Product Name

  • Name

    (±)-5-bromo-6-methoxy-alpha-methylnaphthalene-2-acetic acid

  • EINECS 248-594-2
  • CAS No. 27655-95-4
  • Article Data9
  • CAS DataBase
  • Density 1.483 g/cm3
  • Solubility
  • Melting Point 177-179 °C
  • Formula C14H13BrO3
  • Boiling Point 446.216 °C at 760 mmHg
  • Molecular Weight 309.159
  • Flash Point 223.664 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 27655-95-4 ((±)-5-bromo-6-methoxy-alpha-methylnaphthalene-2-acetic acid)
  • Hazard Symbols
  • Synonyms (±)-5-bromo-6-methoxy-alpha-methylnaphthalene-2-acetic acid;
  • PSA 46.53000
  • LogP 3.79900

Synthetic route

N-[ d,l-2-(5-bromo-6-methoxy-2-naphthyl)-propionyl]-l-aspartic acid

N-[ d,l-2-(5-bromo-6-methoxy-2-naphthyl)-propionyl]-l-aspartic acid

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
With concentrated aqueous hydrochloric acid In chloroform; water; acetic acid94.7%
N-[ d,l-2-(5-bromo-6-methoxy-2-naphthyl)-propionyl]-d-glutamic acid

N-[ d,l-2-(5-bromo-6-methoxy-2-naphthyl)-propionyl]-d-glutamic acid

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
In chloroform84%
2-(5-Bromo-6-methoxy-naphthalen-2-yl)-propionic acid 2-hydroxy-ethyl ester
108791-72-6

2-(5-Bromo-6-methoxy-naphthalen-2-yl)-propionic acid 2-hydroxy-ethyl ester

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
With sodium hydroxide In water Heating;
6-methoxy-2-propionylnaphthalene
2700-47-2

6-methoxy-2-propionylnaphthalene

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 80 percent / bromine / acetic acid / 30 °C
2: 87 percent / toluene-p-sulphonic acid / toluene / 24 h / Heating
3: 1.) sodium / 1.) THF, reflux, 7 h; 2.) THF-DMF, reflux, 11 h
4: 58 percent / meta-chloroperbenzoic acid / methanol / 20 - 25 °C
5: 2M-NaOH / H2O / Heating
View Scheme
Multi-step reaction with 5 steps
1: 80 percent / bromine / acetic acid / 30 °C
2: 87 percent / toluene-p-sulphonic acid / toluene / 24 h / Heating
3: 1.) sodium / 1.) THF, reflux, 2 h; 2.) THF-DMF, reflux
4: meta-chloroperbenzoic acid / methanol / 20 - 25 °C
5: 2M-NaOH / H2O / Heating
View Scheme
2-bromo-1-(5'-bromo-6'-methoxy-2'-naphthyl)-propan-1-one
80336-62-5

2-bromo-1-(5'-bromo-6'-methoxy-2'-naphthyl)-propan-1-one

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 87 percent / toluene-p-sulphonic acid / toluene / 24 h / Heating
2: 1.) sodium / 1.) THF, reflux, 7 h; 2.) THF-DMF, reflux, 11 h
3: 58 percent / meta-chloroperbenzoic acid / methanol / 20 - 25 °C
4: 2M-NaOH / H2O / Heating
View Scheme
Multi-step reaction with 4 steps
1: 87 percent / toluene-p-sulphonic acid / toluene / 24 h / Heating
2: 1.) sodium / 1.) THF, reflux, 2 h; 2.) THF-DMF, reflux
3: meta-chloroperbenzoic acid / methanol / 20 - 25 °C
4: 2M-NaOH / H2O / Heating
View Scheme
2-(1'-bromo-ethyl)-2-(5'-bromo-6'-methoxy-2'-naphthyl)-1,3-dioxolane
80336-61-4

2-(1'-bromo-ethyl)-2-(5'-bromo-6'-methoxy-2'-naphthyl)-1,3-dioxolane

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) sodium / 1.) THF, reflux, 7 h; 2.) THF-DMF, reflux, 11 h
2: 58 percent / meta-chloroperbenzoic acid / methanol / 20 - 25 °C
3: 2M-NaOH / H2O / Heating
View Scheme
Multi-step reaction with 3 steps
1: 1.) sodium / 1.) THF, reflux, 2 h; 2.) THF-DMF, reflux
2: meta-chloroperbenzoic acid / methanol / 20 - 25 °C
3: 2M-NaOH / H2O / Heating
View Scheme
2-(5-Bromo-6-methoxy-naphthalen-2-yl)-2-(1-phenylselanyl-ethyl)-[1,3]dioxolane

2-(5-Bromo-6-methoxy-naphthalen-2-yl)-2-(1-phenylselanyl-ethyl)-[1,3]dioxolane

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: meta-chloroperbenzoic acid / methanol / 20 - 25 °C
2: 2M-NaOH / H2O / Heating
View Scheme
2-(5-Bromo-6-methoxy-naphthalen-2-yl)-2-(1-phenyltellanyl-ethyl)-[1,3]dioxolane
108791-70-4

