55440-54-5

Basic information

• Product Name: 5-CHLORO-2-METHOXYPHENYL ISOCYANATE
• Synonyms: 4-chloro-2-isocyanato-1-methoxybenzene(SALTDATA: FREE);5-Chloro-2-methoxyphenyl isocyanate 98%;2-METHOXY-5-CHLORO PHENYL ISOCYANATE;5-CHLORO-2-METHOXYPHENYL ISOCYANATE
• CAS NO: 55440-54-5
• Molecular Formula: C₈H₆ClNO₂
• Molecular Weight: 183.59
• Product Categories: Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 55440-54-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 58-61 °C(lit.)
• Boiling Point: 271.7 °C at 760 mmHg
• Flash Point: 118.1 °C
• Appearance: White Solid
• Density: 1.22 g/cm³
• Vapor Pressure: 0.00633mmHg at 25°C
• Refractive Index: 1.534
• Sensitive: Moisture Sensitive/Lachrymatory
• BRN: 2719682
• CAS DataBase Reference: 5-CHLORO-2-METHOXYPHENYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-2-METHOXYPHENYL ISOCYANATE(55440-54-5)
• EPA Substance Registry System: 5-CHLORO-2-METHOXYPHENYL ISOCYANATE(55440-54-5)

Safety Data

• Hazard Codes: Xn,T,C,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: 2206
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 55440-54-5(Hazardous Substances Data)

Usage

Description

5-Chloro-2-methoxyphenyl isocyanate, also known as 4-chloro-2-isocyanato-1-methoxybenzene, is an organic building block that contains an isocyanate group. 5-Chloro-2-methoxyphenyl isocyanate is characterized by the presence of a chlorine atom at the 5-position and a methoxy group at the 2-position on a benzene ring, with an isocyanate functional group attached. Its unique structure makes it a versatile intermediate in the synthesis of various organic compounds and materials.

Uses

Used in Pharmaceutical Industry:
5-Chloro-2-methoxyphenyl isocyanate is used as a key intermediate in the synthesis of pharmaceutical compounds. Its reactive isocyanate group allows for the formation of urea and carbamate derivatives, which are common structural motifs in many drugs. 5-Chloro-2-methoxyphenyl isocyanate can be utilized in the development of new medications with potential applications in various therapeutic areas.
Used in Agrochemical Industry:
In the agrochemical industry, 5-Chloro-2-methoxyphenyl isocyanate serves as a valuable building block for the synthesis of active ingredients in pesticides and herbicides. Its structural features can be exploited to create new molecules with improved biological activity and selectivity, leading to more effective and environmentally friendly agrochemical products.
Used in Polymer Industry:
5-Chloro-2-methoxyphenyl isocyanate is used as a monomer in the polymer industry for the synthesis of polyurethanes and other polymeric materials. The isocyanate group can react with various compounds, such as alcohols and amines, to form urethane and urea linkages, which are the backbone of many polymers with diverse properties and applications.
Used in Dye and Pigment Industry:
5-Chloro-2-methoxyphenyl isocyanate is also used in the dye and pigment industry as a precursor for the synthesis of various dyes and pigments. The presence of the chlorine and methoxy substituents on the benzene ring can influence the color and properties of the resulting dyes, making it a useful building block for the development of new colorants with specific characteristics.
Used in Research and Development:
5-Chloro-2-methoxyphenyl isocyanate is utilized in research and development for the exploration of new chemical reactions and the synthesis of novel organic compounds. Its unique structure and reactivity make it an interesting candidate for studying various organic transformations and the development of new synthetic methodologies.

