Conditions | Yield |
---|---|
With sodium at 30℃; for 4h; | 100% |
Conditions | Yield |
---|---|
With methanol; sodium at 30℃; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm2 constant current density); | 100% |
With methanol; sodium at 30℃; for 4h; Product distribution; electrolysis (Pt-anode, Cu-Zn (60:40) cathode, 220 mA/cm2 constant current); reaction with NaBr/CH3OH; | 100% |
Conditions | Yield |
---|---|
at 40 - 45℃; for 5h; Temperature; Large scale; | 95% |
With benzene |
Conditions | Yield |
---|---|
With boron trifluoride In Hexadecane at 110℃; for 12h; Autoclave; | 90% |
Conditions | Yield |
---|---|
Stage #1: methanol; hydrogen cyanide With hydrogenchloride In cyclohexane; water at -15 - 35℃; Large scale; Stage #2: In cyclohexane; water at 50 - 60℃; for 24h; pH=3 - 4; Solvent; Large scale; | 89.7% |
Stage #1: hydrogen cyanide With hydrogenchloride In methanol; mineral oil at -10 - 30℃; for 2.33333h; Large scale; Stage #2: methanol In mineral oil at 32 - 55℃; for 4h; Concentration; Temperature; Large scale; | 87.5% |
With hydrogenchloride |
1'-naphthacetophenone
A
Bromoform
B
methyl 1-naphthoate
C
trimethyl orthoformate
Conditions | Yield |
---|---|
With methanol; sodium bromide at 30℃; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm2 constant current density); | A n/a B 88% C n/a |
1-(4-methoxyphenyl)ethanone
A
Bromoform
B
methyl 4-methoxybenzoate
C
trimethyl orthoformate
Conditions | Yield |
---|---|
With methanol; sodium bromide at 30℃; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm2 constant current density); | A n/a B 85% C n/a |
para-methylacetophenone
A
4-methyl-benzoic acid methyl ester
B
Bromoform
C
trimethyl orthoformate
Conditions | Yield |
---|---|
With methanol; sodium bromide at 30℃; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm2 constant current density); | A 83% B n/a C n/a |
methanol
acetophenone
A
benzoic acid methyl ester
B
trimethyl orthoformate
Conditions | Yield |
---|---|
With sodium bromide at 30℃; Product distribution; Mechanism; electrolysis; other electrolytes, electrodes, other substrates; | A 74% B n/a |
With sodium bromide at 30℃; electrolysis: Pt anode, brass cathode; | A 74% B n/a |
acetophenone
A
benzoic acid methyl ester
B
Bromoform
C
trimethyl orthoformate
Conditions | Yield |
---|---|
With methanol; sodium bromide at 30℃; for 4h; Product distribution; Mechanism; electrolysis (Pt-anode, Cu-Zn (60:40) cathode, 220 mA/cm2 constant current); other electrolyte, other electrolyte-to-substrate ratio, other material of electrodes; | A 74% B n/a C 15% |
With methanol; sodium bromide at 30℃; for 4h; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm2 constant current density); | A 74% B n/a C n/a |
1,3-DIOXOLANE
methanol
A
2-methoxy-1,3-dioxolane
B
4-methoxy-1,3-dioxolane
C
trimethyl orthoformate
Conditions | Yield |
---|---|
With tris (2,4-dibromophenyl)amine; sodium methylate; lithium perchlorate at 40℃; electrochem. oxidation; | A 70.8% B 4.4% C 7% |
With potassium hydroxide; tris (2,4-dibromophenyl)amine; lithium perchlorate at 40℃; electrochem. oxidation; | A 55.8% B 7.9% C 17.7% |
Conditions | Yield |
---|---|
In diethylene glycol dimethyl ether at 120℃; under 2585.81 Torr; for 24h; Solvent; | 70% |
Conditions | Yield |
---|---|
With sodium hydroxide; 1,8-bis(dimethylamino)-1,6-dioxaoctane In dichloromethane | 67% |
With sodium hydroxide; 1,2-bis-(2-dimethylamino-ethoxy)-ethane In dichloromethane Product distribution; other phase-transfer catalysts, other alcohols; | 67% |
