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149-73-5

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149-73-5 Usage

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

Different sources of media describe the Uses of 149-73-5 differently. You can refer to the following data:
1. Trimethyl 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.
2. 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.
3. Trimethyl 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.

Application

Trimethyl orthoformate was used as dehydrating agent in the preparation of surface-modified colloidal silica nanoparticles.MOM protection of Diols using Trimethyl OrthoformateN-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

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.

Synthesis

Trimethyl orthoformate is prepared on an industrial scale by the methanolysis of hydrogen cyanide:HCN + 3 HOCH3 → HC(OCH3)3 + NH3Trimethyl orthoformate can also be prepared from the reaction between chloroform and sodium methoxide, an example of the Williamson ether synthesis.

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-DiolsP. 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 EstersT. Chancellor, C. Morton, Synthesis 1994, 10, 1023.

Check Digit Verification of cas no

The CAS Registry Mumber 149-73-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 9 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 149-73:
(5*1)+(4*4)+(3*9)+(2*7)+(1*3)=65
65 % 10 = 5
So 149-73-5 is a valid CAS Registry Number.
InChI:InChI:1S/C4H10O3/c1-5-4(6-2)7-3/h4H,1-3H3

149-73-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (O0068)  Trimethyl Orthoformate  >98.0%(GC)

  • 149-73-5

  • 25mL

  • 98.00CNY

  • Detail
  • TCI America

  • (O0068)  Trimethyl Orthoformate  >98.0%(GC)

  • 149-73-5

  • 500mL

  • 295.00CNY

  • Detail
  • Alfa Aesar

  • (A13760)  Trimethyl orthoformate, 99%   

  • 149-73-5

  • 100ml

  • 234.0CNY

  • Detail
  • Alfa Aesar

  • (A13760)  Trimethyl orthoformate, 99%   

  • 149-73-5

  • 500ml

  • 411.0CNY

  • Detail
  • Alfa Aesar

  • (A13760)  Trimethyl orthoformate, 99%   

  • 149-73-5

  • 2500ml

  • 1496.0CNY

  • Detail
  • Aldrich

  • (305472)  Trimethylorthoformate  anhydrous, 99.8%

  • 149-73-5

  • 305472-100ML

  • 669.24CNY

  • Detail
  • Aldrich

  • (305472)  Trimethylorthoformate  anhydrous, 99.8%

  • 149-73-5

  • 305472-1L

  • 1,503.45CNY

  • Detail
  • Aldrich

  • (305472)  Trimethylorthoformate  anhydrous, 99.8%

  • 149-73-5

  • 305472-6X1L

  • 6,300.45CNY

  • Detail
  • Aldrich

  • (108456)  Trimethylorthoformate  99%

  • 149-73-5

  • 108456-250ML

  • 222.30CNY

  • Detail
  • Aldrich

  • (108456)  Trimethylorthoformate  99%

  • 149-73-5

  • 108456-20L

  • 11,980.80CNY

  • Detail

149-73-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Trimethoxymethane

1.2 Other means of identification

Product number -
Other names Orthomravencan methylnaty

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:149-73-5 SDS

149-73-5Synthetic route

methanol
67-56-1

methanol

Bromoform
75-25-2

Bromoform

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With sodium at 30℃; for 4h;100%
Bromoform
75-25-2

Bromoform

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
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%
methanol
67-56-1

methanol

formimidomethylester hydrochloride
15755-09-6

formimidomethylester hydrochloride

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
at 40 - 45℃; for 5h; Temperature; Large scale;95%
With benzene
Dimethyl ether
115-10-6

Dimethyl ether

Methyl formate
107-31-3

Methyl formate

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With boron trifluoride In Hexadecane at 110℃; for 12h; Autoclave;90%
methanol
67-56-1

methanol

hydrogen cyanide
74-90-8

hydrogen cyanide

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
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
941-98-0

1'-naphthacetophenone

A

Bromoform
75-25-2

Bromoform

B

methyl 1-naphthoate
2459-24-7

methyl 1-naphthoate

C

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
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
100-06-1

1-(4-methoxyphenyl)ethanone

A

Bromoform
75-25-2

Bromoform

B

methyl 4-methoxybenzoate
121-98-2

methyl 4-methoxybenzoate

C

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
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
122-00-9

para-methylacetophenone

A

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

B

Bromoform
75-25-2

Bromoform

C

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
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
67-56-1

methanol

acetophenone
98-86-2

acetophenone

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
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
98-86-2

acetophenone

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

Bromoform
75-25-2

Bromoform

C

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
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
646-06-0

