13171-00-1

Basic information

• Product Name: Celestolide
• Synonyms: 1-(6-tert-Butyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl)ethanone;1-[6-(1,1-dimethylethyl)-2,3-dihydro-1,1-dimethyl-1h-inden-4-yl]-ethanon;1-[6-(1,1-dimethylethyl)-2,3-dihydro-1,1-dimethyl-1H-inden-4-yl]-Ethanone;4-acetyl-6-tert-butyl-1,1-dimethylindane,97%;Ethanone, 1-[6-(1,1-dimethylethyl)-2,3-dihydro-1,1-dimethyl-1H-inden-4-yl]-;FEMA 3653;CELESTOLIDE;CRYSOLIDE
• CAS NO: 13171-00-1
• Molecular Formula: C₁₇H₂₄O
• Molecular Weight: 244.37
• EINECS: 236-114-4
• Product Categories: Aromatics
• Mol File: 13171-00-1.mol

Chemical Properties

• Melting Point: 68-70°C
• Boiling Point: 117°C/0.6mmHg(lit.)
• Flash Point: 125.5 °C
• Appearance: White solid
• Density: 0.957 g/cm³
• Vapor Pressure: 0.05Pa at 24℃
• Refractive Index: 1.514
• Storage Temp.: Refrigerator
• Water Solubility: 3.29mg/L at 24℃
• CAS DataBase Reference: Celestolide(CAS DataBase Reference)
• NIST Chemistry Reference: Celestolide(13171-00-1)
• EPA Substance Registry System: Celestolide(13171-00-1)

Safety Data

• Hazardous Substances Data: 13171-00-1(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
Celestolide is used as a fragrance ingredient for its long-lasting and musky, sweet, animal odor. It is particularly favored in the composition of perfumes and fragrances due to its ability to provide a unique and persistent scent.
Used in Soap and Cosmetics Industry:
Celestolide is used as a perfuming agent in the production of soap and cosmetics. Its light-stability and strong odor make it an ideal choice for adding a distinct and long-lasting scent to these products.
Taste threshold values:
Celestolide has a taste threshold value of 20 ppm, where it is described as having a solvent-like taste with a dirty, musty brown, and earthy nuance. This characteristic makes it suitable for use in the fragrance industry, where the focus is on the olfactory experience rather than the gustatory one.
Occurrence:
Celestolide has been reported to be found in cooked asparagus, although its primary use is in the perfume and cosmetics industry.

Identification

▼▲ CAS.No.:? 13171-00-1? FL.No.:? 7.133 FEMA.No.:? 3653 NAS.No.:? 3653 CoE.No.:? n/a? EINECS.No.:? 236-114-4? JECFA.No.:? 812

Regulatory Status

CoE: n/a FDA: n/a FDA (other): n/a JECFA: Additional data required (2001).

Natural occurrence

Reported found in cooked asparagus.

Preparation

From tert-butylbenzene

Flammability and Explosibility

Notclassified

Trade name

Celestolide (IFF).

InChI:InChI=1/C17H24O/c1-5-6-7-13-10-15(12(2)18)14-8-9-17(3,4)16(14)11-13/h10-11H,5-9H2,1-4H3

Synthetic route

6-tert-butyl-1,1-dimethylindane (3605-31-0) + acetyl chloride (75-36-5) → Celestolide (13171-00-1)

Conditions	Yield
With aluminium trichloride In dichloromethane Friedel-Crafts reaction;	62%
With tetrachloromethane; aluminium trichloride
aluminium trichloride In hexane

6-tert-butyl-1,1-dimethylindane (3605-31-0) + acetyl chloride (75-36-5) → 6-acetyl-1,1-dimethyl-4-tertbutylindane (102296-26-4) + Celestolide (13171-00-1) + 1-(3,3-dimethylindan-5-yl)ethanone (102296-45-7) + 1-(1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)ethan-1-one (102296-44-6)

Conditions	Yield
With aluminium trichloride In various solvent(s) at 0 - 5℃; for 1h; Further byproducts given;	A n/a B 50.4% C n/a D n/a
With aluminium trichloride In various solvent(s) at 0 - 5℃; for 1h; Further byproducts given;

6-tert-butyl-1,1-dimethylindane (3605-31-0) + acetyl chloride (75-36-5) → Celestolide (13171-00-1) + 1-(3,3-dimethylindan-5-yl)ethanone (102296-45-7)

Conditions	Yield
With tetrachloromethane; aluminium trichloride

5-(tert-butyl)-1,1-dimethyl-2,3-dihydro-1H-indene (38393-97-4) + acetyl chloride (75-36-5) → Celestolide (13171-00-1)

