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4-Methoxyphenylacetic Acid

HCID 7690
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
104-01-8
Standard SMILES
COc1ccc(CC(=O)O)cc1
InChIKey
NRPFNQUDKRYCNX-UHFFFAOYSA-N
Molecular formula
C9H10O3
Average molar mass
166.17 g/mol
Monoisotopic mass
166.06299418

Overview

4-methoxyphenylacetic acid appears as pale yellow or off white colored flakes. Severely irritates skin and eyes. May be toxic by ingestion.

Names & identifiers

Preferred name
4-Methoxyphenylacetic Acid
IUPAC
2-(4-methoxyphenyl)acetic acid
English name
4-Methoxyphenylacetic acid
Molecular formula
C9H10O3
Molecular weight
166.17

Names & synonyms

4-Methoxyphenylacetic acid104-01-82-(4-methoxyphenyl)acetic acidHomoanisic acidBenzeneacetic acid, 4-methoxy-p-Methoxyphenylacetic acid(4-Methoxyphenyl)acetic acid4-Methoxybenzeneacetic acid2-(p-Anisyl)acetic acid(p-Methoxyphenyl)acetic acidp-Anisylacetic acidHomoanisate
Show more names
4MPAAASISCHEM D13364RARECHEM AL BO 01334-Methoxyphenylacetip-Methioxy-toluicacid4-Methoxyphenylacetic
NSC 27799EINECS 203-166-4Acetic acid, (p-methoxyphenyl)-4-methoxyphenylacetatep-Methoxy-alpha-toluic acidAJP2V8U5K6Homo-p-anisic acidAcetic acid, p-methoxyphenyl-

Database identifiers

CAS
104-01-8
PubChem CID
7690
DTXSID
DTXSID1059288
ChEMBL
CHEMBL1760597
ChEBI
CHEBI:55501
UNII
AJP2V8U5K6
EC Number
203-166-4
Nikkaji
J10.116H

Properties

Computed structural propertiesFilling in

XLogP
1.4
Topological polar surface area
46.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
12
Formal charge
0
Complexity
148

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift
LogP · 2 items

1.42

1.48

Solubility18 mg/mL
Boiling Point138.00 to 140.00 °C. @ 3.00 mm Hg
Melting Point87 °C
Physical Description · 2 items

4-methoxyphenylacetic acid appears as pale yellow or off white colored flakes. Severely irritates skin and eyes. May be toxic by ingestion.

Solid

Collision Cross Section · 2 items

122.84 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

137.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Physicochemical properties

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1334 reports by companies from 8 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

Chemical: Benzeneacetic acid, 4-methoxy-

Status: Cease Manufacture Update: 30-06-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/18981

4-Methoxphenylacetic Acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Benzeneacetic acid, 4-methoxy-: Human health tier I assessment
DOT LabelCorrosive
Fire HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Reactive GroupAcids, Carboxylic
Reactivity Profile · 1 item

Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationBenzeneacetic acid, 4-methoxy-: ACTIVE
Applications · 6 items

Uses4-Methoxyphenylacetic Acid is a compound that was found from microbial phenolic metabolites in human feces after the consumption of gin, red wine and dealcholized red wine.

Description4-METHOXYPHENYLACETIC ACID(104-01-8) is used in organic synthesis as well as pharmaceutical industry, especially used as an intermediate of puerarin. It can also be used as potential plasma biomarkers for early detection of non-small cell lung cancer. It is also used in drug industry as an intermediate to make Dextromethorphan.

Uses4-Methoxyphenylacetic Acid is a compound that was found from microbial phenolic metabolites in human feces after the consumption of gin, red wine and dealcholized red wine.

Uses4-Methoxyphenylacetic acid can be used:To prepare methyl 4-methoxyphenylacetate by esterification with dimethyl carbonate using mesoporous sulfated zirconia catalyst.As a ligand to synthesize pharmacologically important dinuclear gallium(III) and phenyltin(IV) carboxylate metal complexes.As a reactant to synthesize hydroxylated (E)-stilbenes by reacting with substituted benzaldehydes via Perkin reaction.

UsesPreparation of pharmaceuticals, other organic compounds.

