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621-76-1

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621-76-1 Usage

Chemical Properties

clear colorless liquid

Uses

Different sources of media describe the Uses of 621-76-1 differently. You can refer to the following data:
1. Tripropoxymethane can be used in the lipase-?catalyzed esterification aimed at the kinetic resolution of racemic acids, circumventing the adverse effects of the water formed in the course of the reaction.
2. Tripropyl orthoformate was used as alcohol donor to investigate the activity and enantioselectivity of Novozym 435 in the esterification of rac-fenoprofen in methylcyclohexane. It may be used as a drying agent during the synthesis of squaraine derivatives.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 3801, 1955 DOI: 10.1021/ja01619a036

General Description

Gas phase reactions of the rare earth metal cations with tripropyl orthoformate were studied by Fourier transform ion cyclotron resonance mass spectrometry.

Check Digit Verification of cas no

The CAS Registry Mumber 621-76-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 1 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 621-76:
(5*6)+(4*2)+(3*1)+(2*7)+(1*6)=61
61 % 10 = 1
So 621-76-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H22O3/c1-4-7-11-10(12-8-5-2)13-9-6-3/h10H,4-9H2,1-3H3

621-76-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A15503)  Tri-n-propyl orthoformate, 97%   

  • 621-76-1

  • 5g

  • 132.0CNY

  • Detail
  • Alfa Aesar

  • (A15503)  Tri-n-propyl orthoformate, 97%   

  • 621-76-1

  • 25g

  • 473.0CNY

  • Detail
  • Alfa Aesar

  • (A15503)  Tri-n-propyl orthoformate, 97%   

  • 621-76-1

  • 100g

  • 1322.0CNY

  • Detail
  • Aldrich

  • (333344)  Tripropylorthoformate  97%

  • 621-76-1

  • 333344-100ML

  • 1,676.61CNY

  • Detail

621-76-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Orthoformic Acid Tripropyl Ester

1.2 Other means of identification

Product number -
Other names Propane, 1,1‘,1‘‘-[methylidynetris(oxy)]tris-

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:621-76-1 SDS

621-76-1Synthetic route

propan-1-ol
71-23-8

propan-1-ol

hydrogen cyanide
74-90-8

hydrogen cyanide

tripropyl orthoformate
621-76-1

tripropyl orthoformate

Conditions
ConditionsYield
Stage #1: hydrogen cyanide With hydrogenchloride In propan-1-ol; mineral oil at -5 - 25℃; for 2.75h; Large scale;
Stage #2: propan-1-ol In mineral oil at 30 - 55℃; for 5h; Large scale;
85.2%
propan-1-ol
71-23-8

propan-1-ol

chloroform
67-66-3

chloroform

tripropyl orthoformate
621-76-1

tripropyl orthoformate

Conditions
ConditionsYield
With sodium hydroxide; 1,8-bis(pyperidin-1-yl)-1,6-dioxaoctane In dichloromethane53%
With sodium
propan-1-ol
71-23-8

propan-1-ol

4-(Methoxymethylene)-morpholinium methyl sulfate
5780-15-4

4-(Methoxymethylene)-morpholinium methyl sulfate

tripropyl orthoformate
621-76-1

tripropyl orthoformate

Conditions
ConditionsYield
With propyl methanoate 1) 16h, 2) 4h, 40 deg C;11.2%
propan-1-ol
71-23-8

propan-1-ol

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

tripropyl orthoformate
621-76-1

tripropyl orthoformate

Conditions
ConditionsYield
With sulfuric acid unter Entfernen des entstehenden Aethanols;
propan-1-ol
71-23-8

propan-1-ol

trimethyl orthoformate
149-73-5

trimethyl orthoformate

tripropyl orthoformate
621-76-1

tripropyl orthoformate

Conditions
ConditionsYield
With toluene-4-sulfonic acid Heating;
1-Butylimidazole
4316-42-1

1-Butylimidazole

tripropyl orthoformate
621-76-1

tripropyl orthoformate

1-butyl-3-propylimidazolium tetrafluoroborate

1-butyl-3-propylimidazolium tetrafluoroborate

Conditions
ConditionsYield
Stage #1: 1-Butylimidazole With tetrafluoroboric acid In water at 0℃;
Stage #2: tripropyl orthoformate at 130℃; for 28h; Inert atmosphere;
93%
4-butanolide
96-48-0

