82815-75-6

Basic information

• Product Name: 4-(4-AMINO-PHENYL)-2-METHYL-BUT-3-YN-2-OL
• Synonyms: TIMTEC-BB SBB010577;ASINEX-REAG BAS 10979688;4-(4-AMINO-PHENYL)-2-METHYL-BUT-3-YN-2-OL
• CAS NO: 82815-75-6
• Molecular Formula: C₁₁H₁₃NO
• Molecular Weight: 175.23
• Mol File: 82815-75-6.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(4-AMINO-PHENYL)-2-METHYL-BUT-3-YN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-AMINO-PHENYL)-2-METHYL-BUT-3-YN-2-OL(82815-75-6)
• EPA Substance Registry System: 4-(4-AMINO-PHENYL)-2-METHYL-BUT-3-YN-2-OL(82815-75-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 82815-75-6(Hazardous Substances Data)

Upstream product

• 115-19-5 2-methyl-but-3-yn-2-ol 
• 540-37-4 p-aminoiodobenzene 
• 106-40-1 4-bromo-aniline 
• 1453813-96-1 tert-butyl (4-(3-hydroxy-3-methylbut-1-yn-1-yl)phenyl)carbamate 

Downstream Products

• 14235-81-5 4-Ethynylaniline 
• 120517-37-5 4-(3-hydroxy-3-methyl-1-butynyl)-1-iodobenzene 
• 67973-34-6 1,2-bis(4-iodophenyl)acetylene 
• 191094-12-9 4-[(4-iodophenyl)ethynyl]aniline 
• 119754-26-6 dimethyl 4-(4-aminophenylethynyl)-2,6-pyridinedicarboxylate 
• 92866-00-7 4-ethynyltolane 
• 120517-38-6 diethyl 4-<4-(phenylethynyl)phenylethynyl>-2,6-pyridinedicarboxylate 
• 120517-40-0 4-<4-(phenylethynyl)phenylethynyl>-2,6-bispyridine 
• 120517-39-7 dipotasium salt of 4-<4-(phenylethynyl)phenylethynyl>-2,6-pyridinedicarboxylic acid 
• 1420536-06-6 C₂₂H₁₆N₂O₂ 
• 1453813-97-2 S-(11-((4-(3-methyl-3-((2-nitrobenzyl)oxy)but-1-yn-1-yl)phenyl)amino)-11-oxoundecyl)ethanethioate 

Relevant articles and documents

Molecular design directs self-assembly of DPP polycatenars into 2D and 3D complex nanostructures

Novel diketopyrrolopyrrole (DPP) based polycatenars characterized with a long π-conjugated rigid calamitic core, different side groups (t-Boc, H or PEO) at the lactam N atoms of the central DPP core and terminal hydrophobic paraffinic chains were prepared

Utilizing a copper-free Sonogashira reaction in the synthesis of the leukotriene a4 hydrolase modulator batatasin IV

Batatasin IV is a dihydrostilbenoid isolated from Chinese yams which was shown to have inhibitory activities against plant growth. Later studies showed that this compound may exhibit anti-inflammatory properties by inhibiting the epoxide hydrolase activity of the leukotriene A4 hydrolase enzyme. To access the dihydrostilbenoid skeleton, a copper-free SPhos-mediated Sonogashira reaction was conceived and the substrate scope was explored. Our results indicate that the reaction can tolerate the presence of free alcohols, aldehydes, nitro groups, and anilinyl groups. However, a substituent with an acidic phenol or carboxylic acid group gave significantly lower yields. Next, a total synthesis of batatasin IV was accomplished in 16% overall yield incorporating the reported copper-free Sonogashira reaction. Finally, we show that batatasin IV inhibits the hydrolysis of alanine p-nitroanilide by leukotriene A4 hydrolase with an IC50 of 91.4 μM.

A photolabile protection strategy for terminal alkynes

We present a strategy for photolabile protection of terminal alkynes. Several photo-caged alcohols were synthesized via mild copper(II)-catalyzed substitution between tertiary propargylic alcohols and 2-nitrobenzyl alcohol to build up robust, base stable o-nitrobenzyl (NB) photo-cleavable compounds. We compare the new photolabile protecting group with the commonly used alkyne protecting group, 2-methyl-3-butyn-2-ol and the results show that NB ethers are stable under the cleaving conditions for the cleavage of methylbutynol protected alkynes. Additionally, we present the synthesis of photo-cleavable NB derivatives containing thiol groups that can serve as agents for photoinduced surface functionalization reactions.