1078-31-5

Basic information

• Product Name: 2-(TRIMETHYLSILOXY)BENZALDEHYDE
• Synonyms: 2-(TRIMETHYLSILOXY)BENZALDEHYDE;2-(TRIMETHYLSILYLOXY)BENZALDEHYDE;o-[(trimethylsilyl)oxy]benzaldehyde;2-(Trimethylsilyloxy)benzaldehyde 97%;2-Benzaldehyde;2-(Trimethylsilyloxy)benzaldehyde97%
• CAS NO: 1078-31-5
• Molecular Formula: C₁₀H₁₄O₂Si
• Molecular Weight: 194.3
• EINECS: 214-081-7
• Mol File: 1078-31-5.mol

Chemical Properties

• Boiling Point: 116 °C
• Flash Point: 142°C/25mm
• Appearance: /
• Density: 1,013 g/cm3
• Vapor Pressure: 0.0729mmHg at 25°C
• Refractive Index: 1.5095
• Sensitive: Air & Moisture Sensitive
• BRN: 1939281
• CAS DataBase Reference: 2-(TRIMETHYLSILOXY)BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(TRIMETHYLSILOXY)BENZALDEHYDE(1078-31-5)
• EPA Substance Registry System: 2-(TRIMETHYLSILOXY)BENZALDEHYDE(1078-31-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36/37/39
• TSCA: No
• Hazardous Substances Data: 1078-31-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(TRIMETHYLSILOXY)BENZALDEHYDE is used as a reagent in various organic reactions, such as the Wittig reaction, Grignard reaction, and nucleophilic addition, for its ability to participate in a wide range of chemical transformations.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(TRIMETHYLSILOXY)BENZALDEHYDE is utilized as a versatile intermediate in the synthesis of various organic compounds, contributing to the development of new drugs and medicinal agents.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 2-(TRIMETHYLSILOXY)BENZALDEHYDE serves as a key intermediate, playing a crucial role in the creation of agrochemicals for agricultural applications.

InChI:InChI=1/C10H14O2Si/c1-13(2,3)12-10-7-5-4-6-9(10)8-11/h4-8H,1-3H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 90-02-8 salicylaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 2549-08-8 3-benzamidocoumarin 
• 137401-65-1 (Z)-4-(2'-hydroxyphenylmethylene)-2-phenyloxazol-5(4H)-one 
• 93782-13-9 β,β-dibromo-o-(trimethylsilyloxy)styrene 
• 80597-60-0 5-Hydroxy-4-[3-hydroxy-3-(2-hydroxy-phenyl)-propionyl]-2,2,6,6-tetramethyl-cyclohex-4-ene-1,3-dione 
• 80597-61-1 5-Hydroxy-4-[3-hydroxy-3-(2-trimethylsilanyloxy-phenyl)-propionyl]-2,2,6,6-tetramethyl-cyclohex-4-ene-1,3-dione 
• 60125-23-7 (E)-3-(2-hydroxyphenyl)propenal 
• 90-02-8 salicylaldehyde 
• 74552-62-8 3-Methoxy-2-phenylbenzofuran 
• 24731-35-9 [2-(Cyano-trimethylsilanyloxy-methyl)-phenyl]-trimethylsilanyloxy-acetonitrile 

Relevant articles and documents

A Tandem Aminoalkylation of Aldehydes; Application to the Synthesis of Substituted Phenols and Naphthols 1

Treatment of a protected salicylic aldehyde (2) and 2-hydroxy-1 -naphthaldehyde (6) with (trimethylsilyl)dialkylamines and various nucleophiles in a 5 M diethyl ether solution of lithium perchlorate gives a variety of N,N-dialkylaminophenols (4) and 1-(N,N-dialkylamino)-2-naphthols (8) in short reaction times and in good yields.

Fast and efficient method for Silylation of alcohols and phenols with HMDS in the presence of bis-thiourea complexes of cobalt, nickel, copper and zinc chlorides

Bis-thiourea complexes of cobalt, nickel, copper and zinc chlorides were used efficiently for rapid and efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) in CH3CN. All reactions were carried out at room temperature within immediate-120?min timeframe to afford trimethylsilyl ether derivatives in high to excellent yields. Investigation of the results exhibited that the prepared bis-thiourea metal complexes show the activity as Co(tu)2Cl2> Ni(tu)2Cl2> Cu(tu)2Cl2> Zn(tu)2Cl2 in their silylation reactions.

Rapid and efficient trimethylsilyl protection of hydroxyl groups catalyzed by niobium(V) chloride

An efficient and convenient procedure for the trimethylsilylation of a wide variety of alcohols, including primary, benzylic, secondary, and phenols with hexamethyldisilazane, has been developed. The reactions were carried out at room temperature in the presence of a catalytic amount of niobium(V) chloride and afforded the corresponding trimethylsilyl ethers in high to excellent yields in short time. Copyright Taylor & Francis Group, LLC.

Sulfonated ordered nanoporous carbon (CMK-5-SO3H) as an efficient and highly recyclable catalyst for the silylation of alcohols and phenols with hexamethyldisilazane (HMDS)

An environmentally friendly catalytic system for trimethylsilylation of alcohols and phenols with hexamethyldisilazane can be successfully carried out for the first time over sulfonated mesoporous carbon catalyst (CMK-5-SO 3H) in dichloromethane at ambient temperature and excellent conversions were obtained. Furthermore, the catalyst displays high activity and thermal stability (to 200 °C) and it can be reused repeatedly for at least 25 cycles without any evidence of loss of activity, confirming the stability of covalent bonding of acidic centers.

Silylation of hydroxy groups with HMDS under microwave irradiation and solvent-free conditions

Phenols and alcohols are silylated with hexamethyldisilazane (HMDS) under microwave irradiation in solvent-free condition in good to excellent yields.

A Simple and Highly Stereoselective Route to E-α,β-Unsaturated Aldehydes

Zinc bromide mediated reaction of α,α-bis(trimethylsilyl)-tert-butylacetaldimine (3) with a wide range of aldehydes takes place under mild conditions and affords the corresponding α,β-unsaturated aldehydes in good yields and with high E stereoselectivity (>98percent).This procedure is successfully applied to the preparation of intermediates for retinoid and natural product synthesis.

THE SYNTHESIS OF VAFZELIN AND SYNCARPIN, CONSTITUTENTS OF UVARIA AFZELII

Efficient syntheses of vafzelin and syncarpin, unusual plant metabolites from Uvaria afzelii, are described.