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Wikipedia

Trimethylsilyl azide

April 01, 2024

Trimethylsilyl azide is the organosilicon compound with the formula (CH3)3SiN3. A colorless liquid, it is a reagent in organic chemistry, serving as the equivalent of hydrazoic acid.[1]

Trimethylsilyl azide
Names
Preferred IUPAC name
Azidotri(methyl)silane
Identifiers
  • 4648-54-8 Y
3D model (JSmol)
  • Interactive image
1903730
ChemSpider
  • 70747 Y
ECHA InfoCard 100.022.798
EC Number
  • 225-078-5
  • 78378
  • DTXSID3063542
  • InChI=1S/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3 Y
    Key: SEDZOYHHAIAQIW-UHFFFAOYSA-N Y
  • InChI=1/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3
    Key: SEDZOYHHAIAQIW-UHFFFAOYAJ
  • [N-]=[N+]=N[Si](C)(C)C
Properties
C3H9N3Si
Molar mass 115.211 g·mol−1
Appearance colorless liquid
Density 0.8763 g/cm3 (20 °C)
Melting point −95 °C (−139 °F; 178 K)
Boiling point 52 to 53 °C (126 to 127 °F; 325 to 326 K) at 175 mmHg (92 to 95 °C at 760 mmHg)
reacts to form dangerous hydrazoic acid
Hazards
GHS labelling:
Danger
H225, H301, H311, H331, H410
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P311, P312, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
Health 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
3
0
Flash point 6 °C (43 °F; 279 K)
> 300 °C (572 °F; 573 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Preparation edit

Trimethylsilyl azide is commercially available. It may be prepared by the reaction of trimethylsilyl chloride and sodium azide:[2]

(CH3)3Si−Cl + NaN3 → (CH3)3Si−N3 + NaCl

Reactions edit

The compound hydrolyzes to hydrazoic acid:[3]

(CH3)3SiN3 + H2O → (CH3)3SiOH + HN3

The compound adds to ketones and aldehydes to give the siloxy azides and subsequently tetrazoles:[1]

(CH3)3SiN3 + R2CO → R2C(N3)OSi(CH3)3

It ring-opens epoxides to give azido alcohols.

It has been used in the Oseltamivir total synthesis.

Safety edit

Trimethylsilyl azide is incompatible with moisture, strong oxidizing agents, and strong acids. Azides are often explosive, as illustrated by their use in air bags.

References edit

  1. ^ a b Nishiyama, Kozaburo; Wang, Cheng; Lebel, Hélène (2016). "Azidotrimethylsilane". Encyclopedia of Reagents for Organic Synthesis. pp. 1–16. doi:10.1002/047084289X.ra117.pub3. ISBN 9780470842898.
  2. ^ L. Birkofer and P. Wegner (1970). "Trimethylsilyl azide". Organic Syntheses. 50: 107. doi:10.15227/orgsyn.050.0107.
  3. ^ Jafarzadeh, Mohammad (2007). "Trimethylsilyl Azide (TMSN3): A Versatile Reagent in Organic Synthesis". Synlett. 2007 (13): 2144–2145. doi:10.1055/s-2007-984895.

April 01, 2024
trimethylsilyl, azide, organosilicon, compound, with, formula, 3sin3, colorless, liquid, reagent, organic, chemistry, serving, equivalent, hydrazoic, acid, namespreferred, iupac, name, azidotri, methyl, silaneidentifierscas, number, 4648, model, jsmol, interac. Trimethylsilyl azide is the organosilicon compound with the formula CH3 3SiN3 A colorless liquid it is a reagent in organic chemistry serving as the equivalent of hydrazoic acid 1 Trimethylsilyl azide NamesPreferred IUPAC name Azidotri methyl silaneIdentifiersCAS Number 4648 54 8 Y3D model JSmol Interactive imageBeilstein Reference 1903730ChemSpider 70747 YECHA InfoCard 100 022 798EC Number 225 078 5PubChem CID 78378CompTox Dashboard EPA DTXSID3063542InChI InChI 1S C3H9N3Si c1 7 2 3 6 5 4 h1 3H3 YKey SEDZOYHHAIAQIW UHFFFAOYSA N YInChI 1 C3H9N3Si c1 7 2 3 6 5 4 h1 3H3Key SEDZOYHHAIAQIW UHFFFAOYAJSMILES N N N Si C C CPropertiesChemical formula C 3H 9N 3SiMolar mass 115 211 g mol 1Appearance colorless liquidDensity 0 8763 g cm3 20 C Melting point 95 C 139 F 178 K Boiling point 52 to 53 C 126 to 127 F 325 to 326 K at 175 mmHg 92 to 95 C at 760 mmHg Solubility in water reacts to form dangerous hydrazoic acidHazardsGHS labelling PictogramsSignal word DangerHazard statements H225 H301 H311 H331 H410Precautionary statements P210 P233 P240 P241 P242 P243 P261 P264 P270 P271 P273 P280 P301 P310 P302 P352 P303 P361 P353 P304 P340 P311 P312 P321 P322 P330 P361 P363 P370 P378 P391 P403 P233 P403 P235 P405 P501NFPA 704 fire diamond 430Flash point 6 C 43 F 279 K Autoignitiontemperature gt 300 C 572 F 573 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Preparation 2 Reactions 3 Safety 4 ReferencesPreparation editTrimethylsilyl azide is commercially available It may be prepared by the reaction of trimethylsilyl chloride and sodium azide 2 CH3 3Si Cl NaN3 CH3 3Si N3 NaClReactions editThe compound hydrolyzes to hydrazoic acid 3 CH3 3SiN3 H2O CH3 3SiOH HN3The compound adds to ketones and aldehydes to give the siloxy azides and subsequently tetrazoles 1 CH3 3SiN3 R2CO R2C N3 OSi CH3 3It ring opens epoxides to give azido alcohols It has been used in the Oseltamivir total synthesis Safety editTrimethylsilyl azide is incompatible with moisture strong oxidizing agents and strong acids Azides are often explosive as illustrated by their use in air bags References edit a b Nishiyama Kozaburo Wang Cheng Lebel Helene 2016 Azidotrimethylsilane Encyclopedia of Reagents for Organic Synthesis pp 1 16 doi 10 1002 047084289X ra117 pub3 ISBN 9780470842898 L Birkofer and P Wegner 1970 Trimethylsilyl azide Organic Syntheses 50 107 doi 10 15227 orgsyn 050 0107 Jafarzadeh Mohammad 2007 Trimethylsilyl Azide TMSN3 A Versatile Reagent in Organic Synthesis Synlett 2007 13 2144 2145 doi 10 1055 s 2007 984895 Retrieved from https en wikipedia org w index php title Trimethylsilyl azide amp oldid 1159829803, wikipedia, wiki, book, books, library,

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