790304-84-6

Basic information

• Product Name: Isoquinoline, 6-(1-methylethyl)- (9CI)
• Synonyms: Isoquinoline, 6-(1-methylethyl)- (9CI);6-isopropylisoquinoline;6-propan-2-ylisoquinoline
• CAS NO: 790304-84-6
• Molecular Formula: C₁₂H₁₃N
• Molecular Weight: 171.23832
• EINECS: 232-940-4
• Product Categories: ISOPROPYL
• Mol File: 790304-84-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 44-45 °C
• Boiling Point: 284.1±9.0 °C(Predicted)
• Appearance: /
• Density: 1.026±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.80±0.10(Predicted)
• CAS DataBase Reference: Isoquinoline, 6-(1-methylethyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Isoquinoline, 6-(1-methylethyl)- (9CI)(790304-84-6)
• EPA Substance Registry System: Isoquinoline, 6-(1-methylethyl)- (9CI)(790304-84-6)

Safety Data

• Hazardous Substances Data: 790304-84-6(Hazardous Substances Data)

Usage

Uses

6-isopropylisoquinoline is a heterocyclic organic compound and can be used as a pharmaceutical intermediate.

Synthetic route

6-bromo-isoquinoline (34784-05-9) + isopropylmagnesium chloride (1068-55-9) → 6-isopropylisoquinoline (790304-84-6)

Conditions	Yield
Stage #1: isopropylmagnesium chloride With zinc(II) chloride In tetrahydrofuran at 0℃; for 1.5h; Inert atmosphere; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran for 0.25h; Stage #3: 6-bromo-isoquinoline In tetrahydrofuran for 12h;	75%

N-[(4-isopropylphenyl)methylene]-2,2-dimethoxyethanamine → 6-isopropylisoquinoline (790304-84-6)

Conditions	Yield
Stage #1: N-[(4-isopropylphenyl)methylene]-2,2-dimethoxyethanamine With sulfuric acid at 140℃; for 0.333333h; Stage #2: With sodium hydroxide In water	15%
With sulfuric acid at 100℃; for 0.5h;

6-isopropylisoquinoline (790304-84-6) + diethyl dicarbonate (1609-47-8) + dimethyl diazomethylphosphonate (27491-70-9, 28447-24-7, 25411-73-8) → ethyl (R)-1-(diazo(dimethoxyphosphoryl)methyl)-6-isopropylisoquinoline-2(1H)-carboxylate

Conditions	Yield
With (R)-6,6’-bis(3',4',5'-trifluoro-2,6-dimethyl[1,1'-biphenyl]-4-yl)-1,1'-spirobiindane-7,7'-diyl phosphate In toluene at -30℃; for 56h; Inert atmosphere; Molecular sieve; enantioselective reaction;	97%

6-isopropylisoquinoline (790304-84-6) → 6-isopropyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (935542-80-6)

Conditions	Yield
Stage #1: 6-isopropylisoquinoline With hydrogen; acetic acid; platinum(IV) oxide for 72h; Stage #2: With hydrogenchloride In 1,4-dioxane	95%

diazoacetic acid ethyl ester (623-73-4) + 6-isopropylisoquinoline (790304-84-6) + diethyl dicarbonate (1609-47-8) → ethyl (R)-1-(1-diazo-2-ethoxy-2-oxoethyl)-6-isopropylisoquinoline-2(1H)-carboxylate

Conditions	Yield
With (R)-6,6’-bis((4-(tert-butyl)-2-methylphenyl))-1,1'-spirobiindane-7,7'-diyl phosphate In toluene at -20℃; for 88h; Inert atmosphere; Molecular sieve; enantioselective reaction;	78%

6-isopropylisoquinoline (790304-84-6) → C12H13NO

Conditions	Yield
With dihydrogen peroxide; acetic acid at 80℃; for 12h;	60%

6-isopropylisoquinoline (790304-84-6) + triethylsilyloxydiethyl phosphonic ester (13716-46-6) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → C19H25Cl3NO5P + C19H25Cl3NO5P

Conditions	Yield
With 1-((S)-1-(N-benzyl-N-methylcarbamoyl)-2,2-dimethylpropyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea In toluene at -50℃; for 72h; Overall yield = 87 %; enantioselective reaction;	A n/a B n/a

6-isopropylisoquinoline (790304-84-6) → 1-chloro-6-isopropylisoquinoline (630422-59-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; dihydrogen peroxide / 12 h / 80 °C 2: trichlorophosphate / 6 h / 50 °C View Scheme

6-isopropylisoquinoline (790304-84-6) → 1-(cyclohex-1-en-1-yl)-6-isopropylisoquinoline

Conditions	Yield
Multi-step reaction with 3 steps 1.1: acetic acid; dihydrogen peroxide / 12 h / 80 °C 2.1: trichlorophosphate / 6 h / 50 °C 3.1: potassium carbonate / tetrahydrofuran / 0.5 h / Inert atmosphere 3.2: 12 h / 80 °C / Inert atmosphere View Scheme

6-isopropylisoquinoline (790304-84-6) → 6-isopropyl-1-(3-methylcyclohex-1-en-1-yl)isoquinoline

Conditions	Yield
Multi-step reaction with 3 steps 1.1: acetic acid; dihydrogen peroxide / 12 h / 80 °C 2.1: trichlorophosphate / 6 h / 50 °C 3.1: potassium carbonate / tetrahydrofuran / 0.5 h / Inert atmosphere 3.2: 12 h / 80 °C / Inert atmosphere View Scheme

6-isopropylisoquinoline (790304-84-6) → C20H25N

Conditions	Yield
Multi-step reaction with 3 steps 1.1: acetic acid; dihydrogen peroxide / 12 h / 80 °C 2.1: trichlorophosphate / 6 h / 50 °C 3.1: potassium carbonate / tetrahydrofuran / 0.5 h / Inert atmosphere 3.2: 12 h / 80 °C / Inert atmosphere View Scheme

6-isopropylisoquinoline (790304-84-6) → C72H80Cl2Ir2N4

Conditions	Yield
Multi-step reaction with 4 steps 1.1: acetic acid; dihydrogen peroxide / 12 h / 80 °C 2.1: trichlorophosphate / 6 h / 50 °C 3.1: potassium carbonate / tetrahydrofuran / 0.5 h / Inert atmosphere 3.2: 12 h / 80 °C / Inert atmosphere 4.1: 2-ethoxy-ethanol; water / 24 h / Reflux View Scheme

Upstream product

• 34784-05-9 6-bromo-isoquinoline 
• 1068-55-9 isopropylmagnesium chloride 

Downstream Products

• 630422-59-2 1-chloro-6-isopropylisoquinoline 

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