1,3-DIOXOLANE

methanol
67-56-1

methanol

A

2-methoxy-1,3-dioxolane
19693-75-5

2-methoxy-1,3-dioxolane

B

4-methoxy-1,3-dioxolane
109620-95-3

4-methoxy-1,3-dioxolane

C

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
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%
trifluoromethan
75-46-7

trifluoromethan

sodium methylate
124-41-4

sodium methylate

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
In diethylene glycol dimethyl ether at 120℃; under 2585.81 Torr; for 24h; Solvent;70%
methanol
67-56-1

methanol

chloroform
67-66-3

chloroform

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With sodium hydroxide; 1,8-bis(dimethylamino)-1,6-dioxaoctane In dichloromethane67%
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
563-80-4

3-methyl-butan-2-one

A

Bromoform
75-25-2

Bromoform

B

Methyl isobutyrate
547-63-7

Methyl isobutyrate

C

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
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
111-13-7

hexyl-methyl-ketone

A

Bromoform
75-25-2

Bromoform

B

2,2-dimethoxy-3-octanol
19841-72-6

2,2-dimethoxy-3-octanol

C

methyl heptanoate
106-73-0

methyl heptanoate

D

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
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
122-57-6

1-Phenylbut-1-en-3-one

A

Bromoform
75-25-2

Bromoform

B

methyl cinnamate
103-26-4

methyl cinnamate

C

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
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
67-56-1

methanol

(methoxymethylidene)dimethylammonium methyl sulfate
21511-55-7, 34643-89-5

(methoxymethylidene)dimethylammonium methyl sulfate

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With Methyl formate 1) 16h, 2) 4h, 40 deg C;50%
methanol
67-56-1

methanol

trifluoromethan
75-46-7

trifluoromethan

A

sodium formate
141-53-7

sodium formate

B

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With sodium hydroxide at 120℃; under 2585.81 Torr; for 24h;A 35%
B 15%
Chlorodifluoromethane
75-45-6

Chlorodifluoromethane

sodium methylate
124-41-4

sodium methylate

A

difluoromethyl methyl ether
359-15-9

difluoromethyl methyl ether

B

trimethyl orthoformate
149-73-5

trimethyl orthoformate

methanol
67-56-1

methanol

dimethoxycarbene
40480-72-6

dimethoxycarbene

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
In acetonitrile at 20℃; Rate constant;
methanol
67-56-1

methanol

3,3-dimethoxydiazirine
114980-39-1

3,3-dimethoxydiazirine

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
at 11.6℃; Thermodynamic data; ΔH;
In pentane at 20℃; Rate constant; Irradiation; primary kinetic isotope effect;
3,3-dimethoxydiazirine
114980-39-1

3,3-dimethoxydiazirine

A

1,1,2,2-tetramethoxyethylene
1069-12-1

1,1,2,2-tetramethoxyethylene

B

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With methanol In pentane at 25℃; Product distribution; thermal decomposition also in presence of water (methanol absent);
Methyl formate
107-31-3

Methyl formate

3,3-dimethyl-2-butanone dimethyl ketal
62038-48-6

3,3-dimethyl-2-butanone dimethyl ketal

A

3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

B

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With hydrogenchloride In methanol at 25℃; Equilibrium constant;
Methyl formate
107-31-3

Methyl formate

A

methoxyoxirane
57346-02-8

methoxyoxirane

B

Methoxyacetone
5878-19-3

Methoxyacetone

C

2,4-dimethoxy-1,3-dioxacyclopentane

2,4-dimethoxy-1,3-dioxacyclopentane

D

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
at -15 - 20℃; for 1.5h; Irradiation; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
chloroform
67-66-3

chloroform

sodium methylate
124-41-4

sodium methylate

A

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

B

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With N,N-dimethyl-formamide In methanolA 48 % Chromat.
B 38 % Chromat.
chloroform
67-66-3

chloroform

sodium methylate
124-41-4

sodium methylate

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

B

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
A 91 % Chromat.
B 3 % Chromat.
chloroform
67-66-3

chloroform

sodium methylate
124-41-4

sodium methylate

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

carbon monoxide
201230-82-2

carbon monoxide

B

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

C

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
for 0.5h; Mechanism; methanol presence;
N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

