ChemicalBook > CAS DataBase List > (+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]

(+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]

Product Name: (+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]
CAS No.: 180186-94-1
Chemical Name: (+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]
Synonyms: Bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)Methane;[3aR-[2(3;3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-Methylenebis[3a,8a;[3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-Methylenebis[3a,8a;(+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-...;(+)-2,2-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE;(+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE;(+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE];(+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] >(+)-2,2'-Methylenebis[(3AR,8AS)-3A,8A-Dihydro-8H-Indeno[1,2-D]Oxazole],98%
CBNumber: CB8327457
Molecular Formula: C21H18N2O2
Formula Weight: 330.38
MOL File: 180186-94-1.mol

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(+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] Property

Melting point:: 225 °C
Boiling point:: 493.2±45.0 °C(Predicted)
Density: 1.48
refractive index: 360 ° (C=1, CH2Cl2)
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
form: powder to crystal
pka: 5.47±0.20(Predicted)
color: White to Almost white
optical activity: [α]22/D +353°, c = 3.7 in chloroform
InChI: InChI=1S/C21H18N2O2/c1-3-7-14-12(5-1)9-16-20(14)22-18(24-16)11-19-23-21-15-8-4-2-6-13(15)10-17(21)25-19/h1-8,16-17,20-21H,9-11H2/t16-,17-,20+,21+/m0/s1
InChIKey: BDHSVQLSNIGJNC-ZCLUNYJNSA-N
SMILES: C(C1=N[C@]2([H])C3=C(C=CC=C3)C[C@]2([H])O1)C1=N[C@]2([H])C3=C(C=CC=C3)C[C@]2([H])O1

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 3
HS Code: 29349990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 464155
Product name: [3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole]
Purity: 98%
Packaging: 500mg
Price: $75
Updated: 2025/07/31

TCI Chemical

Product number: M1401
Product name: (+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole]
Purity: >98.0%(HPLC)(N)
Packaging: 100mg
Price: $24
Updated: 2025/07/31

TCI Chemical

Product number: M1401
Product name: (+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole]
Purity: >98.0%(HPLC)(N)
Packaging: 500mg
Price: $69
Updated: 2025/07/31

TRC

Product number: D452608
Product name: Bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)methane
Packaging: 50mg
Price: $75
Updated: 2021/12/16

Frontier Specialty Chemicals

Product number: JK396000
Product name: (+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole]
Packaging: 250mg
Price: $57
Updated: 2021/12/16

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(+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] Chemical Properties,Usage,Production

Chemical Properties

White powder

Uses

[3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] is a C₂symmetric chiral ligand based on bis(oxazoline) moiety, which can be used in enantioselective catalysis. It easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals. Copper complex of this chiral ligand can be utilized as a reusable catalyst in the cyclopropanation reaction between styrene and ethyl diazoacetate.

Synthesis

136030-00-7

10344-69-1

180186-94-1

Malonylimide diethyl ester dihydrochloride (25.8 g, 0.112 mol, 1.0 eq.) and dimethylformamide (DMF) (320 mL) were added to a 3 L round bottom flask. The mixture was cooled in an ice bath. To the suspension was added (1R,2S)-1-amino-2-indanol (40 g, 0.268 mol, 2.4 eq.) in batches over 20 min. The ice bath was then removed and the reaction mixture was allowed to slowly warm up to room temperature, during which the reaction product gradually precipitated out of solution. After 4 days of continuous stirring at room temperature, a filtration operation was carried out. The resulting white solid was suspended in dichloromethane (CH2Cl2, 450 mL). Next, the mixture was washed sequentially with water (260 mL) and brine (260 mL). The organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated to give an off-white solid. The solid was dried overnight under vacuum to give a final 23.9 g (65% yield) of the target product bis(oxazoline) (4). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.45 (m, 2H, Ar-H); 7.27-7.21 (m, 6H, Ar-H); 5.56 (d, J = 7.9 Hz, 2H, N-CH); 5.34 (m, 2H, O-CH); 3.39 (dd, J = 7.0, 18.0 Hz, 2H, Ar- CHH); 3.26 (s, 2H, -CH2-O); 3.16 (dd, J = 18.0 Hz, 2H, Ar-CHH). The NMR data are in agreement with those reported in the literature WO 00/15599.

