4447-60-3

Basic information

• Product Name: Triisopropyl orthoformate
• Synonyms: TRIISOPROPOXYMETHANE;TRIISOPROPYL ORTHOFORMATE;TIPOF;ORTHOFORMIC ACID TRIISOPROPYL ESTER;2,2',2''-[methylidynetris(oxy)]trispropane;TRIISOPROPYL ORTHOFORMATE ANHYDROUS &;Propane, 2,2,2-methylidynetris(oxy)tris-;2,2′,2′′-[methylidyntris(oxy)]trispropan
• CAS NO: 4447-60-3
• Molecular Formula: C₁₀H₂₂O₃
• Molecular Weight: 190.28
• EINECS: 224-688-9
• Product Categories: Orthoesters;Acetals/Ketals/Ortho Esters;Organic Building Blocks;Oxygen Compounds
• Mol File: 4447-60-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 65-66 °C18 mm Hg(lit.)
• Flash Point: 108 °F
• Appearance: Clear colorless/Liquid
• Density: 0.854 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.29mmHg at 25°C
• Refractive Index: n20/D 1.397(lit.)
• Storage Temp.: Flammables area
• Sensitive: Moisture Sensitive
• BRN: 1700668
• CAS DataBase Reference: Triisopropyl orthoformate(CAS DataBase Reference)
• NIST Chemistry Reference: Triisopropyl orthoformate(4447-60-3)
• EPA Substance Registry System: Triisopropyl orthoformate(4447-60-3)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36-37/39-16
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 1
• F: 21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 4447-60-3(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless liquid

Uses

Different sources of media describe the Uses of 4447-60-3 differently. You can refer to the following data:
1. Triisopropyl Orthoformate (cas# 4447-60-3) is a compound useful in organic synthesis.
2. Triisopropyl orthoformate may be used for the preparation of 2-(diisopropoxymethyl)oxirane.

General Description

Triisopropyl orthoformate (TIPO) is formed during the reaction of dichlorofluoromethane with potassium isopropoxide in isopropyl alcohol. Separation of TIPO from n-hexane by dense carbon nanotube (CNT) membranes by pervaporation has been reported.

InChI:InChI=1/C10H22O3/c1-7(2)11-10(12-8(3)4)13-9(5)6/h7-10H,1-6H3

Synthetic route

trifluoromethan (75-46-7) + isopropyl alcohol (67-63-0) → Triisopropoxymethan (4447-60-3)

Conditions	Yield
With sodium hydride In mineral oil at 120℃; under 2585.81 Torr; for 24h;	90%

di-isopropyl ether (108-20-3) + isopropyl formate (625-55-8) → Triisopropoxymethan (4447-60-3)

Conditions	Yield
With boron trifluoride In Hexadecane at 110℃; for 8h; Autoclave;	88%

hydrogen cyanide (74-90-8) + isopropyl alcohol (67-63-0) → Triisopropoxymethan (4447-60-3)

Conditions	Yield
Stage #1: hydrogen cyanide With hydrogenchloride In isopropyl alcohol; mineral oil at -3 - 30℃; for 2.33333h; Stage #2: isopropyl alcohol In mineral oil at 35 - 53℃; for 5h; Inert atmosphere;	71.84%

formamide (77287-34-4, 77287-35-5, 60100-09-6) + isopropyl alcohol (67-63-0) → Triisopropoxymethan (4447-60-3)

Conditions	Yield
With benzoyl chloride In Petroleum ether at 0 - 40℃; for 2.25h;	58%

trifluoromethan (75-46-7) + isopropyl alcohol (67-63-0) → Triisopropoxymethan (4447-60-3) + sodium formate (141-53-7)

Conditions	Yield
With sodium hydroxide at 120℃; under 2585.81 Torr; for 24h;	A 10% B 40%

4-(Methoxymethylene)-morpholinium methyl sulfate (5780-15-4) + isopropyl alcohol (67-63-0) → Triisopropoxymethan (4447-60-3)

Conditions	Yield
1) 16h, 2) 4h, 40 deg C;	2.9%

thiophene-2-carbaldehyde (98-03-3) + Triisopropoxymethan (4447-60-3) → C11H18O2S (1146221-06-8)

Conditions	Yield
With cerium triflate In isopropyl alcohol; toluene at 20℃; for 0.5h;	99%

Triisopropoxymethan (4447-60-3) + tert-butyl 2'-bromo-5'-formyl-4'-methoxybiphenyl-2-ylcarbamate (1428963-73-8) → tert-butyl 2'-bromo-5'-(diisopropoxymethyl)-4'-methoxybiphenyl-2-ylcarbamate (1428963-58-9)

Conditions	Yield
With N-Bromosuccinimide In dichloromethane; isopropyl alcohol at 20℃; for 6h;	99%

3-phenyl-propionaldehyde (104-53-0) + Triisopropoxymethan (4447-60-3) → 3-phenylpropionaldehyde diisopropyl acetal (64245-42-7)