With sodium |
3-methyl-butan-2-one
A
Bromoform
B
Methyl isobutyrate
C
trimethyl orthoformate
Conditions | Yield |
---|---|
With methanol; sodium bromide at 30℃; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm2 constant current density); | A n/a B 67% C n/a |
hexyl-methyl-ketone
A
Bromoform
B
2,2-dimethoxy-3-octanol
C
methyl heptanoate
D
trimethyl orthoformate
Conditions | Yield |
---|---|
With methanol; sodium bromide at 30℃; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm2 constant current density); | A n/a B 29% C 62% D n/a |
With methanol; sodium bromide at 30℃; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm2 constant current density); | A n/a B 29% C 62% D n/a |
1-Phenylbut-1-en-3-one
A
Bromoform
B
methyl cinnamate
C
trimethyl orthoformate
Conditions | Yield |
---|---|
With methanol; sodium bromide at 30℃; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm2 constant current density); | A n/a B 61% C n/a |
methanol
(methoxymethylidene)dimethylammonium methyl sulfate
trimethyl orthoformate
Conditions | Yield |
---|---|
With Methyl formate 1) 16h, 2) 4h, 40 deg C; | 50% |
methanol
trifluoromethan
A
sodium formate
B
trimethyl orthoformate
Conditions | Yield |
---|---|
With sodium hydroxide at 120℃; under 2585.81 Torr; for 24h; | A 35% B 15% |
Chlorodifluoromethane
sodium methylate
A
difluoromethyl methyl ether
B
trimethyl orthoformate
Conditions | Yield |
---|---|
In acetonitrile at 20℃; Rate constant; |
Conditions | Yield |
---|---|
at 11.6℃; Thermodynamic data; ΔH; | |
In pentane at 20℃; Rate constant; Irradiation; primary kinetic isotope effect; |
3,3-dimethoxydiazirine
A
1,1,2,2-tetramethoxyethylene
B
trimethyl orthoformate
Conditions | Yield |
---|---|
With methanol In pentane at 25℃; Product distribution; thermal decomposition also in presence of water (methanol absent); |
Methyl formate
3,3-dimethyl-2-butanone dimethyl ketal
A
3,3-dimethyl-butan-2-one
B
trimethyl orthoformate
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 25℃; Equilibrium constant; |
diazomethane
Methyl formate
A
methoxyoxirane
B
Methoxyacetone
D
trimethyl orthoformate
Conditions | Yield |
---|---|
at -15 - 20℃; for 1.5h; Irradiation; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts; |
chloroform
sodium methylate
A
N,N-dimethyl-formamide dimethyl acetal
B
trimethyl orthoformate
Conditions | Yield |
---|---|
With N,N-dimethyl-formamide In methanol | A 48 % Chromat. B 38 % Chromat. |
chloroform
sodium methylate
N,N-dimethyl-formamide
A
N,N-dimethyl-formamide dimethyl acetal
B
trimethyl orthoformate
Conditions | Yield |
---|---|
A 91 % Chromat. B 3 % Chromat. |
chloroform
sodium methylate
N,N-dimethyl-formamide
A
carbon monoxide
B
N,N-dimethyl-formamide dimethyl acetal
C
trimethyl orthoformate
Conditions | Yield |
---|---|
for 0.5h; Mechanism; methanol presence; |
N,N-dimethyl-formamide dimethyl acetal
A
tertamethylammonium iodide
B
N,N-dimethyl-formamide
C
methyl iodide
D
trimethyl orthoformate
Conditions | Yield |
---|---|
With iodine Product distribution; | A 12.8 g B 5.2 g C 1.4 g D 6.7 g |
methanol
Chlorodifluoromethane
A
difluoromethyl methyl ether
B
trimethyl orthoformate
Conditions | Yield |
---|---|
With sodium methylate at 25℃; for 2h; Product distribution; Further Variations:; Temperatures; Reagents; |
Conditions | Yield |
---|---|
With Yb(III)-coordinated adamantane-based porous polymer In methanol at 20℃; for 12h; Catalytic behavior; Reagent/catalyst; | 100% |
indium(III) triflate In dichloromethane at 20℃; for 0.0833333h; | 99% |
