liquid

Trimethyl orthoformate Basic Attributes

Molecular Weight：

106.12000

Exact Mass：

106.12

EC Number：

205-745-7

UNII：

XAM28819YJ

NSC Number：

147479

DSSTox ID：

DTXSID7027122

Color/Form：

COLORLESS LIQUID

HScode：

2915130000

Characteristics

PSA：

27.69000

XLogP3：

0.20920

Appearance：

Liquid

Density：

0.9676 g/cm³ @ Temp: 20 °C

Melting Point：

15 °C

Boiling Point：

100.6 °C @ Press: 760 Torr

Flash Point：

13ºC

Refractive Index：

1.378-1.38

Water Solubility：

H2O: 10 g/L (hydrolysis);SOL IN ETHANOL, IN ETHER

Storage Conditions：

Store at RT.

Vapor Pressure：

23.5 mm Hg ( 20 °C)

Vapor Density：

3.67 (vs air)

Toxicity：

LD50 orally in Rabbit: 3130 mg/kg

Explosive limit：

SEE CHLOROFORM: UNPUBLISHED INFORMATION (1948). DURING ATTEMPTED PREPN OF TRIMETHYL ORTHOFORMATE, ADDITION OF SODIUM TO AN INADEQUATELY COOLED CHLOROFORM-METHANOL MIXTURE CAUSED VIOLENT EXPLOSION.

Odor：

PUNGENT ODOR

OH：

6.00e-12 cm3/molecule*sec

Safety Information

Packing level：

Hazard category：

Transport codes：

UN 3272 3

wgk germany：

hazard class code：

R11; R36

safety instructions：

S16-S26-S29-S9

RTECS Number：

RM6650000

Marks：

Stability/Shelf Life：

Stable at room temperature in closed containers under normal storage and handling conditions.

Precautionary statement(s)：

P210-P305 + P351 + P338

Hazard Statements：

H225-H319

RIDADR：

UN 3272 3

Caution Statement：

P210; P305 + P351 + P338

GHS Classification：

|Danger|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 257 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P337+P313, P370+P378, P403+P235, and P501

Fire Potential：

SLIGHT, WHEN EXPOSED TO HEAT OR FLAME; CAN REACT WITH OXIDIZING MATERIALS.

Explosive Limits and Potential：

SEE CHLOROFORM: UNPUBLISHED INFORMATION (1948). DURING ATTEMPTED PREPN OF TRIMETHYL ORTHOFORMATE, ADDITION OF SODIUM TO AN INADEQUATELY COOLED CHLOROFORM-METHANOL MIXTURE CAUSED VIOLENT EXPLOSION.

Drug Information

Human Toxicity Excerpts：

AN IRRITANT TO SKIN, EYES, & MUCOUS MEMBRANES.

Trimethyl orthoformate Use and Manufacturing

Methods of Manufacturing

/IT IS/ PREPARED FROM CHLOROFORM AND METHANOL IN PRESENCE OF SODIUM: SAH, MA, J AM CHEM SOC 54, 2965 (1932).

Uses

Trimethyl orthoformate is the simplest orthoester. It is a reagent used in organic synthesis for the introduction of a protecting group for aldehydes. The product of reaction of an aldehyde with trimethyl orthoformate is an acetal. In general cases, these acetals can be deprotected back to the aldehyde by using hydrochloric acid.The industrial synthesis of this chemical is from hydrogen cyanide and methanol.Trimethyl orthoformate is a useful building block for creating methoxymethylene groups and heterocyclic ring systems. It introduces a formyl group to a nucleophilic substrate, e.g. RNH2 to form R-NH-CHO, which can undergo further reactions. It is used in the production of the fungicides, azoxystrobin and picoxystrobin, as well as for some members of the floxacin family of antibacterial drugs. A number of pharmaceutical intermediates are also made from trimethyl orthoformate.

Intermediates

Manufacturing Info：

Plastic material and resin manufacturing|Methane, trimethoxy-: ACTIVE

Analysis Methods

Name	Column Shape	Active Phase(℃)	Retention index	Temperature Control	Method	Comments	Reference
Kovats' RI, non-polar column, isothermal	Packed	Apiezon L	654.	120.	isothermal	Celite 545	Bogoslovsky, Yu.N.Anvaer, B.I.Vigdergauz, M.S.Chromatographic constants in gas chromatography (in Russian)Standards Publ. House, Moscow, 1978, 192.
Kovats' RI, non-polar column, isothermal	Packed	Apiezon L	660.	160.	isothermal	Celite 545	Bogoslovsky, Yu.N.Anvaer, B.I.Vigdergauz, M.S.Chromatographic constants in gas chromatography (in Russian)Standards Publ. House, Moscow, 1978, 192.
Kovats' RI, non-polar column, isothermal	Capillary	OV-101	702.		temperature ramp	25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; T_start: 50. C; T_end: 250. C	Zenkevich, I.G.Experimentally measured retention indices.2005.

Computed Properties

Molecular Weight:106.12
XLogP3:0.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:106.062994177
Monoisotopic Mass:106.062994177
Topological Polar Surface Area:27.7
Heavy Atom Count:7
Complexity:28.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Synthesis Route

109620-95-3

67-66-3

67-66-3

Material

Sodium methoxide

Methanol

Chlorodifluoromethane

Price Analysis

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Data: 2026-09-27
Price: 12000.00Yuan/ton
Change: 0

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