Conditions	Yield
With cerium triflate In isopropyl alcohol; toluene at 20℃; for 0.0833333h;	98%

Triisopropoxymethan (4447-60-3) + (3-oxopropyl)triphenylphosphonium iodide → (3,3-diisopropoxypropyl)triphenylphosphonium iodide

Conditions	Yield
With hydrogenchloride In dichloromethane; isopropyl alcohol at 0 - 20℃;	97%

Triisopropoxymethan (4447-60-3) + 3-Methylcyclohexanone (591-24-2, 625-96-7) → C13H26O2 (1146221-01-3)

Conditions	Yield
With cerium triflate In isopropyl alcohol; toluene at 20℃; for 0.5h;	95%

tetrafluoroboric acid + Pyrazolo<1,5-a>pyridin-3-carbonsaeureethylester (16205-44-0) + Triisopropoxymethan (4447-60-3) → 3-(carboethoxy)-1-isopropylpyrazolo[1,5-a]pyridin-1-ium tetrafluoroborate

Conditions	Yield
Stage #1: tetrafluoroboric acid; Pyrazolo<1,5-a>pyridin-3-carbonsaeureethylester In water at 0 - 20℃; for 0.5h; Stage #2: Triisopropoxymethan Inert atmosphere;	95%

Triisopropoxymethan (4447-60-3) + (S)-2-(9-methoxy-3,3a,4,5,6,11-hexahydro-2H-pyrrolo[3',2':2,3]azepino[4,5-b]indol-3a-yl)aniline (1312757-32-6) → (-)-trigonoliimine B (1313018-40-4)

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane at 23℃; for 1h; Inert atmosphere;	94.3%

Triisopropoxymethan (4447-60-3) + 2-hexenal (505-57-7) → C12H24O2 (1146221-07-9)

Conditions	Yield
With cerium triflate In isopropyl alcohol; toluene at 20℃; for 4h;	94%

Triisopropoxymethan (4447-60-3) + cyclohexanone (108-94-1) → 1,1-diisopropoxycyclohexane (1132-95-2)

Conditions	Yield
With cerium triflate In isopropyl alcohol; toluene at 20℃; for 0.0833333h;	94%

Triisopropoxymethan (4447-60-3) + (S)-2-(9-methoxy-3,3a,4,5,6,11-hexahydro-2H-pyrrolo[3',2':2,3]azepino[4,5-b]indol-3a-yl)aniline (1312757-32-6) → (-)-trigonoliimine B

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane at 23℃; Inert atmosphere;	94%

Triisopropoxymethan (4447-60-3) + BF4(1-)*C4H5NS*H(1+) → 3-isopropyl-5-methylthiazol-3-ium tetrafluoroborate

Conditions	Yield
at 130℃; for 25h;	94%

Triisopropoxymethan (4447-60-3) + BF4(1-)*C4H5NS*H(1+) → 3-isopropyl-4-methylthiazol-3-ium tetrafluoroborate

Conditions	Yield
at 130℃; for 25h;	94%

5-methylthiazole (3581-89-3) + tetrafluoroboric acid + Triisopropoxymethan (4447-60-3) → 3-isopropyl-5-methylthiazol-3-ium tetrafluoroborate

Conditions	Yield
In water at 0 - 130℃; for 24h;	94%

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + Triisopropoxymethan (4447-60-3) → C23H28O4

Conditions	Yield
indium(III) chloride In acetonitrile at 20℃; for 1h;	93%

Triisopropoxymethan (4447-60-3) + C7H6NS(1+)*C2F6NO4S2(1-) → 3-isopropylbenzo[d]thiazol-3-ium bis((trifluoromethyl)sulfonyl)imide (1227694-43-0)

Conditions	Yield
at 130℃; for 26h;	93%

1,3-Benzothiazole (95-16-9) + Triisopropoxymethan (4447-60-3) + bis(trifluoromethanesulfonyl)amide (82113-65-3) → 3-isopropylbenzo[d]thiazol-3-ium bis((trifluoromethyl)sulfonyl)imide (1227694-43-0)

Conditions	Yield
at 130℃; for 26h;	93%

tetrafluoroboric acid + Triisopropoxymethan (4447-60-3) + 8-methyl-3-phenyl-H-imidazo[1,2-a]pyridine → 1-isopropyl-8-methyl-3-phenyl-imidazole[1,2-a]pyridin-1-ium tetrafluoroborate

Conditions	Yield
Stage #1: tetrafluoroboric acid; 8-methyl-3-phenyl-H-imidazo[1,2-a]pyridine In water at 0 - 20℃; for 0.5h; Stage #2: Triisopropoxymethan Inert atmosphere;	93%

Triisopropoxymethan (4447-60-3) + (S)-3-<(tert-butyldimethylsilyl)oxy>-4-(tosyloxy)butanal (169522-70-7) → (S)-3-<(tert-Butyldimethylsilyl)oxy>-4-(tosyloxy)butanal diisopropyl acetal (169522-71-8)

