p-Anisoyl chloride

HCID 7477CAS 100-07-2

Basic information

Standard SMILES
COc1ccc(C(=O)Cl)cc1
InChIKey
MXMOTZIXVICDSD-UHFFFAOYSA-N
Molecular formula
C8H7ClO2
Average molar mass
170.59 g/mol
Monoisotopic mass
170.01345714

Overview

4-methoxybenzoyl chloride appears as an amber-colored crystalline solid. Melting point 72 °F. Corrosive to metals and skin. Vapors may cause serious burns to the eyes.

Names & identifiers

Preferred name
p-Anisoyl chloride
IUPAC
4-methoxybenzoyl chloride
English name
4-Methoxybenzoyl chloride
Molecular formula
C8H7ClO2
Molecular weight
170.59

Names & synonyms

4-Methoxybenzoyl chloride100-07-2P-ANISOYL CHLORIDEp-Methoxybenzoyl chlorideBenzoyl chloride, 4-methoxy-Anisoyl chloride4-Anisoyl chloride4-Methoxybenzoic acid chlorideBenzoyl chloride, p-methoxy-p-Methoxybenzoic acid chloridepara-anisoyl chlorideNSC 86125
Show more names
4-methoxybenzoylAnisoylchloridP-ANSIOYHLORIDEP-anisoylclorideAKOS BBS-000039074-Anisoylchloride99%
UN1729HSDB 447TV6DMQ94514methoxybenzoyl chlorideBenzoic acid, 4-methoxy-, chlorideEINECS 202-816-4NSC-86125DTXSID9059204

Database identifiers

CAS
100-07-2、1300-64-7
PubChem CID
7477
DTXSID
DTXSID9059204
UNII
TV6DMQ9451
EC Number
202-816-4
Nikkaji
J28.748B

Properties

Computed structural properties

XLogP
2.9
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
11

Experimental & physicochemical properties

Chemical Classes · 2 items

Toxic Gases & Vapors -> Acid Halides

Corrosives

SpringerMaterials PropertiesChemical shift
Density · 2 items

1.26 at 68 °F (USCG, 1999) - Denser than water; will sink

1.261 g/cu cm at 20 °C

Color/FormClear crystals or amber liquid
SolubilitySoluble in ether and acetone. Very soluble in benzene. Slightly soluble in carbon tetrachloride.
Boiling Point · 2 items

504 °F at 760 mmHg (USCG, 1999)

262-263 °C

Physicochemical properties

Melting point
22 °C · 22 °C(lit.)
Boiling point
262 · 262-263 °C(lit.)
Density
1.26 g/mL · 1.260 g/mL at 20 °C(lit.)
vapor pressure
1.853 Pa · 1.853Pa at 25℃
refractive index
20 · n20/D 1.581(lit.)
Flash point
190 °F · 190 °F

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 79 reports by companies from 9 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 4 items

Chemical: Benzoyl chloride, 4-methoxy-

Status: Active Update: 08-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/19721

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

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelCorrosive
Fire Hazards · 2 items

Special Hazards of Combustion Products: Irritating hydrogen chloride fumes may be formed. (USCG, 1999)

· Combustible material: may burn but does not ignite readily.

Health Hazards · 2 items

Vapor irritates mucous membranes. Contact of liquid with eyes or skin causes severe irritation. Ingestion causes severe irritation of mouth and stomach. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Hazards Summary · 1 item

Decomposed by water; Corrosive to tissue; Explosion risk from Sealed containers due to pressure from decomposition at room temperature; [Hawley] May cause serious burns to eyes; Releases hydrochloric acid by hydrolysis; Emergency treatment: acids; [HSDB] Reacts with moisture forming hydrochloric acid; [CAMEO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause edema and chemical pneumonitis; [MSDSonline]

DOT ID and Guide1729 156

Safety & protection

Fire FightingExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 items

INHALATION: remove to fresh air.

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 1 item

If material on fire or involved in fire: Use dry chemical or carbon dioxide. Do not use water on material itself. If large quantities of combustibles are involved, use water in flooding quantities as spray and fog. Use water spray to knock-down vapors. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.