A

tertamethylammonium iodide
75-58-1

tertamethylammonium iodide

B

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

C

methyl iodide
74-88-4

methyl iodide

D

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With iodine Product distribution;A 12.8 g
B 5.2 g
C 1.4 g
D 6.7 g
methanol
67-56-1

methanol

Chlorodifluoromethane
75-45-6

Chlorodifluoromethane

A

difluoromethyl methyl ether
359-15-9

difluoromethyl methyl ether

B

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With sodium methylate at 25℃; for 2h; Product distribution; Further Variations:; Temperatures; Reagents;
furfural
98-01-1

furfural

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2-furaldehyde dimethyl acetal
1453-62-9

2-furaldehyde dimethyl acetal

Conditions
ConditionsYield
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
123-08-0

4-hydroxy-benzaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

4-(dimethoxymethyl)phenol
59276-27-6

4-(dimethoxymethyl)phenol

Conditions
ConditionsYield
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%
salicylaldehyde
90-02-8

salicylaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2-(dimethoxymethyl)phenol
24396-24-5

2-(dimethoxymethyl)phenol

Conditions
ConditionsYield
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%
acetophenone
98-86-2

acetophenone

trimethyl orthoformate
149-73-5

trimethyl orthoformate

acetophenone dimethyl acetal
4316-35-2

acetophenone dimethyl acetal

Conditions
ConditionsYield
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
141-97-9

ethyl acetoacetate

trimethyl orthoformate
149-73-5

trimethyl orthoformate

3-methoxy-but-2-enoic acid ethyl ester
3510-99-4

3-methoxy-but-2-enoic acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride In methanol100%
With hydrogenchloride In methanol100%
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%
benzaldehyde
100-52-7

benzaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
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
1122-91-4

4-bromo-benzaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

1,1-dimethoxy-1-(4-bromophenyl)methane
24856-58-4

1,1-dimethoxy-1-(4-bromophenyl)methane

Conditions
ConditionsYield
Yb-Amberlyst XN-1010 In dichloromethane100%
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
100-19-6

(4-nitrophenyl)ethanone

trimethyl orthoformate
149-73-5

trimethyl orthoformate

1,1-dimethoxy-1-(4-nitrophenyl)ethane
53577-98-3

1,1-dimethoxy-1-(4-nitrophenyl)ethane

Conditions
ConditionsYield
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
149-73-5

trimethyl orthoformate

(E/Z)-3,7-dimethyl-2,6-octadienal
5392-40-5

(E/Z)-3,7-dimethyl-2,6-octadienal

citral dimethyl acetal
7549-37-3

citral dimethyl acetal

Conditions
ConditionsYield
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
Octanal
124-13-0

Octanal

trimethyl orthoformate
149-73-5

trimethyl orthoformate

1,1-dimethoxyoctane
10022-28-3

1,1-dimethoxyoctane

Conditions
ConditionsYield
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%
1,3-dithiol-2-thione
930-35-8

1,3-dithiol-2-thione

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2-methylsulfanyl-2H-1,3-dithiole-2-ylium tetrafluoroborate

2-methylsulfanyl-2H-1,3-dithiole-2-ylium tetrafluoroborate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In chloroform100%
piperonal
120-57-0

piperonal

trimethyl orthoformate
149-73-5

trimethyl orthoformate

5-(dimethoxymethyl)benzo[d][1,3]dioxole
59259-90-4

5-(dimethoxymethyl)benzo[d][1,3]dioxole

Conditions
ConditionsYield
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
15930-53-7

6-bromo-3,4-methylenedioxybenzaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

6-bromobenzo-1,3-dioxole-5-carboxaldehyde dimethyl acetal
74879-22-4

6-bromobenzo-1,3-dioxole-5-carboxaldehyde dimethyl acetal

Conditions
ConditionsYield
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
141-97-9

ethyl acetoacetate

trimethyl orthoformate
149-73-5

trimethyl orthoformate

ethyl (2E)-3-methoxy-2-butenoate
22157-27-3

ethyl (2E)-3-methoxy-2-butenoate

Conditions
ConditionsYield
With hydrogenchloride In methanol100%
With hydrogenchloride In methanol; water96%
acid93%
With sulfuric acid; calcium chloride at 0 - 25℃; Inert atmosphere;74%
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

3,4,5-trimethoxybenzaldehyde dimethyl acetal
59276-37-8

3,4,5-trimethoxybenzaldehyde dimethyl acetal

Conditions
ConditionsYield
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
530-93-8

