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

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