General DescriptionPale yellow or off white colored flakes. Severely irritates skin and eyes. May be toxic by ingestion.

Upstream & downstream products

Upstream raw materials

4'-MethoxyacetophenonePiperazine hexahydrateBenzyl (4-methoxyphenyl)acetate

Related reactions

1,382 records
New reaction record
HRID 6727 reaction equation
HRID 6727As reactantuspto-grants-2006_08
HRID 91467 reaction equation
HRID 91467As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 94876 reaction equation
HRID 94876As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 95181 reaction equation
HRID 95181As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 101882 reaction equation
HRID 101882As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 104320 reaction equation
HRID 104320As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 136341 reaction equation
HRID 136341As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 150254 reaction equation
HRID 150254As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Melting point
84 · 84-86 °C(lit.)
Boiling point
140 °C3 · 140 °C3 mm Hg(lit.)
Density
1.1708 · 1.1708 (rough estimate)
bulk density
440 kg/m3 · 440kg/m3
vapor pressure
0.071 Pa · 0.071Pa at 25℃
refractive index
1.5101 · 1.5101 (estimate)
Flash point
193 °C · 193°C
storage temp.
30 °C · Store below +30°C.
solubility
6 g/l · 6g/l
form
Crystalline Powder and Chunks
pka
1 · pK1:4.358 (25°C)
color
White to light yellow
Water Solubility
6 g/L · 6 g/L (20 ºC)
BRN
1101737 · 1101737
InChI
1S/C9H10O3/c1-12-8-4-2-7(3-5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)
InChIKey
NRPFNQUDKRYCNX-UHFFFAOYSA-N
SMILES
COc1ccc(CC(O)=O)cc1
LogP
1.295 at · 1.295 at 25℃
CAS DataBase Reference
104 · 104-01-8(CAS DataBase Reference)
FDA UNII
2 V8U5K6 · AJP2V8U5K6
NIST Chemistry Reference
4 · Benzeneacetic acid, 4-methoxy-(104-01-8)
EPA Substance Registry System
4 · Benzeneacetic acid, 4-methoxy- (104-01-8)
UNSPSC Code
12352106 · 12352106
NACRES
22 · NA.22
Symbol(GHS)
5 · GHS05
Signal word
Danger
Hazard statements
318 · H318
Precautionary statements
280 · P280-P305+P351+P338
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn,Xi
Risk Statements
22 · 22-36/37/38-20/21/22
Safety Statements
26 · 26-36
WGK Germany
3 · 3
RTECS
8960000 · AI8960000
Hazard Note
Irritant
TSCA
TSCA listed
HS Code
29189090 · 29189090
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
1 · Eye Dam. 1
REACH Registrations
Inactive
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
Hazard Classes and CategoriesAcute Tox. 4 (> 99.9%)

Safety & protection

Fire FightingExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
First AidExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Nonfire Spill ResponseExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Personal Protective Equipment (PPE)Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
AI8960000
hs_code
29189090
risk_code
22-36/37/38-20/21/22
Signal word
Danger
Symbol(GHS)
GHS05
hazard_code
Xn,Xi
hazard_note
Irritant
safety_code
26-36
Storage Class
11 - Combustible Solids
Hazard statements
H318
REACH Registrations
Inactive
Hazard Classifications
Eye Dam. 1
Precautionary statements
P280-P305+P351+P338
tert-butyl 2-(4-methoxyphenyl)acetate

Downstream products

2-Chloro-5-(4-methoxyphenyl)pyrimidine4-Methoxyphenylacetyl chloride3-chloro-4-methoxyphenylacetic acidN-ethyl-p-methoxy-alpha-methylphenethylamine4-Methoxyphenethyl bromide2-p-Anisyl-1,3-indandione(4-Methoxy-3-nitrophenyl)acetic acidEthyl 4-methoxyphenylacetateMethyl 4-methoxyphenylacetate(3-Iodo-4-methoxyphenyl)acetic acid5-Acetonyl-2-methoxybenzenesulphonylchloride

Additional notes

DefinitionChEBI: A monocarboxylic acid that is phenylacetic acid carrying a 4-methoxy substituent. It is used as an intermediate for pharmaceuticals and other organic synthesis. It has been found to inhibit the germination of cress and lettuce seeds.