529-64-6

Basic information

• Product Name: Tropic acid
• Synonyms: DL-3-HYDROXY-2-PHENYLPROPIONIC ACID;DL-A-PHENYLHYDRACRYLIC ACID;DL-TROPIC ACID;3-HYDROXY-2-PHENYLPROPIONIC ACID;ALPHA-(HYDROXYMETHYL)BENZENEACETIC ACID;ALPHA-PHENYLHYDRACRYLIC ACID;2-PHENYLHYDROACRYLIC ACID;2-PHENYLHYDRACRYLIC ACID
• CAS NO: 529-64-6
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 208-465-3
• Mol File: 529-64-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 116-118 °C(lit.)
• Boiling Point: 234.38°C (rough estimate)
• Flash Point: 163.1°C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.1097 (rough estimate)
• Vapor Pressure: 0.000114mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: methanol: 0.1 g/mL, clear
• PKA: pK1:3.53 (25°C)
• Water Solubility: 20 g/L (20 ºC)
• Merck: 13,9849
• CAS DataBase Reference: Tropic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Tropic acid(529-64-6)
• EPA Substance Registry System: Tropic acid(529-64-6)

Safety Data

• Hazard Codes: Xi
• Statements: 22-41-37/38-36/37/38
• Safety Statements: 22-24/25-36/37/39-36-26
• WGK Germany: 3
• Hazardous Substances Data: 529-64-6(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white crystalline powder

Uses

Tropic Acid is a benzoic acid derivative and thus carries anti-fungal properties.

Purification Methods

Crystallise tropic acid from water or *benzene. [Beilstein 10 IV 664.]

InChI:InChI=1/C9H10O3/c10-6-8(9(11)12)7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)/p-1/t8-/m0/s1

Synthetic route

2.2-dimethyl-5-phenyl-1,3-dioxane-4,6-dione (15231-78-4) → Tropic acid (529-64-6)

Conditions	Yield
With samarium diiodide; water In tetrahydrofuran at 20℃; Inert atmosphere;	72%
With samarium diiodide; water In tetrahydrofuran at 20℃;	72%

α-[(acetyloxy)methyl]benzeneacetic acid (37504-67-9, 131682-38-7, 14510-36-2) → Tropic acid (529-64-6)

Conditions	Yield
With sodium hydroxide In methanol	70%

phenylacetic acid (103-82-2) + formaldehyd (50-00-0) → Tropic acid (529-64-6)

Conditions	Yield
Stage #1: phenylacetic acid With isopropylmagnesium bromide In diethyl ether; benzene Heating; Stage #2: formaldehyd In diethyl ether; benzene for 4h;	69.6%
(i) LDA, THF, HMPA, (ii) /BRN= 1209228/; Multistep reaction;

C15H21BO4 → Tropic acid (529-64-6)

Conditions	Yield
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 20℃; for 4h;	57%

2-phenylpropane-1, 3-diol (1570-95-2) → Tropic acid (529-64-6)

Conditions	Yield
With acetate buffer pH 5 In water at 30℃; for 168h; Gluconobacter roseus IAM 1841;	2%
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid 3: sodium hydroxide / methanol View Scheme

phenylacetic acid (103-82-2) + isopropylmagnesium chloride (1068-55-9) → Tropic acid (529-64-6)

Conditions	Yield
With benzene ether anschliessend mit Formaldehyd behandeln;

formaldehyd (50-00-0) + ethyl 2-phenyl-2-bromoacetate (2882-19-1) → Tropic acid (529-64-6)

Conditions	Yield
With zinc

3-chloro-2-phenyl-propionic acid (51545-26-7) → Tropic acid (529-64-6)

tropic acid ethyl ester (3979-14-4) → Tropic acid (529-64-6)

Conditions	Yield
With barium dihydroxide dl-tropic acid;
With sodium hydroxide dl-tropic acid;
With barium dihydroxide; ethanol at 60℃; dl-tropic acid;

methyl tropate (3967-53-1) → Tropic acid (529-64-6)

Conditions	Yield
With barium dihydroxide dl-tropic acid;
With sodium hydroxide dl-tropic acid;
With methanol; sodium hydroxide at 80℃; Temperature; Large scale;

atropine (51-55-8) → Tropic acid (529-64-6)

Conditions	Yield
With ethanol; water

atropine (51-55-8) → Tropic acid (529-64-6) + Tropanol (7432-10-2, 911648-75-4)

Conditions	Yield
With hydrogenchloride at 120℃; weitere Nebenprodukts:Atropasaeure,α-Isatropasaeure,β-Isatropasaeure;
With ethanol; water

atropine (51-55-8) → Tropic acid (529-64-6) + 3-tropanol (120-29-6)

Conditions	Yield
With hydrogenchloride

scopolamine (51-34-3, 138-12-5, 64069-63-2, 124917-17-5) → Tropic acid (529-64-6)