With cerium triflate In methanol at 20℃; for 0.0333333h; | 99% |
4-hydroxy-benzaldehyde
trimethyl orthoformate
4-(dimethoxymethyl)phenol
Conditions | Yield |
---|---|
With lithium tetrafluoroborate In methanol for 0.333333h; Heating; | 100% |
With Decaborane In methanol at 20℃; for 0.0666667h; | 85% |
With methanol; tetra-N-butylammonium tribromide at 20℃; for 2h; | 25% |
Conditions | Yield |
---|---|
With lithium tetrafluoroborate In methanol for 0.666667h; Heating; | 100% |
With Decaborane In methanol at 20℃; for 0.0666667h; | 99% |
With triethylamine In methanol; tetrachloromethane at 0 - 20℃; for 3h; | 86% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol Heating; | 100% |
With lithium tetrafluoroborate In methanol for 5h; Heating; | 99% |
With cerium triflate In methanol at 20℃; for 0.5h; | 98% |
ethyl acetoacetate
trimethyl orthoformate
3-methoxy-but-2-enoic acid ethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride In methanol | 100% |
With hydrogenchloride In methanol | 100% |
Stage #1: ethyl acetoacetate; trimethyl orthoformate With sulfuric acid at 20℃; for 18h; Stage #2: With potassium carbonate for 0.5h; | 38% |
Stage #1: ethyl acetoacetate; trimethyl orthoformate With sulfuric acid at 20℃; for 18h; Stage #2: With potassium carbonate for 0.5h; | 38% |
Conditions | Yield |
---|---|
With [Sc2(C4O4)3]n In tetrachloromethane at 60℃; for 1h; | 100% |
With lithium tetrafluoroborate In methanol for 0.5h; Heating; | 100% |
indium(III) triflate In dichloromethane at 20℃; for 0.0833333h; | 99% |
4-bromo-benzaldehyde
trimethyl orthoformate
1,1-dimethoxy-1-(4-bromophenyl)methane
Conditions | Yield |
---|---|
Yb-Amberlyst XN-1010 In dichloromethane | 100% |
With Yb(III)-coordinated adamantane-based porous polymer In methanol at 20℃; for 12h; Catalytic behavior; Reagent/catalyst; | 100% |
With amberlyst-15 In acetonitrile for 2.5h; electroosmos; | 99.7% |
(4-nitrophenyl)ethanone
trimethyl orthoformate
1,1-dimethoxy-1-(4-nitrophenyl)ethane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol for 72h; | 100% |
With toluene-4-sulfonic acid In methanol at 20℃; | 95% |
With toluene-4-sulfonic acid In methanol at 20℃; for 48h; | 58% |
trimethyl orthoformate
(E/Z)-3,7-dimethyl-2,6-octadienal
citral dimethyl acetal
Conditions | Yield |
---|---|
With lithium tetrafluoroborate In methanol for 0.333333h; Heating; | 100% |
With cerium triflate In methanol at 20℃; for 0.0833333h; | 99% |
With cerium(III) chloride at 0℃; for 4h; Inert atmosphere; | 78% |
With erbium(III) chloride In methanol |
Conditions | Yield |
---|---|
With lithium tetrafluoroborate In methanol for 0.5h; Heating; | 100% |
With cerium triflate In methanol at 20℃; for 0.0166667h; | 95% |
With Pd(PhCN)2(OTf)2 at 20℃; for 0.333333h; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In chloroform | 100% |
piperonal
trimethyl orthoformate
5-(dimethoxymethyl)benzo[d][1,3]dioxole
Conditions | Yield |
---|---|
With lithium tetrafluoroborate In methanol for 0.833333h; Heating; | 100% |
With Montmorillonite K 10 In methanol for 72h; Ambient temperature; | 99% |
With camphorsulfonic acid In methanol at 20℃; for 60h; Inert atmosphere; | 99% |
6-bromo-3,4-methylenedioxybenzaldehyde
trimethyl orthoformate
6-bromobenzo-1,3-dioxole-5-carboxaldehyde dimethyl acetal
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol; benzene at 25℃; for 1h; | 100% |
In methanol; benzene at 80℃; for 8h; Inert atmosphere; Schlenk technique; | 100% |
