2-Naphthyl beta-D-glucopyranoside

Basic Information

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CAS Number

6044-30-0

Molecular Formula

C16H18O6

Molecular Weight

306.31 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Basic Physical Properties

Melting Point

183°C

Boiling Point

567.9°C at 760 mmHg

SMILES

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C1=CC=C2C=C(C=CC2=C1)OC3C(C(C(C(O3)CO)O)O)O

InChI

InChI=1S/C16H18O6/c17-8-12-13(18)14(19)15(20)16(22-12)21-11-6-5-9-3-1-2-4-10(9)7-11/h1-7,12-20H,8H2/t12-,13-,14+,15-,16-/m1/s1

InChIKey

MWHKPYATGMFFPI-IBEHDNSVSA-N

LogP

0.018500000000000405

Topological Polar Surface Area

99.38000000000001 Å²

Hydrogen Bond Donor/Acceptor

4 / 6

Complexity

365

Safety Information

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Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H332 Harmful if inhaled
Acute toxicity, inhalation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Synonyms & References

English

Q27162434
A868977
NS00044887
(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(naphthalen-2-yloxy)tetrahydro-2H-pyran-3,4,5-triol
2-Naphthyl I(2)-D-glucopyranoside monohydrate
beta-naphthol glucoside
2-Naphthylb-D-glucopyranoside
AMY41376
SR-01000463452-1
6044-30-0
HMS654O06
2-Naphthyl b-D-glucopyranoside
2-Naphthalenyl beta-D-glucopyranoside
MFCD00067623
AKOS001660076
b-D-Glucopyranoside, 2-naphthalenyl
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-naphthalen-2-yloxyoxane-3,4,5-triol
2-Naphthyl beta-D-glucopyranoside
ChemDiv1_023898
SR-01000463452
2-naphthol glucoside
(2R,3S,4S,5R,6S)-2-(HYDROXYMETHYL)-6-(NAPHTHALEN-2-YLOXY)OXANE-3,4,5-TRIOL
naphthalen-2-yl beta-D-glucopyranoside
DTXSID50874798
DS-5085
C75823
2-naphthyl beta-D-glucoside
CHEBI:90258
2-NAPHTHYL-BETA-D-GLUCOPYRANOSIDE
EINECS 227-933-8
CS-0322827

MDL Number

MFCD00180742

Customs Code

2932999099

FAQ

What are the physical and chemical properties of 2-Naphthyl beta-D-glucopyranoside (CAS: 6044-30-0)?

2-Naphthyl beta-D-glucopyranoside is a crystalline compound with a molecular weight of approximately 286.28 g/mol. It has a melting point of 118-119°C. This compound is moderately soluble in water and ethanol. It is less reactive compared to simple sugars but can undergo glycoside hydrolysis under basic conditions. Its stability under acidic conditions is good, making it suitable for various applications in organic synthesis.

How is 2-Naphthyl beta-D-glucopyranoside (CAS: 6044-30-0) typically synthesized?

2-Naphthyl beta-D-glucopyranoside is often synthesized via a glycosylation reaction between naphthyl-protected sugar and β-D-glucose. Common protecting groups include benzyl or methyl groups. The synthesis typically involves a condensation step followed by deprotection under suitable conditions. The yield is usually around 70-80%, and the selectivity is high due to the specific orientation of the glycosidic bond.

What industries use 2-Naphthyl beta-D-glucopyranoside (CAS: 6044-30-0)?

2-Naphthyl beta-D-glucopyranoside finds applications in the pharmaceutical industry for the synthesis of complex carbohydrates and drug intermediates. It is also used in the polymer industry for the modification of polymers through glycosylation reactions. Additionally, this compound is utilized in the development of sensors and semiconductors where its unique structural properties are advantageous.

What precautions should be taken when handling 2-Naphthyl beta-D-glucopyranoside (CAS: 6044-30-0)?

When handling 2-Naphthyl beta-D-glucopyranoside, it is important to wear appropriate personal protective equipment (PPE) such as gloves and safety goggles. This compound should be stored in a cool, dry place away from heat sources and ensure good ventilation. In case of a spill, it should be carefully cleaned up using appropriate absorbent materials. For detailed safety information, refer to the Safety Data Sheet (SDS).