4-butanolide

tripropyl orthoformate
621-76-1

tripropyl orthoformate

n-Propyl 4-n-propoxybutanoate
155060-42-7

n-Propyl 4-n-propoxybutanoate

Conditions
ConditionsYield
With sulfuric acid In isopropyl alcohol at 50℃;92%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

N-(5-aminothiophene-2-carbonyl)-L-glutamic acid diethyl ester
106585-63-1

N-(5-aminothiophene-2-carbonyl)-L-glutamic acid diethyl ester

C18H26N2O6S

C18H26N2O6S

Conditions
ConditionsYield
at 80℃; for 2h;92%
4,5-dicyano-1H-imidazole
1122-28-7

4,5-dicyano-1H-imidazole

tripropyl orthoformate
621-76-1

tripropyl orthoformate

1-Propyl-1H-imidazole-4,5-dicarbonitrile
133123-68-9

1-Propyl-1H-imidazole-4,5-dicarbonitrile

Conditions
ConditionsYield
1) 1 h, 105 deg C ) 3 h, 135 deg C;86%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

(2E)-3-phenyl-2-propen-1-ol
4407-36-7

(2E)-3-phenyl-2-propen-1-ol

3-phenyl-(E)-2-propenyl n-propyl ether
14593-45-4

3-phenyl-(E)-2-propenyl n-propyl ether

Conditions
ConditionsYield
With iodine at 20℃; for 0.5h;85%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

Methyl 4-chloroacetoacetate
32807-28-6

Methyl 4-chloroacetoacetate

methyl (E)-4-chloro-3-propoxy-2-butenoate

methyl (E)-4-chloro-3-propoxy-2-butenoate

Conditions
ConditionsYield
Stage #1: tripropyl orthoformate; Methyl 4-chloroacetoacetate With sulfuric acid at 20℃; for 72h;
Stage #2: With phosphorus pentoxide In chloroform for 2h; Reflux;
79%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

isobutyl 4-chloroacetoacetate
97938-39-1

isobutyl 4-chloroacetoacetate

isobutyl (E)-4-chloro-3-propyloxy-2-butenoate

isobutyl (E)-4-chloro-3-propyloxy-2-butenoate

Conditions
ConditionsYield
Stage #1: tripropyl orthoformate; isobutyl 4-chloroacetoacetate With sulfuric acid at 20℃; for 42h;
Stage #2: With phosphorus pentoxide In chloroform for 2h; Reflux;
79%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

triphenylphosphine
603-35-0

triphenylphosphine

triphenyl(propyl)phosphonium 4-methylbenzenesulfonate
101610-04-2

triphenyl(propyl)phosphonium 4-methylbenzenesulfonate

Conditions
ConditionsYield
at 130℃; for 68h; Sealed tube;77%
at 130℃; for 68h;76%
Methylenediphosphonic acid
1984-15-2

Methylenediphosphonic acid

tripropyl orthoformate
621-76-1

tripropyl orthoformate

Methandiphosphonsaeuretetrapropylester
28254-31-1

Methandiphosphonsaeuretetrapropylester

Conditions
ConditionsYield
76%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

ethyl (2-chloroaceto)acetate
638-07-3

ethyl (2-chloroaceto)acetate

ethyl (E)-4-chloro-3-propoxy-2-butenoate

ethyl (E)-4-chloro-3-propoxy-2-butenoate

Conditions
ConditionsYield
Stage #1: tripropyl orthoformate; ethyl (2-chloroaceto)acetate With sulfuric acid at 20℃; for 72h;
Stage #2: With phosphorus pentoxide In chloroform for 2h; Reflux;
74%
Tetrahydro-4H-pyran-4-one
29943-42-8

Tetrahydro-4H-pyran-4-one

tripropyl orthoformate
621-76-1

tripropyl orthoformate

C8H14O2
41939-29-1

C8H14O2

Conditions
ConditionsYield
Stage #1: Tetrahydro-4H-pyran-4-one; tripropyl orthoformate; amberlyst-15 In chlorobenzene at 5 - 20℃; for 16h;
Stage #2: In chlorobenzene at 85 - 125℃; for 16h;
73%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

