1-NAPHTHOYL CHLORIDE

PRODUCT IDENTIFICATION
CAS NO. 879-18-5

1-NAPHTHOYL CHLORIDE

EINECS NO. 212-903-9
FORMULA C11H7ClO
MOL WT. 190.63
H.S. CODE

2916.39.0090

TOXICITY  
SYNONYMS 1-Naphthalenecarbonyl chloride;
alpha-Naphthalenecarbonyl chloride; 1-Naphthalenecarboxylic acid chloride; 1-(Chlorocarbonyl)naphthalene; 1-Naphthoic chloride;

SMILES

O=C(c1c2c(cccc2)ccc1)Cl

CLASSIFICATION

 

PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE clear to yellowish liquid
MELTING POINT 24 - 26 C
BOILING POINT 190 C at 35 hPa
SPECIFIC GRAVITY

1.26 - 1.27

SOLUBILITY IN WATER Decomposes
pH  
VAPOR DENSITY  

AUTOIGNITION

 

NFPA RATINGS

 Health: 1; Flammability: 1; Reactivity: 0

REFRACTIVE INDEX

 

FLASH POINT > 110 C
STABILITY Stable under ordinary conditions.  Moisture Sensitive

GENERAL DESCRIPTION & EXTERNAL LINKS
Acyl is a radical formed from an organic acid by removal of a hydroxyl group. The general formula of acyl compound is RCO-. Acyl halide is one of a large group of organic substances containing the halocarbonyl group, have the general formula RCO·X, where X is a halogen atom (fluorine, chlorine, bromine, iodine, and astatine) and R may be aliphatic, alicyclic, aromatic, and H etc. In substitutive chemical nomenclature, their names are formed by adding '-oyl' as a suffix to the name of the parent compound; ethanoyl chloride, CH3COCl, is an example. The terms acyl and aroyl halides refer to aliphatic or aromatic derivatives, respectively. Acyl halides are made by replacing the -OH group in carboxylic acids by halogen using halogenating agents. They react readily with water, alcohols, and amines and are widely used in organic synthetic process whereby the acyl group is incorporated into the target molecules by substitution of addition-elimination sequence called acylation reaction.  Acylation reaction involves substitution by an electron donor (nucleophile) at the electrophilic carbonyl group (C=O). Common nucleophiles in the acylation reaction are aliphatic and aromatic alcohols, both of which give rise to esters and amines (RNH2) which give amides. The carboxylic acid (X = OH) itself can function as an acylating agent when it is protonated by a strong acid catalyst as in the direct esterification of an alcohol. Two common acylation agents, with the general formula RCOX, are acid halides (X = halogen atom) and anhydrides (X = OCOR). Schotten-Baumann reaction is an acylation reaction that uses an acid chloride in the presence of dilute alkali to acylate the hydroxyl and amino group of organic compounds. There are also other acylating agents.

Wikipedia Linking:http://en.wikipedia.org/wiki/Acyl_chloride

http://mcat-review.org/
General principles

  • relative reactivity of acid derivatives: Acid chloride > Anhydride > Esters > Amides
    • Acid halides are the most reactive derivatives because halides are very good leaving groups.
    • Amides are the most stable derivatives because NR2- is a terrible leaving group. Also, the C-N bond has a partial double bond characteristic. Proteins are made of peptide bonds, and they are very stable.
  • steric effects: bulky groups around the C=O group helps protect the carbon center from nucleophilic attack.
  • electronic effects: groups that can redistribute and stabilize negative charges are good leaving groups. For example, the anhydride has a good leaving group - the carboxylate ion - because the COO- can redistribute the negative charge to both oxygens via resonance.
  • strain (e.g., beta-lactams)
    • Amides have a double bond characteristic between the carbon and nitrogen. This means that the C-N bond can not rotate.
    • Normally, the sigma bonds in a ring rotate as to achieve the most stable conformation, but this can't occur for the C-N bond if the ring contains an amide.
    • Because of C-N bond in an amide can not rotate, rings that contain amides have higher strain.
    • An example of this is the beta-lactam, which is basically a 4 membered ring with 1 amide in it.

http://www.rsc.org/

Acyl chloride ( A compound consisting of an acyl group bonded to chlorine.)
Articles referencing this term..............

1-Naphthoyl Chloride is used as an intermediate for the synthesis of pharmaceuticals, dyes and other organic compounds. Building block in the synthesis of MMP inhibitors
SALES SPECIFICATION

APPEARANCE

 clear to yellowish liquid
ASSAY (HPLC)

99.0% min

MELTING POINT

 24 - 26 C
TRANSPORTATION
PACKING

Steel Drum/P.E. Plastic Drum/Plastic Jerry can (UN Approval)

HAZARD CLASS  
UN NO. 3265
OTHER INFORMATION
Hazard Symbols: C, Risk Phrases: 34, Safety Phrases: 26-36/37/39-45