Storage ConditionsExplosion risk when in closed containers due to pressure caused by decomposition at room temperature.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a structure estimation method(2), indicates that p-anisoyl chloride is expected to have very high mobility in soil(SRC). Volatilization of p-anisoyl chloride from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.8X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). p-Anisoyl chloride is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.014 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2005).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a structure estimation method(2), indicates that p-anisoyl chloride is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 7.8X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 and 50 days, respectively (SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 1.52(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). p-anisoyl chloride is decomposed in water(8), but the rate of this reaction is not known(SRC). However, the hydrolysis half-life of benzoyl chloride, a structural analog, is on the order of several minutes(9), suggesting that p-anisoyl chloride will undergo rapid hydrolysis in the environment(SRC). Biodegradation data were not available(SRC, 2005).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), p-anisoyl chloride, which has an estimated vapor pressure of 0.014 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase p-anisoyl chloride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 19 hours(SRC), calculated from its rate constant of 2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). p-Anisoyl chloride absorbs light greater than 290 nm and may be subject to direct photolysis in the environment; however, the rate of this potential reaction is unknown(SRC).

Adverse EffectsDermatotoxin - Skin burns.
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for p-anisoyl chloride can be estimated to be 37(SRC). According to a classification scheme(2), this estimated Koc value suggests that p-anisoyl chloride is expected to have very high mobility in soil(SRC).

Human Toxicity Excerpts · 5 items

/SIGNS AND SYMPTOMS/ Symptomatology (...ingestion or skin contact): 1) corrosion of mucous membranes of mouth, throat...esophagus, with...pain and dysphagia. Necrotic areas...grayish white but soon...blackish discoloration...and sometimes shrunken or wrinkled texture. /Acid/

/SIGNS AND SYMPTOMS/ Symptomatology.../ingestion/: 2. Epigastric pain...may be associated with nausea & vomiting...intense thirst. 3. Circulatory collapse...clammy skin, weak & rapid pulse, shallow resp...scanty urine. ...shock is often...cause of death. 4. Asphyxial death due to glottic edema. /Acid/

/SIGNS AND SYMPTOMS/ Symptomatology.../ingestion/: 5. Ulceration of all membranes and tissues with which acid comes in contact. Ulcerated areas often perforate, leading to mediastinitis and peritonitis. 6. Late esophageal, gastric and pyloric strictures and stenosis...may require...surgical repair, should be anticipated. /Acid/

/SIGNS AND SYMPTOMS/ Symptomatology: 6. ...permanent scars may...appear in cornea, skin and oropharynx. 7. Uncorrected circulatory collapse of several hr...may lead to renal failure and ischemic lesions in liver and heart. /Acid/

For more Human Toxicity Excerpts (Complete) data for P-ANISOYL CHLORIDE (7 total), please visit the HSDB record page.

Artificial Pollution Sourcesp-Anisoyl chloride's production and use as an intermediate for dyes and medications(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 item

An estimated BCF of 3 was calculated for p-anisoyl chloride(SRC), using an estimated log Kow of 1.52(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Safety data

F
10-21
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
CA0270000
ridadr
UN 1729

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as intermediate for dyes and medicines; [Hawley]

Intermediate for dyes and medicines

Methods of ManufacturingPrepared from p-anisic acid and thionyl chloride: Vanderhaeghe et al, J Pharm Pharmacol 6, 119 (1954).
General Manufacturing InformationBenzoyl chloride, 4-methoxy-: ACTIVE
Applications · 2 items

Uses4-Methoxybenzoyl chloride is used in the synthesis of stilbene and dihydrostilbene derivatives as potential anti-cancer agents. It is also used in the synthesis of coumarin dimers with potential HIV-1 activity.

General Description4-Methoxybenzoyl chloride is one of the reactive acylating agents that can react with carboxylic acids, alcohols and amines to yield respective carboxylic anhydrides, esters and amides. 4-methoxybenzoyl chloride reacts with potassium thiocyanate to yield isothiocyanate derivative via nucleophilic addition-elimination mechanism.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海策嵘生物科技有限公司[email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
Additional notes · 1 item

DefinitionThe hydrolysis of 4-Methoxybenzoyl chloride (OMe) generally occurs through a dissociative mechanism (SN1). The reaction rate is strongly affected by the polarity of the medium and the ability to stabilize the leaving group. Water encapsulated within a reverse micellar system is less polar and less available compared to a continuous aqueous phase; Consequently, the hydrolysis of OMe in the micellar medium is slower than in pure water.

Related reactions

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Linked notes

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