Conditions	Yield
With aluminium trichloride; nitrobenzene; 1,2-dichloro-ethane

6-tert-butyl-1,1-dimethylindane (3605-31-0) + acetyl chloride (75-36-5) → 6-acetyl-1,1-dimethyl-4-tertbutylindane (102296-26-4) + Celestolide (13171-00-1) + 1-(3,3-dimethylindan-5-yl)ethanone (102296-45-7) + 5-acetyl-1,1-dimethyl-6-tert-butylindane (133631-95-5)

Conditions	Yield
With aluminium trichloride In various solvent(s) at 0 - 5℃; for 1h; Further byproducts given. Title compound not separated from byproducts;

6-tert-butyl-1,1-dimethylindane (3605-31-0) + acetyl chloride (75-36-5) → 6-acetyl-1,1-dimethyl-4-tertbutylindane (102296-26-4) + Celestolide (13171-00-1) + 1-(1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)ethan-1-one (102296-44-6) + 6-acetyl-1,1-dimethyl-5-tert-butylindane (132684-99-2)

Conditions	Yield
With aluminium trichloride In various solvent(s) at 0 - 5℃; for 1h; Further byproducts given. Title compound not separated from byproducts;

aluminium trichloride (7446-70-0) + 6-tert-butyl-1,1-dimethylindane (3605-31-0) + nitrobenzene (98-95-3) + 1,2-dichloro-ethane (107-06-2) + acetyl chloride (75-36-5) → Celestolide (13171-00-1)

aluminium trichloride (7446-70-0) + 6-tert-butyl-1,1-dimethylindane (3605-31-0) + acetyl chloride (75-36-5) + CCl2 → Celestolide (13171-00-1)

tert-butylbenzene (253185-03-4, 253185-04-5) → Celestolide (13171-00-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / AlCl3 / nitromethane 2: 62 percent / AlCl3 / CH2Cl2 View Scheme

isoprene (78-79-5) → Celestolide (13171-00-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / AlCl3 / nitromethane 2: 62 percent / AlCl3 / CH2Cl2 View Scheme

6-tert-butyl-1,1-dimethyl-4-indancarboxylic acid (61813-34-1) → Celestolide (13171-00-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: quinoline; CuO; copper-powder / 200 - 230 °C 2: AlCl3; CCl4 View Scheme

1,1-dimethylindan (4912-92-9) → Celestolide (13171-00-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3; CS2 2: AlCl3; CCl4 View Scheme
Multi-step reaction with 2 steps 1: AlCl3; CS2 2: AlCl3; 1,2-dichloro-ethane; nitrobenzene View Scheme
Multi-step reaction with 2 steps 1: concentrated H2SO4 2: AlCl3; CCl4 View Scheme
Multi-step reaction with 2 steps 1: concentrated H2SO4 2: AlCl3; CCl4 View Scheme

4-Phenyl-2-butanone (2550-26-7) → Celestolide (13171-00-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: H2SO4 2: methyl magnesium bromide; diethyl ether 3: aqueous H2SO4 4: AlCl3; CCl4 View Scheme

4-(4-tert-butylphenyl)butan-2-one (65170-86-7) → Celestolide (13171-00-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: methyl magnesium bromide; diethyl ether 2: aqueous H2SO4 3: AlCl3; CCl4 View Scheme

4-(4-tert-butyl-phenyl)-2-methyl-butan-2-ol (72390-27-3) → Celestolide (13171-00-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous H2SO4 2: AlCl3; CCl4 View Scheme
Multi-step reaction with 2 steps 1: aqueous H2SO4 2: AlCl3; CCl4 View Scheme

6-tert-butyl-3,3-dimethyl-1-indanone (38393-94-1) → Celestolide (13171-00-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: N2H4+H2O; KOH; triethylene glycol / 210 °C 2: AlCl3; 1,2-dichloro-ethane; nitrobenzene View Scheme

3-(4-tert-butyl-phenyl)propionic acid methyl ester (1211-99-0) → Celestolide (13171-00-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: methyl magnesium bromide; diethyl ether 2: aqueous H2SO4 3: AlCl3; CCl4 View Scheme
Multi-step reaction with 3 steps 1: methyl magnesium bromide; diethyl ether 2: aqueous H2SO4 3: AlCl3; CCl4 View Scheme

Celestolide (13171-00-1) → 1-(6-tert-butyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl)ethanol

Conditions	Yield
With methanol; sodium tetrahydroborate at 0℃; for 4.33333h; Time;	98.2%

Celestolide (13171-00-1) → 6-tert-butyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-amine (132567-92-1)

Conditions	Yield
With methanol; O-benzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid at 23℃; for 24h; Inert atmosphere;	95%
Multi-step reaction with 3 steps 1: NH2OH*HCl; pyridine / ethanol 2: SOCl2 / CH2Cl2 3: aq. HCl / ethanol / Heating View Scheme