References

[1] Organic Letters, 2017, vol. 19, # 8, p. 2150 - 2153
[2] Journal of the American Chemical Society, 2018, vol. 140, # 1, p. 139 - 142
[3] Patent: WO2004/96764, 2004, A1. Location in patent: Page 38
[4] Organic Letters, 2006, vol. 8, # 3, p. 539 - 542

(+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from (+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] manufacturers

Zhuozhou Wenxi import and Export Co., Ltd

Product: (+)-2,2"-METHYLENEBIS(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO1,2-DOXAZOLE 180186-94-1
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-06-27

Career Henan Chemical Co

Product: (+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] 180186-94-1
Price: US $1.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 100KG
Release date: 2018-12-21

180186-94-1, (+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]Related Search:

(3aS,3a'S,8aR,8a'R)-2,2'-(1,3-Diphenylpropane-2,2-diyl)bis(8,8a-dihydro-3aH-indeno[1,2-d]oxazole) (3aS,3'aS,8aR,8'aR)-2,2'-Cyclopentylidenebis[3a,8a-dihydr o-8H-indeno[1,2-d]oxazole] (3aR,3'aR,8aS,8'aS)-2,2'-Cyclopentylidenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] (3aR,3'aR,8aS,8'a'S)-2,2'-cyclopropylidenebis[3a,8a-dihydro-8H-Indeno[1,2-d]oxazole (3aR,3a'R,8aS,8a'S)-2,2'-(1,3-diphenylpropane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) (-)-2,2'-METHYLENEBIS[(3AS,8AR)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] (3aS,3'aS,8aR,8'a'R)-2,2'-cyclopropylidenebis[3a,8a-dihydro-8H-Indeno[1,2-d]oxazole CIS-1-AMINO-2-INDANOL (R,R)-2,2'-METHYLENEBIS(4-PHENYL-2-OXAZOLINE) (1R,2S)-1-Amino-2-indanol (+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]

(+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]

[3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-Methylenebis[3a,8a

(3aR,3'aR,8aS,8'aS)-2,2'-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole]

[3aR-[2(3'aR*,8'aS*),3'aβ,8'aβ]]-(+)-2,2'-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole]

Bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)Methane

[3ar-[2(3'ar*,8'as*),3'aβ,8'aβ]]-(+)-2,2'-methylenebis[3a,8a-dihydro-8h-indeno[1,2-]oxazole]

(-)-2,2''-METHYLENEBIS-[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] EP

[3aR-[2(3'aR*,8'aS*),3'abeta,8'abeta]]-(+)-2,2'-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] 98%

(+)-2,2'-Methylenebis[(3AR,8AS)-3A,8A-Dihydro-8H-Indeno[1,2-D]Oxazole],98%

[3aR-[2(3

(+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] &gt

8H-Indeno[1,2-d]oxazole, 2,2'-methylenebis[3a,8a-dihydro-, (3aR,3'aR,8aS,8'aS)-

(+)-2,2-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE

3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole

(+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-...

3aR-[2(3`aR,8`aS),3`aβ,8`aβ]]-(+)-2,2`-methylenebis[3a,8a-dihydro-8H-indeno[1,2-]oxazole

3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-Methylenebis[3a,8a

(+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE

(3aR,3'aR,8aS,8'aS)-2,2'-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole

[3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole]

180186-94-1

80186-94-1

Privileged Ligands

BOX

Chiral Catalysts, Ligands, and Reagents

Asymmetric Synthesis

BOX series

Chiral Nitrogen

Asymmetric Synthesis

Synthetic Organic Chemistry

BOX

Chiral Catalysts, Ligands, and Reagents

Privileged Ligands and Complexes