355121-52-7

Basic information

• Product Name: 3,5-BIS-(ALLYLOXY)-4-BROMOBENZALDEHYDE
• Synonyms: 3,5-BIS-(ALLYLOXY)-4-BROMOBENZALDEHYDE
• CAS NO: 355121-52-7
• Molecular Formula: C₁₃H₁₃BrO₃
• Molecular Weight: 297.14452
• Mol File: 355121-52-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,5-BIS-(ALLYLOXY)-4-BROMOBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-BIS-(ALLYLOXY)-4-BROMOBENZALDEHYDE(355121-52-7)
• EPA Substance Registry System: 3,5-BIS-(ALLYLOXY)-4-BROMOBENZALDEHYDE(355121-52-7)

Safety Data

• Hazardous Substances Data: 355121-52-7(Hazardous Substances Data)

Upstream product

• 16534-12-6 3,5-dihydroxy-4-bromobenzoic acid 
• 355121-57-2 3,5-bis-allyloxy-4-bromo-benzoic acid allyl ester 
• 355121-58-3 (3,5-bis-allyloxy-4-bromo-phenyl)-methanol 

Downstream Products

• 355121-66-3 (S)-4-(2-(3,5-bis(allyloxy)-4-bromobenzylamino)-3-hydroxypropyl)phenol 
• 1070782-13-6 (2E)-3-(3,5-bis(2-propenyloxy)-4-bromophenyl)-1-[2-methoxy-4,6-bis(2-propenyloxy)phenyl]-2-propen-1-one 
• 1207843-61-5 3,5-diallyloxy-4-bromo-benzaldehyde (5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl)hydrazone 
• 355121-65-2 carbonic acid allyl ester 4-[(S)-2-[allyloxycarbonyl-(3,5-bis-allyloxy-4-bromo-benzyl)-amino]-3-(triisopropyl-silanyloxy)-propyl]-phenyl ester 
• 355121-64-1 4[(S)-2-(3,5-bis-allyloxy-4-bromo-benzylamino)-3-(triisopropyl-silanyloxy)-propyl]-phenol 

Relevant articles and documents

Large scale synthesis of the Cdc42 inhibitor secramine A and its inhibition of cell spreading

We describe a large scale synthesis of secramine A. Consistent with its ability to inhibit activation of the small GTPase Cdc42, we find that secramine A inhibits cell spreading, a process previously shown to be Cdc42-dependent. The Royal Society of Chemistry 2006.

Experimental and theoretical studies on the thermal decomposition of heterocyclic nitrosimines

A series of substituted 2-nitrosiminobenzothiazolines (2) were synthesized by the nitrosation of the corresponding 2-iminobenzothiazolines (6). Thermal decomposition of 2a-f and of the seleno analogue 7 in methanol and of 3-methyl-2-nitrosobenzothiazoline (2a) in acetonitrile, 1,4-dioxane, and cyclohexane followed first-order kinetics. The activation parameters for thermal deazetization of 2a were measured in cyclohexane (ΔH? = 25.3 ± 0.5 kcal/mol, ΔS? = 1.3 ± 1.5 eu) and in methanol (ΔH? = 22.5 ± 0.7 kcal/mol, ΔS? = -12.9 ± 2.1 eu). These results indicate a unimolecular decomposition and are consistent with a proposed stepwise mechanism involving cyclization of the nitrosimine followed by loss of N2. The ground-state conformations of the parent nitrosiminothiazoline (9a) and transition states for rotation around the exocyclic C=N bond, electrocyclic ring closure, and loss of N2 were calculated using ab initio molecular orbital theory at the MP2/6-31G* level. The calculated gas-phase barrier height for the loss of N2 from 9a (25.2 kcal/mol, MP4(SDQ, FC)/6-31G*//MP2/6-31G* + ZPE) compares favorably with the experimental barrier for 2a of 25.3 kcal/mol in cyclohexane. The potential energy surface is unusual; the rotational transition state 9a-rot-ts connects directly to the orthogonal transition state for ring-closure 9aTS. The decoupling of rotational and pseudopericyclic bond-forming transition states is contrasted with the single pericyclic transition state (15TS) for the electrocyclic ring-opening of oxetene (15) to acrolein (16). For comparison, the calculated homolytic strength of the N-NO bond is 40.0 kcal/mol (MP4(SDQ, FC)/6-31G* + ZPE).