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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]

(+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] Structure
(+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] structure
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;(+)-2,2'3aR-[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] >
CBNumber:
CB8327457
Molecular Formula:
C21H18N2O2
Molecular Weight:
330.38
MDL Number:
MFCD06797115
MOL File:
180186-94-1.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-09-12 18:55:38
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(+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] Properties

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
UNSPSC Code 12352005
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs Respiratory system
PPE dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  3
HS Code  29349990
Storage Class 11 - Combustible Solids
Hazard Classifications Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

(+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] price More Price(32)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 464155 [3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] 98% 180186-94-1 500mg $79.9 2026-04-30 Buy
TCI Chemical M1401 (+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] >98.0%(HPLC)(N) 180186-94-1 100mg $22 2026-04-30 Buy
TCI Chemical M1401 (+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] >98.0%(HPLC)(N) 180186-94-1 500mg $62 2026-04-30 Buy
Strem Chemicals 07-0012 (3aR,3'aR,8aS,8'aS)-2,2'-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole], min. 98% min.98% 180186-94-1 500mg $96 2026-04-30 Buy
Usbiological 284789 (+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] Asreported 180186-94-1 250mg $326 2026-06-03 Buy
Product number Packaging Price Buy
464155 500mg $79.9 Buy
M1401 100mg $22 Buy
M1401 500mg $62 Buy
07-0012 500mg $96 Buy
284789 250mg $326 Buy

(+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] Chemical Properties, Uses, 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 C2 symmetric 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

(1R,2S)-1-Amino-2-indanol

136030-00-7

DIETHYL MALONIMIDATE DIHYDROCHLORIDE

10344-69-1

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

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

(1R,2S)-1-Amino-2-indanol Diethyl malonimidate dihydrochloride

Preparation Products

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

Global Suppliers ( 122)
Supplier Tel Email Country ProdList Advantage
Shanghai Suifu Chemical Technology CO.,LTD. 33738187 19945655289 suifuchemical@163.com China 500 58
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
Meryer (Shanghai) Chemical Technology Co., Ltd. 4006356688 18621169109 market03@meryer.com China 40202 62
TCI (Shanghai) Development Co., Ltd. 021-67121386 Sales-CN@TCIchemicals.com China 24512 81
Energy Chemical 400-0056266 sales8178@energy-chemical.com China 44850 61
Nanjing Habo Medical Technology Co., Ltd. 13376080562 13376090521 sales@habotech.com China 724 60
Shanghai Longsheng chemical Co.,Ltd. 58099637 13585536065 sales@shlschem.com China 9880 59
Daicel Chiral Technologies (China)CO.,LTD 021-50460086-9 15921403865 han_yajun@dctc.daicel.com China 7909 65
Maya High Purity Chemicals +86 (573) 82222445 (0)18006601000 452520369 sales@maya-r.com China 11693 57
Tianjin Derchemist Science & Technology Co., Ltd. 22-58627059 13920586291 zdcomcon@126.com China 4094 50
Supplier Advantage
Shanghai Suifu Chemical Technology CO.,LTD. 58
J & K SCIENTIFIC LTD. 76
Meryer (Shanghai) Chemical Technology Co., Ltd. 62
TCI (Shanghai) Development Co., Ltd. 81
Energy Chemical 61
Nanjing Habo Medical Technology Co., Ltd. 60
Shanghai Longsheng chemical Co.,Ltd. 59
Daicel Chiral Technologies (China)CO.,LTD 65
Maya High Purity Chemicals 57
Tianjin Derchemist Science & Technology Co., Ltd. 50

View Latest Price from (+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
(+)-2,2 2021-07-02 (+)-2,2"-METHYLENEBIS(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO1,2-DOXAZOLE
180186-94-1
 $10.00-15.00 1KG 99%+ HPLC Zhuozhou Wenxi import and Export Co., Ltd
(+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] pictures 2019-07-06 (+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]
180186-94-1
 $1.00 1kg 98% 100KG Career Henan Chemical Co

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

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

180186-94-1 ((+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole]) Related Search:

(-)-2,2'-Methylenebis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] (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) (3aS,3'aS,8aR,8'a'R)-2,2'-cyclopropylidenebis[3a,8a-dihydro-8H-Indeno[1,2-d]oxazole (R,R)-2,2'-Methylenebis(4-phenyl-2-oxazoline) cis-1-Amino-2-indanol (+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole]
(1R,2S)-1-Amino-2-indanol

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[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] > 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] (+)-2,2' 2,2'-methylenebis[(3A-R,8A-S)-3-A,8-A-dihydro-8H-benzene[1,2-D]benzoazole] (+)-2,2'-Methylenebis[(3aR,8aS)-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