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Tritylpropyl ether, also known as triphenylmethylpropyl ether, is an organic compound with the chemical formula C21H22O. It is a colorless, crystalline solid that is soluble in organic solvents and has a melting point of 70-72°C. This ether derivative is formed by the reaction of trityl chloride (C6H5CCl3) with propanol (C3H7OH) in the presence of a base, such as potassium carbonate. Tritylpropyl ether is primarily used as a protecting group in organic synthesis, particularly in the protection of alcohols and phenols, due to its stability and ease of removal under mild acidic conditions. It is also employed as a reagent in various chemical reactions, including the preparation of other trityl derivatives and the synthesis of complex organic molecules.

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  • 13594-77-9 Structure
  • Basic information

    1. Product Name: Tritylpropyl ether
    2. Synonyms: Triphenylmethyl(propyl) ether;Tritylpropyl ether
    3. CAS NO:13594-77-9
    4. Molecular Formula: C22H22O
    5. Molecular Weight: 302.41
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 13594-77-9.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: Tritylpropyl ether(CAS DataBase Reference)
    10. NIST Chemistry Reference: Tritylpropyl ether(13594-77-9)
    11. EPA Substance Registry System: Tritylpropyl ether(13594-77-9)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 13594-77-9(Hazardous Substances Data)

13594-77-9 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 13594-77-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,5,9 and 4 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 13594-77:
(7*1)+(6*3)+(5*5)+(4*9)+(3*4)+(2*7)+(1*7)=119
119 % 10 = 9
So 13594-77-9 is a valid CAS Registry Number.

13594-77-9Relevant articles and documents

Highly efficient protection of alcohols as trityl ethers under solvent-free conditions, and recovery catalyzed by reusable nanoporous MCM-41-SO3H

Gholamzadeh, Zeynab,Naimi-Jamal, Mohammad Reza,Maleki, Ali

, p. 994 - 1001 (2015/01/09)

An efficient method was developed for the protection of alcohols as trityl ethers using triphenylmethanol in the presence of nanoporous MCM-41-SO3H as a heterogeneous catalyst under solvent-free ball-milling at room temperature. Low catalyst loading, high efficiency, reusability are among the advantages of this new solvent-free and environmentally friendly method. The deprotection of the produced trityl ethers was also efficiently achieved using the same catalyst in wet acetonitrile.

Zinc chloride homogeneous catalysis in the tritylation of hydroxyl- and amide-bearing molecules

Maltese, Maurizio,Vergari, Maria Cecilia,Donzello, Maria Pia

supporting information; experimental part, p. 483 - 487 (2011/03/18)

A tritylation protocol based on the transfer of the triphenylmethylcarbenium ion from trityl acetate to substrates having hydroxyls, in the presence of catalytic amounts of ZnCl2, is described. The advantages of this method are broad scope, mild conditions, and easy handling. The comparison with the procedure based on the use of equimolar mixture of TrCl and ZnCl2 in the presence of TEA shows that comparable results are obtained. However, only this method allows reactions of secondary or benzylic alcohols such as oxidation or formation of symmetric ethers to be suppressed. Both procedures are successfully extended to simple and substituted amides. Irrespective of its low solubility in acetonitrile, even asparagine can be directly tritylated on its amide group.

Tetrazoles: XLIV. Synthesis and chemical properties of 5-substituted 2-triphenylmethyltetrazoles

Myznikov,Artamonova,Bel'skii,Stash,Skvortsov,Koldobskii

, p. 1360 - 1369 (2007/10/03)

Tritylation of tetrazole and its 5-substituted derivatives with triphenylmethyl chloride under conditions of phase-transfer catalysis regioselectively yields the corresponding 5-substituted 2-trityltetrazoles which can be used to protect N-H bonds in nitrogen-containing heterocycles and O-H bonds in primary alcohols. Thermolysis of 2-trityltetrazoles in benzonitrile leads to 3,6-disubstituted 1,2,4,5-tetrazines. Thermal transformation of the same compounds in dodecane follows a radically different mechanism, resulting in formation of difficultly accessible 8,8-diphenylheptafulvenes. The structure of the latter was proved by X-ray analysis.

Transetherification of allylic and benzylic ethers in the presence of ferric ion

Salehi, Peyman,Irandoost, Mohsen,Seddighi, Behnam,Kargar Behbahani, Farahnaz,Tahmasebi, Daryush Poor

, p. 1743 - 1747 (2007/10/03)

Alcoholysis of allylic, secondary and tertiary benzylic ethers is proceeded efficiently in the presence of catalytic amounts of ferric ion as anhydrous FeCl3 and Fe(ClO4)3.

Selective and efficient alcoholyses of allylic, secondary- and tertiary benzylic alcohols in the presence of iron(III)

Salehi, Peyman,Iranpoor, Nasser,Behbahani, Farahnaz Kargar

, p. 943 - 948 (2007/10/03)

An efficient and selective method for the conversion of allylic, secondary- and tertiary benzylic alcohols into their corresponding ethers in the presence of iron(III) as FeCl3 and Fe(ClO4)3 under solvolytic condition is d

Alcoholyses and acetolyses of allylic and tertiary benzylic alcohols catalyzed by 2,3-dichloro-5,6-dicyanobenzoquinone

Iranpoor,Mottaghinejad

, p. 2253 - 2260 (2007/10/02)

Allylic and tertiary benzylic alcohols can be converted into their corresponding ethers and acetates selectively and efficiently in the presence of catalytic amounts of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ).

Catalytic and Efficient Cleavage of Allylic and Tertiary Benzylic Ethers and Esters with Ce(IV)

Iranpoor, Nasser,Mottaghinejad, Enayatolah

, p. 7299 - 7306 (2007/10/02)

The reaction of cerium(IV) as ceric ammonium nitrate (CAN) with a variety of allylic and tertiary benzylic ethers and esters has been examined in different alcohols and acetic acid under catalytic and mild conditions.Experiments have been conducted to elu

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