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1-Naphthyl chloroformate

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Identification
Molecular formula
C11H7ClO2
CAS number
4516-87-6
IUPAC name
1-naphthyl carbonochloridate
State
State

At room temperature, 1-naphthyl chloroformate is in liquid state.

Melting point (Celsius)
-15.00
Melting point (Kelvin)
258.15
Boiling point (Celsius)
295.00
Boiling point (Kelvin)
568.15
General information
Molecular weight
204.63g/mol
Molar mass
204.6290g/mol
Density
1.2740g/cm3
Appearence

1-Naphthyl chloroformate is typically encountered as a colorless to pale yellow liquid. It may have a slight odor and is reactive due to the presence of the chloroformate group.

Comment on solubility

Solubility of 1-naphthyl carbonochloridate

1-naphthyl carbonochloridate, with the chemical formula C11H9ClO2, presents interesting solubility characteristics that are important for its use in various chemical applications.

Solubility in Different Solvents

This compound is generally insoluble in water, which is typical for organic compounds that possess a significant hydrophobic aromatic structure. However, it exhibits varying solubility in nonpolar and polar organic solvents.

  • Nonpolar solvents: It is typically soluble in nonpolar solvents such as hexane and benzene, which help to stabilize the aromatic interactions present in its structure.
  • Polar solvents: Limited solubility may be observed in polar solvents like ethanol or methanol. This can be attributed to the presence of the carbonochloridate functional group, which has some degree of polar character.

Factors Affecting Solubility

Several factors influence the solubility of 1-naphthyl carbonochloridate:

  • Temperature: Increased temperature often enhances solubility for most organic compounds.
  • Presence of pressure: In some cases, changes in pressure can affect solubility, especially for compounds released from solid forms.
  • Functional Groups: The presence of substituents can drastically alter the solubility profile, making it essential to consider these aspects in experimental conditions.

In summary, while 1-naphthyl carbonochloridate demonstrates limited water solubility, it is more compatible with organic solvents, making it an intriguing compound for synthetic applications.

Interesting facts

Interesting Facts about 1-Naphthyl Carbonochloridate

1-Naphthyl carbonochloridate is an intriguing compound that belongs to the family of acyl chlorides. It plays a significant role in organic synthesis, particularly in the modification of aromatic compounds. Here are some noteworthy aspects of this compound:

  • Reactivity: As an acyl chloride, 1-naphthyl carbonochloridate is known for its high reactivity. It readily participates in nucleophilic acyl substitution reactions, making it a valuable reagent in many chemical processes.
  • Applications: This compound is used primarily in the synthesis of esters, especially with alcohols that contain nucleophilic sites. It can also be employed in the production of various pharmaceuticals and agrochemicals.
  • Phenolic Substitutions: 1-Naphthyl carbonochloridate can be used to introduce naphthyl groups to phenolic compounds, which can enhance their biological activity. This transformation is particularly important in drug discovery.
  • Side Reactions: While it is useful, the reactive nature of this compound can lead to undesired side reactions if not handled properly. Chemists must carefully control reaction conditions to favor the desired pathways.
  • Safety Considerations: Like other acyl chlorides, 1-naphthyl carbonochloridate can release hydrogen chloride gas upon hydrolysis, which requires appropriate safety precautions when conducting experiments in the lab.

In summary, 1-naphthyl carbonochloridate is not only a critical compound in synthetic organic chemistry but also serves as an excellent example of how reactive intermediates can facilitate the discovery and development of new chemicals. As described by chemists, "Its versatility opens doors to the creation of a wide array of important functionalized compounds."
Understanding its properties and potential not only enriches our knowledge of organic compounds but also allows for advancements in various fields, from pharmaceuticals to materials science.

Synonyms
1-Naphthyl chloroformate
3759-61-3
1-Naphthylchlorocarbonate
Chloroformic acid 1-naphthyl ester
1-Naphthyl chlorocarbonate
Carbonochloridic acid, 1-naphthalenyl ester
alpha-Naphthyl chloroformate
EINECS 223-168-9
Chloromrowczan 1-naftylu
Chloromrowczan 1-naftylu [Czech]
Carbanochloridic acid, naphthyl ester
NSC 106896
BRN 0512216
Chloroformic acid, ester with 1-naphthol
FORMIC ACID, CHLORO-, 1-NAPHTHYL ESTER
DTXSID3063170
DTXCID5039357
223-168-9
naphthalen-1-yl carbonochloridate
naphthalen-1-yl chloroformate
MFCD01726288
1-napthalenyl chloroformate
Chlormethansaurenaphthylester
SCHEMBL878536
.alpha.-Naphthyl chloroformate
Formic acid, 1-naphthyl ester
Chloroformic acid, 1-naphthyl ester
NSC106896
AKOS017390825
NSC-106896
SY296662
DB-238291
1-Naphthyl chloroformate, >=98.0% (GC)
CS-0244329
NS00030224
EN300-275648
G25886