130669-72-6

Basic information

• Product Name: (3AS)-7-BROMO-3A 4 5 7A-TETRAHYDRO-2 2-&
• Synonyms: (3AS)-7-BROMO-3A 4 5 7A-TETRAHYDRO-2 2-&;(3as)-7-bromo-3A,4,5,7A-tetrahydro-2,2-dimethyl-1;(3AS)-7-BROMO-3A,4,5,7A-TETRAHYDRO-2,2-D;[3as-(3aα,4α,5α,7aα)]-7-bromo-3a,4,5,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,5-diol;[3AS-(3AA,4A,5A,7AA)]-7-BROMO-3A,4,5,7A-TETRAHYDRO-2,2-DIMETHYL-1,3-BENZODIOXOLE-4,5-DIOL
• CAS NO: 130669-72-6
• Molecular Formula: C₉H₁₃BrO₄
• Molecular Weight: 265.102
• Product Categories: Chiral Building Blocks;Organic Building Blocks;Polyols
• Mol File: 130669-72-6.mol

Chemical Properties

• Melting Point: 121-124 °C(lit.)
• Boiling Point: 375.69°C at 760 mmHg
• Flash Point: 181.011°C
• Appearance: /
• Density: 1.649g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: ?20°C
• CAS DataBase Reference: (3AS)-7-BROMO-3A 4 5 7A-TETRAHYDRO-2 2-&(CAS DataBase Reference)
• NIST Chemistry Reference: (3AS)-7-BROMO-3A 4 5 7A-TETRAHYDRO-2 2-&(130669-72-6)
• EPA Substance Registry System: (3AS)-7-BROMO-3A 4 5 7A-TETRAHYDRO-2 2-&(130669-72-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 130669-72-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(3AS)-7-BROMO-3A 4 5 7A-TETRAHYDRO-2 2-& is used as a building block in organic synthesis for the creation of more complex molecules. Its unique structure and reactivity make it a valuable component in the synthesis of pharmaceuticals, agrochemicals, or other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (3AS)-7-BROMO-3A 4 5 7A-TETRAHYDRO-2 2-& is used as an intermediate in the development of new drugs. Its chemical properties and reactivity can be harnessed to create novel therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Materials Science:
(3AS)-7-BROMO-3A 4 5 7A-TETRAHYDRO-2 2-& is also used in materials science for the development of new materials with specific properties. Its unique structure and reactivity can contribute to the creation of advanced materials with applications in various industries, such as electronics, coatings, or adhesives.
Further research and analysis are required to fully understand the properties and potential uses of this chemical, as its reactivity and structure may offer new opportunities in various fields.

InChI:InChI=1/C9H13BrO4/c1-9(2)13-7-4(10)3-5(11)6(12)8(7)14-9/h3,5-8,11-12H,1-2H3/t5-,6-,7-,8+/m1/s1

Upstream product

• 130669-75-9 (3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 
• 130669-74-8 (1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol 
• 67451-62-1 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene 
• 108-86-1 bromobenzene 
• 77-76-9 2,2-dimethoxy-propane 
• 82683-92-9 1-Bromo-2,3-dihydroxy-cyclohexa-4,6-diene 

Downstream Products

• 900791-79-9 (1S,2R,5S,6S)-6-(acetyloxy)-2,3,5-tribromo-3-cyclohexenyl acetate 
• 643-10-7 allo-inositol 
• 1393364-60-7 (1R,2R,3R,4R)-1,2-O-diacetyl-5-phenylcarbamoyl-3,4-O-isopropylidenecyclohex-5-ene-1,2,3,4-tetraol 
• 350032-55-2 N-[7-bromo-5-(7-bromo-4-hydroxy-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yloxy)-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yl]-4-methyl-benzenesulfonamide 
• 350032-60-9 N-[7-bromo-5-(7-bromo-5-hydroxy-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yloxy)-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yl]-4-methyl-benzenesulfonamide 
• 1393364-63-0 (1S,2R,3R,4R)-1,2-O-diacetyl-5-phenylcarbamoyl-3,4-O-isopropylidenecyclohex-5-ene-1,2,3,4-tetraol 
• 130698-44-1 (3aS,4R,5S,7aS)-7-bromo-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo-[d][1,3]dioxol-4-ol 
• 372961-82-5 (1S,4S,5R,6R)-2-bromo-4,5,6-tris[(1,1-dimethylethyl)dimethylsiloxy]-2-cyclohexen-1-ol 
• 372961-83-6 (3S,4R,5R,6S)-1-bromo-3,4,5-tris[(1,1-dimethylethyl)dimethylsiloxy]-6-methoxycyclohexene 
• 372961-80-3 (1S,2S,5S,6S)-3-bromo-2,5,6-tris[(1,1-dimethylethyl)dimethylsiloxy]-3-cyclohexen-1-ol 

Relevant articles and documents

Synthesis of a Highly Functionalised and Homochiral 2-Iodocyclohexenone Related to the C-Ring of the Polycyclic, Indole Alkaloids Aspidophytine and Haplophytine

The enzymatically-derived and enantiomerically pure (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol (7) has been elaborated over 10 steps into cyclohexenone 8. The latter compound embodies the enantiomeric form of the C-ring associated with the hexacyclic framework of the alkaloid aspidophytine (2). As such, this work sets the stage for effecting the conversion of the enantiomeric metabolite ent-7 into compound ent-8, and thence, through previously established protocols, including a palladium-catalysed Ullmann cross-coupling reaction, into the title alkaloids.