Celestolide (13171-00-1) → 1-(3-azido-6-(tert-butyl)-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl)ethan-1-one

Conditions	Yield
With trimethylsilylazide; copper diacetate; (S,S)-4,4'-bis(phenylmethyl)-2,2',5,5'-tetrahydro-2,2'-bioxazole; N-fluorobis(benzenesulfon)imide In nitromethane at 30℃; for 24h; Inert atmosphere; Sealed tube;	92%
With sodium azide; iodosylbenzene; C32H46ClMnN2O2 In water; ethyl acetate at 23℃;	74%
With sodium azide; lithium perchlorate In acetic acid; acetonitrile at 25℃; for 10h; Inert atmosphere; Electrochemical reaction;	65%
With sodium azide; 1,10-Phenanthroline; manganese(II) fluoride; lithium perchlorate; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetic acid; 1,2-dichloro-ethane; acetonitrile at 35℃; for 21h; Inert atmosphere; Electrolysis; Irradiation; Schlenk technique;	51%

Celestolide (13171-00-1) → 1-(6-(tert-butyl)-3-chloro-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl)ethan-1-one

Conditions	Yield
With dichloro(1,10-phenanthroline) copper(II); 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one In acetonitrile at 20℃; for 48h; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube;	91%

Celestolide (13171-00-1) → 1-(6-(tert-butyl)-3-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl)ethan-1-one

Conditions	Yield
With xanth-9-one; Selectfluor In acetonitrile at 60℃; for 0.15h; Inert atmosphere; Flow reactor; Irradiation;	88%
With (S,S)-chloro[2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis-[4,6-bis(1,1-dimethylethyl)phenolato]](2-)-N,N',O,O'-manganese; iodosylbenzene; triethylamine tris(hydrogen fluoride) In acetonitrile at 50℃; Reagent/catalyst; Temperature; Time; Schlenk technique; Inert atmosphere;	67%
With (S,S)-chloro[2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis-[4,6-bis(1,1-dimethylethyl)phenolato]](2-)-N,N',O,O'-manganese; iodosylbenzene; triethylamine tris(hydrogen fluoride) In acetonitrile at 50℃; Schlenk technique; Inert atmosphere;
With dihydroxy-methyl-borane; bathophenanthroline; copper (I) acetate; lithium carbonate; N-fluorobis(benzenesulfon)imide In chlorobenzene at 45℃; for 16h; Glovebox; Inert atmosphere;

Celestolide (13171-00-1) → N-(6-tert-butyl-1,1-dimethylindan-4-yl)acetamide (101866-05-1)

Conditions	Yield
With O-benzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid In water; acetonitrile at 23℃; for 24h; Inert atmosphere;	87%
Multi-step reaction with 2 steps 1: NH2OH*HCl; pyridine / ethanol 2: SOCl2 / CH2Cl2 View Scheme

2-(aminoxy)acetic acid hydrochloride + Celestolide (13171-00-1) → C19H27NO3

Conditions	Yield
With sodium acetate In methanol at 20℃;	85.9%

Celestolide (13171-00-1) → 7-acetyl-5-tert-butyl-3,3-dimethyl-indan-1-one

Conditions	Yield
With tert.-butylhydroperoxide In water; acetonitrile at 50℃; for 15h; Electrolysis;	74%
With tetra-O-acetyl riboflavin; ferrous perchlorate; oxygen In water; acetonitrile at 50℃; for 0.416667h; UV-irradiation; Flow reactor;	7%

Celestolide (13171-00-1) + t-butyldimethylsiyl triflate (69739-34-0) → tert-butyl((1-(6-(tert-butyl)-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl)vinyl)oxy)dimethylsilane

Conditions	Yield
Stage #1: Celestolide With triethylamine In dichloromethane at 20℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: t-butyldimethylsiyl triflate In dichloromethane for 3h; Schlenk technique; Inert atmosphere;	70%

2-((trifluoromethyl)thio)isoindoline-1,3-dione (719-98-2) + Celestolide (13171-00-1) → C18H23F3OS

Conditions	Yield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; potassium carbonate In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;	62%

Celestolide (13171-00-1) + (2,2’-bipyridine)Zn(CF3)2 → 1-(6-(tert-butyl)-1,1-dimethyl-3-(trifluoromethyl)-2,3-dihydro-1H-inden-4-yl)ethanone

Conditions	Yield
With zinc diacetate; copper(l) cyanide; zinc trifluoromethanesulfonate; N-fluorobis(benzenesulfon)imide at 20℃; for 24h; Sealed tube; Inert atmosphere;	53%

[bis(acetoxy)iodo]benzene (3240-34-4) + Celestolide (13171-00-1) → 7-acetyl-5-(tert-butyl)-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl acetate