With montmorillonite k-10 at 20℃; Inert atmosphere; | 98% |
ethyl acetoacetate
trimethyl orthoformate
ethyl (2E)-3-methoxy-2-butenoate
Conditions | Yield |
---|---|
With hydrogenchloride In methanol | 100% |
With hydrogenchloride In methanol; water | 96% |
acid | 93% |
With sulfuric acid; calcium chloride at 0 - 25℃; Inert atmosphere; | 74% |
3,4,5-trimethoxy-benzaldehyde
trimethyl orthoformate
3,4,5-trimethoxybenzaldehyde dimethyl acetal
Conditions | Yield |
---|---|
With montmorillonite K10 In methanol at 40℃; for 18h; Inert atmosphere; | 100% |
With camphorsulfonic acid In methanol at 20℃; for 60h; Inert atmosphere; | 99% |
Stage #1: 3,4,5-trimethoxy-benzaldehyde; trimethyl orthoformate With ammonium chloride In methanol for 3h; Inert atmosphere; Reflux; Stage #2: With triethylamine In methanol at 20℃; for 0.0833333h; | 99% |
1,2,3,4-tetrahydronaphthalen-2-one
trimethyl orthoformate
3-methoxy-1,2-dihydronaphthalene
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 20 - 60℃; for 16h; | 100% |
93% | |
With toluene-4-sulfonic acid for 8h; Ambient temperature; | 87% |
In benzene | 1.15 g (75%) |
Conditions | Yield |
---|---|
With lithium perchlorate; methyl iodide Ambient temperature; anodic oxidation at constant current; | 100% |
With poly[4-(diacetoxyiodo)styrene]; sulfuric acid In acetonitrile at 60℃; for 0.5h; | 80% |
With lead(IV) acetate; perchloric acid at 50℃; for 2h; | 46% |
With LiCO4*H2O; methyl iodide Product distribution; Mechanism; Ambient temperature; anodic oxidation at constatnt current; |
1-phenyl-propan-1-one
trimethyl orthoformate
2-phenylpropionic acid methyl ester
Conditions | Yield |
---|---|
With lithium perchlorate; methyl iodide Ambient temperature; anodic oxidation at constant current; | 100% |
With sulfuric acid; N-methyl-N-[3-(4-diacetoxyiodo)phenoxy-1-propyl]pyrrolidinium 4-methylbenzenesulfonate at 60℃; for 3h; Inert atmosphere; | 99% |
With trifluorormethanesulfonic acid; [bis(acetoxy)iodo]benzene In methanol; Cyclooctan at 50℃; for 0.0335h; | 98% |
ortho-anisaldehyde
trimethyl orthoformate
o-anisaldehyde dimethyl acetal
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol at 32℃; | 100% |
With camphor-10-sulfonic acid In methanol at 20℃; for 60h; | 100% |
In methanol at 20℃; for 1h; Inert atmosphere; | 100% |
ortho-bromobenzaldehyde
trimethyl orthoformate
o-bromobenzaldehyde dimethyl acetal
Conditions | Yield |
---|---|
Stage #1: trimethyl orthoformate With montmorillonite K10 Clay at 20℃; for 0.333333h; Stage #2: ortho-bromobenzaldehyde at 20℃; | 100% |
With toluene-4-sulfonic acid In methanol at 20℃; for 2h; Inert atmosphere; | 96% |
With p-toluenesulfonic acid monohydrate In methanol at 100℃; for 12h; Inert atmosphere; | 95% |
2-Bromo-2'-acetonaphthone
trimethyl orthoformate
2-bromo-1,1-dimethoxy-1-(2-naphthyl)ethane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol for 2h; Heating; | 100% |
With hydrogenchloride In methanol for 24h; Ambient temperature; | 81% |
With toluene-4-sulfonic acid In methanol for 3h; Yield given; |
4'-Bromopropiophenone
trimethyl orthoformate
methyl 2-(4-bromophenyl)propanoate
Conditions | Yield |
---|---|
With lithium perchlorate; methyl iodide Ambient temperature; anodic oxidation at constant current; | 100% |
With trifluorormethanesulfonic acid; [bis(acetoxy)iodo]benzene at 20℃; for 24h; | 76% |
With lead(IV) acetate; perchloric acid at 50℃; for 2h; | 65% |
With lead(IV) acetate; perchloric acid at 50℃; for 2h; Yield given; |
3,4-diformylfuran
trimethyl orthoformate