A practical multigram-scale synthesis of allo-inositol

Allo-Inositol was prepared on a multigram scale starting with bromobenzene in seven steps by three different cis-dihydroxylations (enzymatic, OsO4 and RuO4 catalyzed) employed in tandem.

A chemoenzymatic route to chiral siloxanes

An approach employing two enzymes—toluene dioxygenase and immobilized lipase B from Candida antarctica (N435)—was explored as a potential biocatalytic method for the coupling of chiral diols with siloxane species. Analysis of reaction mixtures using1H NMR spectroscopy suggested that up to 66% consumption of the siloxane starting materials had occurred. Oligomeric species were observed and chiral products from the coupling of a cyclic diol with a siloxane molecule were isolated and characterized by MALDI-ToF MS and GPC. Immobilized lipases from Rhizomucor miehei and Thermomyces lanuginosus were also explored as potential catalysts for the coupling reactions, however, their use only returned starting material.

Chemoenzymatic enantiodivergent synthesis of 1,2-dideoxy-2-amino-1- fluoro-allo-inositol

Both enantiomers of dideoxyfluoroamino inositols (+)-9 and (-)-9 were synthesized from bromocyclohexadiene cis-diol 1 obtained by microbial oxidation of bromobenzene with toluene dioxygenase. Selective introduction of the amino group was achieved through S(N)2 displacement of triflates 7, 11. Fluorine was selectively introduced via trans-diaxial epoxide opening with tetrabutylphosphonium fluoride dihydrofluoride (TBPF-DF).

Chemoenzymatic Synthesis of the Antifungal Compound (–)-Pestynol by a Convergent, Sonogashira Construction of the Central Yne-Diene

A total synthesis of the fungal-derived natural product pestynol is reported via a convergent chemoenzymatic approach from the readily available precursors geranyl bromide, ethyl acetoacetate, trimethylsilylacetylene, and bromobenzene. Synthetic (–)-pestynol proved to be identical in all respects to the natural material, allowing confirmation of the structure including absolute stereochemistry.

Synthesis of chiral ADMET polymers containing repeating D-chiro-inositol units derived from a biocatalytically prepared diene diol

Several chiral hydroxylated polymers have been prepared, via ADMET techniques, from the diene diol derived from bromobenzene, obtained by means of whole-cell fermentation with Escherichia coli (JM109 pDTG601).

Chemoenzymatic and Enantiomeric Switching Regimes Enabling the Synthesis of Homochiral Cyclohexa-2,5-dienones Incorporating All-Carbon Quaternary Centers

The enantiomerically pure, bromobenzene-derived metabolite 5 has been transformed into enone 20 using a reaction sequence involving Suzuki-Miyaura cross-coupling and Eschenmoser-Claisen rearrangement processes. Treatment of compound 20 with lithium hydroxide results in an acetonide fragmentation reaction that delivers the 4,4-disubstituted cyclohexa-2,5-dienone 21, reductive de-oxygenation of which leads to congener 22. A closely related sequence of reactions can be used to convert the same homochiral starting material 5 into compound ent-22.

Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer

This manuscript describes the enantioselective synthesis of the aminocyclitol moiety of the antibiotic hygromycin A in eight steps and 39 % overall yield from a non-chiral starting material. The sequence made use of an initial enzymatic step to transfer chirality to an aromatic ring and was followed by selective organic chemistry transformations (oxidation, pro-tection, azidation, hydrolysis) of the six-membered ring in order to achieve the target. The approach is also amenable to the synthesis of other related unnatural analogues as exemplified by the synthesis of the C2 epimer of the natural aminocyclitol. All the intermediates were fully characterized, and the absolute stereochemistry assigned by spectrometric methods.

The Synthesis of Certain Phomentrioloxin A Analogues and Their Evaluation as Herbicidal Agents

A series of 28 analogues of the phytotoxic geranylcyclohexentriol (-)-phomentrioloxin A (1) has been synthesized through cross-couplings of various enantiomerically pure haloconduritols or certain deoxygenated derivatives with either terminal alkynes or borylated alkenes. Some of these analogues display modest herbicidal activities, and physiological profiling studies suggest that analogue 4 inhibits photosystem II in isolated thylakoids in vitro.

The Synthesis of Certain Derivatives and Analogues of (-)- and (+)-Galanthamine and an Assessment of their Capacities to Inhibit Acetylcholine Esterase

Syntheses of certain di- and mono-oxygenated derivatives (e.g., 2 and 3, respectively) and analogues (e.g., 4, a D-ring monoseco-analogue of 2) of both the (-)- and (+)-enantiomeric forms of the alkaloid galanthamine [(-)-1] are reported. All have been assessed for their capacities to inhibit acetylcholine esterase but, in contrast to the predictions from docking studies, none bind strongly to this enzyme.