Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane at 0℃; for 0.5h; | 98% |
Stage #1: Dichloromethyl methyl ether; INDANE With tin(IV) chloride In dichloromethane at -30 - 20℃; Inert atmosphere; Stage #2: With water In dichloromethane at 0℃; | 51% |
With titanium tetrachloride | |
With tin(IV) chloride In dichloromethane |
3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide
2,3-dihydro-1H-inden-5-yl trifluoromethanesulfonate
indan-5-carbaldehyde
Conditions | Yield |
---|---|
With triethylsilane; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium carbonate In acetonitrile at 80℃; for 16h; Inert atmosphere; Sealed tube; | 82% |
Conditions | Yield |
---|---|
With trifluoroacetic acid at 100℃; for 5h; | 84% |
With trifluoroacetic acid at 100℃; Duff Aldehyde Synthesis; | 60% |
With trifluoroacetic acid Duff Aldehyde Synthesis; | 38% |
indan-5-yl-ethan-1,2-diol
indan-5-carbaldehyde
Conditions | Yield |
---|---|
With periodic acid In ethanol; water at 20℃; for 12h; | |
With periodic acid In ethanol; water at 20℃; for 12h; | |
With periodic acid In ethanol; water at 20℃; for 12h; |
(2E,8E)-deca-2,8-diene-1,10-dial
indan-5-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: (2E,8E)-deca-2,8-diene-1,10-dial; pyrrolidine; acetic acid In acetonitrile at -10℃; for 6h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; acetonitrile at 30℃; for 2h; | 81% |
(2E,8E)-deca-2,8-diene-1,10-dial
A
indane-4-carboxaldehyde
B
indan-5-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: (2E,8E)-deca-2,8-diene-1,10-dial; pyrrolidine; acetic acid In acetonitrile at 30℃; for 6h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; acetonitrile at 30℃; for 2h; | A n/a B 83% |
Stage #1: (2E,8E)-deca-2,8-diene-1,10-dial; L-proline In acetonitrile at -10℃; for 48h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; acetonitrile at 30℃; for 2h; |
5-indancarboaldehyde azine
indan-5-carbaldehyde
Conditions | Yield |
---|---|
With selenium(IV) oxide In N,N-dimethyl-formamide at 100℃; for 18h; | 76% |
(2,3-dihydro-1H-inden-5-yl)methanol
indan-5-carbaldehyde
Conditions | Yield |
---|---|
With pyridinium chlorochromate In dichloromethane for 2h; Ambient temperature; | 96% |
With Py*HClCrO3 |
INDANE
indan-5-carbaldehyde
Conditions | Yield |
---|---|
With aluminium trichloride; hydrogen cyanide; 1,1,2,2-tetrachloroethane Reagens 4: wss. HCl; Einleiten von HCl; | |
With aluminium trichloride; chloromethylene-formamidine; 1,1,2,2-tetrachloroethane at 50℃; Reagens 4: wss. HCl; | |
Multi-step reaction with 5 steps 1: 93 percent / AlCl3 / CH2Cl2 / 4 h 2: 89 percent / NaOBr / 1.) 3 h, 0 deg C; 2.) r. t., overnight 3: 94 percent / conc. H2SO4 / Heating 4: 94 percent / LiAlH4 / diethyl ether / 12 h / Heating 5: 96 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 5 steps 1: 93 percent / AlCl3 / CH2Cl2 / 4 h 2: 89 percent / NaOBr / 1.) 3 h, 0 deg C; 2.) r. t., overnight 4: 94 percent / LiAlH4 / diethyl ether / 12 h / Heating 5: 96 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: (i) aq. HCl, H2SO4, (ii) NaOAc, AcOH, (iii) aq. NaOH 2: Py*HClCrO3 View Scheme |
carbon monoxide
INDANE
A
indane-4-carboxaldehyde
B
indan-5-carbaldehyde
Conditions | Yield |
---|---|
With antimony pentafluoride; fluorosulphonic acid at 0℃; under 760 Torr; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
Stage #1: 5-bromoindane With tert.-butyl lithium In diethyl ether; pentane at -70℃; for 1h; Stage #2: N,N-dimethyl-formamide In diethyl ether at -70 - 10℃; for 1h; |
5-chloromethylindane
indan-5-carbaldehyde
Conditions | Yield |
---|---|
With ethanol; hexamethylenetetramine |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: aq. hydrobromic acid; sodium nitrite / 0.33 h / 0 - 5 °C 1.2: 42 percent / copper(I) bromide; aq. hydrobromic acid / 0.67 h / 60 °C 2.1: tert-butyllithium / diethyl ether; pentane / 1 h / -70 °C 2.2: diethyl ether / 1 h / -70 - 10 °C View Scheme |