Furan-3,4-dicarboxaldehyde bis
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol at 35℃; for 20h; | 100% |
4-Ethoxycarbonylmethyl-1,3-dithiole-2-thione
trimethyl orthoformate
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In chloroform | 100% |
3,3-dimethyl acrylaldehyde
trimethyl orthoformate
3-methyl-but-2-enal dimethyl acetal
Conditions | Yield |
---|---|
With indium(III) triflate In methanol at 20℃; for 0.5h; | 100% |
With ammonium nitrate In methanol for 8h; Ambient temperature; | 63% |
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde
trimethyl orthoformate
Dimethoxy-2',2' ethyl-2 trimethyl-1,3,3 cyclohexene-1
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol for 24h; Ambient temperature; | 100% |
(2E,4S,5R)-4,6-diacetoxy-5-hydroxy-2(E)-hexenal
trimethyl orthoformate
(2E,4S,5R)-4,6-diacetoxy-5-hydroxy-2-hexenal dimethyl acetal
Conditions | Yield |
---|---|
With 3 A molecular sieve; toluene-4-sulfonic acid In methanol at 0℃; for 1h; | 100% |
2-bromo-4,5-dimethoxybenzaldehyde
trimethyl orthoformate
2-bromo-4,5-dimethoxybenzaldehyde dimethyl acetal
Conditions | Yield |
---|---|
Stage #1: 2-bromo-4,5-dimethoxybenzaldehyde; trimethyl orthoformate; toluene-4-sulfonic acid In methanol for 3h; Heating / reflux; Stage #2: With sodium methylate In methanol | 100% |
With toluene-4-sulfonic acid In methanol for 3h; Reflux; | 100% |
With toluene-4-sulfonic acid In methanol for 16h; Reflux; Inert atmosphere; | 100% |
Product Name: Trimethoxymethane
CAS No: 149-73-5
Formula: C4H10O3
Molecular Weight: 106.12
Appearance: Colorless liquid
mp : -53 °C
bp : 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
Water Solubility : 10 g/L (hydrolysis)
Sensitive : Moisture Sensitive
IUPAC: trimethoxymethane
Product Categories: straight chain compounds;Orthoesters
Synonyms: Methyl orthoformate ; Tmof ; Orthoformic acid trimethyl ester ; Trimethyl-o-formate ; Trimethoxymethane ; Ch(och3)3 ; Methane,trimethoxy-
Ingestion: The toxicological properties of this substance have not been fully investigated. Expected to be a low ingestion hazard. Causes gastrointestinal tract irritation.
Inhalation: Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Vapors may cause dizziness or suffocation.
Skin: Causes mild skin irritation.
Eyes: Causes moderate eye irritation. The toxicological properties of this material have not been fully investigated.
Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers.
Hazard Codes: XiF
Risk Statements: 11-36
R11: Highly flammable
R36: Irritating to eyes
Safety Statements: 9-16-26-29
S9: Keep container in a well-ventilated place
S16: Keep away from sources of ignition
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
HazardClass: 3
PackingGroup: II
HS Code: 29159080
Fire Fighting:Wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Will burn if involved in a fire. Use water spray to keep fire-exposed containers cool. Containers may explode in the heat of a fire. Extinguishing media: For small fires, use dry chemical, carbon dioxide, water spray or alcohol-resistant foam. For large fires, use water spray, fog, or alcohol-resistant foam. Do NOT use water directly on fire. Use water spray to cool fire-exposed containers. Water may be ineffective. Do NOT use straight streams of water.
Personal Protection:Eyes: Wear chemical goggles. Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear a chemical apron. Wear appropriate protective clothing to prevent skin exposure.
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