Conditions	Yield
With 9-mesityl-1,3,6,8-tetramethoxy-10-phenylacridin-10-ium tetrafluoroborate In dichloromethane at 25 - 40℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;	41%

Celestolide (13171-00-1) → 6-tert-butyl-1,1-dimethyl-4-indancarboxylic acid (61813-34-1)

Conditions	Yield
With sodium hypochlorite; sodium hypobromide
With 1,4-dioxane; potassium hypobromite
With sodium hypobromide In 1,4-dioxane

Celestolide (13171-00-1) → 4-ethyl-6-tert-butyl-1,1-dimethyl-indan (3247-65-2)

Conditions	Yield
With methanol; platinum on activated charcoal; palladium dichloride Hydrogenation;

Celestolide (13171-00-1) + diethyl chlorophosphate (814-49-3) → phosphoric acid 1-(6-tert-butyl-1,1-dimethyl-indan-4-yl)-vinyl ester diethyl ester

Conditions	Yield
Stage #1: Celestolide With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: diethyl chlorophosphate In tetrahydrofuran
Stage #1: Celestolide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: diethyl chlorophosphate In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere;

Celestolide (13171-00-1) → 1-(6-tert-butyl-1,1-dimethyl-indan-4-yl)-ethanone oxime (175136-27-3)

Conditions	Yield
With pyridine; hydroxylamine hydrochloride In ethanol
With hydroxylamine hydrochloride; sodium acetate In ethanol at 90℃; for 2h; Sealed tube; Inert atmosphere;

Celestolide (13171-00-1) → (2E,4E)-6-(6-tert-Butyl-1,1-dimethyl-indan-4-ylamino)-3-methyl-hexa-2,4-dienoic acid ethyl ester (889444-00-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: NH2OH*HCl; pyridine / ethanol 2: SOCl2 / CH2Cl2 3: aq. HCl / ethanol / Heating 4: NaCNBH3; ZnCl2 / methanol View Scheme

Celestolide (13171-00-1) → (2E,4E)-6-[(6-tert-Butyl-1,1-dimethyl-indan-4-yl)-isopropyl-amino]-3-methyl-hexa-2,4-dienoic acid ethyl ester (886861-94-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: NH2OH*HCl; pyridine / ethanol 2: SOCl2 / CH2Cl2 3: aq. HCl / ethanol / Heating 4: NaCNBH3; ZnCl2 / methanol 5: K2CO3 / N,N-dimethyl-acetamide View Scheme

Celestolide (13171-00-1) → (2E,4E)-6-[(6-tert-Butyl-1,1-dimethyl-indan-4-yl)-isopropyl-amino]-3-methyl-hexa-2,4-dienoic acid

Conditions	Yield
Multi-step reaction with 6 steps 1: NH2OH*HCl; pyridine / ethanol 2: SOCl2 / CH2Cl2 3: aq. HCl / ethanol / Heating 4: NaCNBH3; ZnCl2 / methanol 5: K2CO3 / N,N-dimethyl-acetamide 6: KOH / methanol View Scheme

Celestolide (13171-00-1) → (2E,4E)-6-[(6-tert-Butyl-1,1-dimethyl-indan-4-yl)-propyl-amino]-3-methyl-hexa-2,4-dienoic acid

Conditions	Yield
Multi-step reaction with 6 steps 1: NH2OH*HCl; pyridine / ethanol 2: SOCl2 / CH2Cl2 3: aq. HCl / ethanol / Heating 4: NaCNBH3; ZnCl2 / methanol 5: K2CO3 / N,N-dimethyl-acetamide 6: KOH / methanol View Scheme

Upstream product

• 3605-31-0 6-tert-butyl-1,1-dimethylindane 
• 75-36-5 acetyl chloride 
• 38393-97-4 5-(tert-butyl)-1,1-dimethyl-2,3-dihydro-1H-indene 
• 7446-70-0 aluminium trichloride 
• 98-95-3 nitrobenzene 
• 107-06-2 1,2-dichloro-ethane 
• 253185-03-4 tert-butylbenzene 
• 78-79-5 isoprene 
• 61813-34-1 6-tert-butyl-1,1-dimethyl-4-indancarboxylic acid 
• 4912-92-9 1,1-dimethylindan 
• 2550-26-7 4-Phenyl-2-butanone 
• 65170-86-7 4-(4-tert-butylphenyl)butan-2-one 
• 72390-27-3 4-(4-tert-butyl-phenyl)-2-methyl-butan-2-ol 
• 38393-94-1 6-tert-butyl-3,3-dimethyl-1-indanone 

Downstream Products

• 3247-65-2 4-ethyl-6-tert-butyl-1,1-dimethyl-indan 
• 175136-27-3 1-(6-tert-butyl-1,1-dimethyl-indan-4-yl)-ethanone oxime 

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