1,2,3,4-tetrahydronaphthalen-2-one

trimethyl orthoformate
149-73-5

trimethyl orthoformate

3-methoxy-1,2-dihydronaphthalene
40815-23-4

3-methoxy-1,2-dihydronaphthalene

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20 - 60℃; for 16h;100%
93%
With toluene-4-sulfonic acid for 8h; Ambient temperature;87%
In benzene1.15 g (75%)
acetophenone
98-86-2

acetophenone

trimethyl orthoformate
149-73-5

trimethyl orthoformate

benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

Conditions
ConditionsYield
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
93-55-0

1-phenyl-propan-1-one

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2-phenylpropionic acid methyl ester
31508-44-8

2-phenylpropionic acid methyl ester

Conditions
ConditionsYield
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
135-02-4

ortho-anisaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

o-anisaldehyde dimethyl acetal
58378-33-9

o-anisaldehyde dimethyl acetal

Conditions
ConditionsYield
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
6630-33-7

ortho-bromobenzaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

o-bromobenzaldehyde dimethyl acetal
35849-09-3

o-bromobenzaldehyde dimethyl acetal

Conditions
ConditionsYield
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
613-54-7

2-Bromo-2'-acetonaphthone

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2-bromo-1,1-dimethoxy-1-(2-naphthyl)ethane
70891-59-7

2-bromo-1,1-dimethoxy-1-(2-naphthyl)ethane

Conditions
ConditionsYield
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
10342-83-3

4'-Bromopropiophenone

trimethyl orthoformate
149-73-5

trimethyl orthoformate

methyl 2-(4-bromophenyl)propanoate
83636-46-8

methyl 2-(4-bromophenyl)propanoate

Conditions
ConditionsYield
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
7040-25-7

3,4-diformylfuran

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Furan-3,4-dicarboxaldehyde bis
77161-53-6

Furan-3,4-dicarboxaldehyde bis

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 35℃; for 20h;100%
4-Ethoxycarbonylmethyl-1,3-dithiole-2-thione
55436-24-3

4-Ethoxycarbonylmethyl-1,3-dithiole-2-thione

trimethyl orthoformate
149-73-5

trimethyl orthoformate

4-(ethoxycarbonylmethyl)-2-methylthio-1,3-dithiolium tetrafluoroborate

4-(ethoxycarbonylmethyl)-2-methylthio-1,3-dithiolium tetrafluoroborate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In chloroform100%
3,3-dimethyl acrylaldehyde
107-86-8

3,3-dimethyl acrylaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

3-methyl-but-2-enal dimethyl acetal
31525-65-2

3-methyl-but-2-enal dimethyl acetal

Conditions
ConditionsYield
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
472-66-2

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Dimethoxy-2',2' ethyl-2 trimethyl-1,3,3 cyclohexene-1
86558-53-4

Dimethoxy-2',2' ethyl-2 trimethyl-1,3,3 cyclohexene-1

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol for 24h; Ambient temperature;100%
(2E,4S,5R)-4,6-diacetoxy-5-hydroxy-2(E)-hexenal
29581-05-3

(2E,4S,5R)-4,6-diacetoxy-5-hydroxy-2(E)-hexenal

trimethyl orthoformate
149-73-5

trimethyl orthoformate

(2E,4S,5R)-4,6-diacetoxy-5-hydroxy-2-hexenal dimethyl acetal
136011-37-5

(2E,4S,5R)-4,6-diacetoxy-5-hydroxy-2-hexenal dimethyl acetal

Conditions
ConditionsYield
With 3 A molecular sieve; toluene-4-sulfonic acid In methanol at 0℃; for 1h;100%
2-bromo-4,5-dimethoxybenzaldehyde
5392-10-9

2-bromo-4,5-dimethoxybenzaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2-bromo-4,5-dimethoxybenzaldehyde dimethyl acetal
70461-33-5

2-bromo-4,5-dimethoxybenzaldehyde dimethyl acetal

Conditions
ConditionsYield
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%

149-73-5Related news

Dimethoxymethane and Trimethoxymethane (cas 149-73-5) as alternative fuels for fuel cells09/30/2019

The electrooxidation of dimethoxymethane (DMM) and trimethoxymethane (TMM) was studied at different platinum-based electrocatalysts deposited onto a titanium mesh substrate by thermal decomposition of chloride precursors. Half-cell tests showed an increase in oxidation current for the methoxy fu...detailed

Trimethoxymethane (cas 149-73-5) as an alternative fuel for a direct oxidation PBI polymer electrolyte fuel cell09/28/2019

The oxidation of trimethoxymethane (TMM) (trimethyl orthoformate) in a direct oxidation PBI fuel cell was examined by on-line mass spectroscopy and on-line FTIR spectroscopy. The results show that TMM was almost completely hydrolyzed in a direct oxidation fuel cell which employs an acid doped po...detailed

149-73-5Relevant articles and documents

A PRIMARY KINETIC ISOTOPE EFFECT FOR THE O-H INSERTION OF DIMETHOXYCARBENE

Moss, Robert A.,Shen, Shilan,Wlostowski, Marek

, p. 6417 - 6420 (1988)

The primary kinetic isotope effect for the insertion of dimethoxycarbene into MeOH(D) is 3.3 +/- o.5.