4-propylbenzene-1,2-diol
2525-02-2

4-propylbenzene-1,2-diol

(±)-2-propoxy-5-propyl-1,3-benzodioxole

(±)-2-propoxy-5-propyl-1,3-benzodioxole

Conditions
ConditionsYield
With Amberlyst 15 In toluene for 4h; Inert atmosphere; Molecular sieve; Reflux;73%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

benzaldehyde
100-52-7

benzaldehyde

benzaldehyde di-n-propylacetal
13704-53-5

benzaldehyde di-n-propylacetal

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 120℃; for 16h;70%
With sulfuric acid
tripropyl orthoformate
621-76-1

tripropyl orthoformate

1-(3-(5-(4-cyanophenoxy)pyridin-2-yl)-2-(2,4-difluorophenyl)-3,3-difluoro-2-hydroxypropyl)hydrazine-1-carbothioamide

1-(3-(5-(4-cyanophenoxy)pyridin-2-yl)-2-(2,4-difluorophenyl)-3,3-difluoro-2-hydroxypropyl)hydrazine-1-carbothioamide

4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-mercapto-1H-1,2,4-triazol-1-yl)-propyl)pyridin-3-yl)oxy)benzonitrile

4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-mercapto-1H-1,2,4-triazol-1-yl)-propyl)pyridin-3-yl)oxy)benzonitrile

Conditions
ConditionsYield
at 100℃; for 2h;68.6%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

C40H62N4

C40H62N4

C38H52N4(2+)*2BF4(1-)

C38H52N4(2+)*2BF4(1-)

Conditions
ConditionsYield
With tetrafluoroboric acid diethyl ether complex at 150℃; for 24h; Schlenk technique;64%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

3-methylbenzene-1,2-diol
488-17-5

3-methylbenzene-1,2-diol

(±)-4-methyl-2-propoxy-1,3-benzodioxole

(±)-4-methyl-2-propoxy-1,3-benzodioxole

Conditions
ConditionsYield
With Amberlyst 15 In toluene for 4h; Inert atmosphere; Molecular sieve; Reflux;63%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

methallyl 4-chloroacetoacetate

methallyl 4-chloroacetoacetate

methallyl (E)-4-chloro-3-propyloxy-2-butenoate

methallyl (E)-4-chloro-3-propyloxy-2-butenoate

Conditions
ConditionsYield
Stage #1: tripropyl orthoformate; methallyl 4-chloroacetoacetate With sulfuric acid at 20℃; for 42h;
Stage #2: With phosphorus pentoxide In chloroform for 2h; Reflux;
63%
4-aminopyridine
504-24-5

4-aminopyridine

tripropyl orthoformate
621-76-1

tripropyl orthoformate

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

C8H14N2O6P2
1198228-93-1

C8H14N2O6P2

Conditions
ConditionsYield
Stage #1: 4-aminopyridine; tripropyl orthoformate; phosphonic acid diethyl ester for 12h; Reflux;
Stage #2: With hydrogenchloride; water for 8h; Reflux;
61%
di-n-butylphosphine
1732-72-5

di-n-butylphosphine

tripropyl orthoformate
621-76-1

tripropyl orthoformate

tetrabutyl(dipropoxymethylene)bisphosphine

tetrabutyl(dipropoxymethylene)bisphosphine

Conditions
ConditionsYield
Stage #1: di-n-butylphosphine With n-butyllithium In tetrahydrofuran; pentane at -30℃;
Stage #2: tripropyl orthoformate With boron trifluoride diethyl etherate In diethyl ether at -30℃;
61%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

C13H29O4P

C13H29O4P

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; hypophosphorous acid for 3h; Ambient temperature;60%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

O-propyl-O-trimethylsilyl-(dipropoxymethyl) phosphonite
105259-12-9

O-propyl-O-trimethylsilyl-(dipropoxymethyl) phosphonite

Conditions
ConditionsYield
Stage #1: tripropyl orthoformate With hypophosphorous acid; toluene-4-sulfonic acid at 20 - 35℃; under 1 Torr;
Stage #2: 1,1,1,3,3,3-hexamethyl-disilazane Reflux;
60%
With hypophosphorous acid; toluene-4-sulfonic acid 1) r.t., 3 h, 2) 80-100 deg C; Yield given. Multistep reaction;
tripropyl orthoformate
621-76-1

tripropyl orthoformate

di-n-propylphosphine
19357-87-0

di-n-propylphosphine

tetrapropyl(dipropoxymethylene)bisphosphine

tetrapropyl(dipropoxymethylene)bisphosphine

Conditions
ConditionsYield
Stage #1: di-n-propylphosphine With n-butyllithium In tetrahydrofuran; pentane at -30℃;
Stage #2: tripropyl orthoformate With boron trifluoride diethyl etherate In diethyl ether at -30℃;
59%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