1-indan-5-yl-ethanone
indan-5-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 89 percent / NaOBr / 1.) 3 h, 0 deg C; 2.) r. t., overnight 2: 94 percent / conc. H2SO4 / Heating 3: 94 percent / LiAlH4 / diethyl ether / 12 h / Heating 4: 96 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 4 steps 1: 89 percent / NaOBr / 1.) 3 h, 0 deg C; 2.) r. t., overnight 3: 94 percent / LiAlH4 / diethyl ether / 12 h / Heating 4: 96 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme |
indan-5-carboxylic acid
indan-5-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 94 percent / conc. H2SO4 / Heating 2: 94 percent / LiAlH4 / diethyl ether / 12 h / Heating 3: 96 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 2: 94 percent / LiAlH4 / diethyl ether / 12 h / Heating 3: 96 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme |
1-(2-indan-5-yl-2-oxo-ethyl)-pyridinium; iodide
indan-5-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 98 percent / aq. NaOH / Heating 2: 94 percent / conc. H2SO4 / Heating 3: 94 percent / LiAlH4 / diethyl ether / 12 h / Heating 4: 96 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 4 steps 1: 98 percent / aq. NaOH / Heating 3: 94 percent / LiAlH4 / diethyl ether / 12 h / Heating 4: 96 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme |
methyl 5-indanecarboxylate
indan-5-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 94 percent / LiAlH4 / diethyl ether / 12 h / Heating 2: 96 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme |
1-allylcyclopentan-1-ol
N,N-dimethyl-formamide
A
indane-4,6-dicarboxaldehyde
B
indan-5-carbaldehyde
Conditions | Yield |
---|---|
With trichlorophosphate room temp., 30 min, then boiling water bath, 6h; | A 23% B n/a |
Conditions | Yield |
---|---|
With hydrogenchloride; aluminium trichloride; benzene weiteres Reagens: CuCl; |
Dichloromethyl methyl ether
INDANE
A
indane-4-carboxaldehyde
B
indan-5-carbaldehyde
Conditions | Yield |
---|---|
With titanium(III) chloride Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
bei Gegenwart von Benzol, von AlCl3 und CuCl; |
indan-5-carbaldehyde
indan-5-carboxylic acid
Conditions | Yield |
---|---|
With copper acetylacetonate; oxygen; sodium hydroxide; 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In water at 50℃; under 760.051 Torr; for 12h; Sealed tube; | 99% |
indan-5-carbaldehyde
(2,3-dihydro-1H-inden-5-yl)methanol
Conditions | Yield |
---|---|
Stage #1: indan-5-carbaldehyde With sodium tetrahydroborate In ethanol at 0℃; for 0.5h; Stage #2: With hydrogenchloride In water pH=2; | 96% |
With sodium tetrahydroborate at 0 - 20℃; | 59% |
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 1.5h; | 23.1 g |
3,5,6,7-tetrahydro-2H-s-indacen-1-one
indan-5-carbaldehyde
2-(5-Indanylmethylen)-s-hydrindacen-1-on
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 3h; | 95% |
Conditions | Yield |
---|---|
With piperidine; pyridine at 80℃; for 24h; | 91% |
2-bromoprop-1-ene
indan-5-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 2-bromoprop-1-ene With lithium In diethyl ether at -30℃; for 3h; Inert atmosphere; Stage #2: indan-5-carbaldehyde In diethyl ether at -78℃; for 1.5h; | 81% |
Conditions | Yield |
---|---|
With ammonium acetate for 4h; Heating; | 76% |
methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride
indan-5-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride With triethylamine In methanol at 0℃; for 0.166667h; Stage #2: indan-5-carbaldehyde With sodium tetrahydroborate In methanol for 2.5h; | 72% |
