Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, 3-hydroxy- (9CI)

Base Information

• Chemical Name: Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, 3-hydroxy- (9CI)
• CAS No.: 242473-46-7
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.161
• Mol file: 242473-46-7.mol

Synonyms:Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, 3-hydroxy- (9CI)

Chemical Property of Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, 3-hydroxy- (9CI)

Chemical Property:

• Melting Point: 110-112 °C
• Boiling Point: 378.5±42.0 °C(Predicted)
• PKA: 9.96±0.40(Predicted)
• PSA: 44.02000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 1.55548

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, 3-hydroxy- (9CI)

There total 6 articles about Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, 3-hydroxy- (9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1-cyano-4-methoxybenzocyclobutane (56437-05-9) → 3-hydroxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile (242473-46-7)

Guidance literature:

With trimethylsilyl iodide; In acetonitrile; Heating;

Reference yield:

3-(2-bromo-5-methoxyphenyl)propanenitrile (60100-18-7) → 3-hydroxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile (242473-46-7)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonia; sodium amide / 1 h / -33 °C

2: aluminum (III) chloride; dodecyl methyl sulfide / toluene / 3 h / 0 °C / Inert atmosphere

With aluminum (III) chloride; dodecyl methyl sulfide; ammonia; sodium amide; In toluene;

DOI:10.1021/jm2012968

Reference yield:

2-bromo-5-methoxy-benzaldehyde (7507-86-0) → 3-hydroxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile (242473-46-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine; ammonium acetate / toluene / 0.5 h / Reflux

2.1: sodium tetrahydroborate; sodium hydrogencarbonate / methanol; water / 4 h / 0 - 20 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: N,N-dimethyl acetamide / 2 h / 180 °C / Inert atmosphere

4.1: ammonia; sodium amide / 1 h / -33 °C

5.1: aluminum (III) chloride; dodecyl methyl sulfide / toluene / 3 h / 0 °C / Inert atmosphere

With pyridine; aluminum (III) chloride; sodium tetrahydroborate; dodecyl methyl sulfide; ammonium acetate; ammonia; sodium hydrogencarbonate; sodium amide; In methanol; N,N-dimethyl acetamide; water; toluene;

DOI:10.1021/jm2012968

upstream raw materials:

1-cyano-4-methoxybenzocyclobutane

3-(2-bromo-5-methoxyphenyl)propanenitrile

2-bromo-5-methoxy-benzaldehyde

3-(2-bromo-5-methoxyphenyl)-2-cyanoacrylic acid

Downstream raw materials:

1-Aminomethyl-1-(1-hydroxycyclohex-1-yl)-4-hydroxybenzocyclobutane

{3-[(2',6'-dimethylbiphenyl-3-yl)methoxy]bicyclo[4.2.0]octa-1,3,5-trien-7-yl}methanol

{3-[(2',6'-dimethylbiphenyl-3-yl)methoxy]bicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl-4-methylbenzenesulfonate

{3-[(2',6'-dimethylbiphenyl-3-yl)methoxy]bicyclo[4.2.0]octa-1,3,5-trien-7-yl}acetonitrile