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32316-92-0

32316-92-0 Structure

32316-92-0 Structure
IdentificationMore
[Name]

2-Naphthaleneboronic acid
[CAS]

32316-92-0
[Synonyms]

1-NAPHTHALENEBORONIC ACID
1-NAPHTHYLBORONIC ACID
1-NAPHTHYLENEBORONIC ACID
2-NAPHTHALENEBORONIC ACID
2-NAPHTHALENEYLBORONIC ACID
2-NAPHTHENEBORONIC ACID
2-NAPHTHYLBORONIC ACID
AKOS BRN-0020
AKOS BRN-0041
ALPHA-NAPHTHYLBORIC ACID
NAPHTHALEN-1-YLBORONIC ACID
NAPHTHALEN-2-YLBORONIC ACID
NAPHTHALENE-1-BORONIC ACID
NAPHTHALENE-2-BORONIC ACID
NAPHTHALENYL-1-BORONIC ACID
NAPHTHALENYL-2-BORONIC ACID
RARECHEM AH PB 0125
RARECHEM AH PB 0126
2-Naphthalene Boric Acid
2-Naphthylboronic caid
[EINECS(EC#)]

628-070-3
[Molecular Formula]

C10H9BO2
[MDL Number]

MFCD00019722
[Molecular Weight]

171.99
[MOL File]

32316-92-0.mol
Questions And AnswerBack Directory
[description]

2-Naphthalene Boronic Acid is an organometallic iridium complex with applications in catalysis and Pharmaceutical manufacturing. It can be also used in the study of an enantioselective rhodium-catalyzed addition of aryl boronic acids to 2,2,2-trifluoroacetophenones leading to chiral, tertiary trifluoromethyl alcohols.​
[Uses]

2-Naphthaleneboronic acid is a useful research chemical for organic synthesis and other chemical processes.

[Solubility]

Solubility in water: slightly soluble. Other solubilities: soluble in methanol

[Application]

It is used to study the enantioselective rhodium-catalyzed addition reaction of arylboronic acid and 2,2,2-trifluoroacetophenone to generate chiral tertiary trifluoromethanol. 
It can also be used to study the palladium-catalyzed addition reaction of arylboronic acid and nitrile to generate aryl ketones, and aromatic adverbial clauses: palladium-catalyzed addition of oxynitrile to benzofuran.

Chemical PropertiesBack Directory
[Appearance]

yellow crystal powde
[Melting point ]

269-275 °C(lit.)
[Boiling point ]

381.9±25.0 °C(Predicted)
[density ]

1.21±0.1 g/cm3(Predicted)
[storage temp. ]

0-6°C
[Water Solubility ]

Slightly soluble in water
[form ]

Crystalline Powder and/or Chunks
[pka]

8.53±0.30(Predicted)
[color ]

White to off-white
[Detection Methods]

HPLC
[BRN ]

2936449
[InChI]

InChI=1S/C10H9BO2/c12-11(13)10-6-5-8-3-1-2-4-9(8)7-10/h1-7,12-13H
[InChIKey]

KPTRDYONBVUWPD-UHFFFAOYSA-N
[SMILES]

C1=C2C(C=CC=C2)=CC=C1B(O)O
[CAS DataBase Reference]

32316-92-0(CAS DataBase Reference)
Safety DataBack Directory
[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
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
[WGK Germany ]

3
[Hazard Note ]

Irritant
[TSCA ]

No
[HazardClass ]

IRRITANT
[HS Code ]

29319099
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Tetrahydrofuran-->n-Butyllithium-->Trimethyl borate-->2-Naphthol-->2-Bromonaphthalene
[Preparation Products]

10-(2-Naphthyl)anthracene-9-boronic acid-->4-(Naphthalen-2-yl)phenylboronic acid-->2-Naphthalenemethanol-->9-Bromo-10-(2-naphthyl)anthracene-->2,2'-Dinaphthyl ketone-->β-Acetamidonaphthalene-->Benzenamine, 4-(2-naphthalenyl)--->2-(2-phenylethynyl)naphthalene
Hazard InformationBack Directory
[Chemical Properties]

yellow crystal powde

[Synthesis]

To a two-neck 250mL round bottom flask, triisopropyl borate (3.30mL, 29.06mmol) and 3-bromoquinoline (3.00g, 14.49mmol) was dissolved in dry THF (100mL), then n-butyllithium (14.50mL of a 2M solution in hexane, 29.00mmol) was added dropwise via a dropping funnel over 1h under N2 at-78°C. After 2h, the acetone/dry ice bath was removed, and the reaction solution was allowed to warm to 0°C. The reaction was then quenched with a 2M HCl solution, and the pH value was adjusted to 7 with a solution of 2M NaHCO3. The resulting solution was extracted with ethyl acetate (EA) (3×100mL). The combined organic layers were dried with MgSO4 and evaporated to dryness. n-Hexane was then added to precipitated the product 2-Naphthaleneboronic acid as a white solid (80% yield).
Spectrum DetailBack Directory
[Spectrum Detail]

2-Naphthaleneboronic acid(32316-92-0)1HNMR
2-Naphthaleneboronic acid(32316-92-0)IR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

2-Naphthaleneboronic acid, 97+%(32316-92-0)
[Alfa Aesar]

2-Naphthaleneboronic acid, 97%(32316-92-0)
[Sigma Aldrich]

32316-92-0(sigmaaldrich)
[TCI AMERICA]

2-Naphthaleneboronic Acid  (contains varying amounts of Anhydride)(32316-92-0)
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