4-(Trimethylsilylethynyl)benzaldehyde

HCID 2771643CAS 77123-57-0

Substructure search Find similar structures

Basic information

Standard SMILES: C[Si](C)(C)C#Cc1ccc(C=O)cc1
InChIKey: UZQDUXAJFTWMDT-UHFFFAOYSA-N
Molecular formula: C12H14OSi
Average molar mass: 202.32 g/mol
Monoisotopic mass: 202.0813916

Names & identifiers

Preferred name: 4-(Trimethylsilylethynyl)benzaldehyde
IUPAC: 4-(2-trimethylsilylethynyl)benzaldehyde
English name: 4-(Trimethylsilyl)ethynylbenzaldehyde
Molecular formula: C12H14OSi
Molecular weight: 202.32

Names & synonyms

4-(trimethylsilylethynyl)benzaldehydeRefChem:517219878-916-277123-57-04-[(Trimethylsilyl)ethynyl]benzaldehyde4-((Trimethylsilyl)ethynyl)benzaldehyde4-(Trimethylsilyl)ethynylbenzaldehyde4-[2-(trimethylsilyl)ethynyl]benzaldehyde4-(2-trimethylsilylethynyl)benzaldehydeMFCD02093765DTXSID90377990p-trimethylsilylethynylbenzaldehyde

Show more names

DK9024-[(TriMethylsilyl)ethynyl]benzaldehy4-[(trimethylsilyl)ethynyl]bezaldehyde4-[(Trimethysilyl)-ethynyl]benzaldehyde4-[(TriMethylsilyl)ethynyl]benzaldehyde 97%Benzaldehyde, 4-[2-(trimethylsilyl)ethynyl]-4-((Trimethylsilyl)ethynyl)benzaldehyde - [T55948]

4-trimethylsilanylethynyl-benzaldehydeSY081454T38274-(2-(TRIMETHYLSILYL)ETHYNYL) BENZALDEHYDE4-(2-(trimethylsilyl)ethynyl)benzaldehyde4-trimethylsiBenzaldehyde, 4-[(trimethylsilyl)ethynyl]-SCHEMBL701214

Database identifiers

CAS: 77123-57-0
PubChem CID: 2771643
DTXSID: DTXSID90377990
EC Number: 878-916-2
Nikkaji: J1.067.536G

Properties

Computed structural properties

Topological polar surface area: 17.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 3
Heavy atoms: 14
Formal charge: 0
Complexity: 255

Physicochemical properties

Melting point: 66 · 66-70 °C(lit.)
Boiling point: 262.1 · 262.1±32.0 °C(Predicted)
Density: 0.98 · 0.98±0.1 g/cm3(Predicted)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
Appearance: Light brown to brown Solid
InChI: 1S/C12H14OSi/c1-14(2,3)9-8-11-4-6-12(10-13)7-5-11/h4-7,10H,1-3H3
InChIKey: UZQDUXAJFTWMDT-UHFFFAOYSA-N
SMILES: C[Si](C)(C)C#Cc1ccc(C=O)cc1
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: T
WGK Germany: 3 · 3
HazardClass: IRRITANT
HS Code: 2931900090 · 2931900090
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 2931900090
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: T
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Precautionary statements: P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Applications · 2 items

Uses4-(Trimethylsilyl)ethynylbenzaldehyde is a useful reactant for the synthesis of acetylene-substituted naphthalene diimides in polar solvents.

General Description4-[(Trimethylsilyl)ethynyl]benzaldehyde can be synthesized by reacting 4-bromobenzaldehyde and triphenylphosphine in anhydrous triethylamine with ethynyltrimethylsilane and then with palladium(II) acetate under argon. It can also be prepared by Sonogashira coupling reaction between 4-bromobenzaldehyde and (trimethylsilyl) ethynyl.