CAS 131833-93-7 t-Bu-box, (S,S)- (HCID 688208)

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Basic information

CAS: 131833-93-7
Standard SMILES: CC(C)(C1=N[C@@H](C(C)(C)C)CO1)C1=N[C@@H](C(C)(C)C)CO1
InChIKey: DPMGLJUMNRDNMX-VXGBXAGGSA-N
Molecular formula: C17H30N2O2
Average molar mass: 294.4 g/mol
Monoisotopic mass: 294.2307282

Names & identifiers

Preferred name: t-Bu-box, (S,S)-
IUPAC: (4S)-4-tert-butyl-2-[2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]propan-2-yl]-4,5-dihydro-1,3-oxazole
English name: (S,S)-(-)-2,2'-Isopropylidenebis(4-tert-butyl-2-oxazoline)
Molecular formula: C17H30N2O2
Molecular weight: 294.43

Names & synonyms

(S,S)-(-)-2,2'-Isopropylidenebis(4-tert-butyl-2-oxazoline)t-Bu-box, (S,S)-(S,s)-t-bu-box2268A05V3VNSC 648469(S,S)-T-BUBOX(S,S)-T-BU-BOX [MI](S,S)-T-BUBOX, (-)-NSC-6484694-tert-Butyl-2-(1-(4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl)-1-methylethyl)-4,5-dihydro-1,3-oxazoleISOPROPYLIDENEBIS((4S)-4-TERT-BUTYL-2-OXAZOLINE)2,2-BIS((S)-4-TERT-BUTYL-2-OXAZOLIN-2-YL)PROPANE

Show more names

2,2'-ISOPROPYLIDENEBIS[(4S)-4-TERT-BUTYL-2-OXAZOLINE](S,S)-(-)-2,2(S,S)-(-)-2,2'Isopropylidenebisbutyloxazoline2,2-isopropylidenebis((4S)-4-tert-butyl-2-oxazol2,2-Bis[(4S)-4-tert-butyl-2-oxazolin-2-yl]propane2,2’-Isopropylidenebis[(S)-4-(tert-butyl)-2-oxazoline(S,S)-(-)-2,2-BIS(4-TERT-BUTYL-2-OXAZOLIN-2-YL)PROPANE2,2’-Isopropylidenebis[(S)-4-(tert-butyl)-2-oxazoline]

2,2-BIS(2-(4(S)-TERT-BUTYL-1,3-OXAZOLINYL))PROPANEOXAZOLE, 2,2'-(1-METHYLETHYLIDENE)BIS(4-(1,1-DIMETHYLETHYL)-4,5-DIHYDRO-, (4S,4'S)-2,2-Bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propaneRefChem:890148631-344-5131833-93-7(4S,4'S)-2,2'-(Propane-2,2-diyl)bis(4-(tert-butyl)-4,5-dihydrooxazole)MFCD00192243

Properties

Computed structural properties

XLogP: 4
Topological polar surface area: 43.2 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 4
Heavy atoms: 21
Formal charge: 0
Complexity: 422

Physicochemical properties

Melting point: 89 · 89-91 °C(lit.)
Boiling point: 350.4 · 350.4±25.0 °C(Predicted)
Density: 1.04 · 1.04±0.1 g/cm3(Predicted)
refractive index: -118 ° · -118 ° (C=1, CHCl3)
storage temp.: Inert atmosphere,Room Temperature
solubility: 2 O; · insol H2O; sol all common organic solvents
pka: 5.69 · 5.69±0.70(Predicted)
form: Crystalline Powder
color: White to light yellow
optical activity: 20 · [α]20/D 120°, c = 5 in chloroform
InChI: InChI=1S/C17H30N2O2/c1-15(2,3)11-9-20-13(18-11)17(7,8)14-19-12(10-21-14)16(4,5)6/h11-12H,9-10H2,1-8H3/t11-,12-/m1/s1
InChIKey: DPMGLJUMNRDNMX-VXGBXAGGSA-N
SMILES: C(C1=N[C@@H](C(C)(C)C)CO1)(C1=N[C@@H](C(C)(C)C)CO1)(C)C
CAS DataBase Reference: 131833 · 131833-93-7(CAS DataBase Reference)

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (97.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2A (100%)；STOT SE 3 (97.6%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
hs_code: 29349990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335

Chemistry & industry

Applications

UsesChiral catalyst for asymmetric synthesis. C2 symmetric ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.

Preparation methods

Preparation(S,S)-(-)-2,2'-ISOPROPYLIDENEBIS(4-TERT-BUTYL-2-OXAZOLINE) is readily prepared from chiral β-amino alcohols using standard methods for the synthesis of 2-oxazolines.