Selective production of difluoromethyl methyl ether from chlorodifluoromethane using alkali metal carbonates

Lee,Hoon Sik Kim,Sang Deuk Lee,Won Koo Lee,Kim

, p. 133 - 136 (2001)

CHF2OCH3 (HFE-152a), an important starting material for synthesizing various C2 hydrofluoroethers and a prospective alternative to CH3CF2Cl (HCFC-142b), has been found to be effectively produced from the reaction of CHF2Cl (HCFC-22) with alkali metal carbonates in methanol. Some alkali metal carbonates induce selective production of CHF2OCH3 with a small amount of CH(OCH3)3, a major side product. Activities of alkali metal carbonates for producing CHF2OCH3 are in the order of K2CO3 > Na2CO3 > Li2CO3, suggesting that the solubility and ionization tendency of alkali metal carbonate in methanol play important roles in the reaction.

Reactions of dimethoxycarbene and fluoromethoxycarbene with hydroxyl compounds. Absolute rate constants and the heat of formation of dimethoxycarbene

Du,Fan,Goodman,Kesselmayer,Krogh-Jespersen,LaVilla,Moss,Shen,Sheridan

, p. 1920 - 1926 (1990)

Dimethoxycarbene [(MeO)2C] and fluoromethoxycarbene (FCOMe) were photochemically generated from the appropriate diazirines (2a and 2b) and characterized by UV and IR spectroscopy in cold matrices and by UV in solution at 20-25°C. Laser flash photolytic studies determined rate constants for the reactions of the carbenes with ethanol, methanol, chloroethanol, fluoroethanol, trifluoroethanol, hexafluoroisopropyl alcohol, and acetic acid. The reactivity of (MeO)2C with the alcohols spanned 4 orders of magnitude, with kψ for carbene decay in 1 M ROH/CH3CN ranging from 3.2 X 104 S-1 (ethanol) to 6.7 X 108 S-1 (hexafluoroisopropyl alcohol). A Bronsted correlation (α = 0.66) was obtained between log kψ for the decay of (MeO)2C in 1 M ROH/CH3CN and the pK(a) of ROH (in water). FCOMe was much less reactive toward ROH than (MeO)2C; only with hexafluoroisopropyl alcohol (kψ ~9 X 103 s-1 for carbene decay in 1 M ROH/CH3CN) could quenching be observed. Products of some of the carbene/alcohol reactions were characterized. A photoacoustic calorimetry study of the (MeO)2/MeOH reaction afforded ΔH(f) ~ -61 kcal/mol for (MeO)2C;ΔH(f) for FCOMe was estimated at ~ -53 to -56 kcal/mol. The mechanism(s) of the carbene/O-H insertion reactions are discussed. The results of ab initio and semiempirical molecular orbital calculations on FCOMe are presented.

Synthesis method of crude carboxylic ester (by machine translation)

-

Paragraph 0021; 0022, (2020/08/09)

The method is characterized in that the carboxylic ester and the ether are prepared by reacting a carboxylic ester with an ether at a certain temperature under the catalysis of a catalyst at a certain pressure for a certain time. (by machine translation)

Green preparing orthoformate cleaning process

-

Paragraph 0038; 0040; 0041, (2016/10/07)

The invention provides a green process for preparing orthoformate. A hydrogen chloride alcohol solution is prepared from a byproduct hydrogen chloride tail gas of the chlorine-related synthesis industry and then is slowly added into a reaction system, so that loss caused by escape of hydrocyanic acid is reduced, the yield is increased, great equipment corrosion caused by the byproduct hydrochloric acid prepared by the companies is avoided, the economic additional value of the byproduct hydrogen chloride is greatly increased, three wastes are avoided, the byproduct only comprises ammonium chloride, resources are reasonably utilized, and the green process for preparing the orthoformate is an environment-friendly production process and has a good social benefit.

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