Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester

Product Name: Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester
CAS No.: 153559-48-9
Chemical Name: Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester
Synonyms: Bexarotene Impurity Z4f;bexarotene methyl ester;Methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl);Methyl 4-(1-(3,5,5,8,8-pentaMethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate;methyl4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoate;methyl 4-<1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl>benzoate;4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoic acid methyl ester;Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester
CBNumber: CB12502480
Molecular Formula: C25H30O2
Formula Weight: 362.5
MOL File: 153559-48-9.mol

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Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester Property

Melting point:: 160-161 °C(Solv: ethyl acetate (141-78-6); methanol (67-56-1))
Boiling point:: 472.3±44.0 °C(Predicted)
Density: 1.007±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: Chloroform, Methanol (Slightly)
form: Solid
color: White to Light Beige

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: M289820
Product name: MethylBexarotenate
Packaging: 1g
Price: $1265
Updated: 2021/12/16

AK Scientific

Product number: 7704AA
Product name: Methyl4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate
Packaging: 250mg
Price: $394
Updated: 2021/12/16

Matrix Scientific

Product number: 098104
Product name: Methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate
Purity: 95+%
Packaging: 250mg
Price: $643
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CHM0068766
Product name: 4-[1-(5,6,7,8-TETRAHYDRO-3,5,5,8,8-PENTAMETHYL-2-NAPHTHALENYL)ETHENYL]-BENZOIC ACID METHYL ESTER
Purity: 95.00%
Packaging: 5G
Price: $909.56
Updated: 2021/12/16

Matrix Scientific

Product number: 098104
Product name: Methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate
Purity: 95+%
Packaging: 1g
Price: $1428
Updated: 2021/12/16

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Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester Chemical Properties,Usage,Production

Uses

Methyl Bexarotenate is a related compound of Bexarotene (B336750), which is an antineoplastic agent and a selective retinoid X receptor (RXR) agonist.

Synthesis

1779-49-3

153559-45-6

153559-48-9

Methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-carbonyl)benzoate was synthesized by Wittig reaction using methyltriphenylphosphonium bromide and methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate as starting materials. During the synthesis, crystals of compound 35 were found to be suitable for X-ray diffraction analysis. To complete the synthesis of bexarotene, compound 35 was first subjected to Friedel-Crafts acylation using crude monomethyl terephthaloyl chloride (36) to give ketone 37. Subsequently, ketone 37 was converted to olefinic ester 38 by Wittig reaction. finally, olefinic ester 38 was subjected to saponification in the presence of potassium hydroxide followed by acidification with aqueous hydrochloric acid. to obtain the target product bexarotene (39) (Scheme 2).

References

[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 19, p. 5950 - 5966
[2] Patent: WO2011/103321, 2011, A1. Location in patent: Page/Page column 19
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2930 - 2941
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 7, p. 701 - 712
[5] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3368 - 3383

Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

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Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester Suppliers

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153559-48-9, Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl esterRelated Search:

Bexarotene Impurity 8 Bexarotene Impurity 3 Bexarotene Impurity 7 Bexarotene Bexarotene Impurity 2 Methyl 4-[(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl]benzoate Bexarotene Impurity 10 Bexarotene Impurity 1 Bexarotene Impurity 9 Bexarotene Impurity 4 Bexarotene Acyl-β-D-glucuronide METHANE

Methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)

Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester

Methyl 4-(1-(3,5,5,8,8-pentaMethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate

methyl 4-<1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl>benzoate

4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoic acid methyl ester

bexarotene methyl ester

Bexarotene Impurity Z4f

methyl4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoate

153559-48-9