Conditions	Yield
With toluene-4-sulfonic acid In isopropyl alcohol for 2h; Ambient temperature;	92%

Triisopropoxymethan (4447-60-3) + C12H6Cl3F19O3Si → C21H27F19O6Si

Conditions	Yield
In isopropyl alcohol at 60℃; for 3h; Inert atmosphere;	92%

Triisopropoxymethan (4447-60-3) + p-bromo-[4-(trichlorosilyl)butyl]benzene (358642-61-2) → p-bromo[4-(triisopropylsilyl)butyl]benzene (358642-63-4)

Conditions	Yield
at 20℃; for 72h;	91.3%

Triisopropoxymethan (4447-60-3) + methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate (57224-63-2) → methyl (2RS,4S,5R)-3-<(benzyloxy)carbonyl>-2-isopropoxy-5-methyloxazolidine-4-carboxylate

Conditions	Yield
With (CF3SO3)3 In benzene for 12h; Heating;	90%

Triisopropoxymethan (4447-60-3) + cyclopentanone (120-92-3) → cyclopentanone diisopropyl acetal (1146221-00-2)

Conditions	Yield
With cerium triflate In isopropyl alcohol; toluene at 0℃; for 6h;	90%

Triisopropoxymethan (4447-60-3) + ortho-bromobenzaldehyde (6630-33-7) → 1-bromo-2-(diisopropoxymethyl)benzene (1258208-81-9)

Conditions	Yield
With methanesulfonic acid In isopropyl alcohol at 20℃; for 24h;	90%

1-phenylimidazole (7164-98-9) + ammonium tetrafluoroborate + Triisopropoxymethan (4447-60-3) → 1-isopropyl-3-phenyl-1H-imidazol-3-ium tetrafluoroborate (1434057-48-3)

Conditions	Yield
Schlenk technique; Reflux; Inert atmosphere;	90%

Triisopropoxymethan (4447-60-3) + D-glucal triacetate (2873-29-2) → isopropyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside (171228-22-1)

Conditions	Yield
indium(III) chloride In acetonitrile at 20℃; for 1.4h;	89%

Triisopropoxymethan (4447-60-3) + 6-amino-3-methyl-5-(methylamino)pyrimidine-2,4(1H,3H)-dione → paraxanthine (611-59-6)

Conditions	Yield
With sulfonic acid monohydrate In toluene at 90 - 100℃; for 3h;	89%

Triisopropoxymethan (4447-60-3) + taxol (33069-62-4) → 1,1-diisopropyloxy-2,2-dimethyl-3-pentanone (349655-04-5)

Conditions	Yield
With p-TsOH In isopropyl alcohol	88%
With p-TsOH In isopropyl alcohol	88%
With p-TsOH In isopropyl alcohol	88%

Triisopropoxymethan (4447-60-3) + 3,4,6-tri-O-benzyl-D-galactal (80040-79-5) → C23H28O4

Conditions	Yield
indium(III) chloride In acetonitrile at 20℃; for 1.2h;	88%

Upstream product

• 67-63-0 isopropyl alcohol 
• 149-73-5 trimethyl orthoformate 
• 5780-15-4 4-(Methoxymethylene)-morpholinium methyl sulfate 
• 75-45-6 Chlorodifluoromethane 
• 108-20-3 di-isopropyl ether 
• 625-55-8 isopropyl formate 
• 74-90-8 hydrogen cyanide 
• 77287-34-4 formamide 
• 75-46-7 trifluoromethan 
• 67-66-3 chloroform 

Downstream Products

• 35452-52-9 N-(2,5-Dichlor-phenyl)-formimido-O-isopropylester 
• 169522-71-8 (S)-3-<(tert-Butyldimethylsilyl)oxy>-4-(tosyloxy)butanal diisopropyl acetal 
• 175443-57-9 (R)-((S)-1-Diisopropoxymethyl-pentyloxy)-phenyl-acetic acid methyl ester 
• 144647-87-0 ((Z)-6,6-Diisopropoxy-hex-3-enyl)-triphenyl-phosphonium; bromide 
• 61699-62-5 diisopropyl squarate 
• 53-16-7 Estrone 
• 40013-55-6 3-isopropoxy-1,3,5⁽¹⁰⁾-estratrien-17-one 
• 1624-62-0 estrone 3-methyl ether 
• 18864-76-1 4-isopropylbenzophenone 
• 611-59-6 paraxanthine 
• 743468-37-3 1-isopropoxy-1H-isochromene 
• 1434057-48-3 1-isopropyl-3-phenyl-1H-imidazol-3-ium tetrafluoroborate 
• 1304433-63-3 isopropyl N-{4-[3-chloro-5-(trifluoromethyl)phenyl]-1-(pyrimidin-2-yl)-3-(trifluoromethyl)-1H-pyrazol-5-yl}imidoformate 
• 1312953-43-7 (E)-isopropyl N-(3,6-dimethoxy-2-(3-triisopropylsiloxy-prop-1-ynyl)phenyl)formimidate 

Relevant articles and documents

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