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ChemicalBook--->CAS DataBase List--->91424-40-7

91424-40-7

91424-40-7 Structure

91424-40-7 Structure
IdentificationMore
[Name]

3-(tert-Butyldimethylsilyloxy)glutaric anhydride
[CAS]

91424-40-7
[Synonyms]

3-(TERT-BUTYLDIMETHYLSILYLOXY)GLUTARIC ANHYDRIDE
3-[(TERT-BUTYLDIMETHYLSILYL)OXY] PENTANEDIOIC ANHYDRIDE
(3R)-3-[(terbutyldimethylsilyl)oxy]glutaric anhydride
[EINECS(EC#)]

618-749-2
[Molecular Formula]

C11H20O4Si
[MDL Number]

MFCD00075235
[Molecular Weight]

244.36
[MOL File]

91424-40-7.mol
Chemical PropertiesBack Directory
[Melting point ]

79-81 °C(lit.)
[Boiling point ]

302.4±35.0 °C(Predicted)
[density ]

1.030
[Fp ]

>113°(235°F)
[refractive index ]

1.4510
[storage temp. ]

2-8°C
[form ]

Solid
[Appearance]

White to off-white Solid
[Sensitive ]

Moisture Sensitive
[InChI]

InChI=1S/C11H20O4Si/c1-11(2,3)16(4,5)15-8-6-9(12)14-10(13)7-8/h8H,6-7H2,1-5H3
[InChIKey]

RXAJGRHLLRGVSB-UHFFFAOYSA-N
[SMILES]

C1(=O)OC(=O)CC(O[Si](C(C)(C)C)(C)C)C1
[CAS DataBase Reference]

91424-40-7(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
[WGK Germany ]

3
Hazard InformationBack Directory
[Uses]

3-(tert-Butyldimethylsilyloxy)glutaric anhydride was employed as starting material for the preparation of labeling reagents.
[Synthesis]

3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]pentanedioic Acid Diethyl Ester

91424-39-4

3-(tert-Butyldimethylsilyloxy)glutaric anhydride

91424-40-7

The general procedure for the synthesis of 3-tert-butyldimethylsilyloxyglutaric anhydride from diethyl 3-(tert-butyldimethylsilyloxy)glutarate is as follows: B.4 - [[(dimethylethyl)dimethylsilyl]oxy]dihydro-2H-pyran-2,6(3H)-dione Part A: Methylsilyl ether (theoretical value 63.6 g, 200 mmol) was dissolved in methanol (200 ml), NaOH pellets (16.0 g, 400 mmol) were added and stirred at room temperature for 18 h under argon protection. The turbid yellow solution was evaporated to dryness and dried under vacuum to give the disodium salt as a light yellow solid. The disodium salt (42.1 g) was suspended in benzene (400 ml), acetic anhydride (200 ml) was added and refluxed under argon protection for 1.5 hours. The brown mixture was concentrated in vacuum and the residue was partitioned between ethyl acetate and half-saturated and NaHCO3 solution. The organic phase was washed with half-saturated and NaHCO3 and saturated NaCl solution, dried over Na2SO4 and evaporated to give the crude title anhydride as a brown solid. The crude product was dissolved in ether, Darco (3 g) was added, filtered through diatomaceous earth and evaporated. The crystallized residue was ground with cold hexane to give the pure title anhydride (33.26 g, 68% overall yield, based on diethyl 3-hydroxyglutarate) as white plate-like crystals with melting point 205 °C (decomposed) and 77°-78 °C (undecomposed).13C-NMR (15 MHz, CDCl3) δ: 5.22, 17.64, 25.31, 38.88, 61.87 , 165.26 ppm.

[References]

[1] Patent: US4804770, 1989, A
[2] Journal of Organic Chemistry, 1984, vol. 49, # 19, p. 3657 - 3659
[3] Journal of Organic Chemistry, 1988, vol. 53, # 10, p. 2374 - 2378
[4] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1858 - 1873
[5] European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 631 - 638
Spectrum DetailBack Directory
[Spectrum Detail]

3-(tert-Butyldimethylsilyloxy)glutaric anhydride(91424-40-7)1HNMR
3-(tert-Butyldimethylsilyloxy)glutaric anhydride(91424-40-7)Raman
3-(tert-Butyldimethylsilyloxy)glutaric anhydride(91424-40-7)IR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

91424-40-7(sigmaaldrich)
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