94397-40-7

Basic information

• Product Name: 1-(Trimethylsilyl)allyl bromide
• Synonyms: 1-(Trimethylsilyl)allyl bromide;1-Bromo-2-propenyltrimethylsilane;α-Bromoallyltrimethylsilane
• CAS NO: 94397-40-7
• Molecular Formula: C₆H₁₃BrSi
• Molecular Weight: 0
• Mol File: 94397-40-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(Trimethylsilyl)allyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(Trimethylsilyl)allyl bromide(94397-40-7)
• EPA Substance Registry System: 1-(Trimethylsilyl)allyl bromide(94397-40-7)

Safety Data

• Hazardous Substances Data: 94397-40-7(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 593-60-2 Vinyl bromide 
• 106-95-6 allyl bromide 

Downstream Products

• 341525-07-3 (E)-4-Bromo-1-phenyl-but-3-en-1-ol 
• 94397-61-2 ((E)-6-Bromo-3-ethoxy-hex-5-enyl)-benzene 
• 94397-30-5 2-((E)-4-Bromo-1-propyl-but-3-enyl)-cyclohexanone 
• 94397-63-4 ((E)-7-Bromo-4-ethoxy-hept-6-enyl)-benzene 
• 85125-31-1 threo-1-phenyl-2-(trimethylsilyl)-3-buten-1-ol 
• 140150-01-2 (Z)-1-Bromo-4-phenyl-1-pentene 
• 140150-00-1 (E)-1-Bromo-4-phenyl-1-pentene 
• 34602-23-8 1-Phenyl-3-(trimethylsilyl)-4-penten-1-yne 
• 202119-11-7 (3S,4R,5S,6S,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-7-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-5-methyl-3-trimethylsilanyl-oct-1-en-4-ol 
• 299411-65-7 2-(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-trimethylsilylpent-4-en-2-ol 
• 184291-96-1 (+)-tert-butyl-[(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dienyloxy]dimethylsilane 
• 869338-46-5 1-[(Z)-(1S,2S)-1-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-methyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene 
• 869338-64-7 1-[(Z)-(1S,2S)-1-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1R,2R)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-methyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene 
• 479673-25-1 (1R,2R,3S,4S,5Z)-1-{3-(tert-butyldimethylsilanyloxy)-1-[3-(tert-butyldimethylsilanyloxy)propyl]-2,4-dimethylocta-5,7-dienyloxymethyl}-4-methoxybenzene 

Relevant articles and documents

Bioinspired intramolecular diels-alder reaction: A rapid access to the highly-strained cyclopropane-fused polycyclic skeleton

A bioinsipred gold-catalyzed tandem Diels-Alder/Diels-Alder reaction of an enynal and a 1,3-diene, forming the highly-strained benzotricyclo[3.2.1.0 2,7]octane skeleton, was reported. In contrast, a Diels-Alder/Friedel-Crafts tandem reaction occurred instead when silver salts were used as the catalyst. Although both reactions experienced the similar Diels-Alder reaction of a pyrylium intermediate with a 1,3-diene, they have different reaction mechanisms. The former proceeded with a stepwise Diels-Alder reaction, while the latter one with a concerted one. Mother nature knows best! A gold-catalyzed reaction of enynals and 1,3-dienes, giving rapid access to the highly strained benzotricyclo[3.2.1.02,7]octane skeleton, is reported (see scheme; QMD=quinodimethane). Owing to the mild reaction conditions, excellent substrate scope, and high functional-group tolerance, this system holds potential for the construction of complex molecules with the tricyclo[3.2.1.02,7]octane skeleton. Copyright

Highly stereoselective total synthesis of (+)-9-epi-Dictyostatin and (-)-12,13-Bis-epi-dictyostatin

The total syntheses of (+)-9-epi-dictyostatin (1a) and (-)-12,13-bis-epi- dictyostatin (1b), diastereomers of the antimitotic marine sponge-derived macrolide (-)-dictyostatin (1), were achieved by creating 11 stereogenic centers and 4stereogenic double bonds with a high level of stereocontrol. The yield for the 29-step longest linear sequence from Roche ester was 1.53 and 1.52%, respectively. The final key steps to these unnatural products were the addition of vinylzincates C10-C26 to aldehyde C1-C9 (leading surprisingly to complete stereoselectivity for the 9R-configuration in 28a and for the 9S-configuration in 12,13-bis-epimeric 28b), followed by Yamaguchi macrolactonization and global deprotection. (-)-12,13-Bis-epi-dictyostatin (1b) displayed a dramatic decrease of cytotoxicity and of the affinity toward the paclitaxel binding site of microtubules. Eleven stereogenic centers and fourstereogenic double bonds were obtained with a high level of stereocontrol in the total synthesis of (+)-9-epi-dictyostatin and(-)-12,13-bis-epi-dictyostatin, diastereomers of the antimitotic marine sponge-derived macrolide (-)-dictyostatin.

Trimethylsilylation of carbenoids generated in situ from allyl and benzyl halides

Efficient procedures for the trimethylsilylation of the transient carbenoids H2C=CHCH(X)Li and PhCH(X)Li (X = Cl or Br) are described.