2-(5-Bromo-6-methoxy-naphthalen-2-yl)-2-(1-phenyltellanyl-ethyl)-[1,3]dioxolane

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 58 percent / meta-chloroperbenzoic acid / methanol / 20 - 25 °C
2: 2M-NaOH / H2O / Heating
View Scheme
C22H21Br3O3Te

C22H21Br3O3Te

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrazine hydrate
2: 58 percent / meta-chloroperbenzoic acid / methanol / 20 - 25 °C
3: 2M-NaOH / H2O / Heating
View Scheme
2(R)hydroxy-3(R)-[2-(5-bromo-6-methoxy-2-naphthyl)propanoyl]-butanedioic acid diethylester

2(R)hydroxy-3(R)-[2-(5-bromo-6-methoxy-2-naphthyl)propanoyl]-butanedioic acid diethylester

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
With hydrogenchloride In 1,2-dimethoxyethane
N-[ d,l-2-(5-bromo-6-methoxy-2-naphthyl)-propionyl]-l-glutamic acid

N-[ d,l-2-(5-bromo-6-methoxy-2-naphthyl)-propionyl]-l-glutamic acid

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In water
2(R)hydroxy-3(R)-[2-(5-bromo-6-methoxy-2-naphthyl)propanoyl]-butanedioic acid diisopropylester

2(R)hydroxy-3(R)-[2-(5-bromo-6-methoxy-2-naphthyl)propanoyl]-butanedioic acid diisopropylester

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
With hydrogenchloride In 1,2-dimethoxyethane
2(S)-hydroxy-3(S)-[2-(5-bromo-6-methoxy-2napthyl)-propanoyl]-butanedioic acid dimethyl ester

2(S)-hydroxy-3(S)-[2-(5-bromo-6-methoxy-2napthyl)-propanoyl]-butanedioic acid dimethyl ester

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
With hydrogenchloride In 1,2-dimethoxyethane
d,l-2-(5-bromo-6-methoxy-2-naphthyl)-propionic acid 2-bromoethyl ester
80336-88-5

d,l-2-(5-bromo-6-methoxy-2-naphthyl)-propionic acid 2-bromoethyl ester

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
With hydrogenchloride; potassium In methanol; water
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

naproxen
23981-80-8

naproxen

Conditions
ConditionsYield
With hydrazine hydrate In water98%
With sodium hydroxide; sodium borohydrid; palladium/charcoal In water; ethyl acetate
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid
22204-53-1

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions
ConditionsYield
With hydrogenchloride; aluminium trichloride In chloroform; water; toluene; 1,3,5-trimethyl-benzene91%
With hydrogenchloride; aluminium trichloride In chloroform; water; toluene; 1,3,5-trimethyl-benzene91%
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

methyl 2-(6-methoxy-2-naphthyl)propionate
30012-51-2

methyl 2-(6-methoxy-2-naphthyl)propionate

Conditions
ConditionsYield
With hydrogenchloride; sodium hydrogencarbonate; aluminium trichloride In dichloromethane; water; 1,3,5-trimethyl-benzene86.7%
With hydrogenchloride; sodium hydrogencarbonate; aluminium trichloride In dichloromethane; water; 1,3,5-trimethyl-benzene86.7%
With hydrogenchloride; sodium hydrogencarbonate; titanium tetrachloride In dichloromethane; water; 1,3,5-trimethyl-benzene32.7%
With hydrogenchloride; sodium hydrogencarbonate; titanium tetrachloride In dichloromethane; water; 1,3,5-trimethyl-benzene32.7%
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

5-bromo-6-methoxy-2-acetylnaphthalene
84167-74-8

5-bromo-6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With iron(III) chloride; oxygen In N,N-dimethyl-formamide at 110℃;82%
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

2-(5-bromo-6-methoxy-naphthalen-2-yl)-propionyl chloride
99231-35-3

2-(5-bromo-6-methoxy-naphthalen-2-yl)-propionyl chloride

Conditions
ConditionsYield
With pyridine; thionyl chloride In benzene Heating;
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

S-(+)-2-(5-bromo-6-methoxy-2-naphthyl)-propionic acid methylester
136945-97-6

S-(+)-2-(5-bromo-6-methoxy-2-naphthyl)-propionic acid methylester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride; pyridine / benzene / Heating
2: 95.6 percent / CH2Cl2
View Scheme
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

(R)-2-(5-Bromo-6-methoxy-naphthalen-2-yl)-propionic acid methyl ester

(R)-2-(5-Bromo-6-methoxy-naphthalen-2-yl)-propionic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride; pyridine / benzene / Heating
2: 95.6 percent / CH2Cl2
3: Candida cylindraceae lipase / aq. phosphate buffer / 90 h / 30 °C / pH 8.0
View Scheme
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