Stage #1: methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride With triethylamine In methanol at 0℃; for 0.166667h; Stage #2: indan-5-carbaldehyde In methanol for 2h; Stage #3: With sodium tetrahydroborate In methanol | 72% |
2-(1H-pyrrol-1-yl)benzenemethanamine hydrochloride salt
indan-5-carbaldehyde
C21H19ClN2*ClH
Conditions | Yield |
---|---|
In ethanol for 3h; Reflux; | 69% |
N-isopropyl-N-[3,4-(methylenedioxy)phenyl]urea
indan-5-carbaldehyde
1-Isopropyl-6,7-methylenedioxy-4-(5-indanyl)-3,4-dihydro-quinazolin-2(1H)-one
Conditions | Yield |
---|---|
59% |
tryptamine
indan-5-carbaldehyde
1-indan-5-yl-2,3,4,9-tetrahydro-1H-β-carboline
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane for 20h; | 57% |
1-methylcyclopent-1-ene
indan-5-carbaldehyde
Conditions | Yield |
---|---|
With gallium(III) trichloride In 1,2-dichloro-ethane at 25℃; for 24h; Inert atmosphere; | 45% |
indan-5-carbaldehyde
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; palladium(II) trifluoroacetate In decane; water; toluene at 20℃; for 48h; Schlenk technique; Inert atmosphere; regioselective reaction; | 44% |
Conditions | Yield |
---|---|
In toluene at 100℃; | 41% |
Conditions | Yield |
---|---|
Stage #1: thiosemicarbazide; indan-5-carbaldehyde With toluene-4-sulfonic acid In 1-methyl-pyrrolidin-2-one at 100℃; for 1.5h; Microwave irradiation; Stage #2: maleic anhydride In 1-methyl-pyrrolidin-2-one at 110℃; for 4h; Microwave irradiation; | 28% |
Conditions | Yield |
---|---|
With ammonium acetate In methanol Reflux; | 26% |
Conditions | Yield |
---|---|
With ethanol; methylamine hydrochloride; sodium carbonate |
2-thioxo-4-thiazolidinone
indan-5-carbaldehyde
5-indan-5-ylmethylene-2-thioxo-thiazolidin-4-one
Conditions | Yield |
---|---|
With ammonium acetate In acetic acid; benzene Heating; |
acrylonitrile
indan-5-carbaldehyde
3-{N'-[1-Indan-5-yl-meth-(Z)-ylidene]-hydrazino}-propionitrile
Conditions | Yield |
---|---|
(i) N2H4*H2O, (ii) /BRN= 637391/; Multistep reaction; |
indan-5-carbaldehyde
5-indancarboaldehyde azine
Conditions | Yield |
---|---|
With hydrazine |
The Indan-5-carbaldehyde, with the CAS registry number 30084-91-4, is also known as 5-Formylindan. It belongs to the product category of Pharmacetical. Its EINECS registry number is 250-036-8. This chemical's molecular formula is C10H10O and molecular weight is 146.19. What's more, its systematic name and IUPAC name are the same which is called 2,3-Dihydro-1H-indene-5-carbaldehyde.
Physical properties about Indan-5-carbaldehyde are: (1)ACD/LogP: 2.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.76; (4)ACD/LogD (pH 7.4): 2.76; (5)ACD/BCF (pH 5.5): 73.89; (6)ACD/BCF (pH 7.4): 73.89; (7)ACD/KOC (pH 5.5): 757.1; (8)ACD/KOC (pH 7.4): 757.1; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 17.07 Å2; (13)Index of Refraction: 1.61; (14)Molar Refractivity: 45.18 cm3; (15)Molar Volume: 130.1 cm3; (16)Polarizability: 17.91×10-24cm3; (17)Surface Tension: 45.7 dyne/cm; (18)Density: 1.122 g/cm3; (19)Flash Point: 139.7 °C; (20)Enthalpy of Vaporization: 50.01 kJ/mol; (21)Boiling Point: 262.3 °C at 760 mmHg; (22)Vapour Pressure: 0.011 mmHg at 25°C.
Preparation of Indan-5-carbaldehyde: this chemical is prepared by reaction of Dichloro-methoxy-methane with Indan.
The reaction occurs with reagent SnCl4 and solvent CH2Cl2 at temperature of 0°C for 30 minutes. The yield is 98%.
Uses of Indan-5-carbaldehyde: it is used to produce other chemicals. For example, it is used to produce 3-(5-Indanyl)-prop-2-ensaeure.
The reaction occurs with reagent Pyridine and Peridine at temperature of 80°C for 24 hours. The yield is 91%.
You can still convert the following datas into molecular structure:
(1) SMILES: O=Cc1ccc2c(c1)CCC2
(2) InChI: InChI=1/C10H10O/c11-7-8-4-5-9-2-1-3-10(9)6-8/h4-7H,1-3H2
(3) InChIKey: YNGGRNROMJXLCP-UHFFFAOYAX
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