InChI:InChI=1/C8H6ClNO2/c1-12-8-3-2-6(9)4-7(8)10-5-11/h2-4H,1H3

Upstream product

• 75-44-5 phosgene 
• 95-03-4 5-chloro-2-methoxyaniline 
• 29568-33-0 2-methoxy-5-chlorobenzoyl chloride 
• 3438-16-2 5-chloro-2-methoxybenzoic acid 
• 1152958-89-8 C₈H₆ClN₃O₂ 

Downstream Products

• 88451-17-6 1-Benzyl-1-butyl-3-(5-chloro-2-methoxy-phenyl)-urea 
• 335064-79-4 C₁₇H₂₁ClN₄O₂ 
• 202823-21-0 N-(5-chloro-2-methoxyphenyl)urea 
• 919120-19-7 C₂₇H₃₇ClN₄O₃ 
• 919120-18-6 C₂₇H₃₇ClN₄O₃ 
• 1029970-20-4 (2Z)-2-(3-butyl-5-methyl-1,3,4-thiadiazol-2(3H)-ylidene)-N-(5-chloro-2-methoxyphenyl)acetamide 
• 1160165-44-5 1-(1-benzyl-3-oxo-2,3-dihydro-1H-indazol-5-yl)-3-(5-chloro-2-methoxy-phenyl)-urea 
• 1349393-47-0 C₂₁H₁₉ClN₆O₂ 
• 1348143-62-3 C₂₀H₁₇ClN₆O₂ 
• 847024-28-6 1-(5-chloro-2-methoxy-phenyl)-3-(3-{8-[(pyridin-4-yl-methyl)-amino]-imidazo[1,2-a]pyrazin-6-yl}-phenyl)-urea 

Relevant articles and documents

DEUTERIUM-ENRICHED HETEROCYCLIC COMPOUNDS AS KINASE INHIBITORS

The present invention provides deuterium-enriched heteroaryl-containing urea compounds (I) and use of the same for treating conditions mediated by protein kinase such as

Cyclization-Activated Prodrugs: N-(Substituted 2-hydroxyphenyl and 2-hydroxypropyl)carbamates Based on Ring-Opened Derivatives of Active Benzoxazolones and Oxazolidinones as Mutual Prodrugs of Acetaminophen

N-(Substituted 2-hydroxyphenyl)- and N-(substituted 2-hydroxypropyl)carbamates based on masked active benzoxazolones (model A) and oxazolidinones (model B), respectively, were synthesized and evaluated as potential drug delivery systems.A series of alkyl and aryl N-(5-chloro-2-hydroxyphenyl)carbamates 1 related to model A was prepared.These are open drugs of the skeletal muscle relaxant chlorzoxazone.The corresponding 4-acetamidophenyl ester named chloracetamol is a mutual prodrug of chloroxazone and acetaminophen.Chlorzacetamol and two other mutual prodrugs of active bezoxazolones and acetaminophen were obtained in a two-step process via condensation of 4-acetamidophenyl 1,2,2,2-tetrachloroethyl carbonate with the appropiate anilines.Based on model B, two mutual prodrugs of acetaminophen and active oxazolidinones (metaxalone and mephenoxalone) were similarly obtained using the appropiate amines.All the carbamate prodrugs prepared were found to release the parent drugs in aqueous (pH 6-11) and plasma (pH 7.4) media.The detailed mechanistic study of prodrugs 1 carried out in aqueous medium at 37 deg C shows a change in the Broensted-type relationship log t1/2 vs pKa of the leaving groups ROH: log t1/2 = 0.46pKa - 3.55 for aryl and trihalogenoethyl esters and log t1/2 = 1.46pKa - 16.03 for alkyl esters.This change is consistent with a cyclization mechanism involving a change in the rate-limiting step from formation of a cyclic tetrahedral intermediate (step k1) to departure of the leaving group ROH (step k2) when the leaving group ability decreases.This mechanism occurs for all the prodrugs related to model A.Regeneration of the parent drugs from mutual prodrugs related to model B takes place by means of a rate-limiting elimination-addition reaction (E1cB mechanism).This affords acetaminophen and the corresponding 2-hydroxypropyl isocyanate intermediates which cyclize at any pH to the corresponding oxazolidinone drugs.As opposed to model A, the rates of hydrolysis of mutual prodrugs of model B clearly exhibit a catalytic role of the plasma.It is concluded from the plasma studies that the carbamate substrates can be enzymatically transformed into potent electrophiles, i.e., isocyanates.In the case of the present study, the prodrugs are 2-hydroxycarbamates for which the propinquity of the hydroxyl residue and the isocyanate group enforces a cyclization reaction.This mechanistic particularity precludes their potential toxicity in terms of potent electrophiles capable of modifying critical macromolecules.