(S)-2-(5-Bromo-6-methoxy-naphthalen-2-yl)-propionic acid ethyl ester

(S)-2-(5-Bromo-6-methoxy-naphthalen-2-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride; pyridine / benzene / Heating
2: 90 percent / CH2Cl2
3: Candida cylindraceae lipase / aq. phosphate buffer / 105 h / 30 °C / pH 8.0
View Scheme
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

(R)-2-(5-Bromo-6-methoxy-naphthalen-2-yl)-propionic acid ethyl ester

(R)-2-(5-Bromo-6-methoxy-naphthalen-2-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride; pyridine / benzene / Heating
2: 90 percent / CH2Cl2
3: Candida cylindraceae lipase / aq. phosphate buffer / 105 h / 30 °C / pH 8.0
View Scheme
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

2-(5-bromo-6-methoxy-naphthalen-2-yl)-propionic acid ethyl ester
866365-36-8

2-(5-bromo-6-methoxy-naphthalen-2-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride; pyridine / benzene / Heating
2: 90 percent / CH2Cl2
View Scheme
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

d,l-2-(5-bromo-6-methoxy-2-naphthyl)-propionic acid n-butyl ester
103772-32-3

d,l-2-(5-bromo-6-methoxy-2-naphthyl)-propionic acid n-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride; pyridine / benzene / Heating
2: 93.8 percent / CH2Cl2
View Scheme
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

S-(+)-2-(5-Bromo-6-Methoxy-2-Naphthyl)-Propionic Acid
84236-26-0

S-(+)-2-(5-Bromo-6-Methoxy-2-Naphthyl)-Propionic Acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride; pyridine / benzene / Heating
2: 95.6 percent / CH2Cl2
3: Candida cylindraceae lipase / aq. phosphate buffer / 90 h / 30 °C / pH 8.0
View Scheme
Multi-step reaction with 3 steps
1: thionyl chloride; pyridine / benzene / Heating
2: 90 percent / CH2Cl2
3: Candida cylindraceae lipase / aq. phosphate buffer / 105 h / 30 °C / pH 8.0
View Scheme
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

2(R)-(-)-(5-bromo-6-methoxy-2-naphthyl)propanoic acid
92471-85-7

2(R)-(-)-(5-bromo-6-methoxy-2-naphthyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride; pyridine / benzene / Heating
2: 90 percent / CH2Cl2
3: Candida cylindraceae lipase / aq. phosphate buffer / 105 h / 30 °C / pH 8.0
View Scheme
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

2-(S)-(5-bromo-6-methoxy-2-naphthyl)-propionic acid methyl ester

2-(S)-(5-bromo-6-methoxy-2-naphthyl)-propionic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride; pyridine / benzene / Heating
2: 95.6 percent / CH2Cl2
3: Candida cylindraceae lipase / aq. phosphate buffer / 90 h / 30 °C / pH 8.0
View Scheme
D-Glutamic acid
6893-26-1

D-Glutamic acid

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid
27655-95-4

(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

N-[ d,l-2-(5-bromo-6-methoxy-2-naphthyl)-propionyl]-l-glutamic acid

N-[ d,l-2-(5-bromo-6-methoxy-2-naphthyl)-propionyl]-l-glutamic acid

Conditions
ConditionsYield
With sodium hydroxide; concentrated aqueous hydrochloric acid In water; acetone

(1)-5-Bromo-6-methoxy-α-methylnaphthalene-2-acetic acid Specification

The (1)-5-Bromo-6-methoxy-α-methylnaphthalene-2-acetic acid, with the CAS registry number 27655-95-4, is also known as (±)-5-bromo-6-methoxy-alpha-methylnaphthalene-2-acetic acid. Its EINECS number is 248-594-2. This chemical's molecular formula is C14H13BrO3 and molecular weight is 309.16. What's more, its systematic name is 2-(5-Bromo-6-methoxy-2-naphthyl)propanoic acid.

Physical properties of (1)-5-Bromo-6-methoxy-α-methylnaphthalene-2-acetic acid are: (1)ACD/LogP: 3.511; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.66; (4)ACD/LogD (pH 7.4): 0.87; (5)ACD/BCF (pH 5.5): 39.05; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 275.50; (8)ACD/KOC (pH 7.4): 4.37; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 46.53 Å2; (13)Index of Refraction: 1.631; (14)Molar Refractivity: 74.214 cm3; (15)Molar Volume: 208.434 cm3; (16)Polarizability: 29.421×10-24cm3; (17)Surface Tension: 50.3 dyne/cm; (18)Density: 1.483 g/cm3; (19)Flash Point: 223.664 °C; (20)Enthalpy of Vaporization: 74.229 kJ/mol; (21)Boiling Point: 446.216 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)C(c1ccc2c(c1)ccc(OC)c2Br)C
(2)Std. InChI: InChI=1S/C14H13BrO3/c1-8(14(16)17)9-3-5-11-10(7-9)4-6-12(18-2)13(11)15/h3-8H,1-2H3,(H,16,17)
(3)Std. InChIKey: JZRWXNBIQCMXSU-UHFFFAOYSA-N

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