Basic information
- Standard SMILES
COc1ccc(N)c(OC)c1- InChIKey
GEQNZVKIDIPGCO-UHFFFAOYSA-N- Molecular formula
- C8H11NO2
- Average molar mass
- 153.18 g/mol
- Monoisotopic mass
- 153.07897859
Overview
2,4-dimethoxyaniline is a black crystalline solid. (NTP, 1992)
Names & identifiers
- Preferred name
- 2,4-Dimethoxyaniline
- IUPAC
- 2,4-dimethoxyaniline
- English name
- 2,4-Dimethoxyaniline
- Molecular formula
- C8H11NO2
- Molecular weight
- 153.18
Names & synonyms
Show more names
Database identifiers
- CAS
2735-04-8- PubChem CID
- 17652
- DTXSID
DTXSID7043829- ChEMBL
CHEMBL1622132- UNII
- I079354GSI
- EC Number
- 220-355-7
- Nikkaji
- J55.221F
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 44.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 119
Experimental & physicochemical properties
Solubility
less than 1 mg/mL at 63 °F (NTP, 1992)
SLIGHTLY SOL IN WATER; SOL IN ETHER, ALC, BENZENE, HOT PETROLEUM ETHER
Melting Point
92.3 °F (NTP, 1992)
33.5 °C
Physical Description
2,4-dimethoxyaniline is a black crystalline solid. (NTP, 1992)
Black solid; [CAMEO] Black solid; mp = 34-37 deg C; [MSDSonline]
Physicochemical properties
- Melting point
- 33 · 33-36 °C (lit.)
- Boiling point
- 75 · 75-80 C
- Density
- 1.075 g/mL · 1.075 g/mL at 25 °C (lit.)
- refractive index
- 1.464 · 1.4640 (estimate)
- Flash point
- 230 °F · >230 °F
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- pka
- 5.14 · 5.14±0.10(Predicted)
- form
- Crystalline Solid
- color
- Dark brown
- Water Solubility
- 7 g/L · 7 g/L (20 ºC)
- BRN
- 638704 · 638704
- Henry's Law Constant
- 1.6 · 1.6×101 mol/(m3Pa) at 25℃, Ebert et al. (2023)
- Stability
- Stability Stable, but sensitive to prolonged exposure to light. Incompatible with acids.
- InChI
- 1S/C8H11NO2/c1-10-6-3-4-7(9)8(5-6)11-2/h3-5H,9H2,1-2H3
- InChIKey
- GEQNZVKIDIPGCO-UHFFFAOYSA-N
- SMILES
- COc1ccc(N)c(OC)c1
- CAS DataBase Reference
- 2735 · 2735-04-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 79354 GSI · I079354GSI
- NIST Chemistry Reference
- 2 · Benzenamine, 2,4-dimethoxy-(2735-04-8)
- EPA Substance Registry System
- 2 · 2,4-Dimethoxyaniline (2735-04-8)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22-36/37/38-20/21/22
- Safety Statements
- 26 · 26-36-36/37/39-22
- RIDADR
- 2811 · 2811
- WGK Germany
- 3 · 3
- RTECS
- 4200000 · BX4200000
- F
- 8 · 8-10-23
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- HS Code
- 29214200 · 29214200
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Hazardous Substances Data
- 2735 · 2735-04-8(Hazardous Substances Data)
- Toxicity
- 50 · mouse,LD50,oral,1gm/kg (1000mg/kg),Progress Report for Contract No. NIH-NCI-E-C-72-3252, Submitted to the National Cancer Institute by Litton Bionetics, Inc. Vol. NCI-E-C-72-3252, Pg. 1973,
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzenamine, 2,4-dimethoxy-
2,4-Dimethoxyaniline: Does not have an individual approval but may be used under an appropriate group standard
Reactivity Profile
2,4-DIMETHOXYANILINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Safety & protection
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Toxicology
Ongoing Test Status
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. /2,4-Dimethoxyaniline hydrochloride/ [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=54150-69-5]
Non-Human Toxicity Excerpts
... Under the conditions of this bioassay there was no convincing evidence for the carcinogenicity of 2,4-dimethoxyaniline HCl in Fischer 344 rats or B6C3F1 mice. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.
National Toxicology Program Studies
A bioassay for the possible carcinogenicity of 2,4-dimethoxyaniline HCl was conducted using Fischer 344 rats and B6C3F1 mice. 2,4-Dimethoxyaniline HCl was admin in the feed, at either of two concn, to groups of 50 male and 50 female animals of each species. Twenty animals of each sex and species were placed on test as controls. The high and low dietary concn of 2,4-dimethoxyaniline HCl were, respectively, 3,000 and 1,500 ppm for rats and 5,000 and 2,500 ppm for mice. The cmpd was admin in the diet for 104 wk to rats and 103 wk to mice, followed by a l wk observation period for both species. ... Adequate numbers of animals in all groups survived sufficiently long to be at risk from late-developing tumors. ... Under the conditions of this bioassay there was no convincing evidence for the carcinogenicity of 2,4-dimethoxyaniline HCl in Fischer 344 rats or B6C3F1 mice. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.
Safety data
- F
- 8-10-23
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- BX4200000
- ridadr
- 2811
- hs_code
- 29214200
- Toxicity
- mouse,LD50,oral,1gm/kg (1000mg/kg),Progress Report for Contract No. NIH-NCI-E-C-72-3252, Submitted to the National Cancer Institute by Litton Bionetics, Inc. Vol. NCI-E-C-72-3252, Pg. 1973,
- risk_code
- 22-36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 26-36-36/37/39-22
- hazard_class
- 6.1(b)
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H319-H335
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
- Hazardous Substances Data
- 2735-04-8(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used as an intermediate for C.I. basic yellow 11; Not currently manufactured in the US; [HSDB]
CHEMICAL INTERMEDIATE FOR C.I. BASIC YELLOW 11
U.S. Exports
(1977) No Data
(1979) No Data
U.S. Imports
(1977) 3.28X10+7 G (PRINCPL CUSTMS DISTS)
(1979) 1.62X10+7 G (PRINCPL CUSTMS DISTS)
U.S. Production
(1976) PROBABLY GREATER THAN 2.27X10+6 GRAMS
(1979) NOT PRODUCED COMMERCIALLY IN US
Applications
UsesVarious 2,4-dimethoxyphenylsemicarbazones were synthesized starting from 2,4-dimethoxyaniline via a phenylcarbamate intermediate. The hydrochloride of 2,4-dimethoxyaniline was prepared by intro- ducing hydrogen chloride gas into an etheral solution and washing the precipitate with absolute diethyl ether.
General DescriptionBlack crystalline solid.
Upstream & downstream products
Downstream products
Suppliers50 total
Related reactions
Linked notes
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