Conditions	Yield
With barium dihydroxide at 60℃;

α-phenyl-β-propiolactone (27150-91-0) → Tropic acid (529-64-6)

Conditions	Yield
With sodium hydroxide In methanol

tropicamide → 2-phenylacrylic acid + Tropic acid + N-ethyl-N-(4-picolyl)-atropamide + 4-(ETHYLAMINOMETHYL)PYRIDINE

Conditions	Yield
With sodium hydroxide In water for 10h; Heating;

(2S,3S)-<1-14C,3-3H>phenylalanine → Tropic acid (529-64-6) + (+/-)-<1-14C,3-3H>tropic acid

Conditions	Yield
Mechanism; Product distribution; multistep reaction; the stereochemistry of the migration of the carboxyl group was investigated during the biosynthesis of tropic acid;

(2S,3R)-<1-14C,3-3H>phenylalanine → Tropic acid (529-64-6) + 3-hydroxy-2-phenyl-propionic acid-1-14C

Conditions	Yield
Mechanism; Product distribution; multistep reaction; the stereochemistry of the migration of the carboxyl group was investigated during the biosynthesis of tropic acid;

norhyoscyamine + barium hydroxide → Tropic acid

Conditions	Yield
Hydrolysis;

Upstream product

• 103-82-2 phenylacetic acid 
• 1068-55-9 isopropylmagnesium chloride 
• 51545-26-7 3-chloro-2-phenyl-propionic acid 
• 27150-91-0 α-phenyl-β-propiolactone 
• 1570-95-2 2-phenylpropane-1, 3-diol 
• 537-29-1 norhyoscyamine 
• 101-31-5 Hyoscyamine 
• 51-34-3 scopolamine 
• 7647-01-0 hydrogenchloride 
• 51-55-8 Atropine 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 7722-84-1 dihydrogen peroxide 
• 5441-68-9 α-phenyl-β-bromopropionic acid 

Downstream Products

• 25228-98-2 1-methyl-1-(2-tropoyloxy-ethyl)-piperidinium; bromide 
• 37504-67-9 α-[(acetyloxy)methyl]benzeneacetic acid 
• 51-55-8 Atropine 
• 16175-85-2 atropine 
• 30333-92-7 DL-tropic acid-[9-methyl-9-aza-bicyclo[3.3.1]non-3exo-yl ester 
• 49640-36-0 N-Ethoxy-3-hydroxy-2-phenylpropionamid 
• 3967-53-1 methyl tropate 
• 131682-38-7 (+)-3-acetoxy-2-phenylpropionic acid 
• 37504-67-9 (αS)-α-(acetoxymethyl)benzeneacetic acid 
• 17126-67-9 (+)-(R)-tropic acid 
• 22143-89-1 (+/-)-Tropoyl granatan-3a-ol 
• 51-55-8 atropine 
• 51545-26-7 3-chloro-2-phenyl-propionic acid 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Synthesis method of 3-hydroxy-2-phenylpropionic acid

The invention discloses a synthetic method of 3-hydroxyl-2-phenylpropionic acid. The method comprises the following steps: mixing dimethyl sulfoxide, paraformaldehyde, potassium carbonate powder and methyl phenylacetate, heating to 85-95 DEG C, carrying out gas phase monitoring reaction, and cooling to room temperature when the GC content of the product methyl tropine is more than or equal to 70%;adjusting the pH value to be neutral, and performing reduced pressure distillation for desolvation; then adding methanol into the desolventized mixture, dropwise adding a sodium hydroxide solution, and reacting to obtain a mixed solution containing sodium tropine salt; adjusting the pH value of the mixed solution to 2-3, and completely reacting to obtain a crude product; and finally, recrystallizing the crude product sequentially by using methylbenzene of which the ratio of m product to m methylbenzene is 1: (4-6), methylbenzene/water of which the ratio of m product to m methylbenzene to m water is 1: (1-2): (4-6), and water of which the ratio of m product to m water is 1: (4-6) to obtain a pure product of 3-hydroxyl-2-phenylpropionic acid. According to the method, GC is adopted to monitor the reaction, control points are judged quickly and accurately, purification of methyl tropinate is not needed, operation procedures are reduced, and production cost is reduced. According to the method, the purity of the prepared 3-hydroxyl-2-phenylpropionic acid reaches 99% or above while the yield is ensured to reach 76.5% or above.

Gold(I)/copper(II)-cocatalyzed tandem cyclization/semipinacol reaction: Construction of 6-Aza/Oxa-Spiro[4.5]decane skeletons and formal synthesis of (±)-halichlorine

A simple and efficient strategy for the construction of 6-aza/oxa-spiro[4.5]decane skeletons under the cocatalysis of gold(I)/copper(II) was developed, and its potential utility was demonstrated by a formal synthesis of the biologically active marine alkaloid (±)-halichlorine.

Selective reductions of cyclic 1,3-diesters using SmI2 and H2O

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