15356-62-4

Basic information

• Product Name: (-)-MENTHOXYACETYL CHLORIDE
• Synonyms: (-)-MENTHOXYACETYL CHLORIDE;(-)-MENTHOXYACETYL CHLORIDE 98+%;[(2-Isopropyl-5-methylcyclohexyl)oxy]acetyl chloride;[(1R)-2α-Isopropyl-5β-methylcyclohexane-1β-yl]oxyacetic acid chloride;[[(1R)-2α-Isopropyl-5β-methylcyclohexan-1β-yl]oxy]acetyl chloride;2-[[(1R)-2α-Isopropyl-5β-methylcyclohexane-1β-yl]oxy]acetyl chloride;l-Menthoxyacetyl chloride;2-[[(1R)-2alpha-Isopropyl-5beta-Methylcyclohexane-1beta-yl]oxy]acetyl chloride
• CAS NO: 15356-62-4
• Molecular Formula: C₁₂H₂₁ClO₂
• Molecular Weight: 232.75
• Product Categories: chiral;Biochemistry;for Resolution of Alcohols & Thiols;Monocyclic Monoterpenes;Optical Resolution;Synthetic Organic Chemistry;Terpenes;Acid Halides;Chiral Building Blocks;Organic Building Blocks
• Mol File: 15356-62-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 136 °C / 12mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.033 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00189mmHg at 25°C
• Refractive Index: n20/D 1.469(lit.)
• CAS DataBase Reference: (-)-MENTHOXYACETYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-MENTHOXYACETYL CHLORIDE(15356-62-4)
• EPA Substance Registry System: (-)-MENTHOXYACETYL CHLORIDE(15356-62-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 15356-62-4(Hazardous Substances Data)

Usage

General Description

(-)-Menthoxyacetyl chloride is a chemical compound that is commonly used in the synthesis of pharmaceuticals and fragrances. It is derived from menthol, a natural compound found in mint plants, and is often used as a precursor in the production of menthol-based products. (-)-Menthoxyacetyl chloride is a versatile chemical that can be used in a variety of reactions, including acylation and esterification, and is known for its characteristic minty aroma. Its unique chemical structure and reactivity make it an important building block for the synthesis of various organic compounds, and it is widely used in the pharmaceutical and fragrance industries.

InChI:InChI=1/C12H21ClO2/c1-8(2)10-5-4-9(3)6-11(10)15-7-12(13)14/h8-11H,4-7H2,1-3H3/t9-,10+,11-/m1/s1

Upstream product

• 79-11-8 chloroacetic acid 
• 40248-63-3 menthoxyacetic acid 
• 2216-51-5 (-)-menthol 

Downstream Products

• 100921-90-2 3,4-dihydro-8-<3'-(N-isopropyl-N-L-menthoxyacetyl)amino-2'-L-menthoxyacetyl>propoxy-3-nitroxy-2H-1-benzopyran 
• 100921-90-2 3,4-dihydro-8-<3'-(N-isopropyl-N-L-menthoxyacetyl)amino-2'(S)-L-menthoxyacetyl>propoxy-3(S)-nitroxy-2H-1-benzopyran 
• 100921-90-2 3,4-dihydro-8-<3'-(N-isopropyl-N-L-menthoxyacetyl)amino-2'(R)-L-menthoxyacetyl>propoxy-3(R)-nitroxy-2H-1-benzopyran 
• 140380-83-2 ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (10S,11S)-10-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-10,11-dihydro-dibenzo[a,h]acridin-11-yl ester 
• 140380-83-2 ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (10R,11R)-10-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-10,11-dihydro-dibenzo[a,h]acridin-11-yl ester 
• 78549-56-1 (+)-trans-3-bromo-4-menthyloxyacetoxy-1,2,3,4-tetrahydrophenanthrene 
• 78549-55-0 (-)-trans-3-bromo-4-menthyloxyacetoxy-1,2,3,4-tetrahydrophenanthrene 
• 124751-78-6 <1R-(1α,2β,5β,6β)>-<5,6-di(benzoyloxy)-2-methoxy-3-cyclohexen-1-yl> (l)-menthoxyacetate 
• 124647-08-1 <1S-(1α,2β,5β,6β)>-<5,6-di(benzoyloxy)-2-methoxy-3-cyclohexen-1-yl> (l)-menthoxyacetate 
• 80124-35-2 (+)-(3S,4S)-trans-3-bromo-4-menthyloxyacetoxy-1,2,3,4-tetrahydrochrysene 
• 80056-88-8 (-)-(3R,4R)-trans-3-bromo-4-menthyloxyacetoxy-1,2,3,4-tetrahydrochrysene 
• 80433-94-9 ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3S,4S)-3-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-3,4-dihydro-benzo[a]anthracen-4-yl ester 
• 80399-26-4 ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3R,4R)-3-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-3,4-dihydro-benzo[a]anthracen-4-yl ester 
• 80446-24-8 ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (1S,2S)-2-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-1,2,3,4-tetrahydro-chrysen-1-yl ester 