4-methyl-1,2-dihydroxybenzene
452-86-8

4-methyl-1,2-dihydroxybenzene

(±)-5-methyl-2-propoxy-1,3-benzodioxole

(±)-5-methyl-2-propoxy-1,3-benzodioxole

Conditions
ConditionsYield
With Amberlyst 15 In toluene for 4h; Inert atmosphere; Molecular sieve; Reflux;53%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

(Z)-2-Amino-3-{[5-oxo-2-phenyl-oxazol-(4Z)-ylidenemethyl]-amino}-but-2-enedinitrile
874117-16-5

(Z)-2-Amino-3-{[5-oxo-2-phenyl-oxazol-(4Z)-ylidenemethyl]-amino}-but-2-enedinitrile

C18H15N5O3

C18H15N5O3

Conditions
ConditionsYield
for 8h; Heating;52%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

3-Phenylpropenol
104-54-1

3-Phenylpropenol

3-phenyl-(E)-2-propenyl n-propyl ether
14593-45-4

3-phenyl-(E)-2-propenyl n-propyl ether

Conditions
ConditionsYield
With Montmorillonite KSF for 12h; Ambient temperature;51%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

(2E)-3-phenyl-2-propen-1-ol
4407-36-7

(2E)-3-phenyl-2-propen-1-ol

A

3-phenyl-(E)-2-propenyl n-propyl ether
14593-45-4

3-phenyl-(E)-2-propenyl n-propyl ether

B

((1E,1'E)-oxybis(prop-1-ene-3,1-diyl))dibenzene
144759-86-4

((1E,1'E)-oxybis(prop-1-ene-3,1-diyl))dibenzene

Conditions
ConditionsYield
Montmorillonite KSF at 20℃; for 12h;A 51%
B 10%
vinyl acetate
108-05-4

vinyl acetate

tripropyl orthoformate
621-76-1

tripropyl orthoformate

1,1,3,3-Tetrapropoxy-propane
65099-93-6

1,1,3,3-Tetrapropoxy-propane

Conditions
ConditionsYield
With iron(III) chloride; sodium hydrogencarbonate 1) 2 h, reflux; 2) 20 deg C, 2 h;50%
tripropyl orthoformate
621-76-1

tripropyl orthoformate

N,N'-Di(4-methylphenyl)oxalamidine
157368-88-2

N,N'-Di(4-methylphenyl)oxalamidine

2,5-Di-n-propoxy-1,4-di-p-tolyl-1,2,4,5-tetrahydroimidazo[4,5-d]imidazole

2,5-Di-n-propoxy-1,4-di-p-tolyl-1,2,4,5-tetrahydroimidazo[4,5-d]imidazole

Conditions
ConditionsYield
at 120℃; for 10h;41%

621-76-1Relevant articles and documents

-

Alexander,Busch

, p. 554 (1952)

-

Synthesis and Application of α,ω-Bis(dialkylamino)oligooxaalkanes and Their Analogs as Phase-Transfer Catalysts in Heterogeneous Synthesis of Trialkyl Orthoformates

Shtamburg, V. G.,Skobelev, O. L.,Grinev, V. M.,Dmitrienko, A. D.,Pleshkova, A. P.,Pritykin, L. M.

, p. 609 - 612 (2007/10/03)

α,ω-Bis(dialkylamino)oligooxaalkanes, 1,8-bis(alkoxyamino)-3,6-dioxaoctanes, and 1,8-bis(diethylamino)-3,6-dioxaoctane N,N'-dioxide are efficient phase-transfer catalysts, the use of which ensures preparation in high yields of trialkyl orthoformates from chloroform and primary alcohols in the heterogeneous systems CH2Cl2-solid alkali metal hydroxide.

On the Mechanism of Acetalization Reactions with Carboxamide-Dialkyl Sulfate Adducts; a New Method of Preparation of Orthocarboxylic Esters and of Cleavage of Carboxamides.

Kantlehner, Willi,Gutbrod, Heinz-Dieter

, p. 1677 - 1688 (2007/10/02)

It is shown that the efficiency of carboxamide-dialkyl-sulfate adducts in acetalization reactions depends on their alkylation ability.A mechanism of acetal formation using orthoformates as acetalization reagents is proposed.Alcoholysis of carboxamide-dialkyl sulfate adducts 1b, 11, 13 affords orthocarboxylic esters.Carboxamides and carboxmorpholides react with dimethyl sulfate/methanol to give methyl esters.

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