Relevant articles and documents

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Synthesis, structure, and properties of chiral liquid crystal monomers and polymers based on menthol

To study structure-mesomorphism relationships of the monomers and polymers based on menthol, four new chiral monomers (M1-M4) and the corresponding homopolymers (P1-P4) with menthyl group were synthesized. Their chemical structures, formula, phase behavior, and thermal stability were characterized by FTIR, 1H NMR, 13C NMR, elemental analyses, differential scanning calorimetry, polarizing optical microscopy, X-ray diffraction, and thermogravimetric analysis. The selective reflection of light was investigated with ultraviolet/visible spectrometer. The influence of the mesogenic core rigidity, spacer length, and menthyl steric effect on the mesomorphism of M1-M4 and P 1-P4 was examined. By inserting a flexible spacer between the mesogenic core and the terminal menthyl groups, four target monomers and polymers could form the expected mesophase. Moreover, their melting temperature (Tm), glass transition temperature (Tg), clearing temperature (Ti), and mesophase range (δT) increased with increasing the mesogenic core rigidity; whereas the Tm and T g decreased, Ti and δT increased with an increase of the spacer length. M1 and M2 showed monotropic and enantiotropic cholesteric phase, respectively, whereas M3 and M 4 all revealed chiral smectic C (SmC*), cholesteric and cubic blue phases. In addition, with increasing temperature, the selective reflection of light shifted to the long wavelength region at the SmC* phase range and to the short wavelength region at the cholesteric range, respectively. P 1 and P2 only showed a smectic A (SmA) phase, whereas P3 and P4 exhibited the SmC* and SmA phases. All the obtained polymers had very good thermal stability.

Diastereomeric reissert compounds of isoquinoline and 6,7-dimethoxy-3,4- dihydroisoquinoline in stereoselective synthesis

(Chemical Equation Presented) Chiral acid chlorides were reacted with isoquinoline and 6,7-dimethoxy-3,4-dihydroisoquinoline to form diastereomeric Reissert compounds 8-11 and 18-21, respectively. The best diastereoselectivity (80:20) was achieved in formation of the 9-phenylmenthyl derivative 20. The diastereomers of 2-l-menthoxy-carbonyl-1,2-dihydroisoquinaldonitriles (S)-8/(R)-8), formed in equal amounts, were inseparable. However, the individual diastereomers of 2-cholesteryloxycarbonyl-1,2-dihydroisoquinaldonitriles ((R)-11 and (5)-11) and the 2-l-menthoxycarbonyl-6,7-dimethoxy-1,2,3,4- tetrahydroisoquinaldonitriles ((S)-19/(R)-19)) were each readily purified. (S)-8/(R)-8 (1:1) via the corresponding anions (NaH, -40°C, DMF) with pivaldehyde yielded in 82:18 predominance the S-diastereomer of 1-isoquinolyl tert-butyl carbinyl l-menthyl carbonate ((S)-12), which was obtained in pure form by a single recrystallization; hydrolysis produced 99% pure S-(-)-1-isoquinolyl tert-butyl carbinol [(S)-16]. Reactions of the anions of diastereomeric Reissert compounds, either as mixtures or pure single species, with aromatic aldehydes and alkyl halides proceeded with at best modest selectivity (diastereomeric ratios up to 66:34 and 72:28, respectively). Therefore, it is concluded that the Reissert anions are either planar or rapidly inverting tetrahedral structures.